The Knowledge Project with Shane Parrish #81 Jason Calacanis: Intelligent Risk
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Apr 14, 2020 
Jason Calacanis, a tech entrepreneur and angel investor, delves into the high-stakes world of investing and poker. He draws fascinating parallels between the two, emphasizing risk assessment and psychological resilience. The conversation also touches on transforming fear-driven work ethics into meaningful success. Calacanis discusses the rise of no-code tools that democratize entrepreneurship and the shift towards micro VC models, aimed at making investment opportunities accessible to all, fostering diversity, and championing a fairer economic landscape.
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Poker Journey and Tilt Control
- Jason Calacanis recounts his poker journey, starting with low-stakes games and progressing to higher levels.
- He highlights the importance of tilt control and learning from mistakes, emphasizing the need to analyze hands and understand probabilities.
Angel Investing's Potential
- Angel investing offers potentially astronomical returns, exceeding traditional investment limits.
- Calacanis compares angel investing to a casino where you can win not just the chips on your table, but all the chips in the world.
Early-Stage Investing Advice
- Wait until a product is in the market and talk to actual customers before investing.
- Bet small initially to learn and avoid large losses, then increase investment in promising companies.