Definitely disagree, there IS a difference between $10 - $20 Mil and $1 - $1.2 Bil
On a much larger note, I don't feel like there's a big difference beyond $20 Mil if your goal is to continue living the life you're living now, but with total financial security. I know that given the chance, that's all I'd really ask for. Anything beyond that, and the only thing I can think of to spend the money on is philanthropy.
However, I'll bet other people have different aspirations, so I guess I can't really speak on the subject.
... why am I writing this comment ...
That's a huge difference.
At $20 million, there is nothing you can't do. At that point, with some wise long term investments, you wouldn't need to worry about finances.
10million * 3% dividend stocks = 300k per year just having it sit there. Maybe not entirely risk free, but not too risky either.
20M is plenty to live a very well off life, but its not "do anything you want for the rest of your life" money. Look at how many professional athletes/musicians manage to blow many multiples of that amount.
Also, perhaps I'm naive, but I expect tech startup founders to be better with their money than professional athletes. Yes, you could be an idiot, but that doesn't mean 10 mil isn't FU money. It is if you have even a little bit of a brain. You can spend nearly any amount of money, but that's not really the point. You can put your 3 billion all on red and dammit if it didn't come up black. Doesn't make it not FU money. (No casino in the world will take that bet, but you know what I mean).