That first company I started made a lot of money for the venture capitalists - nearly $30 million - but next to nothing for the founders. The companies I started after that varied between failures and mediocre successes. But at no point did I ever consider getting a 'real job.' That felt like a black and white world, and I wanted Technicolor.

Most of the money I make now comes from investments from CrunchFund. And the vast majority of that is what's called carried interest.

We live in a world where you're not being eaten by a lion when you fail, you just have to get another job.

I live a fairly simple life, and that didnt change much after I sold TechCrunch in 2010. I didnt buy a new house or even a new car. The one thing I did splurge on was a boat. Nothing too fancy or large.

Friendships and marriage are far more potent than financial conflicts.

One thing I know from personal experience, judges hate it when parties talk publicly about their cases. There are a lot of things about our criminal legal system that need to be changed, and this is just one of them. Prosecutors know how to play the press. Most defendants don't.

Best startups generally come from somebody needing to scratch an itch.