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Silicon Valley's best kept secret: Founder liquidity

Finbarr
113 replies
13h34m

Secondary at Series A is very rare. Part of the reason more early employees don't get included in secondary sales is because of the Securities Exchange Act of 1934 14e-2. If you have more than 10 sellers involved, the transaction can be considered a tender offer, which triggers additional regulatory requirements and disclosures.

As of 4 months ago I left a very successful stealth startup (which grew to 40M in ARR in two years) to become a founder and that is when it clicked - I expected to feel stressed, pressured, and the weight of all of the risk I was taking.

Please let us all know how that's working out for you in 5-10 years. 4 months in and no stress? Must be easy riding from here!

onlyrealcuzzo
61 replies
5h3m

Especially 5 years down the road when you own ~30% of a $100M company - but you know there's a decent chance you'll walk away with very little, if not nothing - while your peers are all making ~$1M per year working 6 hour days at FAANG with a life partner, maybe kids, and a sizable net worth that isn't going away.

Sure, you've got a decent chance to rocket past them in wealth. But they've got everything they really want. You might have foregone your shot at a partner to build a company to mostly profit someone else who did nothing but write you a check. If you do have kids, you'll be old as hell raising them. All you'll have is extra stuff hardly anyone cares about - except maybe you - if you're the type of person chasing down a decimillion net worth.

I hope these people truly enjoy their boats and their third homes in Aspen! It sure is a lot of work to get them.

icedchai
13 replies
4h13m

Or, based on examples I've witnessed, 5 years down the road you own 20% of a $1M company because your forecasts were off by an order of magnitude. You've gone through a couple down rounds, where investors took at least 20% each time. You feel obligated to your investors and employees, while there is almost zero chance of walking away with anything.

htrp
8 replies
4h4m

One thing that is underappreciated in the startup mythos is just closing up shop and trying again.

moneywoes
7 replies
3h21m

do investors allow that

tomrod
6 replies
3h16m

They don't control it.

nlh
3 replies
1h51m

One of the greatest quotes I've ever heard from a founder buddy was when his startup was going through a particularly dark moment and struggling: One of the investors said to him "Maybe you should seriously think about shutting down and giving us our money back", to which he replied:

"It's not your money anymore."

icedchai
2 replies
1h40m

Yeah, then the investors call a board meeting and bring in a new CEO to provide adult supervision after a 2/3rds vote. The give that guy more equity than you to keep the ship afloat. "It's not your company anymore."

Finbarr
1 replies
1h30m

Your daily reminder of the importance of maintaining board control.

flyinglizard
0 replies
14m

Not realistic to maintain control past A unless you built a real rocketship. The board doesn’t usually want to run your company - they have enough other companies, some evidently better than yours as they don’t require this intervention.

golergka
0 replies
25m

Reputation is a thing. You might need investors in your next startup.

Finbarr
0 replies
2h49m

That very much depends on the stage of the company and how much control has been given up at different points. Do you think the management team of a public company could just decide to shut it down? As you raise consecutive rounds, your control is eroded.

throaway893
3 replies
3h15m

5 years down the road you own 20% of a $1M

What a horrible fate. They only got five years of salary plus 200k extra. I'll include them in my prayers (just kidding, I don't pray).

wordpad25
1 replies
3h1m

They also probably worked many 100 hour weeks while they could've earned more and worked a lot less with less stress

rbranson
0 replies
2h47m

That's how risk works. The FAANG employee friends have exactly a 0% chance at a 9-figure outcome. They'll easily be at top decile if they pull a nominal $10M+ post-tax in 20 years.

icedchai
0 replies
2h7m

Except the "$200K" is purely paper, and has an expected value of closer to zero. Remember, common shareholders are the last ones to get paid. Investors have preferences and get paid back first (often with interest.)

Also realize you were probably forced to take a pay cut and have a below average salary due to cost-cutting measures from the board. We'll ignore the non-financial problems, like tons of stress, complaining employees demanding more equity because you couldn't give them raises...

No, it's not a good situation.

foobarian
13 replies
4h1m

making ~$1M per year working 6 hour days at FAANG

Can you say more on this? I didn't realize FAANG TCO was quite that high. Maybe it's time to swallow some pride and take the adtech money after all...

onlyrealcuzzo
8 replies
3h45m

The average SUCCESSFUL founder is in their earlier 30s. At that point - you should be at least L4 (probably L5) at FAANG. Salaries are about ~$450k at that level and age.

In 5 years, if you work even a fraction of as hard as you need to be a successful founder, you should be L7 - salaries are usually >$800k at that point.

No, it is not like any average slacker straight out of college in 5 years can get to a $1M salary at FAANG. But if you're the type of person that could successfully grow a company to a multi hundred million valuation in 5 years - you can make $1M at FAANG.

dclowd9901
3 replies
3h10m

Big caveats on these numbers:

1. You’ll have to be located in SF or Seattle.

2. Going from L5-L7 is _not_ trivial. It requires a somewhat miraculous combination of being on a productive team with a good boss, a lot of opportunities for showy work and your own gamesmanship around corporate politics.

Is it possible? Sure. But in my short stint at Amazon, I met a lot of people who should have been higher level and were simply not due to missing one of these factors.

onlyrealcuzzo
2 replies
1h20m

Going from L5-L7 is _not_ trivial

It is trivial compared to growing a company successfully from $10M valuation to $100M valuation + an exit.

dclowd9901
1 replies
49m

[citation needed]

Frankly, many more aspects of trying to grow your career from l5-l7 are out of your hands than they are when you're at a startup.

onlyrealcuzzo
0 replies
30m

The vast majority of startup success is luck...

There are literally thousands of people going from L5-L7 at the major tech companies per founder successfully exiting a >$100M company.

kolbe
0 replies
3h17m

Those aren't entirely overlapping skills. There are plenty of founders whose attitudes and generalist skill sets make them unhireable in the management ranks of FAANG.

foooorsyth
0 replies
2h19m

you should be L7

The distribution of the ladder is logarithmic. Most never make L6. L5 is often terminal level IC without any “up or out” obligations. Lots of people spend a long time at L5 and retire.

Xcelerate
0 replies
42m

But if you're the type of person that could successfully grow a company to a multi hundred million valuation in 5 years - you can make $1M at FAANG.

Disagree. Totally different skill sets. Not saying there is no correlation at all, but probably less than one might think.

kilbuz
2 replies
3h44m

You don't start there, but you can get there as you level up. A lot of that would be because the stock on your RSU grants goes up while you work there though. I don't think many SWE have 7 figure targeted comp (highest levels, yes). But plenty get there with refreshers and stock appreciation.

kolbe
1 replies
3h16m

Explain the math on leveling up. Each year, Meta hires more Jrs than there exist L7+'s at the entire company.

throwaway-blaze
0 replies
2h49m

Many people top out at a lower level because they don't play corporate politics games or because the L7s aren't moving on, so there's no real room for promotion among the L5s and 6s.

Microsoft in the Ballmer years (early/mid 2000s) had this problem. Promising L65/L66/L67 (probably equiv to L5/6 at AMZN) would leave because the next step was full. All the "partners" were hanging around and not making room for the next gen of leaders.

gopher2000
0 replies
31m

See levels.fyi. The pay levels for FAANG companies are fairly accurate. But you'd have to be something like L7/E7 level at a Meta/Google to break $1M.

Also note that some comp numbers get heavily inflated by people incorporating stock value increasing between the equity was first issued and the stock actually vested.

ditonal
11 replies
2h15m

You’re obviously overstating the FAANG SWE lifestyle.

But beyond that, it’s interesting you picked FAANG SWE and not startup SWE as the basis of your comparison.

The whole premise of the article is that startup employees are often sold a bag of goods about equity and upside that’s simply a terrible deal. Not terrible in the sense that it’s highly risky, but that it doesn’t even come close to compensating for that risk premium. Its sold as FAANG is low risk medium upside but startup SWE is high risks high upside but really its extreme risk and almost no upside because VCs find dozens of ways to carve it out. And people will say startups pay “market” compensation but they almost always mean base salary only, and the equity is such a horrible deal, it’s borderline fraudulent scam on the part of founders to sell startup employees on the equity as a fair deal.

As an aside, when people think SWEs don’t need unions/ professional associations, they think of teachers unions or autoworker unions where pay is standardized on seniority. Instead, we could have something where our lawyers in our camp could review equity terms and we could collectively advocate for things like liquidity deals. That will never ever happen if you only trust the deals the VCs and founders offer.

Finbarr
7 replies
2h5m

Let's not forget that FAANG companies were all startups at one point. Early employees at those companies experienced significant upside. Startups can be very high risk, and in rare cases, extreme upside.

ditonal
5 replies
1h48m

This is the “startup myth” that lets the scam perpetuate.

The world has changed. Google IPOed just a few years after it founded. Now Stripe, objectively one of the most successful startups ever, still hasn’t IPOed after 15 years.

Liquidity preference Dilution

Even the F in FAANG had a major movie made about early employees getting shafted by dilution!

FAANG is 5 companies founded a long time ago. Since then VCs have completely rewritten the rules of the game. But they’ll still point to extreme outliers in the old rules. The fairy tale of the Google masseuse has probably cost tens of thousands of engineers millions in compensation.

You need to get things in writing and do the math and startups make it as difficult as possible to do that and then the math never adds up. So they resort to fairy tales.

Finbarr
2 replies
1h39m

Many huge private companies, like Stripe, have found ways to provide liquidity to their employees without going public, e.g., through tender offers. Some more recent examples of companies where early employees did very well would be AirBnB, Coinbase and DoorDash.

ditonal
1 replies
1h8m

Early executives at those companies did very well. Early employees did well, but risk-adjusted , not really. I know people who were fairly early at those companies and they own nice SFH in the Bay Area but they're still working as Directors or whatever.

Consider that if you could make 400k (including liquid stock) in compensation at FAANG but you take 180k at the startup, you're basically betting 220k a year on the company. Except unlike any other company you bet 220k on, you won't get a board seat, you won't get access to key metrics, your influence will be dominated by "real" investor's influence.

If your NW is less than 10M, which presumably it is, anyone who's heard even heard of the words "Kelly Criterion" would tell you your nuts for betting 220k a year on one startup. And yet, you get treated like "an employee" and not like "an investor" for taking that insane risk.

So YC has invested in 5000 companies, and you can name 3 that had top-notch outcomes, thats 0.06% success - and you had to work like a dog to realize it! And that money was locked up. Those same early employees could have taken that $220k/ year, put it on Bitcoin or Apple stock, and retired off that. And Bitcoin and Apple were much easier "picks" than an given startup.

The math simply does not add up and the whole system runs off mystique and naivety. And I've worked at startups that gave me a hard time about asking about outstanding shares, about asking about the cap table, about asking about liquidation preference. This is _critical_ information before you invest a significant portion of your life and net worth on a company and that they're guarded about and it should raise the ultimate alarm bells that they don't fall over themselves to explain every part of it.

There's a bunch of propaganda out there "Explaining ISOs, written by a16z" that's a smoke screen of the truth. The math does not add up.

The dream startup employee is really really good at Transformer architectures and really really bad at personal finance. Fortunately for startups, a shocking amount of these people exist. But it doesn't change that if sharp financiers looked at employee equity packages at startups objectively, every single one would agree it's a scam deal.

Finbarr
0 replies
41m

First of all, we're on the same page about the risk profile of working for larger companies being better for employees. But the reality is there aren't enough of those jobs for every single startup employee out there to get one. Some people also like the startup environment - move fast and break things, etc.

Your denominator (5000) is _all_ investments that YC has made. You need to look at investments of a certain vintage, e.g., 10 years or more. You also need to include all the other companies of that vintage where employees did well (way more companies in that cohort have sold or gone public). The result is 0.06% is a gross understimation of the success rate (where success is defined as successful enough for early employees to make a lot of money).

whiplash451
0 replies
1h3m

Can you please explain in what way VCs have completely rewritten the rules? Asking genuinely.

JakeTheAndroid
0 replies
47m

I don't agree it's a myth. Is it an extreme risk? Yes, of course. Do people view the risks to be way too low? Yes. But I worked at Cloudflare pre-IPO, got shares at 1.73, and at one point CF was at 200 a share. That was more or less what I was "promised" from the equity.

Stripe is one example of a successful startup not going public, but there are tons of startups that are going public. And there are many startups that wish they could go public, but they simply don't have the finances or business to do so.

I don't think VCs changed much from when Google went public until COVID. We were seeing massive overvaluations of tech companies for years. Once through 2020, VCs got scared and now the landscape is a bit different. But the AI craze has started to get VCs back out of their shells taking bets on risky projects.

So, yeah, idk what I agree with this assessment. At least it's not been my experience in tech over the last 8+ years.

gopher2000
0 replies
33m

The argument that a startup could be the next FAANG is anchored in lottery-like odds.

jakjak123
2 replies
2h2m

This 100%. Really the only reason to work at a startup as an engineer is if you really want to, because everyone pays low and the tiny bit of equity is essentially worthless in 99% of cases, which gives it a very low value.

nirvdrum
1 replies
1h24m

And, if you exit the company -- either voluntarily or involuntarily -- you often only have 90 days to exercise your options. If you've gotten laid off, eating into your savings while searching for a job is a pretty risky proposition. If you have an appreciable amount of equity, that bill can be rather high. Then there's AMT. Many end up letting the options expire. So, taking that pay cut for equity really didn't work out -- you had less money to exercise the options and because you couldn't, the option portion of your compensation was effectively clawed back.

I very much appreciate the startups pushing to extend the exercise window out to 5 - 10 years, but that's far from the norm. I've debated this with a couple of investors and their stance is if you leave the company then you're not committed enough and shouldn't receive anything. I think that's quite debatable, but that's certainly not the case when folks are laid off. And we commonly discuss people thriving in one particular phase of a company. If you're not in that phase, it's no good for either the company or the employee to continue the relationship just to defer having to exercise options.

Finbarr
0 replies
12m

The 90 day exercise window is the most obviously broken thing about startup equity in my opinion. We changed this to 5 years at Shogun.

dclowd9901
4 replies
3h15m

Ok, please argue in good faith here. Maybe 1 or 2 people who aren’t executives are pulling in that kind of money from FAANGs.

dclowd9901
1 replies
46m

I was under the impression we were talking about ICs here -- your link shows that an upper-middle IC that you'd expect to be choosing between early startup or FAANG will see something around 450 a year, which tracks much closer to what I'd expect.

gopher2000
0 replies
29m

You said 1 or 2 people who aren't executives. There's way more than 1-2 E7s at Meta, as an example.

wordpad25
0 replies
3h0m

If you're CEO at a $100MM company, your peers ARE executives at FAANG

whynotminot
2 replies
4h40m

It’s a shame you were forced to take on this burden and not allowed to be a regular engineer like your peers.

Finbarr
1 replies
4h27m

Nobody is forced to become a founder. A lot of people are naive to the sheer level of stress involved, and think it’s going to be easier than it actually is. You don’t find out just how stressful it is until you’re already super committed, have raised money, have employees, and there’s no easy way out without screwing a whole bunch of people over.

Founders tend to only talk about the good things happening at their companies, and tech press tends to focus on the successes. These things contribute to more people starting companies.

ipaddr
0 replies
2h56m

If you can't stomach screwing people over you shouldn't be a CEO.

throaway893
2 replies
3h26m

You are completely detached from the real world. Even in super rich countries like the US there are a lot of people without savings, living paycheck to paycheck. Most/all software engineers outside the US can only dream of ever earning that much money. And yet here you are, worrying that you'll end up only slightly richer than people earning ~$1M per year.

Thorrez
0 replies
2h31m

And yet here you are, worrying that you'll end up only slightly richer than people earning ~$1M per year.

onlyrealcuzzo is comparing 2 things:

* Being a founder and working mega hours and having no life (e.g. no spouse or kids) and having a decent chance of losing most of your money as the company fails.

* Working at FAANG and making a lot of money while not having to work too much.

onlyrealcuzzo is saying the second option is better.

RhodesianHunter
0 replies
3h20m

I don't think you fully understand the context in which this was written, but you probably should before passing so much judgement.

algobro
2 replies
2h36m

Sir if you live in USA and do not take a dip into the VC money swimming pool, you are stupid, because crazy people with stupid ideas routinely get to $100 Million valuations, like no other place on earth.

Its like going to Disney Land and saying "Oh i'll just sit at the coffee shop". Some people are here for the ride. Some people like the 9 to 5. Like you, obviously. Why dont you go start corporate-drone-news.org, this board is for hackers and founders.

alexvitkov
1 replies
2h16m

I don't mind the shit take, but please don't use underscores in your domains.

algobro
0 replies
2h1m

Good catch, fixed.

Thorrez
1 replies
2h40m

while your peers are all making ~$1M per year working 6 hour days at FAANG

I highly doubt ALL your peers are making that much. And I think the people making $1M per year at FAANG tend to work much more than 6 hour days. You have to be very productive to get $1M per year.

smokel
0 replies
1h12m

The "Four Yorkeshiremen" sketch by Monty Python always lightens my mood when this kind of bragging comes up.

slashdave
0 replies
45m

there's a decent chance you'll walk away with very little

Well, some founders care about their employees and their idea, and the idea of the start up failing is much more than just money.

seansmccullough
0 replies
2h55m

while your peers are all making ~$1M per year working 6 hour days at FAANG

Unless you are a manager, in which case you are working more like 12 hour a day.

dasil003
0 replies
3h59m

Yeah I feel like successful founders natural ambition and optimism is sort of weaponized against them by the VC industry here. From a VC perspective it's worth playing the odds for moonshots. As a founder though, if you can create a $100M company that you own 30% of, you can probably create a $20M company you own 70% of with a much more realistic and sustainable growth targets.

I can't help but feel this would be better for the founders, the employees and the customers of the company. It just doesn't make as much sense for the investors.

chucksmash
0 replies
2h55m

s/deci/deka/

boringg
0 replies
4h15m

"Sure, you've got a decent chance to rocket past them in wealth."

I might rephrase that as you have a non-zero chance. Odds are not that high and certainly not decent.

sneak
24 replies
10h15m

Where would the stress come from? You get a paycheck and there is no personal downside except opportunity cost (and perhaps reputation). You don’t lose any money if your startup fails.

angio
8 replies
10h8m

A lot of people (esp people that performed extremely well in school and in corporate environment) find "failing" and "losing reputation" very stressful.

FactKnower69
4 replies
8h13m

I guess harden the fuck up?

SOVIETIC-BOSS88
2 replies
7h21m

Thank God someone said this. Of course it is stressfull, there is no free lunch. If you can't take the heat just dont enter into a such top-heavy game.

verticalscaler
1 replies
6h59m

Harden The Fuck Up should have been the YC motto as really that's the whole program in a nutshell. Now take a glance at any thread here that is vaguely political.

In a big way there has never been a better time to start companies. It isn't the economy you need to outrun, just the competition.

apantel
0 replies
3h18m

And change.

smeej
0 replies
6h57m

Exactly. Or just don't do it.

I am sure enough that I would crumble under that specific kind of pressure that I don't put myself in situations where I would experience that specific kind of pressure. Works great!

sneak
1 replies
10h1m

Landlords and supermarkets dgaf. There is no real risk, and if they stress over it, that’s more a founder’s own psychological failing than anything else.

If you care what other people think that much, you probably don’t have sufficient quantities of the oft-cited “grit” that founders supposedly require.

zztop44
0 replies
7h34m

I think if the idea of your company failing doesn’t cause you at least some stress then you probably shouldn’t be running a company?

epolanski
0 replies
5h33m

Maybe risky ventures aren't for them.

throwaway98797
7 replies
6h9m

cause if you fail you have to let people go

cause if you fail you have to tell your investors you lost money

cause if you fail is a thought that’s always running through your head as you live it

yard2010
3 replies
5h15m

This is not a real risk you're talking about, but small inconveniences. A risk is losing your house for example, or losing the ability to rent.

Inconveniences are part of life anyway. Being the first engineer means you get all these inconveniences (tell your wife and your kids) plus real risks as above (taking a loan to buy the options and losing it)

naravara
2 replies
5h8m

“Letting people go” is taking on the risk of all of those people being let go losing the ability to rent or pay their mortgages. That seems like more than an inconvenience to me if you take one of the responsibilities of being an employer at all seriously.

zdragnar
0 replies
4h42m

No employee should join a startup with the expectation that the company will be around forever.

Compare startups to restaurants- their failure rate is absolutely massive. Working for a new company is simply always a risk for everyone involved, there's no getting around that.

sneak
0 replies
4h59m

If you are working a tech job and know how to program computers and have no savings slash the loss of a job costs you your house, you have deep and fundamental problems far beyond the loss of one job and it isn’t your former employer’s fault that your life is mismanaged.

shortrounddev2
1 replies
5h45m

My primary motivation as an employee of a startup is fear of personal financial ruin. That the company won't be able to make payroll and I won't be able to pay my rent, that I'll be evicted eventually or that if the company goes under I won't be able to find a new job. There is no mission or any other soft carrot that I care about. I also don't have any faith in stock options.

I can't imagine caring about reputational damage with rich people unless that reputation is in service of not starving in the streets.

sashank_1509
0 replies
4h39m

Perhaps you shouldn’t be working in a startup because your lifestyle is unaffordable, or your company is paying you peanuts.

I have worked in startups in Silicon Valley and have had many friends working for them. Most startups pay a base salary of around 200k$ I reckon (for new grads, perhaps 150k). This might come down to 9-10k after taxes per month. A good 2 bedroom house to rent in a location like San Jose would be 3k$ per month, which leaves you 6k for other expenses. Assuming 1k for car, you should still have 5k in savings per month, in a year of working you will have saved up 20 months of rent, maybe 12 months of living without a job. I find it hard to believe anyone in SV startups, is in risk of “personal financial ruin”, or “starving in the streets” just because they lost a few months of paychecks while searching for another job. That may be true in another country, in another market, but all tech workers in the Bay Area are living well above subsistence and acting like they are living paycheck to paycheck is a fantasy. There is a cost to working in startups, and it is an opportunity cost of not working in a big tech company and cashing out your 200k+ RSU over 4 years and instead receiving paper money stock options that can be worth 0.

LargeWu
0 replies
2h0m

"cause if you fail you have to let people go"

This isn't the founder's risk. It's the employee's risk. And it has the added bonus of, if there is a liquidity event, the employee's don't get the upside.

I was like engineer #3 at a company that eventually was acquired for ~$250MM. My payout was $60,000, after 5 years of employment there. I could have made more by going and contracting at megacorp for a single year. There was never any upside for me.

lettergram
1 replies
6h16m

Starting a company myself, I took 6 months with no salary. After we raised, my salary was massively cut from where it was (30-40% of what I made the year prior). Then you have the fact I gave up guaranteed raises & promotions (to the tune of hundreds of thousands in RSUs).

There’s a pretty large risk to family security. By year two of the startup I have made 15-20% the cash I could have made elsewhere. I have stock that I trust will be worth more in the future (so imo worth it). However, I can see liquidity events being useful if you’re tight on cash after that run

erikerikson
0 replies
2h57m

Investors do it so that the founder can better focus on increasing the value of the company. Having financial stress on top of everything else reduces the probability of liquidity events.

Finbarr
1 replies
4h33m

Hiring, firing, layoffs, making the wrong decisions with limited information and not finding out they were wrong until years later, huge shifts in the tech market around you undermining your business, competitor actions wrecking your business, pressure from investors, pressure from your family to earn more money, uncertainty about whether the business will ever succeed, and an endless list of other things.

You don’t lose any money if your startup fails.

