5min chapter

#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

The Tim Ferriss Show

notes

CHAPTER

A Podcast With Chamath Palaapati

Chamath Palaapati was one of the first people to actually have him on a podcast when I did my two-parter with him. David SACs is an old friend of mine who worked at PayPal with Peter Thiel, went to college with Peter Thiel and created Yammer sold to Microsoft for a billion dollars. And David Freeburg runs a semicolon, the production board, he was an early Google employee,. So he understands science like at a very deep level. The show just caught heat and the dynamic between the four of us, people really started to like and people were at home. Caught heat in a good way.

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Transcript

Episode notes

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, House of Macadamias delicious and nutritious nuts, and LinkedIn Jobs recruitment platform with 800M+ users.

Jason Calacanis (@jason) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital's first Scout, and is the author of the book ANGEL. He also hosts two podcasts, This Week in Startups and All-In.

Please enjoy!

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[05:39] Why is this only the first time Jason’s been on the show?

[06:37] Never underestimate the power of checklists.

[08:56] How Jason’s young life was steeped in blood and taxes.

[11:57] How Jason entered the world of entrepreneurship.

[29:32] What happened when Jason got fired from his own company.

[34:05] Orchestrating a comeback the very next day.

[37:49] The Mercury Club that never was.

[41:37] The origin of “Calacanis.”

[43:01] Building a blogging empire.

[48:36] Finding blog writers.

[52:51] Planning events and making memories.

[58:39] Friendship, loyalty, and collaboration with close friends.