+1 for Startup. I listened to the last episode of season 1 this weekend -- the first half is the most honest discussion of entrepreneurship I've encountered.
Sure listening to his initial pitch to Chris Sacca is horrifying and hilarious, but eventually people just start throwing money at him. Everywhere he turns someone is trying to invest. I'm not saying this doesn't happen, but because of who he is the "money" side of things neatly works itself out for him.
Again, I love the podcast and I think Alex is completely honest in it, but he never has to confront the issue of runway which is probably the most nerve-wracking part of being starting a company.