We Study Billionaires - The Investor’s Podcast Network TIP433: The Art and Science of Investing in Startups w/ Jason Calacanis
9 snips
Mar 25, 2022 
Jason Calacanis, a legendary angel investor known for backing companies like Uber and Robinhood, shares his vibrant journey. He discusses the advantages of being an outsider in Silicon Valley and the realities of startup life. Jason highlights key traits of successful founders and the frequent pitfalls leading to startup failures. He also delves into the importance of syndicates in angel investing and explores the common characteristics of billionaires. This insightful conversation is packed with lessons for aspiring entrepreneurs and investors alike.
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Outsider Status
- Jason Calacanis intentionally cultivates his outsider status, even as his success grows.
- He believes this perspective is valuable in tech, which has historically been driven by rebels.
PayPal Mafia Culture
- The PayPal mafia's culture was known for intense debates, reflecting the high-stakes nature of startups.
- Calacanis witnessed similar debate cultures at companies like Uber.
Startup Reality
- Startups are like wars or sports teams, demanding intense effort and competition.
- Many founders struggle with leadership as it requires a different skillset than initial product development.
