#635: Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and more), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back

In this episode of The Tim Ferriss Show, Tim interviews Jason Calacanis, an angel investor, author, and podcast host. They discuss Jason's early life, including his father's bar and financial struggles, leading to Jason's drive for success. They delve into the origins of Silicon Alley Reporter, the dot-com boom and bust, and the founding of Weblogs, Inc. The conversation explores Jason's approach to friendship, the dynamics of co-hosting the All In podcast, and his strategies for moderating discussions. Jason shares his insights on success, emphasizing enthusiasm and meaningful relationships over monetary wealth, and both reflect on the importance of mental health and addressing trauma.