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.
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...
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.
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.
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'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 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.
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.
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!
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].
> 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”.
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.
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.
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.
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.
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.
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.
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?
> 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.
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.
> 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.
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!
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.
I get the vibe of the dog doesn’t know what to do when they catch the car. Catching the car has been their whole life, and once lost there is nothing 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
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
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
IMHO, RevenueCat exhibits a material dependency on YOU, the founder/CTO, for strategic direction, innovation leadership, cultural alignment, executive decision making, and crisis escalation. In the event of your sudden or prolonged "unavailability" (e.g., illness, accident, burnout, death, departure, etc.), RevenueCat may experience significant disruption to operations, decision velocity, leadership cohesion, and strategic execution. This represents a single point of failure at the executive level and elevates organizational, operational, and valuation risk.
Here are questions I would ask if I were on your board.
1. If you stepped away for six months, what would actually break? not emotionally, but operationally?
2. Which decisions still require your involvement today that should not? and why haven’t you let them go?
3. Is there any executive role at this company you could fully replace yourself in right now? If not, what does that say about how you’ve built the org?
4. Are you rejecting executive candidates because they’re weak or because they would force you to change how you operate?
5. What critical work only exists because it still routes through you?
6. Is OCTO a temporary incubator or a permanent workaround for your inability to decentralize zero-to-one work?
7. How many senior leaders are truly accountable without needing your implicit approval?
8. Are you optimizing this company for scale or for a version of the future where you still feel indispensable?
9. What would have to be true for selling the company to be the responsible decision, not the exciting one?
10. If the company needed you to be less central in order to become great, could you accept that?
Hey poster... Honestly, get over yourself. You suffer from a textbook case of Founder's Syndrome... It smells like a dead fish... You show self-awareness, humility, and care for the team, which makes this harder to see and harder to unwind and the risk comes from attachment, not ego.
Your identity is tightly fused with the company
-- You speak about the company as your primary source of meaning, energy, and long-term purpose.
-- Life outside the company is framed as something that would quickly feel empty or boring for you.
You retain control under the banner of high standards
-- The VP of Engineering search stalled because no candidate met a bar that is implicitly shaped by how you think, operate, and decide.
-- When leverage through delegation feels risky, responsibility naturally flows back to you.
You are the center of cultural gravity
-- Culture, values, language, and priorities are largely authored and reinforced by you personally.
-- Much of the organization's shared meaning still routes through your judgment and voice.
You delegate execution, but not full ownership
-- Even when you are not directly involved, successes are framed as outcomes of foundations you previously built.
-- This keeps you psychologically present in nearly every major win.
You created a parallel structure that still depends on you
-- OCTO exists to do zero-to-one work, unblock hard problems, and pursue opportunistic bets.
-- By design, it reports directly to you and sits outside normal org constraints, reinforcing dependence on your judgment.
You remain the default DRI for existential issues
-- Reliability, support breakdowns, reorgs, executive hiring, culture, and innovation still escalate to you.
-- This conflicts with the principle you explicitly endorse: if there is no DRI, don’t expect it to get done.
You have not made yourself truly replaceable
-- There is no clear path for a future CTO with comparable scope, authority, and trust.
-- The role, as it exists today, is inseparable from you.
Your personal fulfillment shapes strategic decisions
-- The decision not to sell is framed largely through your motivation, energy, and desire to keep building.
-- The company functions as a long-term vehicle for self-actualization now that financial stress is gone.
If this remains unchanged, the long-term risks are predictable:
-- Senior leaders will eventually hit a ceiling.
-- Innovation will bottleneck on your bandwidth.
-- Strong leaders may leave quietly in search of real ownership.
-- Succession becomes a deferred crisis rather than a designed transition.
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
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...
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.
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.
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!
[0] https://web.archive.org/web/20190422235813/https://www.theat...
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”.
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.
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.
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?
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.
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.
You have no idea about me at all, so please don't insult me by thinking that you do.
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.
Also: plenty of meaning outside of running a SaaS. Hell, undergraduate research assistants probably contribute more to societal at large.
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.
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
Here are questions I would ask if I were on your board.
1. If you stepped away for six months, what would actually break? not emotionally, but operationally?
2. Which decisions still require your involvement today that should not? and why haven’t you let them go?
3. Is there any executive role at this company you could fully replace yourself in right now? If not, what does that say about how you’ve built the org?
4. Are you rejecting executive candidates because they’re weak or because they would force you to change how you operate?
5. What critical work only exists because it still routes through you?
6. Is OCTO a temporary incubator or a permanent workaround for your inability to decentralize zero-to-one work?
7. How many senior leaders are truly accountable without needing your implicit approval?
8. Are you optimizing this company for scale or for a version of the future where you still feel indispensable?
9. What would have to be true for selling the company to be the responsible decision, not the exciting one?
10. If the company needed you to be less central in order to become great, could you accept that?
Your identity is tightly fused with the company -- You speak about the company as your primary source of meaning, energy, and long-term purpose. -- Life outside the company is framed as something that would quickly feel empty or boring for you.
You retain control under the banner of high standards -- The VP of Engineering search stalled because no candidate met a bar that is implicitly shaped by how you think, operate, and decide. -- When leverage through delegation feels risky, responsibility naturally flows back to you.
You are the center of cultural gravity -- Culture, values, language, and priorities are largely authored and reinforced by you personally. -- Much of the organization's shared meaning still routes through your judgment and voice.
You delegate execution, but not full ownership -- Even when you are not directly involved, successes are framed as outcomes of foundations you previously built. -- This keeps you psychologically present in nearly every major win.
You created a parallel structure that still depends on you -- OCTO exists to do zero-to-one work, unblock hard problems, and pursue opportunistic bets. -- By design, it reports directly to you and sits outside normal org constraints, reinforcing dependence on your judgment.
You remain the default DRI for existential issues -- Reliability, support breakdowns, reorgs, executive hiring, culture, and innovation still escalate to you. -- This conflicts with the principle you explicitly endorse: if there is no DRI, don’t expect it to get done.
You have not made yourself truly replaceable -- There is no clear path for a future CTO with comparable scope, authority, and trust. -- The role, as it exists today, is inseparable from you.
Your personal fulfillment shapes strategic decisions -- The decision not to sell is framed largely through your motivation, energy, and desire to keep building. -- The company functions as a long-term vehicle for self-actualization now that financial stress is gone.
If this remains unchanged, the long-term risks are predictable: -- Senior leaders will eventually hit a ceiling. -- Innovation will bottleneck on your bandwidth. -- Strong leaders may leave quietly in search of real ownership. -- Succession becomes a deferred crisis rather than a designed transition.
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