[riazrizvi]

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.

[afavour]

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!

[bcantrill]

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...

[afavour]

> 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”.

[bcantrill]

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.

[afavour]

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.

[ridruejo]

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

[throw0101d]

> 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); […]

See perhaps Nick Maggiulli's post "The Ideal Level of Wealth":

> Financial Independence (28.6x Your Annual Spending): $3.5M. Assuming you never wanted to work again, you would need about 28.6x your annual spending to cover your costs indefinitely [$120,000 * 28.6 ~ $3,500,000]. This 28.6 comes from the Kitces research[1] showing that the 3.5% Rule[2] is the safe withdrawal rate for a 40-year time horizon and beyond. This research suggests that if you can make it 40 years while withdrawing 3.5% per year, then you’ll likely make it 50 years (or more).

[…]

> Whether your goal is Coast FIRE or full financial independence, the ideal level of wealth in the U.S. is in the low-to-mid range of Level 4 ($1M-$10M), or $2M-$5M. I know this is a lot of money and many people will never reach it, but that’s why it’s an ideal. It’s something to strive for. It’s enough where you don’t have to worry about money anymore, but not so much that it becomes a burden or warps your identity.

* https://ofdollarsanddata.com/the-ideal-level-of-wealth/

Adjust the $120k annual spend for your own lifestyle and cost of living.

You're not going to fly private, but it will take most of the worry out of life. Morgan Housel, author of the recently release The Art of Spending Money (and previously The Psychology of Money):

> 00:50:16 […] You have the independence to be who you are and wake up every morning and say, I can do whatever I want today. That’s wealth.

* https://ritholtz.com/2025/11/transcript-morgan-housel-spend/

[j7ake]

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

[elwatto]

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.

[j7ake]

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

[ryandrake]

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?

[jonas21]

> 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.

[objektif]

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

[scubbo]

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

[fragmede]

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.

[p1esk]

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

[scubbo]

Companies do not make the world better.

[zbentley]

Individuals can use their roles at companies to make the world better (whatever that means to them).

Also, companies are not the only kind of group someone can join (for money or not) with the goal of improving the world.

[skrebbel]

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

[scubbo]

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.

[stoneforger]

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

[riazrizvi]

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.

[afavour]

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.

[riazrizvi]

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.

[afavour]

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.

[FreakLegion]

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.

[stoneforger]

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.

[rapidfl]

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.

[dmacj]

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

[trollbridge]

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

[jwilber]

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.

[nawgz]

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!

[chollida1]

> 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.

[louthy]

> 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.

[riazrizvi]

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.

[louthy]

> 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.

[jondwillis]

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.

[paradox460]

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

[riazrizvi]

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?

[jazzyjackson]

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.

[j7ake]

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

[what]

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

[websiteapi]

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

[SecretDreams]

> His life has meaning

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

[throw-12-16]

Absolutely hilarious take.