No amount of money will help you make the decision. The size of your network or having Mark Zuckerberg's personal phone number won't make you become less fearful of failure. And past experience (success or failure) won't be the determining factor in whether you'll succeed in future.
I'm not a bad loser in that I'll throw my toys and be a complete twat when I lose; in fact, I can be (somewhat) graceful in defeat and I can (eventually) accept it. But that doesn't mean I have to actually like losing.
In Greek mythology, Icarus tried to escape from Crete where he lived. Icarus' father subsequently constructed wings, made of feathers and wax, for him to fly away. His father however warned him: don't fly too close to the Sun.
When I started to build the very first product, I was the only investor and the only believer.
Ever since the rumours about the Yahoo-Tumblr acquisition running over the weekend (which it turns out weren't just rumours), I've wanted to communicate my opinion on the matter.