> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?

At least for me, regular financial decision making breaks down once the numbers are above a certain amount.

E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall.

The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on building.

That’s the route I took. Paired with obsessive focus on work/life balance, I don’t regret taking this route.

I think of an amount like $10m as “retire well, leave some for the next generation” kind of money. $100m is more like, “retire well, leave passive income for N future generations.” That extra 10x is super compelling.