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.
> - 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.
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".
so many companies raised on sky high evaluations in the '21-'22 vintage, that its going to be a tough ask to keep going now the market has reset and valuations returned to the mean.
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.
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.
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.
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.
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”
> 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.
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!
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.
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.
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.
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.
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?
> 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.
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
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.
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.
> 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.
> 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.
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.
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.
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.
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.
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?).
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?
[+] [-] peterldowns|2 years ago|reply
- 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.
[+] [-] danenania|2 years ago|reply
It’s important to understand who is actually in charge before assigning blame to anyone.
[+] [-] dustingetz|2 years ago|reply
[+] [-] jerrygenser|2 years ago|reply
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.
[+] [-] fishnchips|2 years ago|reply
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".
[+] [-] 1290cc|2 years ago|reply
so many companies raised on sky high evaluations in the '21-'22 vintage, that its going to be a tough ask to keep going now the market has reset and valuations returned to the mean.
[+] [-] rubenfiszel|2 years ago|reply
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.
[+] [-] jeremyjh|2 years ago|reply
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.
[+] [-] gzapp|2 years ago|reply
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.
[+] [-] joeblubaugh|2 years ago|reply
[+] [-] cx42net|2 years ago|reply
[+] [-] mgummelt|2 years ago|reply
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.
[+] [-] epolanski|2 years ago|reply
Company burned more money than it made and winded down, impact on customers have been ultimately negative.
Where's the success?
[+] [-] SmellTheGlove|2 years ago|reply
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”
[+] [-] Rapzid|2 years ago|reply
[+] [-] vasco|2 years ago|reply
[+] [-] typeofhuman|2 years ago|reply
[+] [-] rmnoon|2 years ago|reply
[+] [-] rdtsc|2 years ago|reply
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.
[+] [-] siliconwrath|2 years ago|reply
It's an apt metaphor.
[+] [-] throwaway632|2 years ago|reply
[+] [-] gkapur|2 years ago|reply
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!
[+] [-] rbranson|2 years ago|reply
[+] [-] LewisJEllis|2 years ago|reply
When we heard Airplane was shutting down, everyone's first thought was "can we hire that Yolken guy?"
[+] [-] pritambarhate|2 years ago|reply
[+] [-] arcanemachiner|2 years ago|reply
Open source may be safer than proprietary software in that regard, but it's still not a guarantee. Still far preferable IMO.
[+] [-] gherkinnn|2 years ago|reply
[+] [-] ilrwbwrkhv|2 years ago|reply
[+] [-] Rapzid|2 years ago|reply
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?
[+] [-] hobofan|2 years ago|reply
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.
[+] [-] semanticc|2 years ago|reply
[+] [-] oliyoung|2 years ago|reply
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.
[+] [-] necubi|2 years ago|reply
But so long as you sell for less than your total raise, common shares will be worth nothing even with liquidation preferences of 1x.
[+] [-] gnicholas|2 years ago|reply
> 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.
[+] [-] pm90|2 years ago|reply
[+] [-] mring33621|2 years ago|reply
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
[+] [-] Eridrus|2 years ago|reply
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.
[+] [-] solatic|2 years ago|reply
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.
[+] [-] amerine|2 years ago|reply
[+] [-] stevage|2 years ago|reply
[+] [-] tshaddox|2 years ago|reply
That's a layoff, right?
[+] [-] joeblubaugh|2 years ago|reply
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.
[+] [-] motleyfool|2 years ago|reply
[+] [-] dcre|2 years ago|reply
[+] [-] dang|2 years ago|reply
Airtable acquires Airplane - https://news.ycombinator.com/item?id=38861271 - Jan 2024 (158 comments)
[+] [-] tommoor|2 years ago|reply
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.
[+] [-] submitedit|2 years ago|reply
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.
[+] [-] duxup|2 years ago|reply
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?).
[+] [-] czhu12|2 years ago|reply
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?