Except all the money you lost by not having a proper job along the way. Also it’s not uncommon for founders to float the company at early stage until investment is raised, and they don’t always get a refund for this.

jboggan
0 replies
2h25m

Exactly. I quit Google in 2017 to work on a promising start-up idea (generative AI chatbot for coding, a tad early on that one) and ended up raising barely any money, running up massive CC debt to finance cost of living and GPUs, and taking a huge compounding opportunity cost to not continue growing as a FAANG SWE (not to mention missing out on the stock market run with the extra money I didn't have). I spent the last several years paying off that debt instead of buying a house or investing, etc. I'm massively behind in earnings and net worth compared to my colleagues who talk about their future startup idea but never struck out on their own.

But I'm finally debt free and ready to risk my future yet again on another startup.

rohansingh
0 replies
6h59m

I think for a lot of founders, there is significant financial cost or opportunity cost upfront. Especially if you are bootstrapping.

neilv
0 replies
6h3m

I tend to have large stress in startups, more than in established companies. I won't get into some of the occasional toxic-element sources that can happen anywhere, but some reasons that happen more in startups:

1. Caring about the mission -- the real-world positive impact -- and potentially able to make or break that. Not just taking a shot at making money, for some opportunity cost that I could evaluate quantitatively on a napkin, and walk away from as soon as an option with a higher expected dollars number came along.

2. Livelihoods and investments of time&effort by colleagues hinge to a large degree on decisions I make, ideas I have, and things I have to pull off, and not wanting to let them down. (A bit similar with money investors, but I care more about personal connections, and involvements where it's not just someone buying lots of lottery tickets.)

3. Low "paychecks" for my HCOLA, at that startup and earlier, so personally needing a big win financial exit, and the startup is what I decided to invest my time&energy into. If that fails, it's starting over, and a lot of wading through various startup ickiness to get another good opportunity (or doing FAANG interview BS, and then their promotion-chasing BS).

boringg
0 replies
4h3m

I mean if you don't care about the company mission (if it's mission based), you don't compare about your employees, your word, you don't care about your time or care that you sold people that you were going to take their money to build something... then yes there might be no "personal" downside.

Though if you don't care about anything in the first place what are you doing trying to build a company?

burutthrow1234
10 replies
5h53m

Please let us all know how that's working out for you in 5-10 years. 4 months in and no stress? Must be easy riding from here!

Honestly VC-funded startups seem like a cake walk compared to actually starting a small business. Your biggest challenge is walking into a room full of rich dudes and schmoozing for your pay cheque. If you fail you get acquired and get golden handcuffs.

If you start a real business you can expect to take on debt, and you'll be personally guaranteeing it because nobody cares about equity in your boutique ice cream parlour. Plus a 5-year lease (which you will also personally guarantee).

joenot443
2 replies
5h31m

The most common endgame for a startup is slowly running into the ground until the money runs out and you eventually shut the doors. Failing your way into a happy acquisition isn’t really something to expect as a contingency, I don’t think.

tmpz22
0 replies
2h20m

The contingency isn't golden handcuffs its using one of the hundreds of C-level connections you made as a Founder doing sales and networking (and accelerator programs) to get you a cushy gig as a Product Lead, Operations Lead, or similar title with a strong paycheck and immediate authority.

BeFlatXIII
0 replies
3h26m

Then use those five years to enjoy the fanciest office equipment VC money can buy. Don't cry because it's over; smile because it happened.

boringg
2 replies
4h7m

I don't know why you are trying to make this a me vs them situation. Both situations are difficult in different ways and they are all real businesses.

"Your biggest challenge is walking into a room full of rich dudes and schmoozing for your pay cheque." - Sounds like you are trolling or alternatively incredibly naive.

"If you start a real business you can expect to take on debt". ... Real business? Come on.

No one in this thread is saying starting a business is easy - ice cream business is debt funded because you have a very definitive range of outcomes. Venture funding is completely different animal - failing to see that limits the value of your comment significantly.

owlstuffing
1 replies
3h27m

I don't know why you are trying to make this a me vs them situation.

In terms of economic disparity it _is_ very much an us vs them situation.

Consider the optics over the last 20+ years. The middle class and their small businesses have been decimated while former VC funded companies hoover up their futures on Wall Street.

The level of risk involved starting an average small business is much closer to home compared with a startup seeking VC funding. The former can literally lose his shirt, the latter has to settle for a high six figure salary somewhere else.

Failing to see that limits the value of your comment significantly.

boringg
0 replies
2h39m

This isn't a me vs them. Who is hoovering up the ice cream futures? Different business model, different businesses. Both are difficult. Being a founder of a VC based company is difficult and being a builder of a retail brick and mortar is difficult. It isn't zero sum and both can exist in the same economy trying to make this a Me Vs Them narrative is totally BS.

Making a wedge where there isn't one is disingenuous.

WarOnPrivacy
1 replies
4h33m

Honestly VC-funded startups seem like a cake walk compared to actually starting a small business.

Make this about any brick/mortar businesses and the stresses multiply by another factor. If they're in a federally regulated biz (compliance) or an insurance dominated state (rates, inspections), then multiply again.

burutthrow1234
0 replies
1h1m

This is a comment about brick and mortar businesses, I literally talked about having to personally guarantee a multi-year lease in the post.

And yes, some businesses are even harder due to regulatory requirements

p_l
0 replies
5h48m

Running with VC funds? Oh god, that would be cakewalk compared to even just figuring out how to ensure there's food if you spend money on some necessities for prototype...

mrkurt
0 replies
4h14m

Not that people with VC need defending, but:

Sure, if you magic up a startup with VC funds you suddenly have it easier than a small, bootstrapped business.

Startups almost never start with a round of VC though. There are almost always months or years of the same experience as a bootstrapped business (ie: extreme uncertainty, no money to pay yourself, etc).

Most startups don't manage to raise VC, and most startups that raise VC fail with no acquihire.

Finbarr
10 replies
11h49m

The bigger secret is that stock sold in secondary sales by founders and employees is usually common stock, and the purchasers will often get the right to convert this to preferred stock. This means that the company is instantly encumbered with a greater liquidation preference, without the increase in balance sheet to offset it.

laser
5 replies
10h14m

How is that legal and not considered self-dealing and unjust enrichment? If I was a minority common stock owner in a business I assume I would have standing to sue for damages if a majority owner or officer made my position materially worse while enriching themselves in such a manner? Are you sure such a right is typically granted? I mean even the gap between 409A valuations and preferred valuations, as well as a huge amount of precedent, give a different material value to preferred and common stock. Giving that right out of thin air in a sale by an insider is effectively theft from common holders and I have trouble believing what you’re saying as I’m not sure how that could be kosher, if perhaps infrequently litigated. But is it really standard like you make it sound? That would be a very dirty secret and I expect would and should lead to litigation.

red-iron-pine
0 replies
4h10m

How is that legal and not considered self-dealing and unjust enrichment?

because, ultimately, Capital writes the rules, and they chose to allow this

mountainb
0 replies
5h38m

Who has the cause of action? The majority shareholders. Who authorized the stock sale? The majority shareholders. Are they really likely to sue the founder for something that the shareholders authorized?

Only in some states would minority shareholders have a cause of action. So there are some states in which the courts agree with you. As you might imagine, startups do not typically incorporate in those states.

lancewiggs
0 replies
9h53m

Flip it around - it becomes a condition of the deal happening imposed by investors, who themselves are motivated to present the best deal to founders, and to have founders less economically stressed. No secondaries - no deal, and that doesn’t help anyone.

KingMob
0 replies
6h48m

IANAL, but if you only have options, and not stock, do you still have standing to sue?

Finbarr
0 replies
4h22m

It is very common and usually a condition of closing. Investors know that preferred is way better than common. They are buying highly speculative assets and want strong downside protection.

anxman
3 replies
9h40m

I used Founders Preferred shares to get liquidity at the A (for a now defunct startup).

In our case, we offered all vested employees the option of selling in the same round on the same terms.

I personally don’t recall any disclosure requirements at 10 people; however, we didn’t have that many participate so perhaps it didn’t apply.

In general, Founders Preferred does layer on the preference stack but also hopefully by a relatively trivial amount to the overall funding size.

throwaway-blaze
1 replies
2h48m

Founders never have preferred shares, at least not the same class of preferred (with the same preferences) as investors.

janjongboom
0 replies
2h30m

Not never. E.g. all the capital we as founders put in the business before we raised our seed round was converted into Series Seed Preferred shares at the same rights as angels / seed VC. Small portion of total equity but still.

Finbarr
0 replies
4h38m

Yes, as I mentioned it only applies when you have 10 sellers.

colordrops
2 replies
11h22m

I often hear about these SEC rules that explain why individual contributors get fucked, as if that's a good excuse. Either the requirements and disclosures should be fulfilled and more than 10 sellers allowed, or the rules should change, or both.

llamaimperative
0 replies
8h5m

It sounds like they could’ve fulfilled the requirements and had more than 10 sellers but chose not to.

Finbarr
0 replies
4h30m

I didn’t comment on whether it was a good reason or not. My comment was just highlighting some of the complexities in what the blog author was hoping to achieve.

dclowd9901
0 replies
3h16m

Correct me if I’m wrong, but my perception of most startups at series A is that they’re not usually more than ten-ish employees, and even then, you’d expect more balanced comp packages for employee number 11+, no?

josh2600
84 replies
14h29m

The best startups have a concept which is summed up thusly:

“We all go to the pay window at the same time.”

It’s ok for founders to take a little bit of money off of the table if they extend that to their employees as well. Asymmetry is where things get weird.

I’ve seen many founders who got deep into the fundraising cycles without ever realizing they could take a cent out. VCs will constantly tell you to let it all ride, and sometimes that works out, but for most people, having a little bit of financial security while you’re trying to change the world is necessary.

The best startups figure out how to manage liquidity through financing in a way that aligns incentives, keeps the goalposts at the mission, while allowing their teams to thrive.

It’s about alignment. If everyone is pulling in the same direction you’re going to execute the vision. Whether you win in the startup lottery is up to the threads of fate, but alignment is the straightest path towards a result.

kneath
69 replies
14h22m

I have seen a lot of companies, a lot of rounds. I have known zero founders who have turned down an option to take money off the table (and zero A raises that offered that to employees). I love the idea of your universe, though.

sashank_1509
21 replies
14h2m

The very first startup I joined after grad school allowed all employees to cash out significant chunks of their stock in the Series A round.

Also Elon famously put 200 million of his own money into Tesla and SpaceX to keep it afloat, which is the opposite of cashing out early.

mapt
11 replies
13h16m

If you have 200 million "of your own money" to spare, you are no longer just a person for the purposes of this conversation, you're a walking VC fund, and you're not really risking a substantial change to your quality of life going from 250M to 50M net worth. Your living expenses are already generously compensated for by the large salary that you, the VC fund pays you, the person, out of your personal bank account, and they will be paying you those expenses until the end of your natural life. This isn't "risk" in the same sense as somebody who jumps to supplement their $150k salary with $450k of founder liquidity because it dramatically changes the material security of their life.

throwbigdata
4 replies
9h30m

Life is very different at $50M v $250M

Tepix
3 replies
9h14m

Is it?

BoorishBears
1 replies
9h0m

It's not really compared to an average person's life, but in SV tradition never let the chance to subtly flaunt a wealth gap pass by freely

(This is the part where you say "Yes, having lived both <insert revelation>")

shermantanktop
0 replies
15m

Has 50M: wishes they had 250M

Has 250M: wishes they had 1B

fooker
0 replies
5h19m

50m is the upper echelons of private chaffeur money, 250m is the lower echelons of private jet money.

robertlagrant
2 replies
6h23m

If you have 200 million "of your own money" to spare, you are no longer just a person for the purposes of this conversation, you're a walking VC fund, and you're not really risking a substantial change to your quality of life going from 250M to 50M net worth.

Is that what happened? I thought he had $200m, and put in $200m.

oblio
1 replies
4h16m

Do we know this story from any credible source or are we just trusting Musk's (a famous liar) word about it?

robertlagrant
0 replies
2h19m

It's true that that's what I thought, which is my statement. And it's better caveated than the previous one, which implied uncaveated that he still had $50m, but hasn't attracted the eye of any budding skeptics.

rmbyrro
2 replies
8h24m

You may dislike Elon, but it's pretty absurd to say that what he did is trivial.

llamaimperative
0 replies
8h3m

GP didn’t

KennyBlanken
4 replies
9h8m

...while he was getting loaned $200,000 a month for personal expenses by his billionaire buddies.

https://www.cnbc.com/2017/04/27/the-crucial-decision-teslas-...

Also, that may have kept tesla and spacex 'afloat' but what really saved both companies was billions upon billions of dollars in government contracts, subsidies, preferential loans, and tax breaks. Nevada alone gave nearly two billion dollars to Tesla.

petesergeant
3 replies
8h57m

The government is expecting something in return for these breaks rather than them being some kind of gift, though.

oblio
1 replies
4h15m

The government is not monolithic and politicians might except other things than what their constituents want. It's a bad test of the value of an investment.

petesergeant
0 replies
3h29m

For sure, and it may well have been a terrible investment with terrible returns, but selling to the government and responding to government incentives is an entirely legitimate thing to do, rather than some kind of inherent weakness in a company’s model. A company being “saved” by a government contract is a company being saved by making sales to its largest customer.

nick7376182
0 replies
6h15m

And the government got it, in the form of a cost effective usa-based launch solution.

romwell
3 replies
13h18m

to keep it afloat

Can't "cash out" (early or not) if your company is sinking.

phlo
0 replies
9h35m

Adam Neumann begs to differ.

gorbachev
0 replies
11h12m

Private equity firms do exactly this.

eru
0 replies
13h8m

You totally can. That's what investor money is for.

bradleyjg
21 replies
7h2m

All you’re saying is that in the contemporary context it’s exceedingly foolish to be an employee at an early startup. The VCs and founders have optimized away all the incentive. Eventually the message will reach even naive 22 year olds.

smeej
9 replies
6h51m

I'd tweak this slightly: "It's exceedingly foolish to be an employee at an early startup for the money."

I think there are a lot of us who struggle to fit the larger corporate mold who pretty much only thrive in the startup world. I can't speak for all of them, but I've been very willing to take the balance of lower cash compensation and a fistful of lottery tickets and not having 12 layers of middle management breathing down my neck over more liquidity.

I guess I'm also blessed with inexpensive tastes, which helps, but I'm still able to live somewhere I love and do all the things I care to do, so it works out.

p1esk
6 replies
5h37m

Why does everyone thinks startups don’t pay well? I have worked for various startups all my life, most of them well funded, and competing for talent with faangs. Yes, I could probably make more at Google but I don’t feel like I’m underpaid. At the last 3 startups my base salary was above 250k. I work remotely and I rarely work more than 30 hours a week.

bradlys
4 replies
4h2m

I’d say you’re uncommon. I’ve never seen anyone who is a typical engineer making $250k/yr at a startup that’s below $1B valuation. Same for the amount of work you’re doing and that it’s remote with that compensation.

It’s possible you’d be making $700k+/yr if you were at google. About triple what you are now.

gen220
2 replies
3h6m

I think one component of their point is that the marginal utility of money beyond $200k/year cash comp is quite small, especially if you (1) came to tech early in life (2) plan on staying in it for most of your working life.

With that perspective, $200k/year and $700k/year both reduce to "well-paid".

Also, a Staff title at a Seed or Series A startup can definitely ask for $250k/year, although they'd likely be trading off against equity grants.

whiplash451
1 replies
56m

I would revisit that calculation assuming you are drained at 45 instead of 60, including taxes and the opportunity cost of 500K x a few years at 3% rate for the next 15 years.

gen220
0 replies
12m

That's pretty much exactly the calculation I'm positing. But actually with an even earlier terminus (late 30s or 40 at most).

Assume an "effective" average pay (i.e. "net" pay + retirement and other deductions, inflation-adjusted to today's dollars and averaged over the course of your career) of $120k/year.

From age 22 to 40, you've earned $2.16mm in inflation-adjusted-to-today dollars as a single earner. With a not-unreasonable average savings rate of 30%, not accounting for tax-advantaged growth or any growth at all, you'll come out with $650k of inflation-adjusted-to-today capital in savings.

Realistically, this should end up invested in some kind of equity (housing, stocks, bonds, whatever). If you finance the purchase of a house at 30, you're only 10 years into a traditional 30-year mortgage at this point, for reference. So you're roughly 1/3rd of your way to owning all the equity in your home. That's fairly comfortably a $1mm home (home equity being 30% of your assets at 40).

Of course, if you're DCA-ing into something that yields a modest average of 5%/year in inflation-adjusted returns, that $650k is closer to $1mm inflation-adjusted-to-today capital. And you still have 25 years at that point for your retirement savings to compound. And you can work part-time in something more fulfilling until retirement to supplement your income.

YMMV, but the marginal utility of money beyond $1mm in equity at 40 and $6k/month in expendable (on rental housing, food, travel, social events) income during your 20s and 30s is pretty small for most people. If you add a partner with any kind of income to the mix, it makes the marginal stress of earning more money even less appealing.

Edit: the main thing you ought to avoid like the plague is lifestyle creep. Spending money on things with zero or vanishingly-small happiness ROI. Read this story every year or two, or whenever you get a raise at work. https://www.marxists.org/archive/tolstoy/1886/how-much-land-...

p1esk
0 replies
1h42m

What many people don’t seem to realize is there are a lot of early stage but already well funded (10M+) startups who are desperately looking for top quality people. Once I was approached by a founder who offered 500k base salary (wasn’t a good fit for my area of expertise).

bradleyjg
0 replies
4h8m

Early startup is the part you seem to be overlooking. A well funded startup with few or no runway concerns is a different calculation.

shortrounddev2
1 replies
5h28m

It's a difficult trade off I've found. Large tech companies are boring and slow and you deal with a lot of red tape and BS, and you feel utterly powerless in the security of your own job as economic tidal waves direct the momentum of layoffs and not your personal contribution.

At a startup you have more autonomy and power over your personal position. I wrote 90% of the code that is generating company growth, released 2 months after a layoff. If I had taken longer to release that code or if my code didn't work the company would be in a worse financial position.

But that also means a lot of personal stress. There aren't 4 layers of middle management to catch flak for you. If you fuck something up, you are directly responsible and depending on the environment that can result in some heated conversations. I also work way harder at a startup than I ever did for a big company

smeej
0 replies
17m

Those are the factors that make the tradeoff easy for me. I would vastly prefer direct accountability for my own fuckups, because that means I have the agency to do something to fix it.

What makes me want to put my head through a wall is when I fuck up, and four layers of people above me are the only ones allowed to fix the thing, but they don't, so I keep catching flak for my fuckup without any way to stop it and fix the thing. I have many more heated conversations with those managers, which typically leads to the door.

When I fuck something up, rarely is anyone more upset about that than I am. Nobody's dumping more heat on me than I am on myself, so bring on the heat-- as long as I have the agency to fix the problem.

shmel
3 replies
4h22m

If you only care about money, sure. I have plenty of friends working in FAANG. For some mysterious reason any time I ask them about work, they say something along the lines "ehh... it's fiiiine. Paycheck is pretty good though". Okay, not all, but perhaps 95%. And half of them work massive overtime on regular basis. I can get behind working weekends when you hope to change the world. They often say things like: "yeah, I have to work 60-70h per week because I don't want my boss to yell at me". Those who work normal hours say: "there is not much work to do really, we literally have meetings about meetings to fill the day. I wish I had some real work to do". I truly hope that higher TC compensates for that.

closeparen
2 replies
2h54m

The Bay Area housing market is too competitive for this. If you’re renting a room in your early 20s then sure just have fun, any tech job should cover it. If you want to own a place to raise a family in by your 30s, and you don’t have some exogenous source of wealth, you’re going to need every dollar of liquid compensation you can possibly get.

shmel
1 replies
1h29m

Or you can just live somewhere else. The world doesn't end at Bay Area.

closeparen
0 replies
1h7m

Sure but this thread is about technology startups. The jobs you can get anywhere are business IT departments.

ethagnawl
3 replies
6h35m

All you’re saying is that in the contemporary context it’s exceedingly foolish to be an employee at an early startup.

As a rule, it is and always has been. For every unicorn piñata stuffed with winning lottery tickets, there are hundreds/thousands? of others whose employees walk away with nothing or less (debt, strained relationships, mental health issues, etc.) at worst or a job at AcquiHireCo at best.

bradleyjg
2 replies
6h27m

There was always very high risk, so it was only ever for certain people. But in earlier iterations of SV it was possible to become generationally rich as an early employee. The VCs and founders have fixed the glitch.

To put it another way: early employee equity was always a lotto but now the payout is like some lame scratch off instead of the powerball jackpot.

est31
1 replies
4h40m

The startups where employees get really rich still exist. I'm pretty sure the early employees of OpenAI are generationally rich for example.

It's just that these companies very often are the darlings since their inception, get constantly talked about. Everyone wants to to invest in them and everyone wants to join them. So they have the ability to pick out the best talent, in other words, it's unlikely you'll be able to join that specific startup.

But even 20 years ago, try getting into early Google. From what I heard they had extremely high bars for hiring as well and only lowered them once they got so large that the pool was exhausted.

I'd argue that the total comp at the established companies for engineers has increased precisely because of competition from startups: to make the startup not be the better option.

Does that mean that VCs are not taking a bigger slice than they used to? Absolutely not, but I wouldn't put the blame solely on them.

bradleyjg
0 replies
4h3m

Re: openAI

We’ll see when it happens. If I had to name a company most likely to have massive landmines buried in front of common stock cashing out, it would be at the top of the list.

tivert
0 replies
2h2m

All you’re saying is that in the contemporary context it’s exceedingly foolish to be an employee at an early startup. The VCs and founders have optimized away all the incentive. Eventually the message will reach even naive 22 year olds.

My startup idea is a firm that uses generative AI to flood the internet with pro-startup, pro-VC, pro-founder propaganda, so that message will never reach the naive 22 year olds. Personally, I think it's like saving the environment, since naive 22 year olds are precious resource we cannot allow to be destroyed.

mbesto
0 replies
5h42m

All you’re saying is that in the contemporary context it’s exceedingly foolish to be an employee at an early startup.

As long as naive 22 year olds think have that one friend that stuck around long enough to cash out on an IPO, then yes. On a risk-adjusted basis, this has basically always been the case - you're better off working at FAANG.

lupire
0 replies
6h52m

There's a sucker born every September.

You can find your comment in the HN archives as far back as 2010.

rKarpinski
12 replies
13h20m

I have known zero founders who have turned down an option to take money off the table (and zero A raises that offered that to employees).

Have seen companies offer this to employee's

And companies that let employee's take money off the table at series A are also likely to be generous with meaningless titles; that is they will let early employee's call themselves founders.

adastra22
10 replies
13h10m

At a Series A?!?

That's insane to me. We're talking about the first priced funding round for the company, right?

muzani
3 replies
8h57m

Why is it insane? Some founders take zero salary since the start, and part of the reason for raising funds is that they have to eat too. Anyone who is an "early employee" usually get lower salary than market, and some stock. It's only fair they get to cash out a little early on, or hold on if they're liquid and think it's worth a lot more.

