I’m a big fan of the idea of an Office of the CTO group reporting directly to the CTO that helps with prototyping greenfield projects and exploring innovative ideas. I believe a group like this would be beneficial for larger organizations, like the one I work in. There are numerous opportunities for market disruption, but it becomes increasingly challenging to make bold bets as the company expands. If I had the power to do so, I’d set this up at my company asap.
If that group is necessary then it's a damning indictment of the product/engineering culture. The CTO's job should be to fix the broken culture, not try to side-step it.
Nokia had exactly this kind of CTO office during the 2005 - 2012 years when they lost the entire smartphone market.
The CTO fiddled with greenfield projects that had no path to products while the house burned down.
The best that can be said about it is that inventions outside of the product helped beef up Nokia’s patent portfolio, which played a role in the company surviving the post-phone years and transforming into a pure network company. But they lost a trillion-dollar opportunity and shrunk into an average B2B enterprise.
Traditionally that was R&D and its own department.
Having a CTO pet group isn’t the best use of the CTOs time. If you want to have better architecture and explore greenfield projects, you need an organization that supports R&D through cross functional groups.
A CTO should NOT be doing greenfield projects. A CTO should be setting technical vision and strategy for the entire company.
The wild part to me isn’t 9 figures is good/bad, it’s that in year 8 the company still has a single human as the default DRI for culture, zero‑to‑one work, and existential decisions. If you’re going to turn down generational wealth, the least responsible version is keeping everything psychologically and operationally coupled to you; the grown‑up move is making yourself cheap to replace and designing a succession plan you’d actually be willing to trigger on bad news, not just a term sheet
That was the whole point of writing this series: to show how my role evolves and what I’ve had to give up. Trust me, if it were up to me, I’d still be having fun coding (even more so these days). There’s an entire section on delegation in this year’s post.
I’m not the single DRI for culture at all. We have many strong culture carriers, which has made scaling to 100 people much easier than scaling to 20. That said, culture is still one of the core responsibilities of founders, in my opinion.
Also, OCTO isn’t about me wanting to innovate. It’s about giving certain engineers permission to not be tied to a roadmap and to stay fluid.
That's never quite how it happens, they can't let go. You can see it in the "Office of the CTO" thing. I've seen that one many times before: when confronted with the endless complexity and depth of building a real global product, they recoil. Everything takes too long, is too uninteresting. They instead build up this parallel engineering organization that is showered with money, headcount and C-level attention to build the new moonshots, with the subtext that whenever it's "ready", it will be thrown over the wall to the actual engineering org.
It's a speedrun to make your engineering talent leave.
I’m curious what kind of secondary sale happened? What is normal these days? Is it $5m $10m? Is that excluded from the $50m raised or comes out of that amount. Thanks!
Unless he's pulling a lot of cash out every year it seems unwise to not sell. He can then just go create something highly similar, bankroll it as much as he wants, but still have the back stop of vast wealth on case of failure.
Good read. I had an offer for a mere 7 figures and that was hard enough to turn down. I couldn't imagine 9 figures! But I think I do get it, at least as much as I can get it at my level. It's hard to give up something you've poured so much of your life into -- "your baby." You lose the autonomy to continue shaping what independence looks like for yourself, or at least it felt that way to me.
Working 8 years to get to more than 100,000,000 $ and saying no to that...Maybe I'm just too poor to understand that.
Sure, this is hackernews, so the hustle mindset is stronger here, but the difference you could make in others people lives just with 10 % of that...
I mean, you could house, feed or educate people and you chose to...not do that ? To have more ? Is there a endgame you are not sharing with us, a special number that would make it OK to sell ?
I kind of want to be a CTO somewhere. So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself.
Same, I am looking forward to starting my own company in the next year or two, and exploring the CTO role, especially after so many years as a Staff+ operating as an arm of CTOs and learning the ropes.
Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?
All you find is stuff, presented as super valuable, and people very very keen to sell it to you. They’ll do whatever you want. It attracts a certain kind of person. The people who have the means for this lifestyle seem mostly disappointed.
It’s not the situation this guy has created for himself. His life has meaning, he’s of value to his employees and customers and partners.
I feel RevenueCat is on shaky ground, their market position can only get worse and worse as Apple and Google improve their complimentary offerings and they are forced into more A/B testing that directly competes with others. Recent StoreKit changes this year close a lot of the remaining gap. I would have sold. I wonder why they chose not to.
I’d take the money, spend time with family (he mentioned toddler) and then figure out what to do next. Retiring isn’t everyone’s dream but at least having generational wealth is a big relief.
