One factor that no one seems to have noticed is that both cofounders, Ravi and Joshua, have already built fairly big companies. Ravi was the co-founder at Heap (he took over my co-founder spot after I left), and Joshua was the CTO at Benchling.
Both of those companies have raised >$100M. After that success, the prospect of continuing to run a middling company in the shadow of Retool isn't very appealing.
Very clear and well-written article. I think that the author is likely to be correct that the CEO was overwhelmed by going alone. One thing not mentioned at all, though, is what the investors in Airplane might have wanted to happen. Seriously, ctrl-f for "investor", it doesn't show up even once. In addition to the CEO being overwhelmed and tired, it's very important to realize that:
- Airplane raised a $32mm series B in September of 2022 [crunchbase]
- Tech company valuations fell off a cliff over the course of 2021-2023 [memory]
- By 2023, with slowing growth, it's likely that Airtable was no longer able to raise additional funding. Best case was likely a down-round.
- The investors probably exerted significant pressure, particularly given the departure of the other founder and several key employees, to wind down the venture.
- An acquihire is a reasonable way to end the company, return money to investors, and give employees some sort of payout and a high likelihood of remaining employed.
Just my opinion, but if I were the author I would consider that maybe the remaining founder actually did a decent job of looking out for their team. Signing bonuses of $50-75k is not life changing money, but a job and a signing bonus is a hell of a lot better than nothing.
Right, and another factor to consider is what percentage of the company was owned by investors. After a series B, they may have owned a majority. Apart from exerting pressure, it’s possible that this decision was made 100% by the investors and the founder(s) had no choice. It could also be considered poor form for a founder to make this public if that’s what happened.
It’s important to understand who is actually in charge before assigning blame to anyone.
If that were the case, why wouldn't the CEO say so?
I probably would have in their shoes, but that is one of many reasons I am not CEO. Bosses tell polite fictions that preserve relationships.
I've had some very close relationships with C levels at some big and medium companies. I've caught them lying in varying degrees more than once.
Sometimes though the job demands it. They're potentially not allowed to disclose something which leaves lying or saying nothing as the only other options. This works well until someone already knows the truth -- has their own source of information.
I didn't take offense, I just learned not to take what they said at face value. It's not a bad lesson in general. C level executives often learn to be ruthless, depending on the org, they can end up in real internal power struggles as well.
Polite way to say that. Self-preservation almost always outweighs transparency regardless of the whether the truth is good or bad
It’s important to understand who is actually in charge before assigning blame to anyone.
But also,
It could also be considered poor form for a founder to make this public if that’s what happened.
I mean, they asked the CEO what was going on and he didn't seem to give good explanations. Especially if it wasn't his decision.
maybe he knows the actual explanation that would be satisfactory is also the one he is contractually or professionally bound not to give.
return money to investors
Do the investors care? If they're not making 100x return on an investment, will they truly care about 0.5x return? My feeling is that most would just say "OK, you have a good team, you have money in the bank, pivot and go wild".
This was more likely a 0-0.1x return.
There's no chance the investors were happy with this- if a company had years of runway they almost certainly advised them to tough it out. Even a downround would be preferable compared to a total writeoff
Probably 0x for everyone except the last round investors who would get basically all the cash in the bank due to liquidation preferences, which is probably 0.66-0.84x return IMO.
seed investors might write off a $500k check if their model is to write 30 of them and carry the fund with a 100x-er (and many investors are not so cool with losing), but $32M is not that model. A recent comparable example is Pitch - https://twitter.com/unamashana/status/1745417095809307080
This. As you get into later stages, check sizes become bigger and so does risk aversion + due diligence.
Yes, they care, although this of course varies. Remember that in this situation: one of the founders had already left, another was "giving up", and other key employees had left. Tech companies were laying off like crazy, and your chance of getting your money back via another round was about 0%. Would you be willing to subsidize a bunch of jobs in a bad-trajectory company with disinterested/absent leadership? Or would you instead think to engineer an outcome like this where the employees get a job offer and a bonus, one of your other investments gets a chance at top talent, a serial entrepreneur founder remains happy with you, and you get some money back?
Depending on timing (and here it was just over a year between the round closing and the acquisition), you may be able to easily re-deploy the capital you get back as another investment included in the same fund, and get another shot at a 100x return.
I'd be curious to hear what others think (particularly actual VCs, not just pretend ones like me) but this seems like a very rational outcome to me.
- By 2023, with slowing growth, it's likely that Airtable was no longer able to raise additional funding. Best case was likely a down-round.
