As crazy as this sounds, in my very limited personal knowledge of billionaire investors and almost billionaires — there are two types:
One type actually is quite conservative. They often keep 50% or more in cash or very conservative investments. They sell their stock in their own companies regularly to diversify and minimize risk (quite sensible, that). They use their current income streams (if large) to offset inflation, and to pay “living expenses”. They really don’t want to lose it all. They want more, but know they have “enough”. Importantly — they still prefer to invest Other People’s Money. Which is the ultimate risk hedge.
The others are crazy. They still are going all-in. See Elon Musk. He just put $100m into Tesla’s latest financing. He risks his entire “fortune” regularly, pledging it all these days, investing it all in the past. They prefer to invest their own money, and use other capital sources as a means to an end.
Maybe not as different from all founders as you’d think, really.