The secondary provided that relief. Continuing to work on the company makes perfect sense if you enjoy it, which he clearly does (with the inescapable ups and downs of every start up of course).
you can take the money... and then continue to work. Nothing says you have to retire- I would have taken the money and figured out what's next! Not to mention that hopefully you've given shared ownership with your other early employees, who can also then at least have the opportunity for their own liquidity event.
Honestly, I respect the commitment. It's almost certainly a bad decision, but a founder that can turn down a 9 figure exit at the tail end of a tech bubble he's right in the middle of, has a good chance at having the right mindset to build a great company and survive the collapse. There's a good chance he regrets this for the rest of his life, but you can't argue that he wasn't a true believer or is a sellout.
I had never heard of the company RevenueCat. It looks like a system for mobile app developers to make in app purchases. A few Internet sources say that RevenueCat has about 120 employees. I'm in a completely different field so I'm not going to claim to understand all of that but I have worked for 2 startups.
The author talks about himself and his co-founder Jacob and they went back and forth on whether to sell or not.
I am very interested in what the other 118 employees thought. Did they want the co-founders to sell? What was their equity in the company? What kind of deal would they get? Accelerated vesting? Much larger than normal RSU stock grant at the acquiring company compared to a normal new hire there? Nothing?
I post this link in many threads about startups about how the normal employees often get nothing. The author says "So we decided to raise another round" and I wonder if the co-founders share the liquidation preferences and captables with the other 118 employees.
I posted this comment in a different startup related thread last month but I really wish the CEOs of both startups would have accepted these lower offers.
I don't know what the captable was at the first startup but at the second I would have got around $300K. This would have been a large amount of money for me but the founders wanted more so they rejected the offer.
Almost every "normal" level employee thought we should have taken the deal and then we would have also gotten jobs with normal RSU grants and bonuses at the acquiring company which was a well established company.
It made me decide to never work at a startup again. I don't want a single person to be able to control my financial situation that much. I'd rather have the relatively guaranteed yearly raise, bonus, and RSU grant, and not have to drink the Kool-Aid of the founders.
> I worked at 2 startups. Both failed.
> The first had been around for about 4 years when I joined and had products that made money. They were trying to get acquired. They had partnered with 2 companies making products specifically for them. One of them offered to buy the company for $30 million but the founders thought their company was worth $300 million. They said no and then money started to run out and people started leaving. In the end the assets were sold for $2 million.
> The second startup was created by former coworkers and I joined after it had existed for 4 months. We worked like crazy for the first year and got our prototype out. We had a lot of interest but it took me a while to realize that the 3 founders already had net worths from $5 million to billionaire level. When I heard about offers in the $30 million range they just weren't interested in selling for so little. I left after 3 years and the company floundered another 2 years until they shut it down as people left.
Saying you want to control your company and you want to be around 10 years and then raising VC funding is either naive or dishonest.
VCs aren’t interested in a lifestyle business throwing them maybe a small dividend and a miniscule number of companies go public. Look at YC, they have invested in thousands of companies and only around 20 have gone public and only 3 have had positive returns since going public
tl;dr - delusional founder writes AI slop reflection narrative recast as “vision” and “conviction.”
Makes more sense given a. prototypical cto ego (and insecurity) amplified by b. he’s Spanish (ifyyk)
Thousands of words to justify the rejection of a nine-figure exit and he never seriously addresses what the exit would mean for employees or investors. “I’m a builder,” “I need to work with inspiring people,” “I’d be bored after two weeks.”
Hard to ignore the glaring contradictions amidst the AI slop. He sets “networking with executives” as a top annual goal, then says “networking is mostly bullshit.” He calls out two separate “biggest fires” for the year: first, reliability/support issues; later, hiring velocity.
On one hand he’s bragging about “not having to do anything,” but takes credit for every success (“my foundation-building,” “org design I set up,” etc).
Median senior engineering salaries in Spain are a fraction of those in the U.S. - you can take the founder out of spain…but you can’t…
And yet, the “nine-figure” rejection is repeated over and over. If it was such an easy, confident choice, why does it need so much explanation? Can’t wait to read more about CTO insecurity and a need for public validation. What’s Lemkin got to say?
Why this industry has such a claustrophobic atmosphere? If he was a doctor and had a calling for the profession, I would understand. I was doing an unrelated degree (Econ), but now I am doing a tech degree and I never saw such a depressive mentality towards life among peers.
It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen.
> It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen.
This is a founder/CTO. You don't get to be a founder or C-level without making work a lot more of your life than just a 9-5.
