3min 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

I Could Be an Entrepreneur, I Could Do Something in the World

"I was like, wait a second, I could be an entrepreneur. I could do something in the world," he says. "The adrenaline and the confidence, it felt like, you know, all of a sudden Superman like figures out." The Silicon Valley reporter's first big break came when his magazine went on sale for $100. He now has more than 30,000 fans around the world.

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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.