What is too much is asking an Engineering Manager to start a completely independent product line that may go nowhere. It’s far more effective to rely on senior, staff+ engineers who don’t need management and have experience taking things from 0 to 1. They can build an MVP quick. Once we see real signals of PMF, we can then build a team around it (or drop it)
A CTO is a common title at medium and larger law firms, and an office of the CTO for that org sounds like a great idea.
But HN now is full of people completely removed from any kind of entrepreneurial mindset, people who aren’t “hackers” even in the most generous sense. They will not agree.
Keyboard warriors is probably the best descriptor of HN demo now.
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.
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.
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.
1. We aren’t going to sell.
2. Confiding with your spouse with clear concerns about current levels of stress and time commitment.
3. We can resolve a lot of the stress and sustainability problems by (among other things) raising another funding round!?
I did a double take…isn’t that just inviting more stress, more pressure from investors, more expectation to grow and exit?
I find it hard to relate to this C-suite life and logic, it seems so hyper-capitalist and backwards. There are so many oddly revealing bits of this piece that are like a window into the world of an alien being compared to my perspective.
It’s like Star Trek where there’s an alien race for every personality type and/or representation of a dominant emotion. The C-suite aliens would build their society around building products, meeting customers, finding takeaways, making org changes, etc. Societal enjoyment comes from work accomplishments, and the family decides that stress and time apart is worth it because work is “your baby.” Not really quite like the Ferengi because the Ferengi would have taken the 9 figure exit and dumped it into the next scheme.
Meanwhile the viewer is most familiar with the even-keeled baseline of the Federation where they used their technology to end capitalism and spend their time exploring the galaxy and prioritizing their family and friends. You end the episode with “I’m glad I kept an open mind but I still wouldn’t want to be the C-suite aliens, I like hanging out with the Federation.”
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'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.
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 ;)
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.
Not everthing bought with money is superficial. Certainly a lot is less superficial than dedicating your life to “in app payments made easy”. Turning down generational wealth so you can continue to pursue your dream of being a tech CEO seems like a wildly selfish decision to me. Just start a new company!
Also: plenty of meaning outside of running a SaaS. Hell, undergraduate research assistants probably contribute more to societal at large.
Buy freedom to chose what to do with your life. I've never sold a company and netted 9 figures but i have been lucky enough to work for a hedge fund and make enough that I and my family can do what ever we want from the age of 30 onwards.
That is an incredible amount of freedom and one that I wish most people would have.
You seem to think only in materialistic ways.
But having enough money to not have to work again allows you to be a better and more available parent. To be able to provide your kids and nieces and nephews with schooling to put them apart from other kids.
Its not always about owning another home, Just knowing that my kids are set for life before they start their own lives in case something happens to me was enough for me.
Lots of us think of others before ourselves.
Regain your own time. As a former CTO who has recently exited, recovering my own time again is more valuable to me than the money (although the money means I can retain my own time going forward).
> His life has meaning, he’s of value to his employees and customers and partners.
Your work is not you and if you think that way, you're gonna be crushed when you come to retire. Even though I loved what I did for a career, it's better to do what you love for yourself, not "employees and customers and partners". Many people have other interests outside of building tech, but even if building tech is your only thing, exiting is a chance at starting something fresh and on your own terms.
Did his life not have meaning before he started this company?
Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me.
F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
Speaking as a co-founder CTO, I believe there is a very insidious kind of attachment that forms when you’re dancing with burnout, and working on a successful company that you’ve built from the ground up.
“I want to leave a dent in the universe” I told myself. After 3 months in a hammock decompressing, I very quickly realized that there is more to life than work, and it’s really easy to find fulfillment building things if you get bored. But this viewpoint is really hard to hold onto when you’re buried in the day to day excitement of the job.
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.
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.
This is easier said than done.
The founders of many startups are extremely charismatic. They can get you to sacrifice your personal / family life and work long hours by dangling the big pay day in front of you.
The second startup I worked at let the first 8 employees buy into the company for Class A shares. These in theory were worth more than the Class B shares I was given. This later led to some marital issues when one guy invested $100K into the startup based on the founder taking everyone out to dinner and assuring the wives it was a great idea. Then 3 years later they have turned down 2 possible sales, no exit plan in site, and that $100K would have been useful for the children's tuition who are about to go to college.
I write these posts are warnings to people who get excited about the appeal of working for a startup.
So I would really love to hear the author talk about what his employees thought about turning down the deal and how much money they would have got.
It isn’t reasonable to expect the founders to do an employee’s bidding when it comes to selling a company, but it is reasonable for the employees to feel emotionally invested.
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-...
If anything, it's an endorsement of M&A.
Once you take outside funding, you really have no choice but an acquisition or go public. VCs don’t want to get tiny dividend checks. Even public shareholders will insist on a sale at the right price
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?
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.
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...
Even with such a golden ticket ride to the heavens? You could do anything, focus on your family and build your little castle or depersonalize even, change countries, change your identity, make new connections, live a completely different life...
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.