The author stated they had millions if not 10s of millions in the bank and a bit of runway. And they had already done layoffs. Based on this, they were not under pressure to raise or do a down-round.
Separately and related to a sibling comment, the fact that Thrive Capital invested in Airplane and Airtable means they can now have a positive "tombstone" for Airplane by saying it was an "exit" while receiving a bunch of their original investment back.
You’re right, the point I was trying to make but should have said more explicitly is that they raised at an inflated valuation that would make any subsequent “up” round more difficult to raise in the future, even if the growth trajectory improved.
Airplane and Airtable share a lead investor, Thrive Capital who led both Airplane's Series B and also Airtable's Series D
Lesson for all of us (customers of SaaS companies): never depend of VC backed non profitable companies for critical components of your infrastructure or business processes. Always build on tried and tested open source software.
That's why I never use Supabase.
supabase is open source…
So was ngrok until they abandoned it completely for their cloud hosted v2. Over-engineered JS frameworks might last for a couple weeks in that state if you're lucky. Meanwhile, Rails + Postgres/SQLite need just a couple security fixes per year and they'll keep chugging indefinitely.
The culture that has birthed these mongrol JS frameworks worships shinyness and novelty. These are naturally temporal qualities. It's why for almost no one does it make sense to buy a mid-range Mercedes/BMW. You always lease because you know it will fall apart after the warranty period.
Nope. They are all part of the whole "open source" gimmicky companies where their main focus is the commercial aspect of it. It's a shame they are using "open source" as a marketing gimmick and it's totally against the ethos of open source software.
Even a lot of the open source stuff is runs by companies listed on Crunchbase with millions of dollars of VC backing. That software isn't gonna maintain itself if the cash runs out.
Open source may be safer than proprietary software in that regard, but it's still not a guarantee. Still far preferable IMO.
Yes but if you are already self-hosting it, it really isn't hard to keep it alive. It means there will never be a rug-pull with two months notice.
That is true it gives you time to migrate.
That software isn't gonna maintain itself if the cash runs out.
No, but you can maintain it yourself, or hire people to, or worst case you can at least run it and accept the bugs. You're not going to just get in one morning and find out they've turned off the servers and all the stuff you had in their system is gone.
Look at the mess Vercel created with their Next.js app router.
Was a former employee at Airplane.
We were quite disappointed and surprised by the sudden choice to shut the company down. In many ways, we had good metrics, customers that liked us, a lot of runway, and a great team.
In the end, the decision came to our CEO. While he never gave a clear reason why, it was pretty clear that he burned out and tossed in the towel.
Even if Airplane had been cash flow positive, slowing growth and a demotivated CEO and departure of key employees at an early stage is a tough pill for investors to swallow. See my other comment, but I find it highly likely that your investors were pushing for a way to wind things down and return as much of their cash as they could get, and an acquihire is a fairly employee-friendly way to do that.
The disappointing part was we didn't even get to see the experiment take place before shutting down prematurely. Our sales numbers were still quite solid and there were many paths for us to push forward. As a fraction of our investors' portfolio, Airplane's investment was small. I imagine they would have much more preferred us to continue working hard than to return the bit of capital. In the end, only a few employees chose to join Airtable.
I imagine they would have much more preferred us to continue working hard than to return the bit of capital.
You imagine incorrectly, as revealed by your lead investors' decision to allow an acquihire by another one of their portfolio companies.
Could you share sales numbers to give us a sense of where the company was at?
Don't know any particulars but the real problem here is the misaligned incentives that come from the rather incestuous relationship between founders, investors, and their friends in most companies steroidally pumped-up by VCs. What about the customers and what they want? VCs typically over-rotate on founders they talk to and obsession with comparable companies. Reading between the lines here the real story of a fire sale to Airtable (in some trouble of its own) might have to do with burnout but also machinations with another portfolio company from a lead investor.
I was curious about this article. How much of the AI hype was demoralizing to his perception of the company's future? Attempting to read between the lines, maybe he was down no more than just no-code. He might have thought AI would outperform in the same space where internal tools platforms (Airtable/Retool) currently live. Following that thought, perhaps Airtable/Retool may be looking to pivot away fast from low-code/no-code into AI-first connections to internal knowledgebases & databases.
https://www.airplane.dev/blog/no-code-has-no-future-in-a-wor...
Did the CEO have that many shares that it was his decision? Or did the VCs leave it up to him, and he took the option?
