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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 (#635)

“Jason would never stab you in the back. He might stab you in the face, though.”

— Douglas Rushkoff

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!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor on your favorite podcast platform.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#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

This episode is brought to you by House of Macadamias delicious and nutritious nuts! I love macadamia nuts and have been enjoying them often since keto expert Dr. Dominic D’Agostino recommended them on the podcast in 2015. They taste great, and with more healthy, monounsaturated fat than both olive oil and avocados, 27% fewer carbs than almonds, and more than 50% fewer carbs than cashews, they’re the perfect low-carb, keto-friendly, nutty snack. In fact, I just ate a handful of lightly white-chocolate-covered macadamias about an hour ago to keep me going through the afternoon until dinner. And I will say this: ​House of Macadamias produces the best-tasting macadamia nuts I’ve ever eaten… by far.

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Want to hear an episode featuring another incredible entrepreneur ? Have a listen to my conversation with Automattic’s Matt Mullenweg in Antarctica, where we discussed the surreality of perpetual daylight, the “patient” Antarctican landscape, rollicking penguin imitations, the grieving process, using smartphones to regularly record loved ones, existential revelations, cloned pets, how Matt expresses anger without cursing, gratitude, and much more.

#578: Tim Ferriss and Matt Mullenweg in Antarctica: Exploring Personal Fears, Bucket Lists, Facing Grief, Crafting Life Missions, and Tim’s Best Penguin Impressions

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Jason Calacanis:

Website | Twitter


  • [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.


“When I had no money and then became a millionaire, people treated me differently. All of a sudden, I got 30 more IQ points and I was two feet taller.”
— Jason Calacanis

“[On All-In], I have three partners, and all three of my partners on it have never had a boss. So you’ve literally got four of the most opinionated friends who’ve never had a boss who have four different directions they want to take it.”
— Jason Calacanis

“Have great friends. Build cool shit.”
— Jason Calacanis

“The system is so easy to win, and the system is set up for entrepreneurs to win in this country. Why on Earth would you cheat if it’s so easy to just have a win by just working hard?”
— Jason Calacanis

“It’s important to be, I think, a really good, loyal friend. I have been burned in this regard where I’ve been more loyal to certain people and they have not been loyal to me. And it’s very frustrating for some of the people around me when they see that happen to me. And for me, I say that is that person’s chance to learn how to be a friend. They just haven’t gotten there yet.”
— Jason Calacanis

“47 fucks given.”
— Jason Calacanis


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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