A Gen Xer sold his company for $1.6 billion. He kept less than $100 million and gave the rest away because he doesn't 'believe in billionaires'

O’Kelley’s [sic] says billionaires represent “such an incredibly ludicrous waste of money in a world where there’s so many people who don’t have that,” but he says actually being one is also “othering”—separating you from the limits and consequences that define normal life. “There’s something about keeping connected to normalcy that is really, really important,” the entrepreneur explains. “I don’t want a yacht and I don’t ever want to be able to be without consequences. I think that’s the biggest risk, is, how can we be accountable when we have so much money we can buy anything?”

He gets it. Past a certain point, wealth erodes your humanity. I think I'd have picked $100M too - at a safe 4% return that's $4M per year, plenty for anybody to live on but not megayacht money.

Motherfucking $4MM total is enough to live on with a return like that.
- Sure, but choosing to live on $160k/yr would be a bit much when you're starting with $1.6B. I can't fault him for still wanting to enjoy being wealthy instead of upper-middle-class and definitely don't think it's reasonable to complain that giving away 95% of his wealth is somehow not enough.
- Sadly, not necessarily true. In the US, all it takes is one family member with a severe chronic illness tovery quickly erode that to the point that you are back at work. I think $10MM is the magic number but $100MM is a really good number to ensure that you and.your loved ones are taken care of.
- It doesn't make any sense to keep just enough, because then you may have to worry about weathering any economic storms in the future.
  I think the amount he kept is reasonable, especially when they are pretty much one of a kind for doing this.
Plenty for a normal yacht, the kind you can sail by yourself or with a partner. Megayachts are basically private cruise ships that need a full staff to sail. Even if I had the money I wouldn’t want that!
- The only people that should want one are cruise ship operators and you can rent one for a lot less.
I've always said If I could have enough where I could purchase in cash a cottage in a small cottage town here in Canada with a top of the line internet connection and I'd never have to work or worry about money for the rest of my life I'd be happy. what would I do? nothing. I'd pursue my hobby projects, more FOSS development, gaming, painting, build model kits, drink beer, eat whatever I wanted, and socialize with as few people as possible.
That's all i want. I just want enough money right now to achieve that.
And you would only pick 100mil because of how fucked up the world is. You can easly burn half a million in US if you have a serious health condition.
$4 million a year is absolutely mega yacht territory.
- Not even close - megayachts are 9 figures and that doesn't include the absurd crewing and other operational costs. There's no way he could own let alone operate one on a $4M income.
- Nah, just regular yacht
- It’s definitely really nice yacht territory but can’t afford the floating 100+ room compounds all the billionaires are buying.
Joe Rogan's punk ass couldn't handle $100M

I reserve my praises until I learn how exactly he gave away the money. Family-controlled foundations that only do political lobbing while avoiding taxes are a thing .

I wasn't able to find details with a quick search, but it sounds like it wasn't his own foundation:
After the AppNexus sale, O’Kelley and his wife carefully chose which causes to support. Their donations focus on education, social justice, technology access, and healthcare initiatives.
https://www.ceotodaymagazine.com/2025/08/could-you-give-away-1-5-billion-like-this-ceo/
Perhaps the only good billionaire is one who isn't.
- Their donations focus on education, social justice, technology access, and healthcare initiatives.
  Okay, but you realize the could just be the Gates Foundation, right? Or whatever bullshit charity Zuckerberg runs?
- I honestly hope that's the case. "Hopeful" is a nice change of pace.
- Perhaps the only good billionaire is one who isn’t.
  Duh
well political lobbying would be good if it's lobbying for socialism i'd say
- I would argue that legalized corruption is bad, even if you happen to agree with the cause.
I don't know if there is something much newer and more focused on the foundation aspect, but The Rich and the Super-Rich spends a bit of time on discussing foundations and how they work to preserve wealth.

Should have shared the money with the workers who built the company into a $1.6B valuation and worth acquisition.