It also works well for everyone involved if they're selling their shares to the investors for Series A - investors get shares for cheaper, founders get paid based around the value of those shares, more cash & runway in the bank.

adastra22
1 replies
2h58m

In my industry the series A occurs in the first year of operation, and before the company has really achieved anything. A founder taking money off the table then is ludicrous.

criddell
0 replies
2h12m

Founders who have no need for money in the first year or two are fortunate people who are either already wealthy or have a spouse or family supporting them. Surely those aren't the only types of people worth backing.

owlstuffing
0 replies
4h55m

Correct answer

quartesixte
2 replies
12h39m

I have witnessed small liquidity events at Series A and Series B that allowed for some small percentage of all total equity vested (around 3-5% ish, depending on the terms of your specific options grant) to be cashed out at some multiple of the FMV price. AFAIK the founders held themselves to the same restrictions (5% total, I believe?) to keep it relatively "fair".

Pre-Seed, Seed, and some really really early Series A employees got to cash out fairly significant chunks of equity. Not as much as a founders' 1-2 million, enough for downpayments on homes or slick new cars all cash. The founders apparently were incredibly generous to Seed stage employees.

Still doesn't compare to a Founders' equity, as this article implies.

lmeyerov
1 replies
10h47m

is this zero-interest rate phenomena in action?

meheleventyone
0 replies
10h22m

Nope! Although the availability of funding obviously plays a role so the wider investment environment affects it.

fire_lake
1 replies
12h52m

These days there is typically an institutional seed round before that.

adastra22
0 replies
12h50m

How long is typical for the seed round? Both my prior startups only spent a few months in the seed stage.

rKarpinski
0 replies
11h53m

At a Series A?!?

Yeah, at Series A.

sponaugle
0 replies
3h10m

"> I have known zero founders who have turned down an option to take money off the table (and zero A raises that offered that to employees)."

Nice to meet you. Now you know one. :)

extragood
6 replies
12h18m

It happens.

I was offered the option to liquidate up to 20% of my vested shares at my last company's Series A. It was restricted by tenure though (3 years), so it wasn't available to everyone. In retrospect, I should have liquidated the full amount, but it was a new concept to me at the time and I was more conservative with the amount.

I more recently interviewed with a pre-series A company and they said that they'd include me in a liquidity event when I brought up compensation.

dmurray
2 replies
8h4m

Doing this by tenure seems like a fairer way to distribute the liquidity. The founders still get preferential access to it, but because they really have taken more risk (bigger stake for a longer time period), not just because they have a better individual negotiating position.

hackerlight
0 replies
4h57m

The founders still get preferential access to it, but because they really have taken more risk

It's not related to risk, at least not directly. It's related to the supply of entrepreneurship as a factor of production. Entrepreneurship is scarce, so founders have leverage in any bargaining situation against early employees, who are more numerous and therefore less valuable and less powerful. If 10x the number of people tried to become founders, then founders would hold less leverage and the equity terms would become more "fair" because they'd have no choice but to give generous terms if they wished to hire people.

KingMob
0 replies
6h40m

Tenure/cliffs/etc should already take care of that by gating access to shares/options/etc in the first place. No need to add an extra tenure complication to liquidity as well.

chollida1
1 replies
7h3m

I was offered the option to liquidate up to 20% of my vested shares at my last company's Series A. It was restricted by tenure though (3 years), so it wasn't available to everyone. In retrospect, I should have liquidated the full amount, but it was a new concept to me at the time and I was more conservative with the amount.f

Oh wow, how many companies have a series A after 3 years? How did your company survive without any raises for 3 years and what made your company finally decide to raise money after going 3 year without doing so?

extragood
0 replies
1h32m

That policy was actually one of the major reasons I liked that company and stuck with them for so long. Their goal early on was to avoid raising money if at all possible, and they managed that for a long time by mostly being cash-flow positive/profitable. The trade off is slower, but sustainable growth.

We hit an inflection point in the early pandemic where money was cheap and we had a ton of new customers coming in, so we were able to secure very favorable terms for the Series A and used that money to expand the business. Things continued to go in the right direction for the next ~2 years and we ended up doing a Series B round, and that in retrospect was a mistake. We over-hired in 2022 and couldn't back that up with increased business. And because we had given up so much control to investors in the previous rounds, we were unable to return to the sustainable-growth strategy that had worked for us in the past, and had to adopt faster growth strategies, none of which panned out and ultimately hurt the company and led to many rounds of lay-offs.

anonymousDan
0 replies
9h41m

How would you negotiate that in practice? Would it be reasonable to ask for it to be in your contract? How would you suggest wording it roughly? Sorry I'm inexperienced with this kind of thing and have no idea how I would go about negotiating for it.

chatmasta
2 replies
10h38m

This assumes that the founders are aware of, or offered, the option. If anything this is an argument for why founders should be represented by a banker or lawyer at the closing of every investment round. Let the founders do the negotiating, but once it comes time to sign the papers, bring in the sharks.

newswasboring
0 replies
7h27m

That's not common? I was under the impression that everyone hires at least a lawyer to get through the paper work.

_heimdall
0 replies
6h21m

Honestly if a founder isn't pulling in finance or legal experts prior to signing a funding round they really have no business being in position to begin with. They have to know VCs are leaning on their own financial experts and lawyers, why would you not have your own to protect your own interests?

smallnamespace
0 replies
14h1m

VCs will go along with or sometimes even encourage founders to take a little bit out, but employees rarely don’t have the same level of bargaining power.

imadj
0 replies
13h45m

  A: I’ve seen many founders who got deep into the fundraising cycles without ever realizing they could take a cent out.

  B: I have known zero founders who have turned down an option to take money off the table [...] I love the idea of your universe, though.

Fortunately, our universe is massive with varied different views. Even OP implied that they have experienced both sides firsthand.

darth_avocado
6 replies
14h4m

It’s like trading windows and blackout periods for employee RSUs, but equity selloff on a schedule for the c suite.

jahewson
2 replies
12h48m

That’s really about not falling foul of insider trading laws. Regular employees are free to set up limit orders within their trading windows (eg sell if stock hits $200) if they want. Can’t subsequently cancel it though! It makes way more sense to just sell on the day of vesting and then trade shares that you’re not restricted from trading. No tax or other reason not to do this.

throwbigdata
1 replies
9h28m

I’ve never worked at a public company that allowed limit orders to survive blackout periods.

nick7376182
0 replies
6h9m

I believe they are referring to a 10b5-1 plan that includes price-based sale triggers.

lupire
1 replies
6h46m

Regular employees can also make scheduled trading plans. ETP.

vonmoltke
0 replies
1h41m

We couldn't at Twitter, which is the only company I've worked at that had a blanket trading blackout policy. The closest we could do was elect to sell all RSUs as soon as they vested (even if outside an open window).

hackitup7
0 replies
13h55m

That's not quite how it works. Certain people are required (or strongly encouraged) to sell on a 10b5-1 plan. These plans can trade outside of open trading windows, but they have a meaningful cooldown period before they go into effect and can only be entered into during open trading windows. So it's not necessarily "better."

xbmcuser
2 replies
13h6m

It's not in the interest of the VC that the founders have financial security. Well at least the type of VC's that have come up in since the dot com boom where it was not about building viable businesses but getting sold to the highest bidder when the founder is under financial pressure to sell they can strong arm him into easily compared to a founder that is financially secure and interested in building and running a business

zenlikethat
0 replies
2h42m

It’s literally the opposite to what you suggest. Someone who hasn’t eaten for days isn’t thinking about eating healthy when they walk by a McDonalds.

wrs
0 replies
12h57m

It’s not binary. Enough financial security that they don’t care what their investors think, no. Enough that they’re thinking of how to grow the company rather than how they’re going to pay their mortgage, yes.

nytesky
0 replies
12h3m

I’m sorry, I think the era of “change the world” motivation in tech was eclipsed by “make 42 tons of money” about a decade ago.

Along that line, I would be very surprised that there are founders who don’t seek an opportunity to set aside their nest egg to “de-risk”.

You say you have seen such guileless dedication to the founding first hand, can you share what industry or type of company? Perhaps I’m just exposed to the wrong crowd.

gadders
0 replies
10h0m

>It’s ok for founders to take a little bit of money off of the table if they extend that to their employees as well. Asymmetry is where things get weird.

Yeah, if the founders don't do this I wouldn't want to work for them (not that I'm the target demographic anyway).

fidotron
0 replies
6h51m

I agree with the core of your point, and would extend it to any post-IPO lock in periods.

TimPC
0 replies
8h22m

Assymetry makes a certain amount of sense. Employees don’t take $0 for a long time and generally aren’t having as large a pay cut as founders afterwards. Most of the founders I’ve worked with have had the seniority to justify the top salary in the company and have typically had pay at or near the bottom. Someone operating at that extreme getting to trade equity doesn’t necessarily mean that everyone should get to.

jmward01
73 replies
13h24m

I was mentally, physically and emotionally worn out when I left my previous startup after being an early employee. Despite that I really wanted to stay and be part of what my friends and I were building. Had I had the chance to 'de-risk my life' with some equity to replenish my empty bank account, which was empty from taking an early employee salary, I may have been able to stay but in the end I had to get out.

Getting out for an early employee after funding rounds is expensive because buying options can hit you with massive tax bills on top of the cost of buying the options. Worse, the stats aren't great for a chance on return. Your lotto ticket gets expensive and risky as soon as you decide to leave.

Articles like this one hammer home more and more to me how little VCs actually value early employees. Paying out founders to stay is a strategic move. Keeping them is worth it because they are the face of the company and turmoil at that level hurts their payout. Burning out early employees is not a concern because you can just swap them without drama. In fact, with the way options are structured and the 'industry wisdom' to hold off purchasing, it feels like a strategic move to burn out early employees since many employees that are forced out often can't even buy their options. They are left with nothing after all that work and risk. From a purely cynical view this is a great thing for VCs since now the company got all the benefit of an early employee and just lost all the costs.

I don't know about the other three points, but I can guarantee you point 1 of 'right sizing perceptions' is wrong.

lumost
49 replies
12h53m

This is the model, you can see a lot of early stage founders looking for a "founding engineer" which is really just an excuse to pay founder salaries for 1% of the company rather than 50%. If the founding engineer quits without buying their options, then the founding team recoups the 1% equity. Its a recipe for the founding engineer to be burned out and pushed out.

xandrius
23 replies
12h17m

What if they give 1-2% and good market rate salary (~200k/y) to a founding engineer? Is that still a bad deal?

nevir
8 replies
11h55m

Having been in this exact position multiple times now (once quite successful, others not), you should probably consider it a wash.

Unless the company hits unicorn AND your shares become liquid (secondaries don't count—you generally won't be able to sell enough shares to make a meaningful dent), you'd make just as much or more at a FAANG firm with way less risk.

Of course, I say this while not at a FAANG firm, because I prefer startup type work.

xandrius
7 replies
11h43m

Yeah but I don't think it's fair to compare salaries to FAANG firms, as they are extreme outliers (and not really good companies).

So you would get paid like at another company but get equity on top and it's not a good deal? How comes?

zaptheimpaler
3 replies
11h4m

Depends on the options available to the candidate. Typically someone joining a startup very early probably has the skill to get FAANG salaries with less stress and more free time. There are also hundreds or thousands of mid size companies that pay very well nowadays, its not just FAANG.

xandrius
2 replies
10h24m

Yeah but smaller startups might be more open to non-US applicants, FAANG and other more established companies don't seem to be interested in hiring abroad.

That's what makes the early startup scene the only thing available for some.

cherryteastain
1 replies
7h39m

How come? Most large companies have big legal/HR departments that are very efficient at the whole visa application process. A small company won't have that expertise/staff. I mostly see startups being more concerned about the visa status of applicants.

xandrius
0 replies
4h43m

Remote + non-US is not as welcoming, so the hurdles are way higher as it's not fitting the usual way. While startups have no prior experience anyway, so it's easier to convince 1-2 people instead of changing a whole system (I believe).

jjav
1 replies
11h35m

So you would get paid like at another company but get equity on top and it's not a good deal? How comes?

If it were truly market rate (total comp not just base salary) then sure, it's a good deal. How likely are you to find that in an early startup? It must be pretty close to zero percent chance. But if you find it, sure, it's good.

You'll still work harder and be more stressed but it'll be a different learning experience which is always nice.

eschneider
0 replies
1h27m

A lot of it comes down to management/team quality. Do you want to spend an awful lot of time with these folks? Do you think you'll learn from each other? Do these folks seem to know what they're doing and are the building a product that interests you? If you can say yes to most (all?) of those questions, then all-in-all, it's probably a wash. If not, run.

lumost
0 replies
10h57m

Most early stage companies turn out to be poor companies for employees. Long hours, toxic leadership, unclear roadmaps etc. Working at a small firm doesn't guarantee high quality.

petesergeant
4 replies
11h53m

Market salary with stock upside plus the chance to level up a job title has potential to be a great deal

xandrius
2 replies
11h41m

Yeah, that's my thought too. Many companies give ~$200/y for way less upward mobility, impact and voice, and without any equity.

Maybe you'd lose our on some tiny perk/benefit but that's not always the case.

So I'm not seeing what's wrong with this deal with the only caveat that the engineer has the experience not to overwork/burn out.

lumost
0 replies
10h52m

It depends on the role and company, if you want to get paid 200k per year for the opportunity to do X - then sure. In practice, you may end up doing basic work at a lower quality than a large firm. Such experience doesn't translate the up-leveled title to a more standard position.

geepeeyoudata
0 replies
5h25m

> So I'm not seeing what's wrong with this deal with the only caveat that the engineer has the experience not to overwork/burn out.

The startup can go bankrupt any moment, thats a big deal. You get crappy perks, often poor benefits.

closeparen
0 replies
1h9m

Leveling up seems like a good reason for someone who’s stagnating at a bigger company. My experience is startup people want to recruit their most respected former colleagues, who by virtue of being respected are also getting promoted in place.

Titles obviously don’t transfer back to big companies, we had plenty of ex-cofounders and CTOs hired into the same junior roles as anyone else who could LeetCode.

jonathankoren
2 replies
11h57m

Yes. Because you’re literally the same as the founder, but getting waaaay less equity.

First employee is always a sucker

xandrius
1 replies
11h34m

But you're getting paid a good salary for many while they probably might not. Also I'd be sleeping well at night as I can jump ship the second I'm not happy, my reputation won't be tarnished by that.

So I am not sure it's that easy.

Of course, the idea is to keep the same work/life balance one would have at a more established company.

jonathankoren
0 replies
3h41m

It is that easy. Employee 1 is getting paid below market. That’s why they offer 0.9% equity. Meanwhile, the founders are also getting paid. No one is working for free. One of the first things VCs tell you is to make yourself comfortable so you can concentrate on the company. That’s literally one of the reasons why VCs tell founders to sell equity early, to make up for lost income, while Employees 1+ has to ride the rocket into the ground.

It’s Baby’s First Labor Exploitation.

geepeeyoudata
2 replies
5h27m

> What if they give 1-2% and good market rate salary (~200k/y) to a founding engineer? Is that still a bad deal?

OR....you could just become a founding engineer by actually founding and keep 90% of the equity. You can get that salary with an equity raise, its worth not being the low-person on the totem pole.

xandrius
1 replies
4h41m

That's forgetting what a founder actually has to do and worry about.

blitzar
0 replies
3h40m

Advertise for a founding CEO and offer them 1-2%.

halgir
1 replies
12h0m

If the salary is market rate for that person, I suppose it's by definition a fair deal. I've seen startups hire "founding xyz" two years after they started. Looks to be a vanity title in many cases.

dchftcs
0 replies
11h46m

Total comp needs to be market rate, not just salary. And non-preferred shares should be valued lower than preferred stock. Lumping non-preferred shares with prefereed shares is one of the bigger lies startups tell employees.

extr
0 replies
11h39m

I was recently faced with this exact offer at seed stage vs a series B with a similar salary. YMMV but what I found when I ran the numbers is the series B offer had a lottery ticket with a similar risk/reward profile to the seed stage. Of course I got less total equity, but it was way more likely to ever actually materialize. Plus being employee 80 at a Series B is a lot easier.

matthewsinclair
12 replies
12h16m

This reminds me of how I have seen a few asks lately for roles where a company is looking for a CTO for their “AI startup”. How an “AI startup” (whatever that might actually mean) can _start up_ without a CTO is beyond me, and raises some very big red flags about what that company might be up to.

throwAGIway
4 replies
9h17m

That's simple - they find a CTO.

The really hard thing is marketing and closing big clients.

matthewsinclair
3 replies
8h39m

This is true, but it also depends.

There are a lot of "tech businesses" that are actually using pretty pedestrian tech. What they are _actually_ doing is business model innovation with an underlying tech platform. Often, that tech platform can be commodity or relatively simple tech. There are other startup propositions, though, where the tech _is_ the thing, and if you get the tech right, then some of those other things end up being secondary (not irrelevant, of course) just not primary. This is assuming that you really have punched a hole thru the door with some amazing deep tech breakthrough, which not every company is doing, contrary to what they may claim.

There is a YouTube video [0] (which goes back to 2019) that does a pretty good job of making this point. Well, much better than I can.

To be fair to your original point: you're right that marketing and sales are hard. I'm just adding the subtlety that there are some tech businesses where the tech is _also_ hard, and perhaps even harder.

[0]: https://www.youtube.com/watch?v=C1DlZWfI6rk&ab_channel=YComb...

throwAGIway
2 replies
8h29m

I don't think we disagree. There are definitely deep tech businesses that are very hard to pull off.

My point is - asking "how did they do it without a CTO" is weird, they are hiring a CTO to do it, and they're bringing their business experience and funding - valuable stuff that a tech guy probably finds annoying. The number one suggestion on this forum is to sell before building and when somebody does it, users get wide eyes?

matthewsinclair
1 replies
5h57m

I guess it comes down to what "it" is. My sense (and this is just a personal orientation) is that if a CEO came to me and said, "Hey, I need a CTO for this new business I'm building", the very _next_ thing they say is really important.

If it is a) "Right, I've had this braingasm, and you need to build it, and for the privilege, you get 5% of the company!" versus b) "Right, I've had this idea, done some market validation, lined up our first 3 customers, and now we need to do some technical feasibility and put a team together to build this, and as CTO, I need a 50/50 founder, what do you say?" then I will pick b) over a) every time.

To be fair, those scenarios are cartoons on purpose, but I just wanted to make the point by highlighting the extreme cases.

As far as "sell before you build" goes, I think that really does depend on the problem you're solving. If it's a tech-powered business model innovation (where the tech is a commodity), then we are in 100% agreement. If the tech is a bit trickier and you need to show something special before funding (let alone clients), then I take a slightly different tack.

I'm not sure I get the last point about wide eyes, but I suspect it's immaterial to the bigger point.

sponaugle
0 replies
2h58m

Interesting... My initial reaction about the startup looking for a CTO was the same as yours. I was a founder and CTO, so it seems odd that you would not already have that in the mix... however I can see how there could be an idea, a market, a sales strategy, and a tech idea without the actual tech. In that case you would need to find a CTO to build that tech.

Of course the real gotcha is that there is no 'idea, market, sales strategy' that will be perfect, and the work is finding out where those ideas are wrong and fixing them. The lessons from my successes and failures says it is only worth doing that as a founder, because the failure risks are both high and unpredictable. Time is expensive, so spend it where there is both risk and reward, not just risk.

dcow
2 replies
10h29m

It’s not necessarily a red flag. Sometimes the founder/CEO is technical and decides to solo it with hired engineers until not having a real CTO is a flight risk, or until they’re too busy to be contributing code anymore, or both.

matthewsinclair
1 replies
8h44m

That is fair, assuming the CEO is technical, or technical _enough_. However, I see a lot of non-tech CEOs trying this on and in those cases, it is a red flag for me.

p1esk
0 replies
5h54m

With cofounders it’s fairly typical for one to be technical and the other business savvy.

captaincaveman
1 replies
9h32m

Mostly someone has a Phd and convinced people to give them money to 'change the world', then need someone who has actually built things beyond a script in a python notebook.

matthewsinclair
0 replies
8h45m

Gosh. So much this! The difference between the "average" PhD graduate in data science and the "average" software engineer with genuine experience delivering production software that people use at scale is quite something. I have nothing against data scientists, but in the same way that I wouldn't get a software engineer to build a complex model (above a certain level of complexity), neither would I get a data scientist to build a production app (above a certain level of scale). Both of these things are specialist activities that require a lot of experience, wisdom, and nuance to get right. Being good at one does not (necessarily) mean you will be good at the other.

rimeice
0 replies
11h3m

Founding “CTO” might be more suited to a “Head of Research” role as the company grows beyond a few engineers.

closeparen
0 replies
2h47m

The AI technology consists of templating out ChatGPT prompts.

extr
10 replies
11h43m

I recently applied to a seed stage YC company that was offering me 1.5% equity for a founding eng role which they felt was generous. So basically I get to do all the work for like 1/50th of what the founder has? Get real lol. I even pointed this out to them and they said "it's totally normal, that's the way it's done". Like oh okay, as long as everyone else is getting ripped off too.

titanomachy
4 replies
11h6m

I went through exactly the same discussion in my last job search, and was assured that the offer was in line with industry standards. Even if this tiny company somehow became worth a billion dollars, I’d still make less money than if I’d worked as a senior engineer at Google or wherever. I liked the team and I think it would have been a fun job, but not quite fun enough to work nearly for free. I don’t think I’ll ever work for an early startup as an employee.

throwaway98797
1 replies
6h3m

you should work at google

startups are about the work

sleepingreset
0 replies
5h43m

OP wants to get PAID for their work and rewarded for the all-in effort they'd put in. re-read their comment

lumost
1 replies
4h17m

I recall a discussion where a founder kept insisting that a 10% offer for a pre-funding startup was beyond standard and that I should be lucky to get such an offer.. the experience left a bad taste in my mouth.

Ultimately, this individual needed someone to shape and build the core of their product and the net of a series B would have been at most a wash compared to current employment.

romanhn
0 replies
3h35m

They're not wrong though? 10% is more late cofounder territory, you won't find anyone giving up so much equity for an early employee.

pilingual
3 replies
9h52m

What amount of equity would be fair?

tinco
2 replies
9h25m

In my opinion, you should take the difference between their market salary and the salary they're being offered, and consider that an investment by the employee at the upcoming (not past) valuation.

For example if they're in SF and they're hiring a senior first engineer that would maybe make 250k elsewhere, and they're offering them 125k, and they would take the classic 7% for 125k, then 7% is a good starting point. (Of course if they already have the YC investment, then that would go down dramatically)

If that equity vests over 4 years, then frankly maybe 28% is a better starting point.

But what's fair isn't really relevant. What's relevant is what the market demand and supply is. If there's some dolt who would happily take 1.5% as a first engineer ("founding engineer") for a $125k salary cut, then the founders would be idiots not to take that deal. And frankly, if that $125k salary cut gets them their dream job, then maybe they're not even dumb for doing it.

etothepii
1 replies
3h57m

I think what you are actually describing is that you should value equity at zero. If to work at a startup you would need 28% equity you are describing a founder. That's fine but there is an enormous difference between these two things. There is also the question of where the $125k comes from to pay your base.

tinco
0 replies
2h17m

Value equity at zero? I am not sure what you mean by that. If an employee sacrifices $500k to work at your company, then it would make sense to compensate them with $500k worth of equity is my point. The 28% is tongue in cheek, if you're so early that the amount of equity needed to compensate your first hire adequately is 28%, your company hasn't really started yet, and maybe you should just consider them a founder.

nkohari
0 replies
3h34m

So basically I get to do all the work for like 1/50th of what the founder has?

Who raised the money that the company is using to pay salaries? When investors put money into a seed company, they're largely betting on the founders' perceived skillset and previous experience (or other bona fides like education).

One thing that most people don't realize is that being a founder means that you're inextricably tied to the company for its lifespan. Losing a founder is terrible optics and can be a death sentence for a startup. Regardless of the actual reason, every subsequent investor conversation will involve an explanation of what happened.

