A) He probably didn't own very much of it at that point.

B) Using other people's money is always a lesser risk.

C) Raising big money = big PR ("social proof").

"Raising big money = big PR ("social proof")."

And of course the mafia always needs to be cut into any good deal and requires a "taste" and to dip their beak.

This is his business - the raising of money, not the production of high-quality long-term products...

I asked this of an old boss of mine who cashed out perfectly fine and then raised money for his next business. It's not just about money - having people like Sequoia Capital on your team is more valuable than the money.

The simplest answer: because he could.