My role as a founder-CTO: year 8

1/1/2026 at 12:25:55 AM

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.

by cebert

1/1/2026 at 2:50:53 AM

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.

by phpnode

1/1/2026 at 6:24:07 AM

Hard disagree. Culture isn’t the problem, org structure is. You can call it an experiment or even a hack. Every team is already innovating within their scope, and splitting becomes easier as that scope grows.

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)

by elwatto

1/1/2026 at 4:16:23 AM

Not every company is a product/engineering company.

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.

by TOMDM

1/1/2026 at 7:14:35 AM

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.

by pavlov

1/1/2026 at 7:37:06 AM

well you say that, but blackberry did exactly what you're saying Nokia should have done and we see how much that helped. Truth is iPhone was so far ahead technologically, no other company had a chance. At least Nokia still exists today, which can't be said about majority of other mobile phone manufacturers of that era.

by Yiin

1/1/2026 at 7:34:55 PM

Yes, but it wasn't iPhone that ate their markets, it was Android. Nokia and Blackberry were both at the top because they had their own operating systems, and while they were losing the high end market to iPhone, they would've kept the middle and low end markets where the volume was.

Android changed all that, all of the sudden all their competitors got a good OS for free. Commoditize your complement, Google took their markets.

by distances

1/1/2026 at 1:45:47 AM

Shouldn't this live under the VP of Product?

by nickelbob

1/1/2026 at 2:30:37 AM

That’s a good point. Perhaps where this group lives depends on your organization. Unfortunately, the innovative ideas aren’t necessarily coming from product where I work.

by cebert

1/1/2026 at 6:29:21 AM

No, product shouldn't be the head of an engineering team.

by charlie0

1/1/2026 at 4:56:04 PM

Should engineers be pushing product forward?

by nickelbob

1/1/2026 at 7:12:49 AM

So you're argueing "prototyping greenfield projects and exploring innovative ideas" is something that should come solely out of engineering with no Product input?

by ulfw

1/1/2026 at 4:53:59 PM

That's not what I'm saying. There needs to be a collaboration with product ofc, product shouldn't be the boss though.

by charlie0

1/1/2026 at 4:12:45 PM

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.

by reactordev

1/1/2026 at 8:52:46 AM

Cloudflare has an org whose job it is to do this sort of stuff.

by Seattle3503

12/31/2025 at 8:48:52 PM

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

by orliesaurus

12/31/2025 at 10:53:26 PM

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.

by elwatto

1/1/2026 at 5:22:15 AM

The odd part of this journey to me was basically:

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.”

by dangus

1/1/2026 at 6:35:31 AM

Maybe we are wired differently, but as I wrote in the final part, I’m actually more motivated and see myself going much longer (which is what investors want, as long as there’s growth). It’s linked in the post, but a big part of the round was secondary, which helped reduce financial stress for founders and early employees.

by elwatto

1/1/2026 at 2:53:53 PM

Yes, wired very differently. I think that’s why I used the Star Trek analogy.

This motivation is like a strange curiosity to me. This pursuit of product is so foreign to me, and from the outside it doesn’t seem healthy. But I guess if the Klingon like going into glorious battles to the death better than chilling at home with their family, who am I to question their motivation?

I build stuff at work because it’s a financial obligation, because it’s better than cleaning bathrooms or waiting tables for a living. If I had some kind of better option for paying my bills with less labor involved I’d take it in a heartbeat.

by dangus

1/1/2026 at 8:58:24 AM

I felt the same as you - turned down several acquisition offers, the company was my baby, etc.

Year ten, my partner turned around and stuck a knife in my back, and I found myself railroaded out and battered into submission by lawyers. Exited with token equity, and a small cash payment to get me to fuck off so they could gut the company.

Retrospectively, I should have quit while I was ahead, and I should have realised that while I cared about the company, it did not care about me.

Also, cofounders… you never find out who they actually are until one night you hear the click of the hammer of the gun against your head cocking.

by madaxe_again

1/1/2026 at 6:34:28 AM

raising the round is them selling part of the company. enough of the company that they no longer ever have to worry about money again. yeah that removes a lot of potential stress. the company can fail now and it won't ruin him. gives him more freedom to keep building.

by clarky07

1/1/2026 at 2:46:54 PM

“more freedom to keep building”

This is the disconnect to me. This phrase has tech industry cult vibes to me.

I don’t see “freedom” and “building” as words that mesh together.