Why was the employees' common stock worth $0? Liquidation preference for the outside investors? Related: How can a regular employee joining a startup know beforehand that there isn't a high chance of their equity (which is probably a significant part of their total comp) being worthless even if a big acquisition is made?
assume it's worth zero
sadly, founders who are hiring don't want to hear that and typically don't want to compensate fairly for the high probability that their precious offering of equity is worth zero
I think that's a simplification. The upside is that there is clearly a functioning capital market for valuing and capitalizing high growth, early stage companies where you can make a lot of money very fast. The trade off is that if you don't want the high risk part of committing to a high risk asset, you shouldn't join the company in the first place. For this reason, most people shouldn't join most startups. Some people, of course, make a career from doing this well.
For those people, there's a blend of two things: 1) you think you know something the market doesn't -- it may be something cultural, the product-market fit, maybe you're just really impressed with the people and the momentum you're seeing, maybe you have really deep expertise and insight from previous experiences with the industry 2) you just plain enjoy it more, so the high risk premium is worth it to you overall over a more boring job where with a lower ceiling on rewards and career growth but higher risk-adjusted earnings
Working at a startup is often a mixed bag: an unpredictable, fast-paced, exciting journey full of variety and autonomy, with great highs and often even greater lows.
Most people are neither looking for that nor prepared for that day to day. Others believe they are open to it, but out of a desire to find the positive parts while avoiding the negatives, are fundamentally incompatible with doing what would drive success. I've never seen these kinds of folks achieve much consistently at startups.
It's the people who lean into rather than away from the risk that are instead the ones I've seen most success. They survive the notoriously high attrition and harsh pressure to deliver in high-risk situations without playbooks. They both can scale the company and hang onto leadership roles at scale. This, again, should not be and definitionally is not most employees.
You don’t know. Its a gamble. Sometimes it pays off. Most times it doesn’t.
How can a regular employee joining a startup know beforehand that there isn't a high chance of their equity (which is probably a significant part of their total comp) being worthless even if a big acquisition is made?
You don't.
I've walked into every startup with big promises of stock compensation highly cynical about seeing any of that equity, ever.
Unless the cash is sitting in your account, it doesn't exist.
This wasn't a big acquisition, it was an acquihire. The company essentially failed. They raised ~$40M, and it's unlikely they sold for that much. Investors will get some of their money back, and the remaining founder will get some vesting equity at Airtable as incentive to stay post-acquisition.
But so long as you sell for less than your total raise, common shares will be worth nothing even with liquidation preferences of 1x.
Sounds like they raised tens of millions and had only $10M or so in the bank. Assuming the sale price wasn't in the tens of millions or greater, no common shareholders would have received anything.
How can a regular employee joining a startup know beforehand that there isn't a high chance of their equity (which is probably a significant part of their total comp) being worthless even if a big acquisition is made?
Ask to see the cap table to understand what the company would have to be sold for in order for your shares to be worth anything.
If the product is being shut down, it is definitely not a big acquisition.
The only way to be sure it's worth something is if a secondary market exists for the shares. This is only going to be true for later stage companies, not early stage ones though.
I think the best advice on the topic of early stage options is this blog post: https://www.benkuhn.net/optopt/
The TL;DR for me is: Be more picky about the company than the specific comp package. When you're there, find as much as you can about the revenue growth and retention metrics (assuming B2B), and quit after your cliff if it doesn't look like it is going well enough to justify the valuation.
These colleagues had all been at the company for a while and all had legitimate reasons for resigning unrelated to the revenue slowdown
Obviously not familiar with the particulars, but people don't always say why they are moving on. There is not much of an upside to revealing any negative issues, so it's usually presented as "really wanted to stay, but just found a new exciting opportunity". If all of the sudden 4 people in a few month period "really liked the position, but just found new and exciting opportunities", something else is going on.
Legitimate excuses for leaving. 99% chance what caused them to leave was they saw the writing on the wall and took on a better opportunity.
The fact that it was veterans leaving isn't just a writing on the wall but probably straight up first hand knowledge.
Yes, one must always be sniffing around the books and squinting at the numbers, especially in a startup.
I always think of this article in these situations: https://randsinrepose.com/archives/shields-down/
It's an apt metaphor.
>> The departure cost is always exponentially higher.
And yet no one is going to give you a substantial salary rise unless you sign a resignation letter.
All that questions about the reason why someone wants to leave during recruitment or exit interview are a ceremonial, and people are answering with polite bullshit.
