I don't really know how venture funding works, so pardon my stupid question: Why did he need/want to raise $41m from outside when he sold his company for $850m a few years ago?
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.
B) Using other people's money is always a lesser risk.
C) Raising big money = big PR ("social proof").