#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

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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.

[1:06:00] All-In: When a solo act gets tricked into joining a band.

[1:13:39] Memorable times All-In has gone off the rails.

[1:21:49] With greatly followed podcasts comes great responsibility.

[1:27:38] KeepingAll-In running smoothly with four very different personalities.

[1:34:53] Talent-wrangling techniques.

[1:39:30] Bill Maher’s moderation style.

[1:40:47] Friendly rapport can be contagious.

[1:42:26] Can you see your comfort zone from the Overton window?

[1:45:44] Transfering skills, building popularity, and co-existing with jet blockers.

[1:52:16] What happens when you catch the car?

[1:55:15] Psychedelic therapy and a big win in Colorado.

[2:01:28] Jason’s billboard and parting thoughts.

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