tl;dr; 1. Spent lots of time and money(thousands of pounds) trying to meet with CEO of hedge fund just to get one of the domains in their portfolio. 2. Failed. 3. Explained that he is co-founder of twillio europe. 4. Used above story as some kind of self proof of ability 5. Decided that he failed YC interview because of a silly mistake 6. Drew lots of lessons and conclusions. yawn
I'm kind-of amazed at how much this person was willing to spend at the drop of a hat. I see someone carelessly jumping on planes, spending thousands of dollars without blinking, and I start to wonder if the person may be bipolar and experiencing a manic episode.
There is a relationship between bipolar disorder and creativity; Jameson's Touched with Fire is a good exploration of that. Steve Blank of Lean Startup fame suggests that many founders come from dysfunctional families, because a chaotic home environment makes people comfortable operating in chaos later on:
http://steveblank.com/2009/05/18/founders-and-dysfunctional-...
Living in San Francisco and having just spent the weekend mentoring 100 would-be founders at Lean Startup Machine, it's my firm opinion that entrepreneurs are universally odd ducks. They are my people and I love them, but if they were particularly normal they would have found a lower-risk way of making a living. I think it's especially useful for entrepreneurial types to pay attention to mental health; some kinds of crazy are useful and to be honored, but some are just slowing you down.