Yes, I'm looking for a new job to get more experience, to grow, to get new challenges. Not because I want more money and we all know it is the easiest way to get it. Not because I have an idiot manager. Etc..
Yes, I'm looking for a new job to get more experience, to grow, to get new challenges.
Indeed. There is no upside to provide any criticism or leave on a negative note. It's the other side of the coin why companies don't provide feedback after interviews, there is no upside for them. Same here. What if some coworkers start another company, or the winds change, etc. It's always better to leave on a positive note regardless of reasons.
Of course when 20% of the team leaves in 3 months "to get more experience and jump on an exciting new opportunity" it would be silly not to read between the lines.
To me and others, it seemed like the CEO was tired of the startup grind and simply giving up. Ever since his fellow co-founder quit, he’d been running both the technical and go-to-market sides of the company, and it was clearly very draining. We felt that he wanted a less stressful position with a lower risk payday, and this kind of deal was the best way to achieve that.
Where was the board? Why not hire in a new CEO from the outside?
I appreciate that the author can't actually get inside the founders' heads, but something still smells fishy here.
The company was burning money and growing slowly. Most of the original investment was likely based on the strong founding team.
In that situation, they'd probably just want their money back.
Which seems to be what happened here?
Airtable and Airplane shared a lead investor. After the CEO of ’plane left, the remaining team soon got rolled into ’table and investors got tens of millions back.
If revenue was stalled, the investors would have written it off and deferred to the founders.
If you need to bring in an external CEO to do a large pivot at an early stage company then you may as well just invest the money in a new company. If the original team was there then there's an advantage of having everything in place for that pivot but if it's all brand new then why bother?
Why not hire in a new CEO from the outside?
The fact that both founders with the company were done with it points to the business not going well/not being in a position to go well.
Clearly all the investor interests were very important in making this deal happen, but the root of it is that the individuals with the most investment, knowledge and leverage decided they did not want to pursue the opportunity any more, and the best deal they could scrounge together was an acqui-hire.
If the company had been cash flow positive, or on a path to that soon enough, they probably would have found a new CEO, but if they're just burning down investor cash, it makes sense to wind it down if nobody with power believes in it any more.
"On January 3, the acquisition and product shutdown was publicly announced. As expected, customers were shocked and upset. Many had been using Airplane for critical workflows within their organizations, and they now had to replace huge chunks of internal tooling before the final shutoff on March 1."
Building things on an early-stage no-code platform like this without at least an open source escape hatch feels like a huge risk to me.
It's a danger of all SaaS. If you can't run it yourself, you can't fully prevent this from happening.
Of course, the benefits of taking on this risk may often be worth it. Smart bets don't always pay out.
Escape hatches can work. I took a bet on Mapzen a few years ago - when they shut down my employer had features that depended on their WhosOnFirst API. Because the data behind that was openly licensed we managed to migrate off it to our own (MySQL spatial table-based) solution before the shutdown.
It was still a big pain, but it would have been a whole lot worse without that escape hatch.
Totally. We’ve tried Retool in the past and it wasn’t for me, but I’ve also looked at both airplane and windmill not long ago but decided the risk / reward just isn’t there.
Sucks to be a customer on the other side of this now.
Why not windmill? It's open source, no? I'm only peripherally aware of it, so just curious what people who have dug in on it more think.
I think even for SaaS products, the enterprise customer contracts should include statements around making the source/infra code available under an open license. That would help companies gain confidence in a way that they can always hire the ex-employees and continue using the product.
What's Airplane's best alternative to build internal apps? Windmill and Retool were mentioned but I'm not convinced of them.
Any guidance will be appreciated.
It depends on your use case or development preference. Check us out at Dropbase (https://dropbase.io)
You should take a look at Superblocks. I think you'll find our building blocks both flexible and extensible to solve you use cases.
By app if you mean database frontend this may be interesting: https://visualdb.com
I am building https://github.com/claceio/clace. It is focussed on building operational web apps, with a focus on security. The end goal is to build something between https://www.rundeck.com/ and https://retool.com/, allow automation of operational tasks through a web interface while also allowing fully custom web apps.
Clace also works great for running simple web apps locally. Building and deploying a web app should be as easy and common for backend engineers as creating a CLI app is.
Founder of windmill.dev, the open-source alternative mentioned at the end. This market is tough, our customers are both very demanding and hard on price. We are doing very well because we kept the team very small but I cannot imagine the pressure to deliver when having raised 20x what we did.