If anything he should have invested it into effecting political change. But that other person is right; it's never good enough for you.
- In Russia that's an oligarchy. Yet here you are advocating it?
duckin' A

Wait is this really a good rich person? I have to think something's up

Gen Xer, we're mostly cool. Still some ass hats but most of us try to be cool, do the right things
I'm too lazy to read, but they probably didn't grow up in this wealth they ran into it later and didn't hold on to it long enough to be corrupted.
Better than most but at the end of the day it would have been nice to give that money to the people that built the company he sold for $1.6B.
I would think there’s a lot of talented people that worked hard to build the value of that company such that he could sell it for a huge amount of money.
Definitely better than buying a yacht, but he still got to decide what to do with the value created by others.
AppNexus employs 1000 people across 5 continents. If the ceo has an extra $1.5B kicking around he could have given every person that helped build AppNexus $1.5M, which is a truly life changing amount of money for your average person.
- Yeah that amount of money would change my life I knew there was something wrong about this thank you for pointing this out
In the military there were two kinds of officers: the ones moved from enlisted to officer through schooling and hard work and the ones who started their career in ROTC.
The ones who came up from nothing were always the first to help out the workers and rarely pulled rank. They wanted the entire unit to don well and were not above getting dirty. They were also the most highly respected for it.
The worst and most selfish officers were the ones who came out of ROTC as officers and were essentially police, but with rank only. They sucked and no one liked them and any respect they received was only due to their rank, never to them.
I feel humility and the actual act of working your way to the top is the only way to maintain a connection to your humanity. So many of the current ultra wealthy come from money, didn't work for it, and don't know how to be a human being as a result of it. The last time that kind of generational-wealth was flaunted while the masses starved and suffered, it was in France, and there were a lot of removed heads. The only thing that saved the rich during the Great Depression was the fact there were a lot of them that lost everything as well. Almost everyone was in the same boat.
Those at the top will learn, soon enough, that they only maintain their wealth through the grace of those near the bottom. Squeeze too hard and their whole world will come down around them.
- soon enough,
  The cobwebs are forming..
Also see Chuck Feeney

If only he believed in himself, he could have been a billionaire…

Good for him.

Raise the taxes, remove the cap on FICA contributions, implement universal healthcare.

I love the sentiment but want to make sure it's understood that M4A would cost less, not more, than what we have today. The US government already spends more per citizen on healthcare than most governments with universal programs. The money just doesn't go to healthcare, it pays for profits and unnecessary overhead (like CEO salaries) at insurance companies, physician networks, hospitals, and medical suppliers.
- The US government already spends more per citizen on healthcare than most governments with universal programs. The money just doesn’t go to healthcare
  Then the US is nor spending that money per citizen, now is it?

if i ruled the world no single person would have more than 1bn, hence why it would never happen. (id be very unqualified)

Most of the assclowns running shit now are horribly unfit. At least you have some perspective.
- A lot of people say and/or think that until they have a billion dollars, unfortunately. Absolute wealth corrupts absolutely, absolute power corrupts absolutely, so on and so forth

I'd take just one single measly Canadian million dollars, buy a ~300-400K small house far from the city with enough land to have peace and quiet, and maybe try a greenhouse for vegetables.

That leaves enough money with what I already have to cover never working again, various moving expenses, some repairs and renos, and maybe the occasional weekend transexual escort in my whirlpool.

600K definitely can’t cover your incidentals over 20+ years.
- First I said "That leaves enough money with what I already have " and second CPP and QPP will kick in before that. I can live easily on that. I need little.
- Invested carefully, even at an underperforming 5% return, that's still $30k/yr. Not really enough to live the easy life but it's enough to pay for health insurance while you work on selling artisinal Swedish fire torches.
Kinda buried the lede there at the end... 😂
- I'm only sorta kidding. I would for sure do all the other stuff.

Russian Nobleman paradox. 100 million is still a lot though. Company was AppNexus, name rings a bell. Sold to AT&T.

