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Jason Calacanis on Brooklyn Grit, Big Asks, The Magic of Thinking Big, and More

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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!

[00:00] Start
[00:52] Why is this only the first time Jason’s been on the show?
[01:48] Never underestimate the power of checklists.
[04:12] How Jason’s young life was steeped in blood and taxes.
[07:21] How Jason entered the world of entrepreneurship.
[24:06] What happened when Jason got fired from his own company.
[28:51] Orchestrating a comeback the very next day.
[32:28] The Mercury Club that never was.
[36:20] The origin of “Calacanis.”
[37:46] Building a blogging empire.
[43:28] Finding blog writers.
[47:37] Planning events and making memories.
[53:30] Friendship, loyalty, and collaboration with close friends.
[1:01:12] All-In: When a solo act gets tricked into joining a band.
[1:09:02] Memorable times All-In has gone off the rails.
[1:17:10] With greatly followed podcasts comes great responsibility.
[1:23:14] Keeping All-In running smoothly with four very different personalities.
[1:30:41] Talent-wrangling techniques.
[1:35:26] Bill Maher’s moderation style.
[1:36:42] Friendly rapport can be contagious.
[1:38:23] Can you see your comfort zone from the Overton window?
[1:41:50] Transfering skills, building popularity, and co-existing with jet blockers.
[1:48:51] What happens when you catch the car?
[1:51:54] Psychedelic therapy and a big win in Colorado.
[1:58:25] Jason’s billboard and parting thoughts.

About Tim Ferriss:
Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 800 million downloads and been selected for “Best of Apple Podcasts” three years running.

Connect with Tim Ferriss:
Sign up for “5-Bullet Friday” (Tim’s free weekly email newsletter):
Visit the Tim Ferriss PODCAST:
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