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$100 million invested into dividend stock would gross him $1-5 million per year. About 1/3 of that will be paid in taxes, depending on what kind of dividends those are.
Me personally, I think I'd be happy with $10 million but I guess you get hungry when there's a lot of food in front of you.
Depends if you want rich people play money or just comfy people play money.
Also if you want to say buy a beach front house in california or a nice mountain home in Colorado. That alone can run you a few millions dollars upfront not to mention a the on going costs.
100m is honestly not a lot of money if you plan to not for for the next handful of decades and want to actually enjoy a rich life style.
10 mill will put you in a nice middle class home and keep you living a middle class life style for the same length of time.
Wealth to life style scales pretty well from 10 to 100 million dollars when your looking at a 35 year span.
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.
Just a general reminder to anyone to use a site like Charity Navigator to find good causes to donate to.
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.)
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.
How many more people/companies do we need to see doing this before we see change?
I am praising the action not the individual :)
Should have shared the money with the workers who built the company into a $1.6B valuation and worth acquisition.
duckin' A
Jesus Christ, it's never good enough for you, why even bother trying.
At the end of the day, stolen wages are still stolen wages.
Lol, i know, right?
So many upvotes for the guy above you defending billionaires
Just because he gave it away, doesn't remove his responsibility for how he "earned" it.
Look, at least he does not seem to have raped anyone.
I agree, but it doesn’t sound like his choices are bad. There’s a comment further down.
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.
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.
I honestly hope that's the case. "Hopeful" is a nice change of pace.
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.
Well, the current method of taking the high ground to make change for good ain’t exactly working out too well.
Lobby for removing that legalized corruption?
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.
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.
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.
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, you among many others in this thread are just describing communism, at least on some level.
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.
Oh. I thought this was The Onion for a second when I saw the title.
If only he believed in himself, he could have been a billionaire…