If you want more equity, you should ask for it! And you definitely shouldn't take a job where you'd feel under-compensated! But realistically, if you want a "founder-level" equity, you have to start your own company.

blitzar
0 replies
9h38m

a lot of early stage founders looking for a "founding engineer"

I always just assumed that the Entrepreneur, Founder & CEO had come up with an amazing idea like "build an startup (Ai probably) that makes a lot of money" and got some funding - but don't know what software is, don't know how to code and isn't really sure what Ai is does or can be used for; so need someone to put the pieces together to execute their vision with (for) them.

Opportunity to get in the ground floor with a future Unicorn - must have 25 years experience, Salary $25,000, 2% equity with 5 year lock-in.

inhumantsar
5 replies
12h44m

the lottery ticket analogy doesn't quite hit the mark imho.

I've been seeing really shitty vesting schedules more often these days. a year in an early stage startup is often more intense than years in larger companies, yet they feel the need to push vesting schedules like 5/15/30/50 on people.

even if you do stick it out and exercise those options and eat the tax burden, those shares can still be ignored in an acquisition or diluted into oblivion in an IPO if the agreements are structured to allow that.

with a fat carrot dangling at the end of year four and the promise of an IPO Soon™, a lot of people will be more than happy to ignore important parts of their lives and financial well being for the chance of maybe, just maybe, getting access to that lottery ticket.

I think a better analogy might be like gambling in a casino. investors get to write the rules and hold all the leverage. the worst places are mobbed up, the rest might be legit but either they have every incentive to keep selling you the dream of winning big. in all likelihood, if you keep making that bet you'll walk out worse off than you were when you walked in.

if a startup or VC truly gave a shit about anyone outside the c-suite, they'd have an employee ownership program of some form and assign actual equity, not just options. I've yet to see many of them do this though because founders are the most likely ones to be gambling in those kinds of casinos.

torginus
2 replies
5h5m

Sorry I'm a total dumbo when it comes to startups, but what do you 'vest'? I thought vesting is for stock options (maybe stake?). And your startup is not on the stock market, and won't ever be unless it gets a billion-dollar valuation.

Even stake might be worthless, if the company fails, despite you building a kickass backend for it.

munchbunny
0 replies
3h38m

Yes, you vest stock options, and given that risk for startups is very much front-loaded, vesting schedules that are back-loaded are a big red flag for incentive misalignment. And that's ignoring all of the problems with stock options as opposed to RSU's.

The baseline is something like a 4-year vesting schedule with a 1 year cliff and monthly after that, uniform distribution. Anything more back-loaded or worse than that is a red flag.

inhumantsar
0 replies
3h6m

most startups don't offer actual equity even though that's what everyone calls it. they offer options. the idea is that the options you'll receive will have a strike price much lower than what the stock will be worth in future funding rounds or when the company is acquired or IPOs. the vesting schedule defines when you can start to exercise those. typically you'll receive 25% of your options after the first year, then the other 75% will vest every month after.

and yes, liquidity in a private company is always going to be an issue.

all of this is why I tell everyone that their options are worthless right up until they're not. anyone who's burned out or looking at a new opportunity shouldn't include them in their decision making process.

xandrius
1 replies
11h37m

What would you suggest to someone who wants to work at interesting (non-evil) companies, wants a decent comp ($200k+) and doesn't mind being one of the first to lay the foundation with the possibility of upward mobility in the future?

inhumantsar
0 replies
3h13m

be a founder or a consultant, not a founding engineer. build up a set of specialized skills in something you love doing, network your face off, keep lifestyle inflation under control, and keep a large amount of your savings liquid(ish). if the right people and opportunity comes along, be ready to tap those savings and live off them for at least a year while you build the company or be selective about your next consulting job. like the old cliche says, luck is where opportunity meets preparation.

if you're not that ambitious and simply want to live comfortably, then go to those early stage startups and negotiate for higher cash comp and a smaller slice of the options.

you can make great money as a SWE, but there's a massive leap between that rung on the income ladder and the ones above it. it takes a dedicated effort to get there.

CalChris
3 replies
13h2m

If you were early, why didn't you purchase your options and file an 83b?

yieldcrv
1 replies
12h51m

requires having cash to tie up indefinitely, privilege alert

we did this on our crypto token grants though. once we realized we can play with the prices much more than with securities and that vesting isn’t standardized by any law, we granted ourselves deeply discounted tokens in a vesting schedule of like 3 months, the whole grant being a couple hundred dollars and launched the token the next day. mailing the IRS the election was beautiful.

novok
0 replies
11h57m

If your early enough (like seed stage), it's like $300 for %5.

throwawaythekey
0 replies
11h7m

I'm not the GP but was one of the first engineering hires in a startup. In my case I got caught in the cross-fire of one of the co-founders backstabbing the other which meant that by the time we closed the series A I had been diluted by 80%. To 'make this up to me' the company gave me a new grant that would counter the dilution. The downsides were that this restarted the vesting clock and the new options would cost a year worth of savings to exercise - this was much more than the few hundred dollars my original grant cost.

Fast forward four years of toil with multiple cycles of doubling and then halving headcount as well as endless leadership changes. We are now on our fourth CTO in as many years. On the upside things are starting to look up! The newest sales team have worked out how to sell the original product we built, not the bells and whistles we pivoted to on the wisdom of the overpaid CPO. We can now celebrate as we have about a year's worth of runway and can confidently project being cash flow positive in about six months.

The new ex-FAANG CTO earning three times as much as anyone in the original team has great news! As a result of the positive development we are now able to hire an extra development team in South America! This shouldn't cost us too much and they can start on the next greenfield effort. The existing developers need not worry about being replaced as the existing team has all of the experience with the money making side of the business, and besides the new devs will be working on a parallel offering anyway.

Four weeks later and we've onboarded two offshore devs. The VCs have demanded we cut our burn rate and my position is being made redundant. I have 90 days to exercise but my options are underwater, both when compared to the funds we raised a few months ago and also the FMV. Essentially to buy them now I would be worse off than someone walking straight off the street.

onion2k
2 replies
12h16m

The irony of being an early engineering employee (and any engineer really) is that the better job you do the easier it is to replace you with someone who can maintain what you built. Accepting a below market salary and then doing a great job is a huge risk.

repomies69
0 replies
11h56m

Accepting a below market salary and then doing a great job is a huge risk.

By doing bad quality work on purpose will not make you learn anything. Better idea is to leave your underpaid position, start your own startup or join another that has better salary and compensation.

aorloff
0 replies
10h58m

Sure, in startups that don't grow.

In startups that experience internet growth, you find yourself trying to build systems so fast and hire people that you aren't so worried about someone replacing the job you used to have because the nature of your job is changing as the company scales.

And if the startup is not growing, you can stop worrying about the equity package

jjav
1 replies
12h37m

Getting out for an early employee after funding rounds is expensive

Early exercise and 83(b) is a must, or forget about it.

When considering joining an early startup ask if they will allow you to early exercise as soon as you start (well, it'll be after board approval but as soon as that happens).

If they don't allow that or if the price is too high for your comfort level, don't join that startup.

deepGem
0 replies
11h58m

Every startup CEO must demystify 83(b) for their employees.

If you don't have cash on hand to pay for early taxes, the company can pay a signing bonus or something for those who elect 83(b) to pay for the upfront taxes.

OR

Just pay market salaries and leave the choice to employees to do whatever they want with cash. You want to buy our company stock great here's the grant. You want to put your money in S&P index go ahead.

The employee equity part needs a lot more simplification. I don't know why it is not as simple as

Here are 2 options for you

Salary 200K OR Salary 100K Equity 100K If equity 100K exercise 83(b) - pay taxes at 200K income OR defer taxes for the subsequent exercise dates. (Could land a huge tax bill) OR defer the exercise date for a liquidity event/secondary sale.

Those who value risk will take the last option and those who don't will stick to full salary. 83(b) exercise, when presented like this, doesn't seem all that rosy.

There could be some legalities that I am unaware of, but broadly this should work.

jahewson
1 replies
12h52m

90 day exercise window is a big part of the problem here.

gafferongames
0 replies
5h46m

If you're certain the stock is worth something, just take some risk and exercise.

ZhadruOmjar
1 replies
11h55m

In my experience there has never been a good time to be a founding engineer even in companies that have later made it. It's much better to join the company 1-3 years prior to IPO/Sale where you get many of the benefits but significantly less stress. If I had worked at startups I would have been taking a 30-40% pay cut compared to the roles I did work and none of those startups have gone anywhere with most crashing and burning.

bambataa
0 replies
9h54m

I’ve heard this a few times. Could you elaborate why? Surely at that point, less you are hired to a very senior role, you are going to get a very small equity % and a lot of the capitalisation growth has already been priced in? In exchange it is far less risky.

Do you just go for the market salary and treat the equity as a minor plus?

FlyingSnake
1 replies
13h16m

I’m really sorry to hear about your burnout, I hope you’ve made a recovery and are at a better place now.

I thought it was the prevailing wisdom here on HN that being the first employee almost always is bad for the employee. You’re right, the cards are stacked against them

jmward01
0 replies
13h9m

Much better now actually, thank you.

palata
0 replies
5h4m

how little VCs actually value early employees

Do they even pretend that they care about anything other than money? Like... ever? Maybe to family and friends (not even sure), but I mean professionally?

chermanowicz
0 replies
12h47m

I can also guarantee you points 2 & 3 are pretty wrong as well. Funny (and also sad) how different peoples realities can be. I have been worn out sitting on both sides of the table to tell you the truth. (One thing I will say is that within VC, the vast majority of the folks actually doing the work are sympathetic and helpful to companies, working with early/senior employees, but it gets lost up the food chain so to speak and there's usually just one or two people making decisions at the end of the day about a particular deal or a whole portfolio- and these people are generally very self-interested.)

throwailearner
31 replies
5h56m

Posting from throwaway so I can be very open.

I joined a YC startup as engineer #1 with close to $200k salary and 2% options vesting at the usual 4 years, with a 10 year window.

I feel like this was bettern than usual, and for a while felt like I struck an awesome deal, but as time went on I realised I was building everything single-handedly, while getting (at best) 2%, which started to annoy me deep down.

Over two years in I'm considering quitting, for multiple reasons. I still believe there is a good chance of getting to an exit at some point, but I don't like the vibe and culture here, and honestly between cashing out 1.X% and cashing out 2% I don't see the point.

If I had been given a much higher chunk (>5%) there is a good chance I would've stayed, so we'll see if they value me enough with a counteroffer when I give my notice.

All in all, and reading through all of this I would never join a startup under these terms again, if I'm engineer #1 then I'm getting at least 10% and essentially being a cofounder. Otherwise I want a salary that's on par to a bigger company.

palata
6 replies
5h7m

$200k? Do you live in a place where this is considered a bad salary?

CSMastermind
2 replies
4h52m

It's normally considered a bad salary in comparison to what you could be making. I won't speak for the poster but I left a ~$1m / year TC job ($300k base the rest RSUs) to join a startup. I have a good salary compared to the population at large but it's a fraction of what I could be making on the hope that my equity turns into something meaningful that makes up for it.

palata
1 replies
2h56m

I wish I knew how to get to $200k. Not even mentioning 1m/year, that seems absolutely insane to me.

hedora
0 replies
1h25m

The easiest way is to move to the SF area. However, you'll end up spending most of the after-tax pay on housing, food, etc. For example, rent on a 1 bedroom apartment in the suburbs is going to be $30-60K per year:

https://www.zillow.com/santa-clara-ca/apartments/1-bedrooms/

The cost of pretty much everything around here reflects that cost of living. Businesses have to pay workers enough to allow them to live in the area.

BiteCode_dev
2 replies
4h39m

It's not just a matter of place, but what you can have if you work for Google instead. I can make $200k as a freelancer in France, but much more as a Google employee.

palata
0 replies
2h57m

$200k is extremely high for France. Even half of that is high. I wish I could do that.

cosmic_quanta
6 replies
5h31m

I've been thinking about the equity split amongst early employees. Our startup is reserving 20% of equity for early employees. How about a division by 2 every time? First employee gets 0.5 x 20%, second employee gets 0.25 * 20%, etc.

Early employees are better rewarded for the risk, but later employees (e.g. #10) will get basically nothing. It's all about tradeoffs

romanhn
5 replies
3h54m

At 10 employees the company is still incredibly risky. With this scheme you'll never grow past that size.

cosmic_quanta
4 replies
3h49m

Well, the alternative (which appears to be the status quo) is to give lower % equity to the first ~50 employees.

What do you think is the ideal breakdown of equity for early employees?

zenlikethat
3 replies
3h13m

people already do a variant of “earlier gets more, later gets less” that’s a lot smoother/linear than your scheme and can be customized and adjusted to roles (engineers get more than salespeople as an example). With what you describe, offering some exec down the line 0.5% or whatever is impossible.

You need flexibility because at any moment some killer candidate might come along that you need to juice the grant for. Just being earlier doesn’t mean they contribute more to the company

RhodesianHunter
1 replies
1h38m

Just being earlier doesn’t mean they contribute more to the company

No, but being earlier does mean taking on more risk, which is the whole argument founders and seed investors make for their cuts.

zenlikethat
0 replies
13m

But you can leave easily. and in 2024 I think people should insist on getting a decent salary (FAANG is impossible, but for most of the country, “even just” $170K is eye watering), and work life balance (sure, you will have to put in extra hours sometimes, but if it’s a 12 hours a day shop, don’t join). Founder should work a lot more aggressively, live a lot more spartan, and obviously is shackled to the damn thing with no optionality.

cosmic_quanta
0 replies
1h58m

That makes sense, thanks

sleepingreset
4 replies
5h46m

out of college directly, would you recommend a similar position? looking for early career options

shortrounddev2
1 replies
5h41m

I don't think you could get hired as engineer #1 straight out of college

disgruntledphd2
0 replies
5h37m

And even if you could, you probably shouldn't. Go get experience with a bigger company first, so that the startup experience is more useful to you.

djbusby
0 replies
4h31m

I'd say take a startup. Those early companies don't have a lot of staff so you can try lots of things, wear lots of hats. Good experience. Take cash, don't get played by options/equity. When you find the hat you like move into a more stable role.

aketchum
0 replies
3h20m

i joined as founding engineer as my second job, 2 years after college. The founders were the same age which I think let them consider a young founding engineer. It worked out for me and I think if you have the opportunity then it is a great time to take the plunge. Knowing what I know now I would likely not take the same role at 30 due to lifestyle requirements (have wife and house now, back then I was paying very little for rent with roomates and had no issue with 12 hour days. I think the risk can make sense early in your career but most founders probably dont want to risk it on an untested dev with sub 3 YoE.

stevesthrowaway
3 replies
3h43m

throwaway acct here. I left a flagship tech company with $500k total comp and joined a startup as engineer #1 with 5% options over 4 years. My salary is current $120k and I'm losing money each month, although I've been promised that will changed as soon as we raise more.

We are going to raise a Series A in the next few months. I know a little bit about this stuff, but not enough that I'm confident in exactly what to expect over the next few years, nor enough to know that I've negotiated properly (thought I did lol) and are protecting myself enough. This thread is scaring the shit out of me. I have a good relationship with the two founders and not afraid of being candid with them. Would appreciate any advice.

gen220
1 replies
3h11m

You should be candid with them that you're uncomfortable with the cash portion of your comp.

5% is an unusually high % of equity, the founders likely assumed you were happy to trade-off cash for equity. Series A is usually a dilutive round and it's normal to grant people like yourself more options to compensate for the dilution (i.e. to keep you at 5% of the new cap table).

My 2¢: I know people in your position who have ~$200k cash comp in addition to meaningful equity. Don't feel bad about asking for more cash, if your founders have a good relationship with you and you're providing value for the company, they'd rather invest the marginal cash in you and keep you happy + comfortable.

RhodesianHunter
0 replies
1h40m

I know people in your position who have ~$200k cash comp in addition to meaningful equity.

That's great, so long as its taken within the context of "200k is way more than the average US engineer makes without any equity"

moneywoes
0 replies
3h15m

hate to blow your bubble but this sounds like a bad deal. do you even know the denominator on equity? look at liquidation

sashank_1509
1 replies
4h25m

10% to a founding engineer almost never happens. You’re in cofounder territory. There really are 2 reasons to stay in the startup,

1. The startups reaches a great valuation. If it reaches a 1B valuation, then even assuming 50% dilution, you have 10M for 2+ years of work, almost 3-5M per year TC! Yes your founders are earning much more but comparison is the thief of joy, you just got a salary that no big tech company could match (unless you’re in C suite)

2. The startup doesn’t reach a large valuation but grows rapidly making you in charge of a large group. This too is useful, promotions in big tech have a very standard time schedule, it takes 8-9 years to reach staff (or never) and then 4-5 years for every subsequent promotion if it happens. With a startup, if as a founding engineer you gain experience leading a team of 50 people, you’re scoped for staff and above in your next job hop. Of course you need to sell this in your interviews but I’ve seen this happen and it can be worth it, if you played your cards right.

If none of this is possible, you should leave.

darkwizard42
0 replies
2h55m

TC isn't TC if it will remain illiquid for a number of years. That is the issue described in the blog post. Founders get great secondary liquidation in each round which helps realize some of those gains. For you as the early employee you get stuck with a now more valuable potential lottery ticket, but no clarity on when it can be cashed in.

mrkurt
1 replies
3h58m

This sounds like a bad job and you should find another.

At some point you were happy with $200k and 2%. Now you aren't. I don't think there's a bump that they could give you at this point that would make you want to tolerate the shit that's bad about the job.

Note that this is a bad job. Startups are more prone to creating bad jobs.

The math for employee #1 at a startup is almost never ideal if you're being completely rational about expected value. That is, I think, a separate problem than you're dealing with.

zenlikethat
0 replies
2h51m

The ideal reason to be engineer number one tbh is if you want a playground (for lack of a better way of putting it) to build the system out the way you want. That will be of high value to specific people (Architects, not the LinkedIn kind) and low value to most of the population who just sees a job as a means to an end.

But for some people, direct access to an AWS account and license to build as they please is intoxicating.

zenlikethat
0 replies
2h45m

Compensation wise, that’s a great startup job, especially with such an insanely generous exercise window. Where I think you maybe went wrong is, if you are building everything, it’s not a collaboration with the founders, which is half of the fun of everything.

I suspect it’s more about the culture than the numbers. You say on one hand, oh I’d probably stay for 3% more, yet, you don’t see the point to earn another 1%. Your salary is pretty good man. Meanwhile they are burning $250K every month into smoke

10% is not realistic. That’s the whole employee options pool. I mean imagine if at your current job, someone worked there for a year before you, then walked away with more than your entire current equity grant, never to be heard from again. That’s what you’re describing.

moneywoes
0 replies
3h16m

how much effort are you putting here wrt to your previous job

aeyes
0 replies
3h37m

What I don't get is that you are engineer #1 but you say the vibe and culture are bad.

Why didn't you build a better culture? I very much doubt that the management team took all the hiring decisions on their own after they got you on board. I'd say the most important part of my job as #1 was to hire and build the team.

VHRanger
0 replies
2h26m

If you're building everything singlehandedly, then you have leverage over your employer and investors.

You should use that leverage to renegotiate your pay. You'd lose nothing because you're considering quitting anyways.

koalaman
26 replies
6h49m

I recently left a long career in FANG to roll the dice on an early startup. I was pretty surprised by the uneven terms between founders and early employees. From what I could tell the early employees takes more risk than the founders because they don't get that magic token dollar turning into their share of the founding equity event and have to pay the fictional valuation of the seed to convert their options. Depending on how hot your startup is that can be a lot of money.

Anyway that ended in tears, but I got what I was looking for from it. A look under the covers of the hot VC backed startup roller coaster. I may be getting old and cynical, but it looked considerably more exploitative than what I saw at Google. Obviously depends on the character of the founders and leaders, but the structure seems to be setup for toxicity.

geepeeyoudata
9 replies
5h38m

I worked at a Series A startup as an employee, and wont be doing that anymore. Early engineers have all the risk (lose job the second things go bad) but little upside. They would offer 500 options, or 1000 options, or 30,000 options -- but when you look at the prices, that was worth $100-$10,000. Why would anyone take all this risk, and lower base salaries for that lottery ticket?!

Secondly, they wont share the cap table, so you dont know what the denominator is. 30,000 shares of What!? No one would tell you. You should run.

Third, the VCs installed a buddy from SV as CEO who was creative with revenue. Great -- so they make their bonuses based on creative revenue, but the company gets saddled with VC rounds they have to dig out of w/o showing real revenue growth. Once you get SV insiders being placed into the company, often with their entourage of cousins and neighbors' kids as Director of HR or Director of Finance -- RUN FAST. The company is being strip-mined for cash, while Engineers slave away trying to code their way out of the wreckage left by locusts.

The C-Suite operated in a separate tier of the company with a heads-i-win-tails-you-lose setup. You could tell -- no way you are all driving Tesla Plaid on a "startup salary" -- the "startup salary" was for suckers, engineers, and those not in the VC-back-scratch loop.

My advice to everyone -- if you want risk, be a founder. Not Engineer #1 or #10. If you want balanced risk, go to a Series C or D company where you dont have the risk of fake accounting. If you want money, go to a public company with real accounting rules, visible revenue, visible liabilities, and more accountability.

randerson
4 replies
3h26m

My experience was similar, right down to the $10,000 worth of options. Eventually the company went public and those options would have been worth $5M if I'd had the foresight (and cash) to exercise them (which I didn't). The co-founders did not have exercise costs or AMT of course. It is an unfair system indeed. I'd encourage those seeking to be early engineers to go work at a FAANG for a few years before joining a startup so that you have the cash reserves to take the risk.

davedx
3 replies
2h39m

Wait, you couldn’t find the 10k cash to exercise 5m worth of options?

xnx
0 replies
1h51m

You typically don't know what they're worth when you exercise the options. Often it turns out to be nothing.

randerson
0 replies
1h33m

The paper value was far lower during the exercise window & no guarantee it would ever be liquid. The AMT would also have dwarfed the 10k.

hylaride
0 replies
1h12m

What they likely meant was that the options would eventually be worth $5m, but not when they left the company and could exercise them.

zenlikethat
0 replies
3h5m

Even if you don’t see the cap table, any company you talk to should be clear and consistent in disclosure of facts like number of shares outstanding, including viewing it in tools like Carta. You are basically describing the abusive version of a startup and then saying all startups are bad.

I actually think going to a Series C or D is not the ideal play. It’s better to join an early company, with good leadership, reasonable if not mind blowing salary and cheap shares. Then, work hard, but not brutally hard. Somewhere that you enjoy the people, the work/product, and you can level up a lot. The options are cheap, and you can bail to FAANG at any time if you burn out. Realistically, that’s your shot at making 1% of $Xmm without completely hating your life. It will be a rare company so, yeah- be picky. I don’t know why all startups get lumped into one when there’s a lot out there for the discerning employee.

pragma_x
0 replies
4h8m

but when you look at the prices, that was worth $100-$10,000. Why would anyone take all this risk, and lower base salaries for that lottery ticket?!

I was in a company when my options were "purchased" from me at the strike price, when the company itself was sold. We never made it to IPO. I've learned to not overvalue options and phantom stock, and just chalk it up to another bonus down the road. The real money is, or already has been, made elsewhere.

What really steams my biscuits is when I figured out how the payout was worth less than the unpaid overtime (never more than 50 hours a week), weekend support time, and travel time spent in my years there.

e40
0 replies
2h57m

Spot on, and I say this as a founder of a company that didn’t fuck over the employees. 40 years and still going, and most people have been with us for more than 25 years.

