In his last year of breather, Aaron Sorkin started a news letter business. He says he realized it wasn't going to do the imperson thing that he had been planning undoing. After one year and three months, he decided to start an investment bank. But after learning from this mistake, Sorkin went on to find success in real estate.
In the news segment, Jason covers unicorn SaaS Startup called HeadSpin has been accused of a massive fraud by the SEC and DOJ (2:06), and Pacaso real estate startup offering fractional ownership of vacation homes is causing outrage in wine country (17:35). Then, Jason interviews Not Boring's Packy McCormick (34:41), about his time at WeWork competitor Breather (36:14), turning his newsletter into a venture fund (59:12), and Packy's vision for crypto - it's one of the best explanations we've heard (1:03:17).