2min 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

How Do You Start With Such a Blue Sky Blank Page?

I started calling people out. What are you working on? What's happening? And then this one person was making this photo sharing site flicker. Another person was doing a bookmarking site called Delicious. There's just this little underground of people who were building stuff for the web. So how do you even begin with such a blue sky blank page? How do you even start where you just pulling from random bits and pieces floating around? Did you have some approach?

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Transcript

Episode notes

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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.