I didn’t get rich because I wanted to sleep at night, but people in my orbit (probably me in theirs?) advised me very differently.

djbusby
0 replies
4h37m

If you are early and they not sharing the cap-table it's a red-flag.

palata
2 replies
6h1m

I have been working in multiple startups, I've come to think that it's a Ponzi scheme for the founders.

Generally underpaid and quickly toxic. It is an experience, but it's important to know it.

RhodesianHunter
1 replies
1h55m

It's a Ponzi scheme for VC and other investors.

Founders just get greased palms along the way if they're successful.

koalaman
0 replies
1h41m

Yeah agreed to both of you. I had the same thought.

oblio
2 replies
4h21m

You have the current unicorns, basically anything from about the time YC started, and then you have the old school unicorns.

For comparison, Microsoft IPOed in 1986:

The company's 1986 initial public offering (IPO) and subsequent rise in its share price created three billionaires and an estimated 12,000 millionaires among Microsoft employees.

https://en.wikipedia.org/wiki/Microsoft

I would really, really want to know if anything more recent has gotten to that level of widespread distribution of the riches.

I kind of doubt it, such an event would probably be considered Communist by modern standards :-)

kaiokendev
0 replies
2h59m

Facebook, although it didn't have nearly as many employees upon its IPO

ilamont
0 replies
2h38m

an estimated 12,000 millionaires

One of them is my neighbor, an early Microsoft employee. She basically retired in her 30s.

carterklein13
2 replies
5h27m

I did a similar thing to you. However, I do feel like cutting your teeth as a "founding engineer" at an early startup has 2 major benefits:

1. You get to see what it's like under the covers, as you said. It's not nearly as glamorous as it looks from the outside. And yes, as an early engineer, you share in a lot of the downside without nearly an equal share of the upside.

2. You get to leave. Unfortunately, the startup I joined entered a tailspin. But, my name wasn't attached to the company, and I didn't have a fiduciary obligation to our investors. I had a lot of "stake" myself after putting in years of 12-hour days, nights and weekends, but at a certain point I saw that my career was actively being harmed by staying. That "founding engineer" role on my resume got me the job I'm at now, at a level that skews higher than my YOE.

Do those two points mean you should get a fraction of the equity (or rather, a fraction of the options) as the founder? Honestly... maybe. I've now seen a few founders fail. It can really be a career-killer.

zenlikethat
0 replies
2h57m

Getting to leave is so underrated. Nothing keeps your head above the doom and gloom like knowing you aren’t shackled to the thing, and the world’s your oyster if you need to move on. We live in a weird world if people don’t think a gig with $160K salary, 2% of the company, where you can work hard but not 24/7, and _leave any time you want_ is a bad gig. That 0.25-0.5% after one year that you get is PERMANENTLY gone for them even if you just fuck off after a year. Years later it could be worth millions.

But anyway, as founding engineer you get to set the systems, culture, language etc. maybe some people don’t want the responsibility but for others it’s an opportunity to build things out in our own image and learn a lot.

palata
0 replies
5h9m

Do those two points mean you should get a fraction of the equity (or rather, a fraction of the options) as the founder? Honestly... maybe. I've now seen a few founders fail. It can really be a career-killer.

And I have seen a few founders fail and enter bigger companies at a pretty high position. Not sure I would relate that to how much money they should get in case their startup is one of the lucky ones.

wnolens
1 replies
2h31m

I almost left for an ultra early startup, still running on seed money. They offered a typical SDE2-Senior salary + 1%. I was kind of offended. I'd be inventing their core technology (which didn't exist yet and which their CTO wasn't fit to do) and probably interviewing every engineer and growing them.

Even IF they achieved a 100-300M exit, after dilution I would be compensated at best par with a FANG Senior over about 5-7y.

I was pretty excited about joining and would have been all-in. So I asked for 2-3% and was denied. Looking back, I'm glad because even 3% isn't worth it. Not when the founders are taking 10x.

indymike
0 replies
1h3m

. I'd be inventing their core technology (which didn't exist yet and which their CTO wasn't fit to do) and probably interviewing every engineer and growing them.

I see this a lot in failing startups:

The CTO is a pure manager who can't do any actual engineering. The result is that the shares and salary that could have been traded for getting product to market faster & better ends up being burnt on an empty chair.

jejeyyy77
1 replies
3h38m

most i know who work as eng #1 (non founder), are new grads who couldn't get into FANG. So mainly just looking for experience/inflated job title to boost their resume.

So not like these startups are getting top senior talent who obv will want to get PAID.

tmpz22
0 replies
1h42m

I went this route and now have a resume of inflated titles. I learned a lot and believe I can do some things in the top 10 percentile, just not the things many companies are currently hiring for (top 10 percentile in a narrow development skillset such as ML, or a specific language, or algorithms).

Im cynical and ultimately an rebuilding my dev career around a platform that will give me opportunities for entrepreneurship AND individual contributor work as an employee (Apple Ecosystem - iOS client development + product dev/mgn).

If I were to do it over again I 100% would've avoided startups early in my career when I could lean on junior positions to grow in a more mainstream manner. I'd have more money in my pocket, less stress, and less cynicism.

--

The problem is there is objectively zero way for fresh grads to learn these lessons. Even with prominent threads like these being available to some, the bearish attitude in every other thread will be more appealing to a fresh grad.

sackfield
0 replies
5h27m

As an engineer you really have a finite amount of good working years, and accepting startup salary vs big tech compensation is a bigger risk than founders are willing to generally admit.

o283j5o8j
0 replies
3h55m

I did early employee several times because I didn't know any better, didn't have anyone around to tell me not to. I won't do that again. All the risk, none of the reward. 1% of $10-20M after 4+ years of 80hrs/wk is less than the difference between a startup salary and a good salary over that same time.

hliyan
0 replies
4h25m

There was an oft-repeated response back in the day (but gladly rarer now) when you dig too deep into employee benefits at startups: "If you're offered a seat on a rocket ship, don't ask what seat!"

To this, I usually reply "Unless the seat happens to be in a stage that gets jettisoned before reaching orbit".

keeptrying
26 replies
14h18m

Founder liquidity doesn’t make up for much in the average situation.

Making $400k after making $100k for 4 years doesn’t really change much.

It gets you upto junior engineer level.

The underestimated play is becoming a cofounder to a great CEO 2nd time founder.

Sytten
22 replies
13h58m

Getting out of the SV bubble this is an insane amount of money. I boostrap my business and I make 40k a year. Most senior SWE around here make less than 100k.

hn_throwaway_99
19 replies
13h47m

Obviously everything is local. 40k is about $20/hr, which where I live is just a tad above what new fast food workers make. Fresh CS grads make more than $100k (or at least they did, obviously the past year and a half has been brutal). This is not in SV.

adastra22
18 replies
13h8m

In most of the world (even just considering developed nations) fresh CS grads do not make more than $100k. Senior software engineers don't even make that much anywhere in Europe or most of Canada.

selestify
14 replies
12h51m

Why the disparity? Especially with Canada - no language barrier and no time zone differences. Why doesn’t the free market equalize Canadian dev wages with American ones?

FactKnower69
4 replies
8h2m

This is not speculation, it is what multiple Canadians I've tried to poach have told me: they don't want to move to a country where one medical emergency can put them in 6 figures of debt

Sytten
3 replies
5h1m

Not that our health care system is going that well these days but true. Also being called a freaking non-resident "alien" is so demeaning, sorry I am human.

hn_throwaway_99
2 replies
4h14m

None of those reasons make any sense to me. The US health care system is truly fucked, but nearly all the companies paying well for SWEs also provide good health care plans. It sucks that things are so complicated (deductibles, copays, coinsurance, in-network, out-of-network, etc.), but people with good health insurance aren't getting bankrupted by health care costs. And I've seen plenty of colleagues with super-expensive conditions in my lifetime ("million-dollar babies", cancer, losing limbs in car accidents, etc.)

And bitching about bureaucratic terms like non-resident alien? All countries have silly bureaucratic language and words can have multiple meanings. Nobody thinks "alien" in this context means you're a little green man from Mars.

Sytten
1 replies
2h8m

Sure until you lose your job, I think having your health insurance tied to employment is really scary for a lot of people (me included). Not everybody has the same tolerance to risk. Our safety net isn't what they have in europe, but it is still better than the US.

No offense but it is spoken like a true American. I have dealt with European immigration and it was pleasant/painless for the most part. In the US they make you feel unwelcome and they drown you in paperwork. Not that Canada is much better these days, but I am a citizen so don't need to deal with it.

hn_throwaway_99
0 replies
1h55m

Sure until you lose your job, I think having your health insurance tied to employment is really scary for a lot of people (me included)... Our safety net isn't what they have in europe, but it is still better than the US.

100% agree, but we weren't talking about which system is better, we were talking about why Canadians may be reluctant to relocate to the US. It's not like Canadians who come to work in the US give up their citizenship. Worse comes to worst and you lose your job and health care and have a major medical issue, the Canadian safety net is still there for you.

extragood
3 replies
12h0m

I am convinced that the WFH movement is responsible for the recent offshoring trend.

Before 2020, it was fairly uncommon to work remotely and most employees were expected to physically come to the office. You would relocate if you got a job in another state, and employers had to go through a painful visa process to access foreign workers or set up expensive international satellite offices.

The great WFH experiment kicked off by the pandemic concluded that no productivity was lost, so many employers realized that they did not actually need to hire domestically at all. Everyone can be remote and work from wherever. LCOL in the US is still extravagant compared to many other regions, so a top engineer can now be hired for pennies on the dollar. I think there's a very good chance that tech salaries in the US have begun to and will continue to equalize with the rest of the world as a result.

hn_throwaway_99
1 replies
4h8m

I definitely agree with this. In addition to WFH, consumer-grade Zoom/Meet/etc. got good enough right around the pandemic (just before really) where it made off shoring really feasible. I've especially seen an explosion of offshoring to Latin American and Eastern Europe. The time zones make things much more workable than, say, India or China.

extragood
0 replies
41m

Yep. My previous company almost exclusively hires in Latin and South America now. The interesting thing to me is that it hasn't affected the executives themselves yet. If employees from one region work just as well as employees from another for other roles (or at least cost to performance is favorable), then it seems hypocritical and counterproductive for them to insist on US-based execs. The vindictive part of me hopes that it catches up with them next.

keeptrying
0 replies
4h27m

True. WFH was the real trial of offshoring especially to similar time zones.

Also it took the risk off the CEO plate that remote might fail. Further the market is rewarding them for it now.

jahewson
2 replies
12h33m

How much do Canadian tech companies earn per employee? There’s your answer.

PeterisP
1 replies
7h50m

So many of the companies are global, or at least have offices both in USA and Canada. Why do they hire devs in USA instead of Canada?

hn_throwaway_99
0 replies
2h1m

In my experience the best Canadian devs came to the US specifically because they could make so much more. Not sure if that's changed much over the past 5 years given the explosion of remote work.

adastra22
1 replies
12h49m

The better question is why doesn't the free market lower Silicon Valley pay to be comparable to the rest of the world. SV is the outlier. Even other forms of engineering don't pay compensation anywhere near what SV software devs get.

hn_throwaway_99
0 replies
4h4m

In winner-take-nearly-all industries, it makes sense to pay top dollar for talent if that gives you a better chance of being "the winner".

jahewson
1 replies
12h35m

They definitely do, take a look at how much big US tech companies pay in London.

adastra22
0 replies
12h28m

take a look at how much *big US tech companies* pay in London
dubbel
0 replies
9h36m

Senior software developers definitely can make that much in parts of Europe, and not just at banks or the big 5. But also 100k USD isn't what it was 5 years ago.

seattle_spring
1 replies
12h53m

Where is "around here"? No way it's any city in the US.

randunel
0 replies
11h8m

They're Canadian.

parentheses
2 replies
14h11m

This assumes how much of the founders' shares they sell and the size of the raise. The $400k figure is just arbitrary here. I imagine when companies are raising Series B or later, founders are walking away with millions.

keeptrying
1 replies
13h56m

$1-$2M after 6 years of working at $100k isn’t really much either in the Bay. (Which is the only place you’d get that.)

Even that averages to a senior Eng salary for the very very few founders who get there.

This has to be tempered by other realities - no social life - working 80 hours a week easily - risking personal finances - health problems - good chance of divorce / no deep relationships

Starting a company is no joke.

Very few get to series B/C.

newshackr
0 replies
5h16m

That may be true, but it is also true of early employees who stick it out for similar amounts of time and get nothing. $1-2 million may be the total amount they would get after a billion dollar exit.

corry
18 replies
2h45m

Three interesting part of the discussion:

(1) The opportunity cost to the founder of taking early liquidity:

If a founder cashes out 10% of their position for $500k @ $25M Series A valuation, that de-risks a lot of their personal life. But when the startup ends up selling for $250M, that $500k of 'early' selling would have been worth $5M (less any dilution between rounds) - hard not to regret the choice in that case even if hedging is going to be the correct choice 99% of the time.

(2) Meaningful vs. not-meaningful amounts:

From my prev example, the founder sells 10% of their position for $500k. Well, if all employees were allowed to sell up to 10% of their positions too, would that even matter to them? If you were an employee and had $200k total value in your options, and you could sell 10%, you're getting $20k. Not really enough to de-risk your life although still might be welcome (and employees would appreciate having the choice).

(3) Sellers need buyers:

In order for there to be a seller of shares, there needs to be a buyer. The founder is effectively choosing his buyer and future business partner by taking investment and choosing to give that buyer more control over the corp by selling him even more shares (his personal shares). The buyer wants to make the founder happy and de-risk their downside so they can be more aggressive or big-picture or whatever, plus is happy to own more of the company assuming it's a hot round.

But what does the buyer want to achieve by purchasing the employees shares? Just to own a little bit more % of the corp? For amounts that might not even matter for the employees and may de-incentivize them?

It's all very complicated and perhaps there are nuances that make every situation unique.

neilv
3 replies
2h28m

If a founder cashes out 10% of their position for $500k @ $25M Series A valuation, that de-risks a lot of their personal life. But when the startup ends up selling for $250M, that $500k of 'early' selling would have been worth $5M (less any dilution between rounds) - hard not to regret the choice in that case even if hedging is going to be the correct choice 99% of the time.

IMHO, it's very easy not to regret, with those particular numbers.

I'd take $500K now plus possibly $45M later -- over $0 now and possibly $50M later.

I'd take that deal even if "possibly" were "guaranteed".

(Who might regret that is a founder who was otherwise already wealthy.)

simonebrunozzi
0 replies
1h3m

You are not taking into account QSBS. [0]

When you sell your stocks before 5 years of holding period has passed, you pay significantly higher taxes. So you don't get 500k net, you get 500k gross, or probably 300k net. Which makes the de-risking less compelling.

[0]: https://www.investopedia.com/terms/q/qsbs-qualified-small-bu...

remus
0 replies
41m

Not to mention that in reality there is no guarantee you'd end up selling for $250m. $500k now would look pretty damm good if the whole thing tanks and the other 90% of your shares become worthless.

brightball
0 replies
57m

Exactly. About 15 years ago I was offering equity in a good little startup. I didn't take it because I just wanted to go somewhere with a higher salary.

When they finally sold about a decade later I ran the numbers and determined it would have been about $40,000 based on the actual sale price.

There's no guarantee of a $50M exit for anybody.

rybosworld
2 replies
1h11m

None of this is very good justification for founders being the only employee that have the option to sell part of their stake.

If you were an employee and had $200k total value in your options, and you could sell 10%, you're getting $20k.

It obviously depends on your financial situation, but having the option vs not will certainly matter to some employees. Not to mention that the stake could well be worth $0 in the future.

earnesti
1 replies
1h3m

I don't think it needs any justification, really. The investor decides, whom to sell to and how much. If the founder doesn't want to organize a sale for employees, then he doesn't do that. He would probably have to pitch it and include it in to an already complicated funding round.

I totally understand why a typical founder doesn't want to do that. If for you as an employee it is a deal breaker, then you can complain about it, change company or whatever. It is not like the founder owes anything to the employees (unless he has promised that). Everyone in the equation are adults and have to decide themselves, if the position they are in makes sense for them with the terms they have.

rybosworld
0 replies
38m

I don't think it needs any justification, really

From a founder's perspective sure, you can do what's best for you.

That's not what this article is about. This article is highlighting that there's a tendency in SV for founders to cash out early, and secretly. And along with that, there's a tendency to paint a narrative that the founders haven't sold a share. It's hard to see that as anything other than deceptive.

It's one thing to join a startup that you know may not succeed in the long run. It's another to join a startup that has a founder whose been secretly cashing out along the way.

Justification does seem necessary in that second scenario, at least from a morality perspective.

thunkshift1
1 replies
1h47m

Also bake in the fact in your calculations that 9/10 startups will not see the kind of success you are talking about. And the authors point still stands.. the founder made some money at liquidity event at round A vs … making even more money later if he doesnt sell?

galaxyLogic
0 replies
1h24m

Bird in hand is better than 3 in the bush

fragmede
1 replies
38m

to put it bluntly asf, you're being poor (and I'm being insensitive). what's $500k going to do for you if you come from a rich family? you already have your rent paid for until you die, and vacations paid for. all you have to do to do is put up with your annoying family, which isn't the worst if you've been through therapy. your mom or dad's abusive? if you've been through enough family therapy, that's not a problem.

if you ask you mom or dad, whichever believes in you, they have enough money to fund your dreams (if you care enough to ask) of joining or starting a startup to become an (x) CEO/salesman/builder/marketer/whatever for whatever you want to build, and that includes signing onto some startup that won't pay you a living wage until it fail-exists for $5 million and everyone goes to burning man/Berlin/ibiza on the founders dime (including rent for everyone N months).

Matticus_Rex
0 replies
4m

Yes, there are people who won't get the same benefit from hedging like this.

But they're a small minority. Not that many people meet your description here.

cashsterling
1 replies
1h30m

Great points... as to #3, investors are often happy to be buyers. They are buying shares anyways that would otherwise have to be created. Allowing founders and employees to sell shares lowers dilution vs. creation of new shares... usually this is not a large effect, but still not bad for current & future investors.

yuliyp
0 replies
59m

I mean it effectively means that the amount of cash going into the business is less than it otherwise would have been. The company wanted $5M of cash. With the owner selling $500k worth of shares it means they had to find $5.5M to be invested.

The only reason it happens is that the founder is negotiating both on behalf of the business and a bit for themselves.

PheonixPharts
1 replies
1h24m

hard not to regret the choice

If you can't handle "regret" in these cases, then you probably shouldn't be in a position where you're deriving the vast majority of your income/weatlh from investments (which is fundamentally what a CEO does).

It's astounding how many ICs can't wrap their heads around the concept that holding onto your RSUs make absolutely no financial sense. With rare exceptions, this doesn't make sense for anyone. And yet, fear for "regret" keeps people holding.

But it's not shocking that even in tech many ICs are not good at reasoning financially. But if you want to be a co-founder, and hold a lot of your wealth in investments it's essentially that you learn to reason, plan and accept outcomes accordingly. Otherwise you're more-or-less a professional gambler.

skybrian
0 replies
4m

I believe in diversification and index funds for most people, but this seems overdone.

The issue here is that sometimes if you procrastinate about diversifying, it pays off very well. As a Google employee (who joined after IPO), it was by far my best investment and funded my retirement.

I guess that's accidental gambling. I did have other investments.

ipsento606
0 replies
2h27m

hard not to regret the choice in that case even if hedging is going to be the correct choice 99% of the time

in the scenario you outline the founder sells the remaining 90% of their position for $45MM?

I don't think many people would experience any real regret at "only" getting $45.5MM instead of $50MM, due to declining marginal utility of money

WalterBright
0 replies
1h26m

For me, it's always regret:

1. If I buy stock, and the stock goes down, I regret buying

2. If I buy a stock, and the stock goes up, I regret not buying more

There's no winning :-/

MisterBastahrd
0 replies
50m

$500K right now would pay off my home and do a good job of setting me up for retirement in the future.

$5M when you already have $45M doesn't move the needle much.

carliton
14 replies
12h54m

Many companies don’t get to Series A and very few companies get to Series B. Even if they do get to Series A or B, they won’t be able to raise the amounts you see in the news and have heavy dilution.

Very few founders have double digits percent ownership by Series B and Series C.

Liquidity of $400k or more is a lot and isn’t available for many founders.

All of this after 7 to 10 years of working 80+ hours week, no social life, loosing family, sacrificing health, taking less than $100k/year salary, constant worry of failure, dealing with ups and downs of employees, being a support system of everyone in the company while not being one for their own families, and no guarantee of success. All of this for seeing their dream come true because failure would be worse.

I think the OP should work on his company for more than 4 months and have more than 10 employees for at least a year to truly understand what it is to be a founder.

Also 20% option pool and exercising options up to 10 years are not uncommon.

Source: 2nd time founder.

palata
5 replies
5h58m

I think the OP should work on his company for more than 4 months and have more than 10 employees for at least a year to truly understand what it is to be a founder.

Have you been an employee in a startup? Because in my experience it has a lot of the downs of the founder, but none of the ups.

gafferongames
3 replies
5h51m

So start your own company then.

palata
2 replies
5h13m

Maybe I should, so that I could abuse from the employees and then explain how I deserve to get rich if MY startup succeeds but my employees don't (because it is MY startup, you see? I don't need them).

che_shirecat
1 replies
4h53m

Good luck with this! Let us know how it goes.

Founders have leverage, because they started the company. If you don't like it, start your own and don't join someone else's.

palata
0 replies
2h54m

Where I come from, that's an ultra-liberal point of view. "Instead of saying that Elon Musk does not deserve 68b as a salary (because no human does), then maybe you should become ultra-rich yourself".

Sure. You just completely missed my point.

nkohari
0 replies
3h43m

Have you been an employee in a startup? Because in my experience it has a lot of the downs of the founder, but none of the ups.

Have you been a founder? If not, I'm not sure you fully realize what goes into the job. Everyone wants to be a founder, but nobody wants to _be_ a founder.

joeblubaugh
2 replies
11h48m

After the Series B for my last company the three founders owned something like 45% of the outstanding shares, and when they sold took out something like 40% of the price. What were the rounds like that led to less than 10% after 3ish rounds?

sokoloff
1 replies
10h43m

I read GP as very few founders individually have double-digit ownership, not collectively.

sunk1st
0 replies
6h27m

45 divided by three is 15 is double digit.

ivalm
1 replies
12h7m

All of this after 7 to 10 years of working 80+ hours week, no social life, loosing family, sacrificing health, taking less than $100k/year salary

If you are taking less than $100k/year salary for 7 to 10 years while also absolutely no-lifing then that’s on you.

It’s true that early on you prob take ramen salary, but that’s for one or two years. You can prob scale to 200k by year 3 if your thing is viable. No-lifing when your startup is in year 5 is just a personal choice. If by year 5 you aren’t on a path of unicorn then prob it’s time to evaluate if it’s worth so much sacrifice or if you should run it as a lifestyle business (or just go do something else).

ZhadruOmjar
0 replies
11h53m

If the product isn't making enough money to pay people by year 5 you're not a startup founder you're just unemployed with a side project.

gitfan86
1 replies
7h5m

I don't the the author is saying that founders don't deserve 400k after 7 years of hard work.

He is saying that it is sketchy that this is hidden from employees.

elzbardico
0 replies
5h37m

No. the author is not saying that.

gen220
0 replies
1h9m

I often think about how if more people understood the median cap table life cycle from Seed to Acquisition/Shut-down/IPO, there'd be half as many VC-funded companies and twice as many bootstrapped companies every year. Thank you for sharing your experience towards that goal.