I love what I'm doing and I feel very fortunate for the opportunity to build a startup in a domain that I cherish, devtools, and have grown to love demanding customers as people that care about our product. But if I wasn't passionate in it and its technical challenges, I think there are easier opportunities out there to make a successful startup and can easily imagine how disappointing this segment is with the track records they had as founders.
your product is really cool and i think you made a good decision by going OSS - it reduces the risks your customers take by migrating to the product.
I migrated to windmill.dev a couple of weeks ago and couldn't be happier. Honestly the product is simply better than Airplane. I looked at Windmill.dev a 18 months ago when I adopted Airplane, and it was less mature - but it was open source and I wish I'd given that more weight.
For my shop this was not really a big deal - we did not leverage Airplane's apps or workflows, we just used it to productionize some scripts that support edge cases in our platform and the migration for that is not too bad. Of course, I didn't feel that way when I got the email on Jan 3rd.
Heya, ex-Rundeck engineer and founder of https://stepwisehq.com .
Will likely end up releasing MVP OSS this month and have to go back to work while continuing to bootstrap. Would love to chat sometime; may be some ideas in here you'd find interesting.
You have a massive acquire opportunity here ...
Several people on the team confronted the CEO, but he denied that there was an acquisition brewing.
If there actually was an acquisition brewing at that time, and it's true that the CEO denied to employees that there was, that's one way to spoil any existing culture of honesty and goodwill.
Another angle: If a CEO denies to employees that an acquisition is in the works, to retain employees, but there actually was an acquisition in the works, and an acquisition happened, and it included employees' stock becoming officially worth $0 (or some other arguable financial harm)... could that constitute legally actionable fraud?
Or, if it really was an acquihire, then you don't run around telling this to employees, not to scare them off .. (certaily this was a clause in the LOU/SPA)
It's probable that he was legally bound by a confidentiality agreement.
Probably you want to avoid signing an agreement that could necessitate actively lying to someone else.
If already under such an agreement, find a way not to lie.
Being proactive can help. The first example that comes to mind was when a highly-placed colleague (who I trusted, and with whom I had a good rapport) asked me directly whether I knew whether of anyone in the department who was job-hunting. I didn't know of any, but I told them I generally couldn't answer that question, as a matter of policy. Because that's the kind of question for which we can anticipate a hard conflict someday, between betraying a trust, and lying to someone else. And that's an easy conflict to avoid.
"If I knew, I probably couldn't tell you." is a useful phrase.
As a customer and one of those early adopter and champions of Airplane this really was particularly frustrating to experience.
I was also surprised at how poorly the shutdown was communicated, a single email went out and there was never any followup. I wouldn't be surprised if there was a reasonable percentage of their customers that were shocked on March 1st to find out they could no longer login to the product.
It actually hasn't been shutdown yet, so that moment will still be coming. My theory is there is no one left to even turn it off and it will continue to run until it's hosting bill is past due and the servers are shutdown.
It's gone, the sign-in page is there but it doesn't function
That’s interesting - it works for me accessing app.airplane.dev. Scheduled jobs are still running too. I’m using Google authentication. Today there is a pop up message that everything will be shutdown over the course of the month.
While I can't vouch for Ben's time at Airplane, I worked adjacent to Ben at Segment and can say his reputation there was unimpeachable and his work was top notch, so it doesn't surprise me that he'd publish something so thoughtful and informative.
As an Airplane customer, Ben was the man, always super helpful when we had questions.
When we heard Airplane was shutting down, everyone's first thought was "can we hire that Yolken guy?"
If you are at a large company, he'd love to decompress there for now!
That's a shame. I really think the world of software infrastructure needs a "more user friendly, batteries included service orchestrator" as an alternative for K8s and public clouds offerings.
Thanks to OP for the candid view. I was confused by Airplane.dev since it seemed like it was taking Temporal and putting SaaS + UX chrome over it. Temporal seemed like the hard part. It also made me wonder why Temporal wasn't doing something end-user friendly in parallel with their Cloud offering. I do enjoy Temporal and have shared my OSS related to it (Terraform modules and a half-baked Terraform Provider).
Regarding that service orchestrator, even before seeing Airplane et al, I've wanted to take my Terraform + Nomad + Temporal + Ops experience (coupled with all the other diverse HPC + UX stuff on my GitHub) and make a nice OSS PaaS out of it.
But I didn't because Nomad is "Business Source Licensed" -- so once I put all that work in and try to make it customer-supported, HashiCorp could shut down any commercial hopes once they finally decide to put Nomad on HCP (why not yet OMG?!). But I get why it's licensed like that, no shade on HashiCorp, any of the big clouds could otherwise host Nomad and crush them.
