Angel investing, which is backing and investing in companies at the earliest stages, is a high-risk, high-reward game.

Jason Calacanis, who was one of the first investors for billion dollar startups Uber and Robinhood, came from a difficult beginning. As a scrappy kid from Brooklyn who lost out on a $20 million buyout offer for Silicon Alley Reporter when the dotcom bubble burst, Jason refused to give up and made his fortune as an angel investor. Still not satisfied, Jason is setting his sights even higher to impact the world at scale. Within the episode, he tells host Geoffrey Woo that he is aiming to become the greatest investor in the history of Silicon Valley.

In this discussion, you'll discover:

• How and why Jason plans to become the greatest investor in Silicon Valley
• The impact of social media and identity politics on conversation and discourse
• Techniques for developing a self-aware, self-improving mindset

 

Check out a full transcription and highlights for the episode.

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