Unless you're doing some niche b2b thing where you have no personal connections (in which case, why are you doing it at all?), the differential financial returns of going with VC are often negative, if not neutral. The main diff is you can "fail up" into the investor class if you prove your worth but the business goes sideways. But even that is a dissatisfying career for most founder-type people.

To whoever needs to read this: start your own company, avoid raising money.

doodda
13 replies
7h39m

This post has managed to piss off everyone: employees who didn't realize founders were getting liquidity events while they're still sitting on their more-often-than-not valueless equity, and founders who feel they've earned it and don't like the implication they haven't.

boringg
4 replies
3h51m

Good point. Its interesting to see the comment thread here.

The part to me that I see as surprising is dismissal of the stress of taking VC money and being a founder. It is a job thats incredibly demanding. Which is eye opening to me that that's how people see it.

If it was so easy why aren't there more of them and more companies?

Early employee is tough - unless the company is on a significant trajectory the options should be valued at zero. That said being an early employee has other benefits such as being part of an interesting team and work problem. Definitely not a cushy job though (and nor is a founder) - both are significantly hard and for a certain personality type.

Everyone else go join a FANGG and get paid if thats what you are looking for comfy life benefits.

pydry
2 replies
2h42m

The part to me that I see as surprising is dismissal of the stress of taking VC money and being a founder. It is a job thats incredibly demanding.

Sounds like you're dismissing the idea that being an early employee is hard.

boringg
1 replies
2h35m

>"Early employee is tough".

^^ Literally in my comment.

pydry
0 replies
2h21m

Yes and the people dismissing how hard it was to be a founder were comparing it to being an early employee.

So, you're saying that it's hard but "not that hard actually".

peter422
0 replies
3h12m

The main advantage of being an early employee is that you can leave.

Founders generally need to go down with the ship, early employees do not. If the growth trajectory starts to falter after 1.5-3 years, just get out of there and try another company. Let the founders clean it up (and you have equity in case they do).

blitzar
2 replies
6h42m

You managed to make both parties sound like absolute tools.

arolihas
0 replies
4h59m

How does the employee sound like a tool here?

JonChesterfield
0 replies
5h51m

Not the founders clearing life altering capital returns from the pre-revenue company seeking product market fit. They're winning.

rk06
0 replies
5h21m

Yeah, this one lives up to headline!

reportgunner
0 replies
5h44m

Oh yes it's time to shoot the messenger.

mattgreenrocks
0 replies
7h18m

The mark of a good post!

matsemann
0 replies
6h52m

It also reminded me about another post I read here, probably a few years ago, that outlined how stuff works. And my takeaway from that one, was yet another way that early employees get shafted, as they get diluted a lot, and other employees being brought on later end up with a better exit in the end. But I can't remember the details or find it.

largbae
0 replies
4h51m

If I hadn't found your comment I was going to say this is the best HN I've seen in months.

NullHypothesist
13 replies
14h31m

Having only worked for larger companies (RSU stage), I'm curious what the typical breakdown of founder to early employee to investor to later employee equity looks like. I'm sure it differs pretty wildly, but I'd love to know what a 'typical' case for mid-to-late-stage start up looks like.

parentheses
11 replies
14h9m

I can share some details.

Employee 1: ~1%

Employee 10: ~0.1%

Employee 1000: 0.01%

I'm extrapolating from past experiences in SaaS companies where I was employee number X and X has varied fairly widely.

atomicnumber3
9 replies
13h30m

This always seems like a huge scam to me. Employee 1 gets 1%? It seems unfair from multiple perspectives.

One is just a straight up naive sense of fairness. If I'm going to be in the trenches with you, I had better be able to see my ownership % in a pie chart with my glasses off. If we're out here both making chairs and when we sell a chair for $100, you get $85 (assuming someone took one of the standard-ish seed rounds that are usually 10-20%?) and I get $1? No thanks.

The other sense is aware that the founder is taking various risks and blah blah blah. Ok whatever. Let's pretend somehow 1% is a fair number and just look at it from a payoff perspective. 1% of stripe? Yeah I'll take that. 1% of the other 1000 startups who had mediocre exits or just muddle along to finally do some kind of tender? I'm barely breaking even. 1% of the other 10000 startups that just folded? At least I can mop the sweat off my brow with the paper I signed.

It seems like the only reasonable way to look at this is you either join a company for a competitive wage and get WLB, or you join a rocket ship in the hopes of becoming genuinely wealthy while pouring your blood, sweat and tears into it. So taking 1% and a shitty salary and having terrible WLB sounds like a huge suckers game.

xandrius
3 replies
11h12m

Are you talking about 1% and no pay or 1% and a pay?

If I'm getting no pay, I'm definitely a co-founder, but I'm getting a pretty good salary from day 0, I don't think that's too bad.

Say you get offered $200k/y +1%, if things go well, in 4 years you got $800k in cash and your 1%. If things go south, you still got $800k, a cool title, worked on a hopefully interesting product with a nice team. Doesn't sound awful to me. No?

segfaltnh
2 replies
8h2m

Glad to see someone else say this. I feel like I'm crazy reading these replies about being ripped off. I've been working startups my whole career, earning salaries, working with good people and having fun at times. Sometimes the equity even pays out, but that's not my only financial "egg".

newshackr
1 replies
5h13m

Startup founders often take salaries too

xandrius
0 replies
4h40m

Only after they managed to raise any money, which is not as common as many people assume. And whatever you pay yourself as a founder initially eats into your runway, so that's always a tradeoff.

kolinko
1 replies
12h28m

If you don’t believe a startup can be the next Stripe, then you definitely shouldn’t take 1% and work as one of the first employees.

Also, the risk profile and expectations are vastly different between founders and first employees. E.g. founders are expected to not quit unless the company collapses completely, first employees can quit whenever they wish. Also, if the runway is short, founders work for free and can even go into debt, whereas employees have a stable salary.

temp90210
0 replies
6h32m

Outside US but I never regret getting equity/options and usually it went hand in hand with the higher paying jobs (paltry compared to US standards!) rather than being a salary/equity tradeoff. Atlassian is a great example though I have not worked for them.

I think companies here tend to have less fuck you over terms in employment share schemes but OTOH are less likely to get rich but one company made several employees rich (does 8 figures count?) here.

zamfi
0 replies
12h19m

This isn't a terrible take, but there doesn't seem to be a shortage of people for whom this doesn't feel like a scam.

I'm not particularly fond of the founder hype train, and the typical line is indeed "various risks and blah blah blah" but what's often left out is that employee #1 at a post-funding startup is a pretty different job/profile than co-founder.

Most employee #1's don't have relationships with investors, might not be as employable outside the startup world, and they don't sit on the board, don't have the same formal responsibilities, and rarely are able to raise money to found their own startup -- in fact, this is the often the key reason they're even interested in being employee #1.

It's a market, and as a market I'm not sure it's that skewed.

Want 25%+ of the company? Start it. There's no cabal preventing you from doing that. Have better options than 1% of a likely-dead startup, that pay more and have better WLB? Take them.

After all, few industries give any employees equity. First employee at an ice cream parlor? 0%. First employee of a hedge fund? 0%. First employee of a medical practice? 0%.

Equity grants can be motivating and aligning, and frankly more industries should probably consider them. But not that many people are in a position to found a startup that can raise money (larger equity grants are much more common for pre-external-funding employees) and this differential reflects that.

Btw, "1% of the other 10000 startups that folded" is worth about the same as a founder's 40%: $0. The issue is the middle ground, but there the equity grant is often not worth the paper it's written on: typically the acquirers dictate who gets the money. 1% or 5%, unless the acquirer is trying to retain you, chances are you'll see nothing even if the nominal payout is large.

Anyway, the upshot is what people have been saying for decades: don't do a startup for the money. Do it because you want to be part of that kind of thing, and treat any exit money as a bonus.

jahewson
0 replies
12h10m

Unicorn or bust is the name of the game. Once you understand that it’s not so bad.

It’s also possible to level-up pretty well from an acquisition, where maybe the equity was not life changing but you’re now in a bigco at a higher level than you’d otherwise be. The trap there is that many startup folks are not cut out for bigco life.

But yeah if you were dreaming of sailing off into the sunset you need to be a founder (or remarkably lucky). That’s one reason why there’s so many startups.

cbsmith
0 replies
12h44m

It's not even remotely fair, but it does follow the golden rule: he who has the gold makes the rules. The founders were the ones who investors were willing to trust their money with. Employee #1 was not.

o11c
0 replies
13h44m

If my math is correct, this fails catastrophically for companies with more than 15 tredecillion employees.

molsongolden
12 replies
14h34m

I’d also push for allowing early exercise along with secondary sales restricted only by a short right-of-first-refusal period.

JumpCrisscross
11 replies
14h29m

allowing early exercise along with secondary sales restricted only by a short right-of-first-refusal period

Do you mean cashless exercise?

JumpCrisscross
7 replies
14h13m

Does anyone restrict 83b elections? Is that even allowed?

stanleydrew
2 replies
13h59m

What would this even look like? An 83b election is something I file with the IRS. Are you suggesting a company might have me sign a contract committing me to not file an 83b election?

How would they ever find out if I did file, and why would they care?

tdiggity
0 replies
13h48m

It's been a possibility in my options contracts. However, the company must agree to it, cash your exercise check, and send the necessary paperwork to the IRS. If they choose not to cooperate, you're out of luck.

jahewson
0 replies
12h22m

My understanding is that 83b applies to stock, not options, so you have to first exercise the options and hold unvested stock. That requires early exercise.

dilyevsky
2 replies
14h10m

Ive seen it restricted so yes

jjav
1 replies
12h22m

I think there's a confusion between the related events. Filing the 83(b) form with the IRS is between you and the IRS. Company isn't involved so not something they can restrict.

However, filing that 83(b) only makes any sense if you are allowed to early exercise and that is indeed entirely up to the company. So if they don't let you early exercise you also won't be filing the 83(b).

Pro tip: Never join a startup that does not let you early exercise!!

dilyevsky
0 replies
1h37m

Yes i assumed parent was referring to early exercise but maybe i misread. Imo early exercise doesn’t make a ton of sense when the company no longer qualifies for qsbs especially if long exercise window is offered so probably why it’s not offered - to avoid a ton of drama later on

molsongolden
0 replies
13h58m

Not a restriction of the 83b election but a restriction of when you can exercise. Without early exercise you are stuck exercising as you vest so there’s more likely to be a taxable spread between your option strike price and the value of the stock. With early exercise you are exercising and making the 83b election when there’s no taxable spread.

stanleydrew
0 replies
14h5m

No, although it could also be cashless.

Early exercise is purchasing shares before your options vest, making you a shareholder sooner and solving a bunch of tax issues. The company retains the right (basically the obligation) to repurchase any unvested shares should you leave the company before fully vesting.

molsongolden
0 replies
14h11m

Sorry, separate concepts executed at separate times.

Early exercise (yep, 83b in the US) when options are issued then allowing employees to sell shares down the road, outside of fundraising events (Forge, EquityZen, sales to angel SPVs, etc.).

iEchoic
11 replies
14h24m

Making less money isn't really the risky part about founding a startup. The risky part is missing out on years of other life experiences, stressing (or losing) your closest personal relationships, failing and feeling personally responsible for disappointing everyone you convinced to believe in you, and developing an anxiety disorder (or worse) from chronic long-term stress.

Author's suggestion that they could have taken a "similar level of risk" as an early employee by taking secondaries as a founder is way off, IME.

jmward01
7 replies
14h13m

Having been employee #10 a couple times now, there is a lot of that even when you aren't a founder. It would be nice if the 'de-risk your life' stuff this article describes for founders was also available for early employees.

toomuchtodo
6 replies
14h1m

Work a high salary job and buy lottery tickets or 0DTE options instead. Half joking. Look at the success rate of outlier comp through liquidity as an early startup employee. If professional stock pickers can’t pick better than index funds, what makes you think you can do better picking startups, spending non renewable time, working for years vesting common shares that you might get liquidity for eventually, assuming they have any positive value.

If you want to get wealthy, there are more efficient, less effort ways. If you want to suffer with low chances of success based on all available data, well, help yourself to the firehose of startup jobs.

bjt
3 replies
13h53m

You're not just "picking a startup". That early, you're also a big factor in whether it succeeds. Betting on yourself is different than buying a lottery ticket. (Maybe just as irrational for a lot of people, but still.)

toomuchtodo
0 replies
13h49m

You (not “you”, but the persona for this discussion) are not special and will likely fail, based on startup failure rates. Certainly, you will put effort forth, but that is only tangential to odds of success. If you enjoy the experience and don’t need monetary resources, sure, knock yourself out. Just recognize the opportunity cost, that the odds are stacked against you, and if you succeed, you were as lucky as you were skilled.

I’ll take the lottery ticket over me any day, not because I suck, but because I am human. Even exceptional humans fail. I don’t drink the exceptionalism koolaid.

skeeter2020
0 replies
13h44m

People, especially sw devs, love this narative but it's just not true. It's not all luck like the lottery but the combination of things outside your control might as well make it so for early employees at a startup. But hey, you did get that vp of whatever title...

freddie_mercury
0 replies
13h40m

Advanced sports stats have the notion of "contribution above replacement value", the idea being it isn't just what you do, it's what you do relative to whoever they could (relatively easily) replace you with.

The startup failure/success rate already have some level of "smart, motivated staff" baked in. So you're really making a bet on how much better you are than the average early stage startup employee.

patmorgan23
0 replies
4h56m

When you work for a start up you can have a material impact on the company's success (or failure).

ivalm
0 replies
11h50m

When you work for a startup you have a ton of insider information not available to outsiders, even investors. If you think your startup won’t be successful then obviously just find a different job.

AnarchismIsCool
1 replies
14h3m

Having been a key early employee at a failed startup, horseshit.

The employees bear the burden too, if they're working their asses off at an early stage startup they believe in the cause just as much. Viewing founders as somehow magically special is a symptom of the broader misguided hero worship the US has right now.

bps4484
0 replies
2h0m

I'm sorry this isn't true. Your name wasn't on the line when you took the investment, and the OP pointed out with his "5 startups in 10 years" line, it's very easy for early employees to walk away. That isn't as available to founders. There is much more burden (reputational, financial, emotional) on the founders.

I've been a founder, and I've been a key early employee. It is very different.

beambot
0 replies
14h16m

Perfectly illustrated by this statement:

I have been an early or first engineer at five different companies and have had three liquidity events in a 9-year career.

A "big" success is a 10+ year journey. For an early employee, it is perfectly acceptable to give a few weeks' notice and move on to the next lotto ticket. This doesn't work for a key founder-exec -- they're likely going to commit to a decade working on one big problem, and investors want to incentivize them to shoot for the moon & stick with it for the long haul.

It's definitively not the same for an early employee.

rytill
10 replies
14h27m

Only a small percentage of tech companies raise a series A or beyond.

To me, this just seems like a capital-efficient alternative to the founder increasing their salary that could be negotiated. I had no such perception that this was some “secret” thing, I assumed it happened since you can do whatever you want if the investors and founders agree that it makes sense.

adastra22
8 replies
13h6m

This whole thread is leaving me very confused. Series A is the first priced round. You're saying only a small percentage of tech companies raise a priced round?

mtremsal
5 replies
12h46m

A significant portion of startups that raise a Seed round (or equivalent) never get to a Series A. Maybe 30 to 50% fail at this stage.

adastra22
4 replies
12h42m

Are we talking about just YC-style internet/app startups? Two of my startups have been deep tech where you can't do shit without a Series A, and the third was crypto in the start of that boom where VCs were begging to lead your Series A. So maybe I just work in a vastly different field.

throwaway2037
1 replies
9h27m

What is "deep tech"? Like, not a CRUD web app? Hardware? AI/ML?

adastra22
0 replies
3h2m

Fusion, fabs, manufacturing, defense, etc.

quartesixte
1 replies
12h35m

Yeah deep-tech (which I am also in) plays on a different scale when it comes to funding rounds, simply because of how expensive hardware is and how big the headcount gets to just make MVPs.

My friends in software startups balk at the sheer burn rate and funding rounds at mine. $100mm for a Series A is unheard of in software.

Thank you Thiel for setting the bar so high (the famous, "you need $1billion in total capital to successfully pull off hardware startups" quote).

rytill
0 replies
12h12m

As you noted below, it depends on the industry.

But for software, and my impression is that it is even more like this in most other industries, a huge amount of tech ventures never receive any funding. Many of these are never even properly incorporated and may not be included in datasets. Then, for the ones that do raise seed money, usually with SAFEs, 50-60% of them would fail before raising a significant priced round (series A).

The overall point being, there’s a lot of risk between starting a company and raising a sizeable priced round for most people.

DandyDev
0 replies
5h40m

The company I work for raised a $1M pre-seed round, $10M seed and $25M series A

I imagine other companies went through a similar scenario but failed before series A

cbsmith
0 replies
12h50m

It is a bit funny how founders get the special access at a lot of companies. Not all places work like that, but it seems disingenuous.

throrway12
9 replies
12h12m

I worked at a preseed company recently. Here's my experience:

- Work 9 to 7 everyday. 6 days a week.

- People are working 9 am - 5 am in crunch time. Then joining again at 10 am.

- Monetary Comp is exactly market average.

- Equity Comp is even more paltry since founders raised at a huge valuation.

- Founders make unrealistic promises. Eg: It took a competitor with 7 people, 3 months to make a product. The founder told us Saturday that he wanted it built by Monday (with 3 total devs).

- Founders message you 24 x 7. If you don't reply, there's a "serious discussion" to be had next time.

- Non Accomodating of anything because "It's a startup".

I left the place after 10 weeks. I saw 3 people leaving the 6 person company in these 10 weeks. The ones who stayed were under heavy financial stress or had drank the kool aid.

grvdrm
2 replies
5h34m

Honest question: do people with young kids do these jobs well, or at all?

I'm sure the answer is sometimes, yes. But, as a 41-yr-old father of two kids (6, 2) and a wife in PE, the pace and stress strike me as contradictory to being present in a marriage, being present with my kids, managing my health, etc.

I'd love to hear how the people with families manage (or fail) this pace?

Spoom
1 replies
3h17m

There are many reasons that startups tend to have young employees.

As someone in a similar place in my life, I'd never take a job like that either.

grvdrm
0 replies
1h6m

Yeah - financial risks aside. It just seems difficult to do this without major disruptions to family life as I am a part of it. Of course, you can hire as many people as you need (if you have the means) to resolve the logistical problem. But my absense isn’t replaceable like that.

torginus
1 replies
4h59m

Sorry if founders already raised a huge valuation, why didn't they hire more devs?

I'm sure what can be done with 996 style slave labor with 3 devs can be done with 6 devs working 9 to 5. It's not like they couldn't afford the salaries (and you mentioned they weren't paying that much anyways).

throrway12
0 replies
1h33m

because they are cheap ass people. Pivoted 3 times since 2021 to the latest hype, currently building another generic AI app. They still have 5-6 years of runway left with current burn-rate.

If they go all out in 12 months, they would actually be considered a winner/failure. Purgatory is comfortable.

throwaway2037
1 replies
9h29m

This is a great post. No need for the throwaway account!

   > Founders message you 24 x 7. If you don't reply, there's a "serious discussion" to be had next time.
That one is my favourite.

blitzar
0 replies
6h38m

Founders message you 24 x 7. If you don't reply, there's a "serious discussion" to be had next time.

You drop them a bunch of messages to get signoff for the thing that absolutely had to go live on Thrusday and dont hear from them till Sunday because they are tripping on Ayahuasca in the desert.

There's a "serious discussion" to be had next time about your work ethic.

shoo
1 replies
7h56m

it's important to figure out where to set your own boundaries. people out to exploit you will seek to see how far they can push. congratulations for leaving.

one thing that catches out some junior folks is that they may believe this kind of behaviour from bosses is normal and unavoidable as they have only worked for exploitative bosses at places with toxic cultures. you can do better, you're worth it. get out. find a more mature company with professional managers, where it's normal to leave the office on time and turn off all your work comms and leave all work-related messages unanswered until you're back in the office and getting paid to think about work again.

grvdrm
0 replies
5h27m

I think this is the right point, but it's tough.

People don't like to say "no" or "can't do it in that timeline" and other permutations of these statements. If you can't even challenge or disagree with anything, then you're doing something wrong, or you're in the wrong environment, or both.

20 years into my career and still practicing this.

One hack: I can't respond when I'm asleep! So, I head to bed pretty early (9:30-10 EST).

AlwaysBCoding
7 replies
43m

The situation I recently went through reads like a horror story:

was the founding engineer at a startup, essentially do co-founder work for 18 months getting the company off the ground.

company is a breakout success, raises a large growth round.

founders each take a couple of million dollars off the table in secondaries, no option for employee liquidity.

founders start thinking about early employees as "problems" because they have too much equity and could easily hire multiple FAANG engineers for the equity comp they're paying the early team. push all early employees out of the company.

horrible ego-based decision making such as this kills the company culture and runs the company into the ground. company is a mess, stock is now worth significantly less.

---

early employees have to pay money to exercise their stock options which are worth millions on paper. early employees have to front money to pay taxes on the capital gains on the stock.

founders have pocketed millions, off the backs of other people's work, while the employees who built the company all owe huge tax bills and have no path whatsoever to ever seeing liquidity with the floundering company.

all of this is because the employees did their jobs too well, the company grew too fast, and the founders egos got completely out of control.

To be blunt, situations like this should be illegal. joint-stock companies aren't slush funds for three people to personally enrich themselves off the labor and capital investment of others, they're supposed to be entities where all shareholders participate in the upside of the value creation together. Until there's some sort of legal framework for pursuing class-action lawsuits against founders who defraud their employees like this I don't think this situation will ever get better. There are already laws against self-dealing transactions by company executives, I don't see what is different in cases of extreme founder liquidity off the backs of other people's work.

tomp
1 replies
10m

employees aren't shareholders

they get options, not equity

personally, I never understood why they don't get actualy equity (in particular, given that the options are "fairly priced" i.e. the call price is the latest equity round price, making them worth literally $0!)

and that equity should have the same terms as investors get (no "liquidation preference" lol) because - guess what - you're literally exchanging your labour (== money) for them!

georgeecollins
0 replies
4m

That's elective. It's fine and not uncommon to just give employees stock (actual shares, not options) in a company as compensation. Famously Wizards of the Coast gave shares to employees and vendors to create alignment.

Someone is going to point out that giving actual shares is a taxable event. And that is sometimes the rational for options. But there are work arounds: you can put shares in a 401k for example. 401ks were originally created to be employee incentives, but morphed into being used for retirement, but you can still do it either way.

gedy
1 replies
36m

Not to put you on spot, but this behavior is unprofessional, and you should name names IMHO.

AlwaysBCoding
0 replies
16m

The company is Phantom, and the VCs are Paradigm.

nine_k
0 replies
10m

If we talk about stock options, the company is still private, and no stock was issued.

Paying taxes on options for stock that may never materialize, or never be worth much, sucks.

I won't (and didn't) buy options before an IPO or an acquisition is scheduled, even if they had been granted, unless I have money to gamble on it. I won't consider options as a part of my pay, unless I'm a founder %) They are but a lottery ticket, even when your personal effort may significantly affect the odds of it winning.

georgeecollins
0 replies
9m

I wonder if this problem could be avoided if the early technical founder insisted on having the same class of stock as the founders. IANAL but in my (limited) experience these games are easier to play when the founders (or often the C-suite people) have a different class of stock then key employees. Or that's how I have seen the game played where one employee can have a liquidity event and another doesn't, or the dilution is unequal.