Even still, $100m is more than enough to live a very comfortable life and secure your family's future. No one needs $1b.
- What about $300b though?
  That’s like, occasionally order off the value menu rich
100 million is still a lot though.
To be fair, the article does mention that he's considering using that as a way to fund his current startup if it ever needs a cash injection, rather than turning straight to more VCs, which is probably good in the long run in terms of reducing how much the company could have to cater toward predatory investors over customers, so I'd consider at least part of his remaining wealth just a means to fund a separate venture from his private life, but still, he probably does have more than enough even after that.
Also, I'd never heard of the Russian Nobleman paradox before, but I looked it up and it seems interesting. Thanks for sharing it.
I'm not criticizing him for keeping enough to keep him and his family comfortable for a few generations. Giving away a comma is a big request that he did without needing to be asked.
AppNexus is a cloud-based software platform that enables and optimizes programmatic online advertising. It was founded in 2007...
- I felt like this guy was doing the right thing but the amount of visual pollution he must have enabled in his career is wild. I hope it keeps him up at night.
- Yeah, I would feel bad keeping all of the money from that, too.
TIL
A young Russian nobleman intends to give his estate to peasants upon inheriting them. He also realizes that over time, his ideals might fade. Thus, he puts his ideas down into a legal document that can only be revoked by his wife. He makes her promise not to consent if he changes his mind later on.
\ At the time, he argues these core beliefs are an essential part of him, stating: “If I lose these ideals, I want you to think that I cease to exist.”
\
\ Now suppose 50 years later, he changes his mind and asks his wife to revoke the documents. The wife made a promise to the young nobleman. Is the old nobleman, with all his memories and new beliefs, the same person as the young nobleman? What should she do?
- Is the old nobleman, with all his memories and new beliefs, the same person as the young nobleman?
  Count Theseuski
- What should she do?
  Obviously as she promised, it doesn't matter what happens after that. Promises are made to be kept, don't make them unless you keep them. Only good reasons I can think of for breaking a promise would be something like if you were lied to when making that promise, or saving lives or maybe prevent nature destruction etc. Old dude changing his mind isn't a proper reason; if he feels like he was young and stupid back then, that's his problem
- If the old nobleman is considered a different person than his younger self - then the entire concept of promises is voided.

How many more people/companies do we need to see doing this before we see change?

I am praising the action not the individual :)

Oh. I thought this was The Onion for a second when I saw the title.

Just a general reminder to anyone to use a site like Charity Navigator to find good causes to donate to.

Seems to be only American
- Because most other Western countries have social security networks paid for by taxes, which are infinitely more efficient than the temporary bandaid which is charity.
or GiveWell if you want causes ranked according to their impact as measured in QALYs. They research these things pretty carefully to determine the impact. If you're not a utilitarian then you may not see the point of doing this (though on the other hand, if you're not a utilitarian, I don't know if there's any way to evaluate charities well.)

The question is: does it bring lasting benefits to the people?

If he gives away a billion once, eventually it will be consumed and then we're stuck in the same situation again. The rich must give money away repeatedly, that's the only way to sustain society going forward. For that, solid and robust policy changes will have to be implemented.

Well, yeah, I mean you are not wrong but in this case the guy sold his company for a billion (or rather more) and I assume that company wasn't running for just a few months. So in order to do it again he'd first have to start another company that reaches that selling price.
Other billionaires of course would need to keep giving back money they continuously amass, yes.
Well, you among many others in this thread are just describing communism, at least on some level.

I've said stuff like that before, but I bet we can do even better. You don't just tax the extra money they make and be done. You publicize the great things the money does, and you give the people awards, titles, and attention in whatever way seems effective.
So maybe next year AWS keeps growing like crazy and Jeff Bezos's yearly "donation" is like 30 Billion dollars. He never sees that money, yet he still lives a billionaire lifestyle. The government uses that money to have schools offer every child in the country three hot nutritious meals per day, and some hallway in DC gets a plaque that says Jeff Bezos: Savior of the Children and the Future of American Brainpower. We all win in the ways we care about.
If it's ok for companies to psychologically manipulate and/or physically harm people in pursuit of profit, then it's ok for we the people to use the bottomless narcissism and ambition of the CEO class as an energy source.
Well that's certainly nicer than how the French handled it

He's not wrong. Being circled by scavengars like some kind of dying leviathan is not a sane way to live.

When a billionaire gives money away, it's usually to their own charity, and it's to avoid paying taxes. Of course it sounds good to say they gave it away but it reality, they give it to a charity they fully control.