I much prefer Nomad to K8S for what I do (HPC on-prem + cloud-edge). And HCP itself runs on Temporal!
Wanted to shout also out to this Cron Atlas project [1], who put nice chrome and functionally over Temporal, focused on scheduling serverless functions. It is OSS, with a commercial offering. I haven't used it, but saw it on the Temporal Slack and appreciated the work.
I'm always puzzled by stories like this:
Why not just cut staffing to a minimal number of people -- go back to existing customers, and renegotiate existing contracts down (due to reduced support), and try to balance out the revenue with costs to get back to some level of profitability.
2-3 person indie hackers that bring in 400k in revenue are considered wildly successful. I have to imagine airplane.dev was bringing in enough revenue to support a team of 10 - 15 people who could forever be a thorn in the side of companies like retool. Maybe there could even be an exit one day for the people staying behind.
Even the founders could leave, just hand it off to a group of employees who are still interested in working on the problem, will have more control over the company, get better work life balance, etc. Rather than just scrapping it all
I'm sure it isn't this easy, since that seems to never actually happen, but can anyone illuminate me on why?
Likely triggered by investors
Yeah, it would be interesting if a company like this could be sold to a handful of employees. But I imagine part of the reason this happened is that the CEO felt responsible for finding a landing spot for the Airplane team (pun intended). An acquihire accomplishes this, and is probably better for his resume and/or ego as well. But for customers, yeah it would be better if this were kept as a going concern.
He then explained that the Airplane product would be shut down, but that most of us would be getting “extremely strong” offers from Airtable. However, we’d have to do interviews for leveling purposes, and the financial details wouldn’t be made available to us until later.
That's a layoff, right?
I went through an acqui-hire with the same structure - ironically, it was to be part of Ben's group at a different company.
In our case, they genuinely wanted the whole engineering team, so the interviews were pretty friendly, and our offers were fair. I'm not sure that was the case here, and I'm sure that came through in the tone of the conversation.
However, we'd have to do interviews for leveling purposes, and the financial details wouldn't be made available to us until later.
"Everyone has to re-interview for their job" is a terrible thing to do to people, IMHO.
You could instead have deal clauses about retaining the employees for some period, and how the leveling and compensation maps. If the acquiring company isn't willing to do that, then I think that tells you that you're selling out the employees to a worse environment.
Re-interviewing is one reason I wouldn't sell to Google, at least not without checking with the employees first. "So, uh, if we were to get acquired, how would people feel about having to do especially jerky re-interviews for their jobs, if, uh, it paid really well?"
"So what makes you think you're a good fit for this job?"
"I already have it."
extremely ironic that the founders wrote a blog post entitled "How to gain conviction to work on a startup idea for 10+ years" https://www.airplane.dev/blog/how-to-gain-conviction-to-work...
let those among us who is without sin cast the first stone
I'd say given the startup's shutdown being offered a signing bonus and a job at another company was the best outcome for the employees.
The employees didn't get a job at another company. They got the opportunity to interview for a job at another company. I don't know about you, but I usually do fine at making that happen myself.
I really hope this trend of non-informative, common noun names for software comes to an end. Airplane, seriously? Why not Skateboard or Plywood or Shovel? I guess I have noticed it's a signal that the actual product is yet another boring productivity tool.
"Airplane" starts with "AI", and it sounds like their work involved AI (I have never heard of them, so don't know).
Something about this narrative doesn't make sense though.
Why would Airtable go through all this trouble just to get a product owner for something unrelated?
Did Airtable even pay anything for Airplane.dev or was this just a face-saving maneuver? I don't understand how the Airtable board would sign-off on this if they are just tossing the tech AND all the users. Outside of those assets, acquihires happen with the aquirer wants the same tech built into their offerings. They are hiring a proven team with existing domain knowledge to reduce the risk of adding this tech. But none of that is happening.
Why not find a way to do right by their customers if Airtable truly isn't interested in the product? Open source it, or find a company willing to take the product and customers on?
As other comments pointed out Airtable and Airplane share an investor in Thrive Capital, which made negotiating a deal probably easier. But yeah, Airtable probably didn't pay a lot for Airplane.
It still makes sense for Airtable, as they do get someone with a proven track record of building tech products in general to build out an important division of their company. You say that it's for something "unrelated", but integrating AI capabilities (Airtable isn't looking to build new foundational models I assume), should definitely be in their ballpark. Though of course that's a gamble with a very low bus factor.