I am no expert! Can someone explain to me if having the same class of stock as the founders is a meaningful protection?

carbocation
0 replies
34m

I'm focusing on a tiny technical detail here but from the description, it sounds like the ISOs weren't set up with an 83(b) election which is another bummer.

jensneuse
6 replies
11h27m

As a founder with multiple years of experience I can say that this post and a lot of other comments are coming from people who don't understand the life of a founder. It's not so much about risk. My peers earn 5-10x my salary. I'm paying my employees more than myself. I have to provide for 3 kids and we have a lot of debt on the house. I'm working day and night, 24/7. I don't like the phrase "taking money off the table". If I can sell some equity, this is none of your business. I started this company with my co-founders. Start your own company and try reaching Series A. It's almost impossible. Most people are not capable of getting there.

erremerre
2 replies
10h54m

So you either you are neglecting your kids, or you are calling work at building legos with your kids?

erremerre
0 replies
6h18m

My point is that he is not working 24/7 as he says. He just have a business to run, that does not mean they work all the time, as they try the rest to convince us.

Neither working all the time should be rewarded with a status in which they can't be critised, but even if such reward shall exist, he aint working that much.

tock
0 replies
10h34m

Aren't most early employees also working very long hours for 1/4th the pay and maybe 1% equity? A lot of them also have kids and debt. The life of a "founder" is not really that different from how most people in the world make ends meet. Heck most small businesses run on loans not VC money and are a ton more stressful.

throwaway2037
0 replies
9h35m

It's sad this post was so downvoted. You speak the truth from your view. We need more of that here.

    > My peers earn 5-10x my salary.
I need to troll a little bit here. So... their package sounds much better. Way lower risk. Are you shooting for the moon (want to be 1B+?)... or what?

colordrops
0 replies
11h15m

To be frank that's your call to work 24/7 with 3 kids and not the business of your employees. They are free to negotiate how they please and we are free to take issue with certain founder behaviors. It's all business and it's a free world.

surfingdino
5 replies
11h57m

This and my own experience with employee stock options led me to reject any work for startups that offer stock options. It is a way to make you work hard and allow to be treated like dirt for less money. The lowest point was having to walk across town to the office to eat energy bars from the office kitchenette, because I could not afford a bus fare or food as my pay was delayed by a week over Christmas. Meanwhile, the founder was holidaying in Dubai, driving a BMW X7 to work, and showing off a house with a small park and a pond bought in leafy Berkshire. Employee #1 treated the rest of us like dirt. I got laid off in a round of cuts just before my options kicked in and thought it was unjust, but a year later the company was sold to a competitor and the investors got a nice return, the founder got another pot of gold, and the employees with stock options got nothing, because it was a private sale and not an IPO. Employee # 1 was in a bit of a shock allegedly.

segfaltnh
4 replies
8h15m

I don't believe a private sale entitles one to ignore a stock options legal rights. What are the relevant details here I'm missing?

throwawaythekey
0 replies
4h45m

1) The common stock that employees get via options is the last in line for the pot of gold.

2) There's plenty of bullshit that can be used to cheat an employee out of their options. One example here [1].

[1] https://techcrunch.com/2011/06/26/skypes-worthless-employee-...

surfingdino
0 replies
5h23m

It was 10+ years ago. I don't have the details, but the riches they were underpaid for never came true. The founder made out like a bandit.

hylaride
0 replies
48m

For IPO sales, all options can eventually be converted into common shares then sold (often after various lockup periods giving other investors chances to cash out first).

For private sales, which can be structured in a variety of ways, there's a bucket order that can vary depending on the share structure (remember options aren't shares until converted). Most VCs have terms that they get paid out first to recoup their investment (and often then some) before common or option holders get paid out.

So for a simple example (I'm making these numbers and percentages up): Say if VCs invested $10m for 30% of a startup with a guarantee of first rights to get that back and 50%, then a founder class of shares owns a percentage, say 50%, and then there's a class of common shares/options that are in theory 20% of the company. So in thoery, the investors own 30%, employees on 20%, and founder(s) 50%.

Let's say then that the company then sells for $20m. The investors get their $10m back, plus $5m for their 50% return guarantee. The founder class of shares has rights to 50% of the company, but all that's remaining is the $5m left over which is 25%; they get it all. Everybody else gets shit unless the buyers want to retain any employees and give them anything extra (this can happen).

Things like this happen a lot. I knew people that worked at 500px (the photo site) and eventually the investors forced a sale after the business stagnated that even the founders got nothing in the end.

hmottestad
0 replies
4h45m

Maybe if the founder has a majority they can sell their shares to someone and the company keeps on running. If the new owners don't intend to ever do an IPO I guess the existing employees end up with options to buy stock in a company that they will never be able to sell. Only upside would be if new owners take out a dividend, since that would assumably be a fixed amount per stock regardless of who owns the stock, unless of course the new owners are able to circumvent that by doing an unequal dividend payout that only goes to certain owners.

ajhit406
5 replies
14h30m

Love the movement and glad there are founders out there pushing the envelope for their team.

(aside: 51 points but only 1 comment? It's a front-page worthy article, but sort of feels like there's some vote gaming happening. I've never seen 50 points w/ 1 comment.)

kortilla
1 replies
14h23m

It’s a vote bait title. (Type of thing people upvote without reading the article)

bigiain
0 replies
13h58m

I wonder if that's something the algorithm can detect?

Measure the time between when someone clicks a link to the article and when they upvote it, compare that to one of the "estimated reading time" metrics of the linked page...

(Which, of course won't work, because at least some people (ie me) open a bunch of tabs for everything that looks interesting on the homepage, then spend a few minutes at a time over the entire morning choosing a tab and reading/voting...)

wiradikusuma
0 replies
14h24m

I'm one of those people who upvoted without commenting. I think it's just a way of saying, "I found this article interesting / I agree with the content, but I don't have anything of value to add".

But hey I just commented :)

neilv
0 replies
14h2m

The usual problem of late on HN is people commenting without upvoting, even if they like the article.

On this post, I started reading, then paused to hurry back and upvote on HN, to do my part to keep it from falling off the front page, before I returned to finish reading.

dang
0 replies
14h26m

That's actually a lot more common than people assume it is, and comments like "I can't believe there are X points but only Y comments" are more common than you'd think they'd be as well!

My theory is that it's a sign of a good article, because more energy is going into reading it than into posting quick comments (which are usually less valuable comments). But I don't have the data.

Edit: well... we have the data (to test this), but it would be enough of a pain to do the analysis that other things will probably take precedence forever.

varenc
4 replies
13h5m

I always thought there was another reason for VCs encouraging founders to sell shares: giving them a taste of wealth. If you're a founder that sold 2M in stock a year ago and a 200M acquisition offer comes along, you'd be less tempted now that you appreciate the difference between small millions and big millions.

If you thought you had a real chance of going much bigger, having cash already makes you more willing to take that risk. And since VCs tend to make most of their money off a couple very big wins, it's worth it to have founders that won't settle for less than billions.

JumpCrisscross
3 replies
12h26m

another reason for VCs encouraging founders to sell shares: giving them a taste of wealth

VCs are wealthy. Some of them weren't born wealthy. The best among them recognise that removing the worry about e.g. paying rent will make a better CEO.

repomies69
1 replies
12h10m

It is about aligning risk preferences. Being "all-in" is not likely a good thing for a founder. The founder prefers to take less risk which results to mediocre exit for the investor. The investor would rather have bigger exit or nothing, and giving the founder some money is helping to aling the risk preferences a bit towards the same direction.

As for employees? They are typically not calling the shots about company direction. I don't see a reason why investors would care about employees.

mezyt
0 replies
4h35m

As for employees? They are typically not calling the shots about company direction.

They can be motivated or not, knowing that the founder made big bucks and they made nothing is bound to lower motivation. Thus the title of the article, founder's liquidity is a well guarded secret.

blitzar
0 replies
9h32m

removing the worry about e.g. paying rent

Only once the startup has matured at least a little, too much money too early and your hungry founders become lazy.

tompetry
4 replies
13h20m

The single data point here is Adam Neuman, so I have a hard time taking this seriously.

I have raised 6 equity rounds as a founder of 2 companies. Never took a dime off the table, was never offered it, never asked for it. We actually did have early employees ask about it, and we encouraged them to not sell.

Why would you, especially at early stage valuations? You're either bad at math, or you know you're about to fail. And who is buying these secondary shares? I don't know a VC or angel who would "de-risk" an early founder like this; it's not aligned with their model. It also complicates QSBS status if I recall correctly.

adastra22
3 replies
13h7m

Never took a dime off the table, was never offered it, never asked for it

Well they certainly wouldn't volunteer the offer without you asking for it.

tompetry
2 replies
13h3m

The founder in this scenario was offered $400,000 of liquidity at Series A and $750,000 at Series B and encouraged to do so by their board of investors to de-risk their own life.

This is from the article. I would tend to agree with you.

adastra22
1 replies
12h52m

I straight up don't believe the article. (Edit: not saying author is lying, but that they're extrapolating from bad data.) I've worked as employee #3 at one startup, co-founded another which achieved >$3bn valuation, and am now solo-founding a third. I've networked with lots of other founders. I've never, ever heard of a secondary liquidity offer in a Series A.

I think the paragraph above that quote explains it. They're talking about founders that "mortgaged their house and lived on ramen noodles for years." It actually sounds like they got screwed out of some equity. Rather than pay themselves a reasonable salary to support their lifestyle as they build the company, they instead traded equity for a one-time payment. That's a shitty deal, and I want to know who this predatory VC is so I make sure I never take money from them.

ivalm
0 replies
11h55m

This so much. So many folks in this thread are talking about series B+ and only paying themselves under 100k/yr and that’s just a scam. Once you have institutional money you can just start paying yourself enough to live ~comfortably.

dmitrygr
4 replies
14h26m

The title of the article is mostly clickbait. Anyone who's lived in SV for a decade or so knows this well. Startups are a scam unless you are a founder. They are a meat grinder that runs on naive young new college grads who buy into the bullshit that their options are worth anything.

iwontberude
2 replies
14h15m

Even founders get shafted in later rounds where they are diluted out of their voting rights because they can't raise the capital to maintain their share. The only people not getting scammed regularly are the VC.

dmitrygr
0 replies
14h13m

Founders have control of how things go, and have many ways to make money along the way (one such way documented by this article). How often do the first 2-5 engineers get any such chances?

bigiain
0 replies
13h51m

The only people not getting scammed regularly are the VC.

Not to want to sound like I'm standing up for Vulture Capital, but while it's not "getting scammed" as such - I suspect most VCs lose money on most startups they invest in. And not all VCs land enough 100x exits to make up for all those losses. (The "successful" VCs are the ones who make all the losses end up in pension fund balance sheets, while ensuring most of the profits land in their friends and their own pockets.)

babl-yc
0 replies
13h19m

Founders cashing out early may be more of an "open secret" but it warrants more discussion. I don't find the title overly clickbait-y.

And a counterpoint to your perspective, I joined a startup a couple years out of college, had the most fun of my career, and the options were very much worth something. Working for a well-funded start-up is something I'd especially recommend early in your career when you can take more risk even if the equity doesn't always work out.

If anything, I'd discourage becoming a founder as a new grad more than SV typically discusses. I really appreciated taking time to build up my savings and get experience before taking a shot at that.

blobbers
4 replies
14h10m

I think founders generally have 20 to 50x what the first employee has, in my experience. Employees rarely have more than 1%. Founders tend to start out with about 20-40% depending on number of cofounders.

khazhoux
3 replies
13h19m

Yeah that line in the article is completely off:

Ask most venture-backed founders why they get 10x more equity than employee #1

Employee #1 typically gets 1%. Sometimes could be up to 2%, but 1% is standard. So then the founder gets 10%? No way.

I posit that very, very few early non-founding employees in SV startups have a true notion of how cheap they're working compared to the founders. Founders do founder-y stuff, the early engineers build and launch the full product, and if all goes well, the founders fly private the rest of their lives while early engineers make good progress towards a down payment.

pojzon
2 replies
10h1m

And what happens in case it does not work out well ?

temp90210
0 replies
6h36m

Employee gets fired and founder may get something or nothing but get “fired” last and turn off the lights on the way out I would guess.

khazhoux
0 replies
1h12m

If startup goes to zero, then everyone goes home with nothing. The founders typically don't lose any money of their own -- that cost is shouldered by angel and series-A investors.

Often though, the startup has a "soft landing" where it's acquihired by a larger company, and then the founders typically get executive or very senior roles (with large bonuses, etc) meanwhile the non-founders get standard employee packages.

throwaway-blaze
3 replies
13h45m

I must be an idiot, I've been a cofounder or first hire in 6 startups (2 successful) over the last 25 years and have literally never been offered secondary during a Seed or Series A or B.

xyzzy4747
0 replies
7h32m

You don’t necessarily get offered it, you demand it as a term. If it’s a “hot startup” you pick and choose your investors so if some don’t like it they can walk.

damezumari
0 replies
12h45m

It depends a lot on the startup. I have similar number of startup experiences, and only one had early stage secondary sales ( but those were even for non founders ). Mainly money comes from IPO or other exit.

askafriend
0 replies
13h40m

How has your time in startups panned out? Were those 2 successes worth the failures?

benjaminwootton
3 replies
11h47m

I think it’s entirely reasonable for a founder to take money off the table.

The founder possibly walks away from a 6-7 figure opportunity cost working for a big corporate or FAANG. In return they take zero salary.

All of the money that begins to come in is then used to pay employees.

Maybe they raise some funds and pay themselves a below market salary for years.

A few years later they are over $1 million in opportunity cost and still owning a lottery ticket.

By this time they are a bit older, have a family, want to buy a house etc.

They are also massively wedded to the project for as long as it takes, so strapped in for the long haul.

The founder should be able de-risk at the next funding round and not continuing to roll it all for the benefit of VCs.

The same is probably true of early employees, but a lot of the factors above are dialled down. They didn’t work for zero, salary wasn’t under market by such a degree and they haven’t had such a high opportunity cost.

xandrius
1 replies
11h23m

In what world 6-7 figures at FAANG is something a founder is actually "walking away" from?

First of all, it assumes everyone wants to work for those companies and assumes all founders could get such high paying jobs with a snap of the finger.

benjaminwootton
0 replies
5h2m

Not everyone can but most founders I know could be earning a very high salary in industry.

gafferongames
0 replies
5h42m

^--- This

saulrh
2 replies
12h18m

The founders I've known were already wealthy when they decided to do a startup. They aren't at risk because even if the startup falls through without making a cent they have enough money in their bank account to withdraw $200k/year for thirty years. There's no risk there.

bux93
1 replies
9h22m

Most can even file for personal bankruptcy and then lounge around in their parent's home for a bit. (Or a house in the name of their spouse-with-a-prenup.) My parents didn't have a garage for me to found a business in.

When people helpfully suggest, why don't you start your own business, they usually have a substantially bigger than average support network and liquidity to begin with. I never get those suggestions from people who've actually experienced hardship due to job loss or financial stress.

FactKnower69
0 replies
8h6m

Why, simply pawn some of Father's apartheid emeralds to Tiffany's, why didn't any of you lazy imbeciles ever think of that?

knappe
2 replies
12h43m

Look, I've worked for 5 companies, 1 of which I knew would never sell and I had inklings that one other probably wasn't going to sell and instead was a lifestyle business for the founders, and the other 3 had successful exits. I won the lottery 3 times but I quit the game because I was tired of making VCs and founders rich while taking home breadcrumbs, comparatively.

My first startup I walked with a paltry sum and the owners suddenly went from being doctors with a side hustle to private investors. That was my first warning sign and really drove home the need to invest in myself because it certainly wasn't going to be someone else doing it, despite the talk of changing the world. It was really, really obvious that the payouts were stacked in one direction and it certainly wasn't on the side of employees, early or not. I still enjoy working for small companies, but the hype and bullshit are really tiring and so very cultish. I'd really suggest treating the startup life like a scratch lottery ticket, because that is all it is. If you win, you're gonna get paid but it won't be life altering money, just like a scratch lottery ticket. Plan around it being worth zero and go in eyes wide open.

throwaway2037
1 replies
9h23m

    > Plan around it being worth zero and go in eyes wide open.
This is the best advice I have seen on HN about start-ups. Note: I have seen it repeated multiple times.

_heimdall
0 replies
3h43m

I've joined two startups now as the 2nd and 4th engineer. I went into both expecting nothing from options or shares, and knowingly accepted a lower than market salary because I liked the teams and projects.

I couldn't be happier. Neither panned out for me with regards to stocks, and I definitely didn't get rich in the process, but I very much enjoyed the jobs and when I decided to leave it was only because the business direction wasn't a fit for what I wanted to spend my time on.

It sure sounds like a privledged position, but it more came down to us living cheaply compared to our income and having the breathing room to trade a higher salary for work that I really enjoyed. I hope more people can make that tradeoff, it's much more fulfilling in my opinion

dsign
2 replies
14h21m

We are talking SV here, and that's very different from my European experience. I've known of founders in Scandinavia who walked out from startups that weren't doing so bad and that could have gone for another round of investment because they were earning as much as a bus driver, had zero savings, and were experiencing burn out after almost a decade of work. Maybe that bit of SV culture that lets founders be on par with a highly paid engineer at a big company is up to something. Maybe if it were more of a thing in other parts of the world, we would be more competitive.

ilrwbwrkhv
0 replies
13h49m

Yes and that is why we call them Europoor out here.

givemeethekeys
0 replies
14h3m

Having cofounded both bootstrapped and funded startups, I can say that in each case there was a deadline associated with success: for bootstrapped, we set hard targets in terms of maximum spending and time in order to test our hypothesis. This allowed us to fail fast in our own way and go back to a better paying day job.

For funded startups - at least with a healthy seed round, the investors expected us to burn fast and hard in order to prove our hypothesis or fail trying as quickly as possible, but they also expected us to not pay ourselves very much. As we found product-market fit and raised Series rounds, it was understood that we would pay ourselves competitive salaries.

Being stuck at the seed stage for 10 years is not healthy - neither in Europe, nor in Silicon Valley.

wafriedemann
1 replies
11h31m

The question I am most interested in is: How do people even get funding (or in other words: Who gets funding)

I'd assume it's 'references', i.e. which school you went to, which university you went you, who you know/who knows you

Where are early employees from? Are they still from the same elite circles?

Terretta
0 replies
7h7m

How do people even get funding (or in other words: Who gets funding)

Second question first, early employees are from anywhere, just make sure they are hungry to ship. You want devs able to self-organize and self-manage amid ambiguity and pivots, and filled with an urgency to get working software in the hands of users to get feedback to iterate, and you want sales/product able to listen and drive focus on product that users believe could be 10x better than however they meet their need today.

Answering your first question, this answer sounds cynical, but this is how the math usually has to work for VC to give outsized returns to pools of investors in VC funds:

You need to have a 20% to 5% chance at 2x - 10x annualized growth generating high cash flow and high margins reinvestable in the business with ability to switch modes and cash out or IPO in 5 years to let investors exit by year 7.

In other words, don't aim for a solid dependable low risk business plan. Aim for a unicorn business plan. To get funding, your business plan should be so compelling that in a funding round of 10 startups, yours is the one delivering returns that make up for the other 9 blowing up, and still giving the investors in the venture fund returns that are a multiple of the stock market.

Remember VC have customers too, their investors. Their investors want a basket of startups that handily beat just parking their money in a market-beating ETF of Apple, Meta, Tesla, Nvidia, Netflix, Alphabet, Microsoft ...

In practical terms, your business plan must convincingly show that the startup can grow exponentially (not just "up and to the right" but a curve) and overcome inherent risks (show you're risk aware, and already planning to beat the risks). Investors are looking for ideas that can stand out in a portfolio where the rare successes can de-risk returns that far outweigh the more common failures, for their portfolio to generate overall profitable returns.

To get funding, position your startup as a standout gem for a portfolio.

sealthedeal
1 replies
1h7m

I think its less about more risk etc, and its more like, they are the ones starting the company lol.

1. They are providing jobs 2. They are responsible for growing business 3. They are accountable to not only the employees but to board and investors, etc.

They take money off the table because they are in a much different position than say an engineer. It might be bad to say, but the engineer is responsible for one part of the business, the founders and CEO etc are responsible for all aspects of the business, and should be compensated appropriately for it, whether secondaries or higher salaries etc.

Also, secondaries at seed and A are not as common as they were during the 2020-2022 run up.

bink
0 replies
56m

Are founding engineers not also taking on risk? They're typically taking a much lower salary in exchange for their shares. They're avoiding vacations, nice cars, fancy houses, and other expenses that they could purchase if they worked for a larger, public company. In the example from the article WeWork founding engineers would've gone 9 years without seeing any value from their shares while the CEO was cashing out billions.

The difference in responsibilities is already accounted for in their disparate salaries and ownership stakes. I don't think it's very relevant to whether or not they should have the option of cashing out some of their stake during funding rounds.

mapasj
1 replies
14h13m

How common is this? How many founders that raise series A are liquidating? What are the amounts typically?

parentheses
0 replies
14h6m

It's fairly arbitrary, but there is at least one constraint on how much you can liquidate: You cannot liquidate much more than 10%, because you're taking money from the company and investors would not appreciate that.

dumbfounder
1 replies
7h55m

I don’t agree with this sentiment: Investors, founders, and employees all believe that founders are taking more risk than early employees (this isn’t true once founders have exclusive access to liquidity)

This completely discounts how much risk and stress go into the early stages before money is raised, or before enough money is raised to pay founders properly. They often go into debt, put many aspects of their lives on hold, and undergo outsized stress that is largely alleviated by the liquidity event, enabling them to plow forward and shoot for the moon. There are outliers that are insane, but you can’t throw the baby out with the bath water.

KingMob
0 replies
6h11m

...? Much of what you described applies to early employees, too.

bux93
1 replies
9h17m

I thought "founder liquidity" would refer to the supply and fungibility of founders. I've heard that, although ZIRP is over, there is still a large supply of capital, which implies that there's not enough good idead / founders to go around?

ergocoder
0 replies
9h1m

Supply and fungibility is more for kpop idols

blackeyeblitzar
1 replies
13h45m

Why is it a secret that founders get liquidity in many venture rounds? Because it undermines the narrative of the founder who is "all-in." The story of the founder who mortgaged their house and lived on ramen noodles for years is compelling.

A lot of startup compensation seems to rely on people not having transparency and honesty. The founders, investors, etc. all have very different risk and reward situations compared to typical employees and even non-founder executives. But for most it seems like a raw deal compared to working at a big tech company, unless you’re lucky and strike gold at a place like OpenAI or whatever.

Another area where there is a lot of obscure but important detail is in the cap table, stock plan documents, and so forth. If company financials and cap tables were transparent, and if it was clear the various ways in which a company could screw over employees through various clauses deep in their documents, no one would take those jobs.

jslakro
0 replies
6h42m

This is a solid argument to motivate startups to build confidence on employees through any of the captable solutions available out there

apinstein
1 replies
2h3m

The only fair way to analyze this is by looking at opportunity cost, which isn’t what TFA does.

Founders often have slightly higher market value (though not always) than first employees, so they are giving up more to go the startup route.

Separately, TFA further underestimates founder risk as they are typically not taking salary during pre-seed, and no or low salary during seed. However employees 1-5 typically get mostly cash, often much closer to market.

Thirdly, there is also often a lot more stress in being the founder. It is a complex, all day job. You have the weight of keeping things going for all employees, and when cash is low it’s your paycheck that gets delayed/cut first, not your employees.