Or to reinvent their image, and not be look upon as a terrible person. Aka, gates
- Basically he paid the cost of buying the Benevolent Nerd Dad image when you're primarily known for running a company with some of the most anti-competitive practices ever around.

Thats fucked up, why sell it? Give it back to the workers.

Sell it, keep $100M, distribute $1,500M to the employees who built the company with you.
...sit on the beach with your former employees as just people, discussing who has the cutest little umbrella in their drink and laughing at the stock value of the global conglomerate that bought a business that no longer has employees.
- No, just distribute ownership amongst the workers. Keep a majority share if youre worried they arent responsible enough.

Gave the rest… to his employees… right??

Lol, they probably set up a foundation and now don't have to ever pay taxes again

yea well trying to increase your wealth to billions is pretty much an addiction much akin to gambling addiction.

There's also his age as a factor, he's probably more aware of his limited remaining lifespan than he would have been if he cashed out at 25, let's say.

Cashing out 1.6billion at any age is generational wealth.
- I understand, but I think a 25 year old wouldn't think first of donating most of it.

why didn't he pay a bunch of that to the employees?

Because that's against how the system works. Shareholders can and will sue your company if you don't maximise profits. I honestly do not believe that we will achieve an acceptable distribution of wealth under capitalism.
- That's a certainty as equitable distribution of wealth is diametrically opposed to the fundamental working of the capitalist system.

Good for him tbh, being a billionare WILL slowly corrode your mind and soul

Sounds good

Put it in the bank and live off the interest

There's nothing wrong with billionaires in themselves, that'd be stupid. A billion's js a number slowly losing it's value as time goes on. It's how the money's acquired that matters.

A lot and overwhelming amt of billionaires in places like america make their money thru fistfucking their entire country and the destruction of society, but they don't notice money's just a number, a value and once that society's destroyed you can't eat money. Like I said nothing wrong with making money but it depends on how you make it.

Most billionaires make their money from coming out of the right womb.
- Which is why inheritance tax is a thing even tho most find ways to avoid it.
  As long as they pay their dues, instead of leaving us plebs to run their own state for them, which granted a lot of them don't, idrc. I want to make P's as much as anyone else but if the game's rigged against my favour we need to change the game.
  Same way how in sport people win and lose, that's not the issue, but the game has to be fair, we can't allow doping, the playing field has to be even.
Soft disagree. I think even numerical wealth past a certain number is a sign of, at best, incoherent markets.

That's stupid to just "give it away" because there are so many unsolved problems in the world you'd think they'd use it to start another company which improves recycling rates or invest in nuclear power.

You might want to actually read the first sentence of the article before posting... Jus sayin'
- "Brian O’Kelley banked less than $100 million after selling his $1.6 billion startup AppNexus to AT&T—and gave the rest to charity."
What are you on about?
Give it away is cool af.

He accomplished an ideal that if every other billionaire upheld and followed suit, we wouldn't have the problems we do.
- The Woz(tm) recently commented on this topic: https://yro.slashdot.org/comments.pl?sid=23765914&cid=65583466
  by SteveWoz ( 152247 ) on 2025-08-11 20:36
  I gave all my Apple wealth away because wealth and power are not what I live for. I have a lot of fun and happiness. I funded a lot of important museums and arts groups in San Jose, the city of my birth, and they named a street after me for being good. I now speak publicly and have risen to the top. I have no idea how much I have but after speaking for 20 years it might be $10M plus a couple of homes. I never look for any type of tax dodge. I earn money from my labor and pay something like 55% combined tax on it. I am the happiest person ever. Life to me was never about accomplishment, but about Happiness, which is Smiles minus Frowns. I developed these philosophies when I was 18-20 years old and I never sold out.
- [replied to the wrong comment]
He accomplished donating 1.5 billion dollars to causes and charities, and still got to live worry free for the rest of his life. I'd say at that point he shouldn't be expected to live like a struggling laborer just to prove himself to unimpressed dickheads who don't recognize a good thing.
More than what was expected.
More than you have, I’d guess.