As much as people complain about the C-suite not doing anything and spending all their time golfing, they're basically on work mode 24/7. I've never worked with a C-level who didn't check emails on the weekend, wasn't willing to travel at a moment's notice to close a deal, not willing to work to resolve business or tech emergencies at 1am, etc.
On top of that they always represent the company, even in their off time. Stuff that wouldn't matter for a regular employee might lead to termination or forced resignation. For example, kissing a woman who isn't your wife at a concert.[0]
This is all true even outside of tech. Ever talk to someone who owns a restaurant? They spend weekends and nights talking to suppliers, figuring out staffing, etc...
This doesn't represent typical non-executive jobs in the software industry. Most are largely 9-5. The ones with oncall expectations tend to pay more.
There is a real mentality in many of the teams I've worked with that the "grind", "sacrifice", as the pound of flesh that must be offered up for success.
In reality it's far different. We need to make something of value and charge fairly for that value.
Teams can do this without the grind, and still be wildly successful. Teams can do the grind only and are typically not.
It's a false idol, and a lot of folks in the industry only have this to look up to so they don't know better.
It's because those of us doing the opposite, getting there with balance, aren't writing career focused articles around the holidays. Virtue signaling our work ethic. We're spending time with ourselves, our families, quietly succeeding.
cebert|2 months ago
phpnode|2 months ago
pavlov|2 months ago
The CTO fiddled with greenfield projects that had no path to products while the house burned down.
The best that can be said about it is that inventions outside of the product helped beef up Nokia’s patent portfolio, which played a role in the company surviving the post-phone years and transforming into a pure network company. But they lost a trillion-dollar opportunity and shrunk into an average B2B enterprise.
nickelbob|2 months ago
reactordev|2 months ago
Having a CTO pet group isn’t the best use of the CTOs time. If you want to have better architecture and explore greenfield projects, you need an organization that supports R&D through cross functional groups.
A CTO should NOT be doing greenfield projects. A CTO should be setting technical vision and strategy for the entire company.
Seattle3503|2 months ago
orliesaurus|2 months ago
elwatto|2 months ago
I’m not the single DRI for culture at all. We have many strong culture carriers, which has made scaling to 100 people much easier than scaling to 20. That said, culture is still one of the core responsibilities of founders, in my opinion.
Also, OCTO isn’t about me wanting to innovate. It’s about giving certain engineers permission to not be tied to a roadmap and to stay fluid.
stefan_|2 months ago
throw03172019|2 months ago
IncreasePosts|2 months ago
unknown|2 months ago
[deleted]
ezekg|2 months ago
Geste|2 months ago
I mean, you could house, feed or educate people and you chose to...not do that ? To have more ? Is there a endgame you are not sharing with us, a special number that would make it OK to sell ?
Sparkyte|2 months ago
throw-12-16|2 months ago
I've been the CTO twice in my career, and am in a pure engineering role now and get a lot more satisfaction out of my job.
RamblingCTO|2 months ago
How so? I think it's possible. Network, linkedin etc. And in startups it's not that bureaucratic in my experience. I think you can achieve that ;)
vinnymac|2 months ago
MagicMoonlight|2 months ago
elwatto|2 months ago
fourseventy|2 months ago
asah|2 months ago
riazrizvi|2 months ago
All you find is stuff, presented as super valuable, and people very very keen to sell it to you. They’ll do whatever you want. It attracts a certain kind of person. The people who have the means for this lifestyle seem mostly disappointed.
It’s not the situation this guy has created for himself. His life has meaning, he’s of value to his employees and customers and partners.
harmonic18374|2 months ago
DANmode|2 months ago
throw03172019|2 months ago
ridruejo|2 months ago
ipython|2 months ago
jimbo808|2 months ago
lizknope|2 months ago
The author talks about himself and his co-founder Jacob and they went back and forth on whether to sell or not.
I am very interested in what the other 118 employees thought. Did they want the co-founders to sell? What was their equity in the company? What kind of deal would they get? Accelerated vesting? Much larger than normal RSU stock grant at the acquiring company compared to a normal new hire there? Nothing?
I post this link in many threads about startups about how the normal employees often get nothing. The author says "So we decided to raise another round" and I wonder if the co-founders share the liquidation preferences and captables with the other 118 employees.
https://www.reddit.com/r/startups/comments/a8f6xz/why_didnt_...
I posted this comment in a different startup related thread last month but I really wish the CEOs of both startups would have accepted these lower offers.
I don't know what the captable was at the first startup but at the second I would have got around $300K. This would have been a large amount of money for me but the founders wanted more so they rejected the offer.