So it's a win-win-win for Airtable, the CEO/CTO and the investors. Airtable gets a capable leadership person to de-risk their AI endeavours (where IIRC they were lagging a bit behind competition like Notion). The CEO gets to work in a less stressful position, and maybe something that's a more interesting topic to him. The shared investor is happy as it strengthens their already strong unicorn company at the expense of a company that probably wouldn't be able to grow to notable size for them. Many of the other investors that are individuals I'd wager were happy that their money isn't tied up in Airplane anymore and that they can place new bets in a hot AI market (just a guess based on who is on that list).
Why not find a way to do right by their customers if Airtable truly isn't interested in the product? Open source it
Presumably because the cost of that is significant for little to no gain for them, especially if you factor in the opportunity cost.
or find a company willing to take the product and customers on?
I think the buyers that make most sense there would be e.g. Retool, which are too close of competitors to Airtable that they want to directly sell marketshare to them. It's probably better for Airtable to let the customers spread across all their competitors.
This guy's specialty is working at startups that get acquired
Thanks for the clear explanation. Had wondered at the time why this would happen.
Not to play the blame game but sounds like it comes down to cofounders just losing interest in their own company. Rest was just a side effect.
Unfortunately this is becoming more and more common. The cult of the irrational, warrior founder/CEO who takes the startup journey as literal life or death is even rarer.
What is even more weird to me is that I know founders who sleep 2-3 days in the office trying to make their startup work and grow, year after year.
They are hiring for people like you. They always get rejected for some reason.
Yet Silicon Valley natives get their way easily with great engineers like the ones in your team. I don't mean to offend anything, I have been just really curious what makes great people like your team go with founders who give up eventually. Cos I used to think you can sort of sense a founder who is not in it for life and death.
Huge kudos to the author for this article. I'm the founder of the competitive bootstrapped product https://uibakery.io. So I was really surprised to hear that Airplane was shutting down at the beginning of the year. This story provides an insider's perspective on what happened and helps to understand their situation better.
However, it's still sad that in the end, the customers suffered the most. While I agree that the founder probably did fairly well in his situation, it's unfortunate that he did not consider or did not manage to achieve other options, such as buying out the company from investors. They had a decent product that could have become a successful and profitable business within its niche.
It also struck me as rather cowardly for the CEO to drop this bombshell from his home office rather than flying across country to be with the team.
"software is a force multiplier" well maybe that's the point. I am a superstitious b*tch but maybe the Universe doesn't want our force to be multiplied any more!!!!
Very interesting. I didn't know the cofounder quit earlier. That's rough.
I empathize for the co-founder who was CTO and became CEO. I imagine some of the challenges come from the fact that there was a big chunk of equity owned by the original founding CEO. As the remaining co-founder, I can imagine feeling like I was climbing a grueling uphill battle to just get back to the most recent $300 million (!) valuation and a large amount of the upside of that battle was going to someone who abandoned me/the team. That said, I'm not privy to any equity adjustment that happened after the original founding CEO left.
That said, the after-the-fact communication feels lacking. It sounds like your CEO could have at least explained things in more detail after the fact (ie. Why he felt a pivot would be necessary to get to where the business needed to go.)
Such is life, I guess. I'm wishing you and the team the best for the future!
The title made me think this was an announcement by the company and it took me a minute to realize it was someone's personal experience there. I suspect the context of HN and the title confused me a little.
I do find commentary on the level of "interest" and behavior of various individuals interesting when it never mentions the actual fundamentals of the business (making any money?).
This underlines what a shame it is that we so rarely get to read postmortems on startups from people without a strong motivation — whether social or financial — to paint a rosy picture.
Related:
Airtable acquires Airplane - https://news.ycombinator.com/item?id=38861271 - Jan 2024 (158 comments)
I love posts like this. I wish more employees would share tales like this.
If the sole purpose was to get the CEO they could have just made him an offer he can't refuse, stick some other new CEO into airplane and call it good.
Would effectively be a risky, but free bet on a growing company.
Quite baffling that success is measured in how much you raise.
Company burned more money than it made and winded down, impact on customers have been ultimately negative.
Where's the success?
The success is in convincing the investors to give money.
The subsequent execution might or might be another success.
Sure, but wouldn’t users be hesitant to use Ravi and Joshua’s products in the future? Businesses depended on Airplane and even paid for the service so having the rug pulled from under them will leave a bad taste.