I see “building” as something I’m obligated to do to pay my bills. I do it because it’s preferable to other forms of labor. As soon as I have the financial means to stop doing it, I’m out.

by dangus

12/31/2025 at 9:00:06 PM

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.

by stefan_

12/31/2025 at 10:11:33 PM

Oh wow you just described our last CTO to a T.

by throwway120385

12/31/2025 at 11:25:27 PM

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!

by throw03172019

1/1/2026 at 6:58:31 PM

This guy is going to end up offing himself when the company slowly goes to zero and he could have had 400 million.

by MagicMoonlight

1/1/2026 at 7:32:09 PM

I wouldn’t have had 400M. But I am fine.

by elwatto

12/31/2025 at 10:23:20 PM

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.

by ezekg

1/1/2026 at 9:29:08 PM

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 ?

by Geste

1/1/2026 at 6:03:05 AM

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.

by Sparkyte

1/1/2026 at 3:41:44 PM

> So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself.

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 ;)

by RamblingCTO

1/1/2026 at 11:50:13 PM

Would need to know a startup.

by Sparkyte

1/1/2026 at 6:30:15 AM

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.

by vinnymac

1/1/2026 at 6:51:50 AM

Check out the earlier posts in the series. They’re probably more relevant for that stage. What I’ve learned over the years is that the CTO role varies a lot depending on the company and personal context. I just tried to share my journey.

by elwatto

1/1/2026 at 7:39:57 AM

If you enjoy building its kind of a pain in the ass.

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.

by throw-12-16

1/2/2026 at 12:03:45 AM

I think the problem I see with every place I have been is a lot bad practices. As a CTO I could guide people out of those bad practices. I love engineering too, but every place I have been as of late has been a squeeze on workers and always a lack of focus.

by Sparkyte

1/1/2026 at 8:29:12 PM

Building is so much fun, probably my #1 favorite thing to do, but a bad company culture can ruin it. I love being a CTO so I can build and set the culture that keeps it fun.

by calderwoodra

1/2/2026 at 12:04:53 AM

I like that a lot.

by Sparkyte

12/31/2025 at 10:33:23 PM

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.

by IncreasePosts

12/31/2025 at 7:33:19 PM

Unless you are already worth billions if an exit would net you 9 figures its a no-brainer to sell.

by fourseventy

12/31/2025 at 8:40:56 PM

almost: just cut a deal to allow partial liquidity, ideally via a vehicle that avoids tax events, e.g. loan

by asah

1/1/2026 at 9:36:15 PM

Can you expand on this please?

by objektif

12/31/2025 at 8:15:33 PM

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.

by riazrizvi

12/31/2025 at 8:31:11 PM

So that you have security for the rest of your life and your children have security for the rest of theirs. And likely their children as well.

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!

by afavour

12/31/2025 at 8:43:41 PM

I know from the outside this seems very simple, but it's more complicated than that. Certainly, if the objective is (merely) security for one's children, that can be secured with much (much) less money (and likely was secured in the secondary that the author makes reference to); having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated. To appreciate this dynamic, read Graeme Wood's outstanding 2011 piece in The Atlantic, "The Secret Fears of the Super-Rich"[0].

[0] https://web.archive.org/web/20190422235813/https://www.theat...

by bcantrill

12/31/2025 at 8:53:19 PM

> having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated

Sure, but I’m pretty sure if you asked those parents if they’d rather lose all their money to make parenting easier their answer would be a resounding “no”.

by afavour

12/31/2025 at 9:16:58 PM

Those aren't the choices. You don't understand how the poster passed on nine figures -- but if the secondary sale netted 7 figures (likely), the choice is in fact between having enough wealth to have total security for one's family versus having so much wealth that the wealth itself creates anxiety.

by bcantrill

12/31/2025 at 9:27:42 PM

Then have someone manage the money away from you. Put it in a lifetime trust, whatever. The idea that you’d turn down that sum of money because of the anxiety it would cause you is simply not logical.

by afavour

12/31/2025 at 10:02:22 PM

Correct. The secondary provides the safety net to confidently swing for the fences.

by ridruejo

1/1/2026 at 1:10:04 AM

You forgot to account for the 100+ employees. The liquidity event would have helped their families as well.

by j7ake

1/1/2026 at 6:27:50 AM

I won’t disclose details out of respect for the other party, but no, not necessarily. As I wrote, it was a good deal for the founders and some investors, but not for everyone, including employees. There are many ways to structure a sale, and unfortunately not all of them split the cake equally.

by elwatto

1/1/2026 at 5:25:23 PM

At 9 figures I’m sure the founder can trickle down a few for everyone including employers after the sale.

by j7ake

12/31/2025 at 8:37:15 PM

I just don't understand the mentality of the author. 9 figures is generational wealth, potentially perpetually with good multi-generational money management plan. With that kind of money invested, you have beaten the game, and can literally do any side quest you want to do, forever. This is the biggest no-brainer ever. What the fuck are you waiting for?

Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want and yet you voluntarily continue to amass more?

by ryandrake

12/31/2025 at 10:23:06 PM

> Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want

Has it occurred to you that perhaps what they want is to be the CxO of a big tech company? There’s a lot of power, prestige, and impact on society that you can’t easily have if you quit. Maybe they really enjoy the work itself too.

by jonas21

1/1/2026 at 9:37:28 PM

Yeah what he is not understanding is they are already doing what they wanted in life.

by objektif

12/31/2025 at 10:35:24 PM

You can just say "sociopath", it's faster.

by scubbo

12/31/2025 at 10:30:19 PM

Because it's genuinely not about the money for them. It's hard to believe, but some people really do want to make the world better in their way, with whatever tools they have that their disposal.

by fragmede

1/1/2026 at 2:16:55 PM

Wanting power usually has little to do with making the world better.

by p1esk

12/31/2025 at 10:36:55 PM

Companies do not make the world better.

by scubbo

1/1/2026 at 10:51:34 AM

The company that made my robot vacuum cleaner definitely made my world better.

by skrebbel

1/1/2026 at 5:21:38 PM

No, your robot vaccuum cleaner itself made _your_ life better. The _company_ made _the_ world worse, by over-charging, exploiting, and polluting. The fact that they happened to create a product that you personally enjoy does not negate the overall negative effect.

by scubbo

1/1/2026 at 6:24:29 PM

If the consumer thinks of himself as the center of the world, The Main Character so to speak, then the robot vacuum cleaner "made the world better."

by ryandrake

12/31/2025 at 11:24:38 PM

The Kool Aid is strong, remember this is the forum of an incubator. One has to believe to drink the whole cup.

by stoneforger

12/31/2025 at 8:40:45 PM

Anyone can have security by living very safely within their means, by learning how to be satisfied. What people really mean when they say what you are proposing, is “guarantee a certain future lifestyle”. But the appeal of future lifestyles depends on not obtaining them. Without an ability to be satisfied, acquisition is always disappointing. It’s why a pay raise in a job that doesn’t address your needs, loses its shine after a month or so.

by riazrizvi

12/31/2025 at 8:43:42 PM

As someone who has experienced family adversity in my life (health, disability) I couldn’t disagree with you more.

Things happen. Expensive things. The security to be able to afford expansive cancer care without worry, to pay for therapy and specialized schooling for your child… these are huge, huge things and they happen to you (or your children, or your children’s children) no matter what you do or don’t do. This isn’t just about being happy to be frugal.

by afavour

12/31/2025 at 8:59:07 PM

Things happen, it’s true. And in the world there are many enterprises that spring up to present solutions as long as you fork over all your cash, and here in the USA, based on the market, that means lots and lots of cash.

That’s just a perspective on hardship, it’s not the only way. People deal with hardships with many many tools. My favorite tools are dignity, grace, courage, personal strength, and ingenuity. Money is another tool, yes, but it tends to prevent mastery of the others.

Elsewhere in the comments there was talk about legacy. You can give your kids a bank account, and the examples that you had money to pay off problems. Or you can give them something else through your example. I choose the latter.

by riazrizvi

12/31/2025 at 9:17:38 PM

With respect, those words feel very empty. Face the prospect of, say, chemotherapy you can’t afford or death. See how you feel about dignity and grace then.

by afavour

1/1/2026 at 7:55:57 AM

We're deep in a thread questioning a founder's choice not to sell their company. a) The company is 8 years old, b) the founder's stake is 9 figures, and c) they've done at least one secondary, meaning d) the founder has almost certainly cashed out $10m exempt from federal taxes (founder has held shares > 5 years for QSBS treatment, and $10m < 10% of founder's stake, a common threshold of concern for investors).

Your hypotheticals simply aren't relevant here.

by FreakLegion

12/31/2025 at 11:27:00 PM

So people who can't afford a broken system cannot afford dignity or grace? We should be ashamed we allow this kind of collective paranoia.

by stoneforger

1/1/2026 at 2:21:46 AM

If he had children, the decision would have been influenced by that. So that was my first guess, he probably has no kids.