Almost every "normal" level employee thought we should have taken the deal and then we would have also gotten jobs with normal RSU grants and bonuses at the acquiring company which was a well established company.
It made me decide to never work at a startup again. I don't want a single person to be able to control my financial situation that much. I'd rather have the relatively guaranteed yearly raise, bonus, and RSU grant, and not have to drink the Kool-Aid of the founders.
> I worked at 2 startups. Both failed.
> The first had been around for about 4 years when I joined and had products that made money. They were trying to get acquired. They had partnered with 2 companies making products specifically for them. One of them offered to buy the company for $30 million but the founders thought their company was worth $300 million. They said no and then money started to run out and people started leaving. In the end the assets were sold for $2 million.
> The second startup was created by former coworkers and I joined after it had existed for 4 months. We worked like crazy for the first year and got our prototype out. We had a lot of interest but it took me a while to realize that the 3 founders already had net worths from $5 million to billionaire level. When I heard about offers in the $30 million range they just weren't interested in selling for so little. I left after 3 years and the company floundered another 2 years until they shut it down as people left.
moomoo11|2 months ago
Don’t take it so personally. I did once too.
If the employees think they know better, there’s nothing stopping them from starting their own businesses and destroying their boss.
raw_anon_1111|2 months ago
VCs aren’t interested in a lifestyle business throwing them maybe a small dividend and a miniscule number of companies go public. Look at YC, they have invested in thousands of companies and only around 20 have gone public and only 3 have had positive returns since going public
https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-...
airstrike|2 months ago
If anything, it's an endorsement of M&A.
Lionga|2 months ago
adiazyc|2 months ago
[deleted]
OGEnthusiast|2 months ago
__turbobrew__|2 months ago
[deleted]
adiazyc|2 months ago
tl;dr - delusional founder writes AI slop reflection narrative recast as “vision” and “conviction.”
Makes more sense given a. prototypical cto ego (and insecurity) amplified by b. he’s Spanish (ifyyk)
Thousands of words to justify the rejection of a nine-figure exit and he never seriously addresses what the exit would mean for employees or investors. “I’m a builder,” “I need to work with inspiring people,” “I’d be bored after two weeks.”
Hard to ignore the glaring contradictions amidst the AI slop. He sets “networking with executives” as a top annual goal, then says “networking is mostly bullshit.” He calls out two separate “biggest fires” for the year: first, reliability/support issues; later, hiring velocity. On one hand he’s bragging about “not having to do anything,” but takes credit for every success (“my foundation-building,” “org design I set up,” etc).
Median senior engineering salaries in Spain are a fraction of those in the U.S. - you can take the founder out of spain…but you can’t…
And yet, the “nine-figure” rejection is repeated over and over. If it was such an easy, confident choice, why does it need so much explanation? Can’t wait to read more about CTO insecurity and a need for public validation. What’s Lemkin got to say?
cityzen|2 months ago
[deleted]
weslleyskah|2 months ago
It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen.
Honestly disgracefully.
mjr00|2 months ago
This is a founder/CTO. You don't get to be a founder or C-level without making work a lot more of your life than just a 9-5.
As much as people complain about the C-suite not doing anything and spending all their time golfing, they're basically on work mode 24/7. I've never worked with a C-level who didn't check emails on the weekend, wasn't willing to travel at a moment's notice to close a deal, not willing to work to resolve business or tech emergencies at 1am, etc.
On top of that they always represent the company, even in their off time. Stuff that wouldn't matter for a regular employee might lead to termination or forced resignation. For example, kissing a woman who isn't your wife at a concert.[0]
This is all true even outside of tech. Ever talk to someone who owns a restaurant? They spend weekends and nights talking to suppliers, figuring out staffing, etc...
This doesn't represent typical non-executive jobs in the software industry. Most are largely 9-5. The ones with oncall expectations tend to pay more.
[0] https://www.cnn.com/2025/07/19/business/andy-byron-astronome...
iancmceachern|2 months ago
There is a real mentality in many of the teams I've worked with that the "grind", "sacrifice", as the pound of flesh that must be offered up for success.
In reality it's far different. We need to make something of value and charge fairly for that value.
Teams can do this without the grind, and still be wildly successful. Teams can do the grind only and are typically not.
It's a false idol, and a lot of folks in the industry only have this to look up to so they don't know better.
It's because those of us doing the opposite, getting there with balance, aren't writing career focused articles around the holidays. Virtue signaling our work ethic. We're spending time with ourselves, our families, quietly succeeding.
unknown|2 months ago
[deleted]
farceSpherule|2 months ago
[deleted]
themanmaran|2 months ago
farceSpherule|2 months ago
[deleted]