That said I am all for reasonable early stage liquidity where it makes sense, but as many other commenters have mentioned, it tends to not be life changing super early for most early employees. Most employees would rather keep the bet on the table. Also, I am strongly against large founder secondaries. I think it’s helpful for founder to remain feeling “not financially successful”, especially first time founders, so that they keep their heart in the game. I followed this practice with my companies.

openmajestic
0 replies
1h12m

Thirdly, there is also often a lot more stress in being the founder. It is a complex, all day job. You have the weight of keeping things going for all employees, and when cash is low it’s your paycheck that gets delayed/cut first, not your employees.

I've seen startups from a founder perspective and from an employee perspective (VC style startups). I agree there is more stress as a founder, but people really underestimate the toll as an early employee - the gap is smaller than many people think. Particularly those ideal missionary-type early employees, they take on just as much mental ownership burden as the founders. It is also an all-day job. Let me tell you, when the money runs low, it is immensely stressful as an early employee - it is both hard to be the one making the decisions and it is hard to not be the one making the decisions. The ability to walk away isn't a benefit, it's a burden.

Their jobs can be different (or can be very much the same - depends on people and every startup is its own beast) with founders needing to deal with fundraising, board management, and ultimately having the impossible problems land at their feet which is often out-of-scope (and out-of-sight) for early employees. But the same core problem exists for both - your actions will dictate the success of the company.

And there is a huge amount of understanding of the founder burden and support for them, from financial to emotional to reputational. Where are the support networks for early employees? People will say the founders, but this is a load of crap for the same reason that founders rely on relationships with other founders rather than talking to their board or teammates.

Early employee is probably the worst engineering gig in Silicon Valley on most dimensions. Unless you just want to 0 to 1 build things. Then I haven't seen a job that can compare.

JumpCrisscross
1 replies
14h30m

Hmm, I’ll be controversial. Twinned secondaries, i.e. secondaries tied to a primary, are almost always a give away to senior management and the buyer. (They’re frequently syndicated at double-digit spreads.)

If the company sucks, senior management gets cash back first while the investor gets top-of-stack liquidation preferences. If the company is doing great, the investor gets to buy stock at a price almost always lower than market.

They’re common in Silicon Valley, because they’re good for founders and the Board members. But they’re rare in public markets. The closest thing I can come up with is the current clusterfuck with Shari Redstone.

s17n
0 replies
3h19m

They’re frequently syndicated at double-digit spreads

What does this mean?

EternalFury
1 replies
14h26m

You get Founder Liquidity because you managed to convince people who do just as much work that they couldn’t do just as much work without you. LOL I am so cynical.

its_ethan
0 replies
14h13m

To be fair, there is a skill in getting people to believe your vision and to take the risk to work for you. They also need to convince VC's of that vision to get the money to pay you in the first place.

Generally they make more decisions that directly effect the odds of the company existing 6 months or a year down the line than the average employee does (with some exceptions obviously).

You can still be cynical, I think all employees should be given the ability to get liquidity early, but it's not like it's totally unjustifiable.

yieldcrv
0 replies
3h50m

Delaware allows for employee shareholders to demand some transparency, but it doesn't apply to options holders.

VCs and Founders should be far more forthcoming to sweat equity participants. Delaware could mandate that too.

I've been on both sides, where leadership gaslights candidates and employees about why their tiny stock grant is so generous, diluted in the best case scenario. And on the other side where leadership is confused why someone with prior financial success would want to be an employee at all since its so obviously shit. That's sad to me that they can put on two faces, and its enabled in a way that securities laws were made to mitigate.

totorovirus
0 replies
2h55m

What shines better in a resume? ex-founder or ex-founding engineer? If ex-founder is a better role for next job, I think founders are taking much less risk than founding engineers. They get all the exposure to talking to rich people, VCs, learning how financial game works, which i regard much more rewarding career-wise.

tempusalaria
0 replies
9h9m

One under appreciated dynamic that has changed is that companies with limited revenue/PMF are raising more money at higher valuations. This mean that more early employees are being hired into less certain, less profitable situations, and the equity they are getting is a smaller percentage behind more liquidity preferences.

E.g. There are numerous AI startups I’ve spoken to in the past year with negative gross margins, 8 figure raises, and >100x ARR multiples. $1mln in paper equity in such a company is probably intrinsically worth <$100k.

Being an early employee at a startup right now is a really bad financial decision imo

stratigos
0 replies
3h8m

As someone who has worked in startup environments for 20 years, its rather offensive that anyone in 2024 would claim that employees arent taking risks.

In todays salary brackets, one could be comfortably making 220k as a staff dev some huge healthcare/pharma tech firm. One may also feel the job is boring, soulless, and mostly uncomfortable. Then one may choose to work at an exciting AI startup for ~160k, and suddenly find themselves way happier, growing more, and engaged. One just took ~60k worth of risk right there, not to mention that it could be come $0 tomorrow, and one likely now has crap healthcare benefits, given the startup status.

That 60k could be a million dollars in ~15 years if invested wisely.

steveBK123
0 replies
7h15m

I was aware something along these lines was going on when a profitless not-quite-unicorn (and still private & profitless 6 years later) startup founder bought the nicest penthouse apartment in my building some years ago... and then spent more money gut renovating it.

It wasn't Adam Neumann sized liquidity but certainly mid single digit millions at least. His company meanwhile has floundered with wave after wave of layoffs post ZIRP era.

sneak
0 replies
10h16m

We allow employees to exercise options up to 10 years after they leave instead of 90 days.

This always struck me as completely unethical. Your vested options are part of your pay; you should be able to exercise them years after leaving. I would never work for a startup that evaporates my vested options 90 days after leaving. That’s like clawing back cash comp, in my view.

s17n
0 replies
14h4m

I think most employees are mostly well aware that founders take a money off the table in every round, and I think that it absolutely does negatively affect morale.

riemannzeta
0 replies
2h9m

This is a wonderful article and kudos to the author for his moral sensibility here. The lack of liquidity and anti-dilution rights for any except a handful of key persons is a dirty secret of Silicon Valley. Most startup employees do not end up better compensated than they would at a larger company on a net present value basis even when their startup is successful -- and they don't as easily get liquidity along the way although there are more private secondary market brokers than there used to be.

The other angle worth observing here is the tax angle. In many cases, the founders are taking liquidity at valuations that are only loosely tied to tax valuations of the company. These valuations are fine for the founders and preferred by the buyers/investors, but undercut the premise of the tax system that was redesigned after the options backdating scandals of the early 2000s, in part, to ensure that taxes were getting paid in accordance with the actual capital gains.

rasengan
0 replies
6h0m

This is weird AF.

I gave 20pct to my employees and didn’t have to write a blog post about it.

paulddraper
0 replies
12h37m

IDK how secret this is.

But the reason for founder equity -- as with anything in a free market system -- has nothing to do with deserve and everything to do with demand/supply.

There are many more we early employees willing to take 1% equity than founders willing to offer it.

palata
0 replies
5h53m

Founders often feel guilty that they are getting liquidity (they shouldn’t)

Well they should not feel guilty that they are getting liquidity, but I think they should feel guilty that their employees get pretty much nothing in comparison.

Investors, founders, and employees all believe that founders are taking more risk than early employees (this isn’t true once founders have exclusive access to liquidity)

As an employee in multiple startups, I can tell you that I never thought that. One startup went well, the founders got rich and I did not even compensate the salary compared to being in an established company (and I'm not even talking FAANG). When the startup goes bad, then the employees are screwed as well.

Employees actually have the risk of getting fired, of being lied about the finances of the company, etc.

p0seidon
0 replies
3h14m

This thread is more entertaining than both TikTok and Netflix combined, which is truly exceptional.

notanadvice
0 replies
1h48m

People are talking about angry founders and angry employees, but there is another side to this post:

Prospective founders who work in big tech companies and have a family which depend on them. I include myself in that group, and I thought I needed 10 years worth of savings to venture on creating my own startup. But from the discussion, in about four years it is possible to match big tech compensation.

I feel more motivated to start a company now.

not_a_dane
0 replies
9h9m

The entire system seems like a scam. Thankfully, the COVID-19 pandemic and the Ukraine war have deflated startup valuations a bit. I believe another crisis is looming in the near future, and once it passes, we should be in a better place for the next 5-10 years.

nimish
0 replies
4h9m

Being a "founding engineer" is a sucker's game unless you have some very specific goals.

Nearly all the same risk, 99% less reward.

nikisweeting
0 replies
9h10m

Wait wtf founders are taking liquidity in second rounds?!

Had I known this was possible I would have totally changed my strategy years ago.

I've founded 3 startups and always thought I could only take out whatever ramen salary I could defend to the most scrutinizing investors. I've given a heck of a lot more in employee bonuses than I've ever taken directly out of the investor pot, where was this "de-risk your own life" essay all those years ago!

nbardy
0 replies
2h34m

I’ve got a job as a ML Researcher without a degree. I have experience building multimodal generative products. Because I was able to learn on the job at startups. I get to work on the problems of my dreams for the rest of my life now.

10 years ago the only jobs for machine learning were for PhDs at big companies. If you want to join a nascent industry and you’re not a top college graduate you have to find a way in the back door.

Don’t do startups for the money do it for the career growth.

10 years in startups out of college.

Even with two good exits. I didn’t make much money as an early employee, even in success, compared to FAANG peers.

If I went to big companies I most likely end up doing a lot of web development and Im rich off the stock market.

moss2
0 replies
9h17m

It is too bad it is up to the founders themselves to offer liquidity to employees. Founders are financially incentivized to not offer anything, so you're counting on their sense of justice and morals to overcome their sense of personal gain. This should be regulated.

(Yes, this is a political opinion. No, I am not American.)

matco11
0 replies
3h0m

Yeah. This misses the point that founders often go unpaid for long periods of time.

Those payments catch founders up to being able to have a “normal” lifestyle - which enables them to perform their CEO or CTO jobs better. A CEO having issues with making ends meet at home, having personal debt, and eating ramen can sustain that additional pressure forever. It’s in the interest of VCs to arrange things so that founders can focus 100% on the success of the company.

logicallee
0 replies
10h8m

Wouldn't most 9-5 employees stop working if they had a sizable liquidity event?

light_triad
0 replies
2h22m

While I agree that employees should get more equity and liquidity, I think it comes down to supply and demand:

- If the founders are de-risking appropriately it will take years of no pay/low pay work before they can even consider taking on employees. Building a valuable asset is not done overnight and takes extreme commitment - plus reputational & financial risk, opportunity costs etc.

- It's very rare for companies to get past the Series B stage. When they do, the founders have accumulated non trivial and non replicable knowledge about the market and the customers. The liquidity they get should be worth much more down the road.

Now of course if you are an early employee that is expected to 'make the startup work' like a founder and get none of the benefits there's a problem. On the other hand employees are replaceable & 'swappable' in a way that founders are not.

librish
0 replies
13h50m

My guess would be that it has to do with the amounts involved. In a typical series A/B only the founders have enough equity (they have larger share, plus they've been at the company the longest so they've vested the most) to be worth the transaction cost of a secondary sale.

lenerdenator
0 replies
5h13m

Accumulating capital becomes easier as you gain more capital, which is exactly why we need to abolish stock option pay packages and tax these people. Film at 11.

joshuamerrill
0 replies
10m

Founder liquidity events are done in secret in startup land. There's a simple reason for that.

It's wrong.

Startup employees, especially early ones, take on most of the risk that founders do. They take pay cuts. They work insane hours. They sacrifice.

And they have the same liquidity needs, too.

It's wrong to make them wait a decade for a fraction of the liquidity that founders got in the Series B.

It's wrong to force them to absorb the risk of the Series B, C, D, E, F, and IPO. All while the founders were set for life years ago.

If founders are going to take money off the table, they should extend the same liquidity offer, pro-rata, to their employees. Period.

jaksmit
0 replies
3h45m

dunno why the writer opted for this: "Our equity packages vest over 3 years instead of the industry standard 4-year period."

given it takes a long time to build companies; so on the contrary, many startups are instead opting for like 6 year windows.

"We allow employees to exercise options up to 10 years after they leave instead of 90 days." - the reason that 90 days is more standard is that it's more tax effective than having options exercisable for 10 years, though many companies are making a compromise on this recently

ilrwbwrkhv
0 replies
13h51m

This is another reason why American companies beat out Canadian and many other companies by so much.

In Canada even at Series A Canadian VCs will not offer you liquidity while at the same time allotting pennies in the first place. Absolutely conservative poor people.

If things are working, derisking the founder so that they can focus all in on the problem is the best thing you can do as a VC.

hemloc_io
0 replies
3h57m

Damn I was writing a blogpost about this exact problem inspired by a talk w/ a friend of mine.

Being an early engineer is the worst deal in all of tech, the people I've seen do it are either comfortably wealthy or just don't care about money.

golly_ned
0 replies
12h34m

I wish I had known so much more about this before joining a hot AI startup a few years ago. It raised its Series C at $850MM valuation. The business was doing terribly; investment was exclusively speculative with no business success to speak of.

The founders made tons of cash. Layoffs ensued. They're still kicking; they've pivoted to Gen AI which has given them new life. I had no idea how terrible the deal was. I regret so much about that time and the opportunity cost of joining that place.

goalonetwo
0 replies
26m

In my 20s I joined a couple startups as "early engineer" or "founding engineer".

I quickly realized those are the absolute worst positions to be in. You take almost as much risk as the founders but almost none of the upside. One startup died, the other one sold for 100m$. Out of that I saw 400k$ as an exit. Not too bad but even with that exit I ended up making way less than if I joined a FAANG. In both cases the founders made millions (through the exit or through liquidity)

Now I'm a realist. Either you create/found a startup or it's not worth joining one as an employee. You have way more upside at a FAANG/pre-IPO mid-life startup that already found a great product market fit.

Essentially, founders are pushing a crazy narrative of Startups being worth it to early employees because they need them. It was sometimes fun but I wish I just joined a FAANG like most of my friends, I would have a couple millions by now if I did.

gardenhedge
0 replies
6h26m

The difference is: no founder === no company at all. no first employee === not a problem, hire another one.

gafferongames
0 replies
5h53m

Two words: opportunity cost.

franciscop
0 replies
8h57m

I feel like the article contradicts itself in this point:

Investors and founders both tend to think that if employees knew founders were getting liquidity that that would negatively impact employee morale (it wouldn’t)

If employees realize they are taking more risk than the founders, [...] maybe they'll start yelling: "I'M TAKING SO MUCH RISK, IT'S SO HARD TO BUILD A COMPANY, I DON'T EVEN HAVE ACCESS TO LIQUIDITY!!!". And maybe they're right.

How is "not impact morale" and giving an example of employees shouting as a possible outcome when they find out not contradict each other?

divbzero
0 replies
1h34m

Startups are far more founder-friendly than they used to be (thanks in part to YC’s contributions) but we have a ways to go to make them more employee-friendly too.

To call out the employee-friendly equity policies that OP has instituted at his new startup:

Our employee option pool is 20% which is double the average

We have a 3-month equity cliff which is 9 months sooner than the average.

We allow employees to exercise options up to 10 years after they leave instead of 90 days.

Our equity packages vest over 3 years instead of the industry standard 4-year period.

… only taking liquidity if I can also offer it to employees as well.

The 10-year exercise window is especially noteworthy since the cost to exercise options can be substantial.

didgetmaster
0 replies
2h31m

I joined a startup as an engineer about 30 years ago. I was one of the first employees and one of the last to get some 'founder stock'. I took a big risk (low initial salary and even lent them money to make payroll) but it paid off. When the company was purchased 8 years later I did fairly well. Not enough to retire wealthy, but well worth the risk I took. I am glad I did it, but it could have turned out to be a big mistake.

Everyone working for a startup might have a different story to tell. Some good. Some bad. Tread lightly if you wade into the startup waters. It CAN be very rewarding but it can also lead to nowhere.

demondemidi
0 replies
6h40m

“ Being a software engineer who has a strong preference for creativity, problem-solving, and autonomy”

That’s nearly every engineer or programmer I’ve ever met, not some rarity.

danw1979
0 replies
5h20m

Investors and founders both tend to think that if employees knew founders were getting liquidity that that would negatively impact employee morale (it wouldn’t)

It would. Knowing that founders are cashing out and I’m not able to would be a very good reason to walk away, in my rather old, maybe slightly cynical opinion.

I get the need to hedge your bets, but employees should be able to that too.

classified
0 replies
12h26m

I couldn't care less. They can keep their secret and stick it where the sun doesn't shine.

bob1029
0 replies
4h8m

I just got off the ride (at a small startup) after ~9 years. Not much to show for it economically, but I did gain a lot of confidence and experience around how to actually run a business. I've picked up a lot of lessons, most in what not to do. I'd say it was absolutely worth it compared to alternative paths that I was previously on.

My biggest takeaway is to focus on compelling problems, rather than delusions of financial grandeur. I've learned that solving a hard thing and hearing the feedback from the customer brings me a lot more joy than hypothetical promises of extra cash in the bank. The money is a mind killer for me, especially when it's not real yet. Stock options are no longer something that interest me. I'll negotiate additional salary instead. The only company with stock options I am interested in would be a company that I personally found and retain control over.

One other lesson is to pull the rip cord the microsecond you think something doesn't feel right with management/leadership. I started thinking things like "does anyone care about the sales funnel?", "Why are we only talking to one prospect at a time!?", etc... The chances you will be able to "fix" some other person in this setting are pretty much zero, unless they actively want to be helped. I feel like I could have jumped off this ride at the ~7 year mark and walked away with 99% of the wisdom I have right now.

billy99k
0 replies
1m

When I was younger, I worked for multiple startups and received stock in each one. How much is that stock worth now? $0. I no longer will put that much time and effort into something, unless I am the founder.

benreesman
0 replies
11h25m

Silicon Valley’s best kept secret is how Altman made his first few bucks.

Everyone just buys that someone with a failed startup has capital that better founders lacked.

Invested in X with what Y bro?

api
0 replies
6h20m

It’s all relative. Founders that actually make it to series A levels have options to take money off the table (usually) and often what most Americans would consider a great salary, but if you do the math vs getting a massively overpaid FAANG job and include the odds of the startup imploding founder is actually a tougher gig.

I refer to dilemmas like this as "zeroeth world problems."

Of course like I said… relative. It is nowhere near as tough a gig as schoolteacher or service industry worker, at least financially, though there can be a lot of stress and some mental health risks.

albroland
0 replies
13h22m

Nice article, but it is wrong about liquidity events at WeWork. The author only discusses a tender offer that fell through at the end of 2019 after the failed IPO and collapse, implying there was nothing ever before.

There was a tender offer in 2017 with the first SoftBank investment, and again in early 2019 (pre IPO attempt, closed in April) associated with the second investment by SoftBank. It is possible there were earlier events, but I had joined in 2015.

That isn't to say things were roses; I know many early employees who, in the lead up to IPO, exercised their options and took enormous loans to pay AMT and were left in a terrible situation.

abpavel
0 replies
4h40m

It's clear that the author is first time founder. The article is disingenuous in that it talks about secondary availability, but the solution is longer exercise and shorter vesting? That wouldn't solve WeWork situation at all. Also, the risk of founders and employees is not comparable. A good analogy of the relationship is Landlord vs. Tenant. Founder burdens statutory obligations, is responsible with their personal belongings, has to lay the groundworks, and get the investors. Employee has to pass a job interview. If company fails, both lose a job, so that part is shared. First employees are sometimes special, but they are not founders. Musk was not even an employee and he became founder of Tesla.

aaronbrethorst
0 replies
12h59m

If employees realize they are taking more risk than the founders, maybe they'll ask for more compensation, maybe they'll congratulate the founders and move on with their day, maybe they'll start yelling: "I'M TAKING SO MUCH RISK, IT'S SO HARD TO BUILD A COMPANY, I DON'T EVEN HAVE ACCESS TO LIQUIDITY!!!". And maybe they're right.

This is why I think the term "Founding Engineer" is often just a fancy way of saying 'sucker.'

MobileVet
0 replies
6h2m

This is a great post and I am glad it is getting high visibility. Everyone involved in a startup should understand this and consider it as part of their 'do I join' calculation. Additionally, founders shouldn't try to hide it nor should they horde the returns.

Clearly founders are the reason the business exists, but the whole team is the reason it succeeds, everyone deserves a piece of the reward. Mark Cuban is a famous founder that understands this and distributing gains well before his big win. [1]

One piece of feedback on the terms, 3 month w/ 10 yr window is pretty rough for the company. You will end up with a bunch of random people on the cap table... people that didn't really contribute much in the overall picture. That is annoying as you raise and downright frustrating when you exit. I would suggest you go back to a 12 month cliff w quarterly going forward and maybe set the window at years served, rounding down. My 2 cents.

[1] https://www.businessinsider.com/mark-cuban-employees-million...

KaiserPro
0 replies
9h54m

As an early stage engineer that was bought out by a FAANG, I can assure you that most of the hype surrounding buyouts is mostly an exaggeration.

Sure some people get millions, but most people do not, even early stage engineers.

Think about it, you as an engineer, have deliberately avoided working at $bigCorp, and are about to be given $5m in shares. Would you continue working at $bigCorp? no, you'd take the money and fuck right off.

Ok Ok you say, but look at the headline buyout figures Google buys a company for "450 million" that startup having raised 65m in capital for a valuation of x.

so, you as an employee have an option for 0.1%. Awesome, you're gonna get 450k right?

No.

The 450M is the headline figure, The PR figure. Its not actually how much the company is bought for (well it rarely is)

Google will pay off the 65M from investors, plus some amount, maybe give some shares. This will value the company at say 85-100M in terms of cash paid for actual shares.

oh sweet, so you'll get 0.1% of 100M right? well not always. There is debt seniority and weird structures that mean that certain investors are paid more per share than others.

So it might mean that the pool of employee money would be 10M or 1M. or even none. The structure is normally bespoke and deliberately opaque.

Ok, so fuck, not that much money.

If you are lucky, you'll get a job offer from google. This is where the head line figure comes in. Say Google pays 100M for the actual company, in actual cash, the rest of that headline figure comes from share offerings.

That is, if you join google, you'll get the standard level of pay, plus the normal share offer. However you'll then get an additional share offer from the headline figure. This could be double, or many multiples of the normal share offering.

TL;DR:

The headline buyout figure for startups is mostly fiction. You'll only get lots of money, if you are part of the 0.01% that IPO and stay long enough to get the full offering, even then thats not a given. The second best outcome is getting bought out and serving your golden handcuff period.

Joel_Mckay
0 replies
13h56m

"Silicon Valley's [worst] kept secret: [Loyalty will not be rewarded]"

The fact remains that sweat-equity deals rarely work out in a founding employees favor.

i. IP selloff to umbrella firm for $10

ii. contract restructuring or share dilution

iii. jettisoned from a company months before an IPO

Most techs have seen all of these events unfold... if you are around long enough.

People always have their own strategic truths once significant money is on the table. Even moderate success can destroy peoples memory, and anything not legally watertight is just hot air.

Best of luck, =3

HarHarVeryFunny
0 replies
4h13m

I've read that Sam Altman's net worth has ballooned from hundreds of millions (mostly tied up in Helion) while at OpenAI to billions, and that despite all his protestations of not making a penny from OpenAI, he also has/had a $10M investment in the (~100x profit capped) for-profit part of OpenAI...

Given Altman's slippery relationship with the truth, I have to wonder if his sudden significant increase in wealth, if true, is due to having participated in an early "liquidity event" as the article describes. Did he sell part of his shares to Microsoft, perhaps ?