Will accept, I have no idea about his personal situation. Also feel the HN crowd may downvote my comment because it is not phrased correctly.

by rapidfl

12/31/2025 at 8:21:41 PM

I’m sure there are many other more meaningful options, none of which start with the word “buy”.

by dmacj

12/31/2025 at 8:27:25 PM

But then money has nothing at all to do with such options.

by trollbridge

12/31/2025 at 8:36:05 PM

> Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?

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.

by chollida1

12/31/2025 at 8:30:40 PM

you're seriously lacking in imagination if all you can think of is that.

by websiteapi

12/31/2025 at 8:39:49 PM

> Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?

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.

by louthy

12/31/2025 at 8:53:32 PM

You can live in the heart of San Francisco on $2k/mo, including rent. You don’t need to work 10hours a week as a software developer, to support that lifestyle.

I could fit a solar system in the gap between your two options of a) full time CTO or b) 9 figures to ‘win back your time’.

Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.

by riazrizvi

12/31/2025 at 9:01:02 PM

> Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.

You have no idea about me at all, so please don't insult me by thinking that you do.

by louthy

12/31/2025 at 10:15:54 PM

Bro, what? $2k? I just double checked and everything available for less than $2k is awful if you care about, IDK, having a family, a pet, a kitchen, outdoor space, green space, not having to share everything, including peace and quiet, with a revolving cast of characters.

Not that these things are required to “live,” but I certainly am not interested in making these tradeoffs.

by jondwillis

12/31/2025 at 10:30:46 PM

Nah see you live in a SRO in Chinatown and get all your meals at the Catholic mission.

by paradox460

1/1/2026 at 12:34:06 AM

Yes I exactly did that! Moved into an SRO on the edge of Chinatown. It's a nice tiny apartment, I'm on the edge of a mecca of affordable grocery stores, and I'm two blocks from my part-time job that gives me free-time to self-fund my software hustle. But there are other options. What's wrong with living with good people in a room share?

by riazrizvi

1/1/2026 at 12:56:06 AM

Finding good people to live with is a miracle and not a permanent one. All it took is one good roommate to decide he didn't need to take his antipsychotics anymore for me to never want a roommate again.

So enjoy your situation while the good times roll, no shade, but people have their own reasons to never consider living in an SRO besides mere materialism.

by jazzyjackson

1/1/2026 at 1:08:34 AM

Fair point.

BTW I was originally searching for an SRO but I landed a 'micro-apartment' (I just double-checked terms), it has its own kitchen/bathroom. Had I stopped looking I wouldn't have found this great situation. Great enough that when I won a housing lottery the following month, for a nicer apartment at the same rate, I was content to give it up and let someone else receive it.

by riazrizvi

1/1/2026 at 1:14:09 AM

Do you have a family or people you need to take care of? Life is more than sustaining your own existence.

by j7ake

1/1/2026 at 1:09:36 AM

How are you living in SF on 2k/month? How many people sleep in the same room as you?

by what

1/1/2026 at 7:42:20 AM

Absolutely hilarious take.

by throw-12-16

12/31/2025 at 8:40:54 PM

You must be fortunate to have a lived experience where the answer isn’t immediately (and obviously) financial security.

Also: plenty of meaning outside of running a SaaS. Hell, undergraduate research assistants probably contribute more to societal at large.

by jwilber

12/31/2025 at 8:33:00 PM

You're right, financial freedom is completely unfulfilling, instead it's really meaningful and impactful to be involved in a tech economy whose primary value has been in undermining democracy and social systems!

by nawgz

1/1/2026 at 2:02:25 PM

> His life has meaning

Did his life not have meaning before he started this company?

by SecretDreams

12/31/2025 at 9:20:33 PM

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.

by harmonic18374

1/1/2026 at 6:24:03 AM

Users, while not at the top of the list, is probably on the list.

by DANmode

12/31/2025 at 9:49:11 PM

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.

by throw03172019

12/31/2025 at 10:10:09 PM

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).

by ridruejo

12/31/2025 at 10:49:33 PM

I dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction.

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.

by theptip

12/31/2025 at 11:12:38 PM

> 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?

At least for me, regular financial decision making breaks down once the numbers are above a certain amount.

E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall.

The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on building.

