James Beshara is a founder, investor, and encourager. He has started a few startups, sold one (Tilt, acq by Airbnb), and has invested in a few multi-billion dollar companies in his career. He has written angel cheques into gusto, clubhouse, bolt, mercury, openAI, 50+. His portfolio companies have a market cap of $50Bn. Timeline : 00:00 Top Moments 00:38 Intro to pod with James. 02:18 How did James get into angel investing, and what made him do the fund? 05:44 What made James take such a bold and risky bet into Gusto? 08:55 How did James decide the fund size, cheques, and investment stages during the fund's inception? 14:14 What was James' strategy for differentiating from other investors, gaining access to deals, and targeting LPs for his first few funds? 20:39 What is James' deal sourcing process, his big wins and misses, and his learnings from that? 29:42 What is James' relationship with India? 35:27 If money and attention are not needed anymore, what would James work on? 38:08 What do James' friends know him for? 39:33 What is James most obsessed about lately, and what is draining him?