Airplane was a startup in a competitive market, it wasn't Google Reader shutting down. Anyone using it was an early adopter and in my experience, most early adopters understand the risk. Maybe it's possible that folks will be hesitant, but after multiple successful exits, maybe that's a hypothetical that won't matter any more, often founders move on to be advisors/board members, and I think any board would be lucky to have Ravi's experience on tap.
Such a founder perspective.
Here is another; they fucked over their customers. Didn't even open source it on the way out?! Nobody with a memory for this is going use their products without second thought in the future.
But peoples memories are short and a sucker is born every day.
Would a board be lucky to have Ravi on it? Sure, maybe. So their personal success is secured fuck their users; slow clap.
I'm an airplane user, and have already moved our tooling over to retool. Fuck over their customers? I'm sorry, but you have a choice in what tools you acquire, buy, and invest in, if you don't take into account that the company is small, new, and requires VC funding to exist, I just can't empathize with you if you are angry about it not working out. I use new software because it usually gives me access to the team in a way that lets me build with them and get features that a larger incumbent won't provide, but that doesn't mean it will make the company successful, and if they fail it sucks, but it's not like they are actively trying to hurt me.
There are so many reasons it's not easy or straight forward to open source the software of a startup that failed. I don't know what to tell you, I guess since I've only worked for startups I kind of understand what risks are involved when working with them, but there are also benefits, it's a trade off that you should be making when you're informed.
If you want stability, buy from a profitable and stable company that can pen multi-year contracts that include liability clauses, and if your company has the leverage, get source code/on prem written into your MSA.
All that said: please, don't use new software or tools, avoid startups and steer clear of emerging technology, you'll feel less betrayed.
*I'm not a founder, never have been a founder, and never could be a founder.
Yeah, I'm sorry you can't see that.
I'm guessing zero effort was made to continue service for existing customers. If there were efforts made that failed, they would have mentioned it for PR.
Doesn't change what happened.
Apparently you don't need to be to have a founder perspective.
"Fuck over" to me implies malicious intent, if it doesn't to you then that may explain why we have differing points of view.
How many startup founders have you worked closely with in your career when the company they ran was < 50 employees?
Early on, my business relied heavily on Zapier in 2015 and they were just as big as Airplane at that point. If they sold the company and shut it down, I would swear never to do business with the parent company again. Yes I could migrate to something else or just code it if that were to happen, but that is a fuck over.
Indifference can be malicious. Or at least it would qualify for fucking over the customers IMO. At least give them (and the employees) a bit more warning.
I suggest think bootstrapped alternatives. (Disclaimer we are one of them )
A shame that is what constitutes "success" in the business world today.
As far as I can tell that applies to neither Heap nor Benchling which were the companies OP cites as successes.
You are right I might have interpreted the message in a bad way.
It's a proxy for size of company, and often one of the two public ones (the other being the number of employees you can count on LinkedIn). It's not perfect, of course; there's always a Zapier which raises 1.3M and then grows sustainably. But for VC funded companies, this lets you compare them, if not perfectly.
I think everyone would agree that revenue, ARR, and profitability are all more important. But those metrics are rarely shared for private companies.
How does one take over a co-founder role? Is it a job title now? If he took over for you he didn’t actually found the company, right?
I’m not asking this sarcastically. Trying to understand how this works because I’ve always taken “co-founder” to mean “I was one of the people that started this company from day 1”
You can buy the "co-founder" title. That's how Elon Musk is associated with Tesla.
In this context, Ravi who became cofounder of Heap certainly didn't take that route. He was and is fantastic and if anything I'm surprised Airplane wasn't even more successful because of his involvement.
I don't have all the early context, but my understanding (vaguely) is that Heap went through two different incubators, and after one Ravi came on to be cofounder at YC where Heap raised its seed round.
The early stages of many companies are pretty nebulous as you're exploring different ideas/positioning and building the basics.
It's reasonable that someone joining <1 year in would be considered a co-founder if they had founder-level commitment.
How did I not know you were an original cofounder at Heap?
I was only there for a few months!
I was employee six and didn't know (though I did know there was a history to Heap before it joined YC and there was another cofounder, I just never knew/didn't dig into who)
Do you know how Heap is doing these days? I see many similarities to the article we're commenting on.
Heap was bought by ContentSquare late last year. Product is still around but I imagine they're working to consolidate the products.
"fairly big companies" != "amount raised"
The prospect of screwing over their customers and becoming an also-employee at Airtable is much better? Something isn't quite adding up.