That’s the route I took. Paired with obsessive focus on work/life balance, I don’t regret taking this route.

by cj

1/1/2026 at 4:43:15 AM

I think of an amount like $10m as “retire well, leave some for the next generation” kind of money. $100m is more like, “retire well, leave passive income for N future generations.” That extra 10x is super compelling.

by twodave

1/1/2026 at 6:30:57 AM

Thanks for your message and point of view. You’re probably the only person here who has been presented with a similar scenario, and this is exactly how I felt.

by elwatto

1/1/2026 at 2:05:39 AM

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.

by ipython

12/31/2025 at 11:29:56 PM

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.

by jimbo808

12/31/2025 at 9:28:56 PM

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.

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.

by lizknope

12/31/2025 at 10:08:02 PM

Startups (businesses in general) are a game and the employees are resources.

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.

by moomoo11

12/31/2025 at 10:16:21 PM

> Don’t take it so personally. I did once too.

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.

by lizknope

12/31/2025 at 10:30:55 PM

Yeah, just don’t get emotionally invested in a chance of paying off your mortgage immediately. Don’t get your hopes up about materially bringing down your retirement age.

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.

by eptcyka

12/31/2025 at 8:44:05 PM

Not taking a nine-figure exit is insane to me.

by OGEnthusiast

12/31/2025 at 8:56:16 PM

[flagged]

by __turbobrew__

12/31/2025 at 9:52:41 PM

They do another startup of course.

by operatingthetan

12/31/2025 at 10:08:36 PM

Yeah. I know someone that started 4 companies and another that started 5. Out of those they had about a 50% success rate in selling to a larger company, stay about 3-4 years to vest, then leave to make a new start and repeat the cycle. Unfortunately I worked at 2 of the startups that failed.

by lizknope

1/1/2026 at 1:38:57 AM

[dead]

by adiazyc

12/31/2025 at 8:43:01 PM

[flagged]

by cityzen

12/31/2025 at 8:48:23 PM

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.

Honestly disgracefully.

by weslleyskah

12/31/2025 at 9:07:55 PM

> 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.

[0] https://www.cnn.com/2025/07/19/business/andy-byron-astronome...

by mjr00

12/31/2025 at 9:11:16 PM

Everybody wants to be the CTO until it's time to do CTO things.

by nradov

12/31/2025 at 11:59:34 PM

I agree with this 100%. The thing you have to watch out for is when they try to pin similar levels of responsibility on you for very little upside.

by charlie0

12/31/2025 at 9:16:59 PM

Perhaps I'm just a naive young imbecile.

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...

by weslleyskah

12/31/2025 at 9:31:19 PM

I don't think you're an imbecile. People just like living differently. "Work to live" vs "live to work" and all that.

Some people like working a stable but boring 9-5. Some people like working a challenging job, even for longer hours and lower pay. Some people like building things; some people like coordinating teams and managing people; some people like maximizing financial returns and seeing numbers go up.

As to why this specific person didn't take a 9-figure cashout (assuming it's true); I would imagine it's at least partly because this person thinks it could be worth more in the future. Crazy as it sounds, he may not be wrong. Remember that Larry and Sergey tried to sell their "Google" research project to Yahoo for a life-changing amount of $1 million (in 1998, they could have each bought a house!). Or a million-dollar sale that did happen, Roy Raymond selling Victoria's Secret for a million in 1982. (Multiple houses!)

Obviously 9 figures is a lot different than 7, especially in 2025. But he's also the CTO and has access to financials and company strategy. Who's to say that the $100,000,000 he would get won't be $250,000,000 in an acquisition next year? Even "just" a 25% bump in a year would be an extra $25 million, which in itself is life-changing. It's obviously a risk, but saying "this guy is crazy and/or an idiot for not taking a 9 figure cashout" isn't fair unless you can peer into the future.

by mjr00

12/31/2025 at 9:46:41 PM

I can definitely understand you. Interesting you mentioned Victoria's Secret, another area that I am highly interested and could make money is fashion. I could mention the cases of models (Tatjana Patitz, Gisele Bundchen) climbing this money ladder of luxury, but too off-topic for this site.

Different adventures, different life obsessions...

by weslleyskah

1/1/2026 at 2:38:51 PM

Some people have made being the boss their entire personality.

by throw-12-16

12/31/2025 at 9:34:45 PM

Ive worked with a lot of people who sent emails at 2am and in each case it was not necessary but it was performative.

by pydry

12/31/2025 at 9:57:22 PM

Night owls who check in before they go to bed probably. I've done it, and I wasn't like "oh I will get some points for this!"

by operatingthetan

12/31/2025 at 9:00:07 PM

Totally.

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.

by iancmceachern

12/31/2025 at 7:35:56 PM

[flagged]

by farceSpherule

12/31/2025 at 7:41:39 PM

Did you just generate a GPT rant and find-replace every — with --?

by themanmaran

12/31/2025 at 8:12:33 PM

Those were most likely from a multi-line list that was converted to a single line when the comment was processed on submission.

by thaw13579

12/31/2025 at 7:43:15 PM

Why does everyone assume that everything posted is based on GPT? There are people in this world who know how to write.

by farceSpherule

12/31/2025 at 8:11:52 PM

Because your account was created after general access to chatGPT and other LLMs was available to the public and your writing style looks similar.

Anonymous text on the internet, especially from accounts made after 2022/2023, are like steel post nuclear tests. Everything on the planet is tainted and the only things that can be relatively trusted are steel/text created prior to the tainting event

by lovich

12/31/2025 at 9:44:30 PM

Because only a complete sociopath (or someone replacing AI's –) would have this much -- in their copy

by HHaan

12/31/2025 at 7:41:17 PM

[flagged]

by farceSpherule

12/31/2025 at 7:22:31 PM

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

https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-...

by raw_anon_1111

12/31/2025 at 7:39:39 PM

The problem with that analysis is it ignores all the companies that exited through an acquisition rather than public markets.

If anything, it's an endorsement of M&A.

by airstrike

12/31/2025 at 8:08:24 PM

My “analysis” was the idea of a private company that seems to want to stay independent and control their own destrone like the author of the submission wants. There are only two ways to stay independent - stay private forever or go public.

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

by raw_anon_1111

12/31/2025 at 9:09:43 PM

Going public doesn't keep you independent, though, unless you were already the kind of unicorn that has enough pull to own a massive amount of shares and/or a special class of them

by airstrike

12/31/2025 at 9:49:08 PM

Isn’t that what I just said?

> Even public shareholders will insist on a sale at the right price

by raw_anon_1111

12/31/2025 at 9:57:49 PM

Yes, but that isn't all you said and it isn't even right.

Public shareholders generally don't insist on anything as they are dispersed. They may elect directors to the board, but that question gets into all sorts of dynamics about who actually really votes when annual meetings come around, board independence, activist shareholders and whatnot.

Put all of that aside and assume for a second that directors are a perfect representation of shareholder interests. Boards do not "insist on a sale". Instead, they may have the _fiduciary duty_ to consider bona fide acquisition offers and take the decision that maximizes shareholder value, triggered upon certain conditions (cf Revlon Duties)

by airstrike

12/31/2025 at 10:23:20 PM

How many times have the board refused a sell for the right amount of money.

by raw_anon_1111

12/31/2025 at 10:34:35 PM

That is not "insisting on a sale". Selling for the right amount of money is literally the right decision to make!

by airstrike

12/31/2025 at 11:35:46 PM

The entire submission is about someone who doesn’t want to be acquired even at “the right price”. You don’t have that option when you take outside investors.

by raw_anon_1111

1/1/2026 at 1:10:06 AM

That's right. And that's why I said "There are only two ways to stay independent - stay private forever or go public" is not accurate.

by airstrike

1/1/2026 at 7:31:56 AM

Not at all, we believe the asset is worth a lot more :)

by elwatto

1/1/2026 at 7:24:19 PM

I believe you.

I don't know the specifics of your company so I can't give you valuation advice, but I'd just like to add that, in my experience, I've seen lots of C-level teams and Directors refuse to sell even when a great offer was on the table because they believed they were worth more. In numerous cases, it turns out they were wrong and the company either fizzled out or sold to a different buyer a year or two later for much less than they could have gotten.

I'm talking refusing a $3.5 billion offer because you think you're worth $4B, only to sell for $2B later.

Not every deal is a good deal, but remember as an insider who's built the company you're also likely somewhat biased. There's nothing morally wrong about selling if it is quote-unquote "the right price".

I can't really name names in public, but email is in profile if you ever want to chat

by airstrike

12/31/2025 at 8:24:31 PM

Talk about dumping your trash on retail, YC is a lot smarter then I thought

by Lionga

12/31/2025 at 8:27:57 PM

The house always wins.

by trollbridge

1/1/2026 at 1:41:58 AM

[dead]

by adiazyc