Jason Calacanis on Brooklyn Grit, Huge Asks, Angel Investing (Uber, Calm, Robinhood, and extra), The Magic of Pondering Huge, and St*bbing Folks within the Face however By no means within the Again (#635)

“Jason would by no means stab you within the again. He would possibly stab you within the face, although.”

— Douglas Rushkoff

Jason Calacanis (@jason) has invested in additional than 300 startups prior to now decade (Uber, Calm, Robinhood, and extra), was Sequoia Capital’s first Scout, and is the writer of the ebook ANGEL. He additionally hosts two podcasts, This Week in Startups and All-In.

Please take pleasure in!

Take heed to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor in your favourite podcast platform.

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#635: Jason Calacanis on Brooklyn Grit, Huge Asks, Angel Investing (Uber, Calm, Robinhood, and extra), The Magic of Pondering Huge, and St*bbing Folks within the Face however By no means In The Again

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Wish to hear an episode that includes one other unbelievable entrepreneur ? Have a take heed to my dialog with Automattic’s Matt Mullenweg in Antarctica, the place we mentioned the surreality of perpetual daylight, the “affected person” Antarctican panorama, rollicking penguin imitations, the grieving course of, utilizing smartphones to frequently file family members, existential revelations, cloned pets, how Matt expresses anger with out cursing, gratitude, and way more.

#578: Tim Ferriss and Matt Mullenweg in Antarctica: Exploring Private Fears, Bucket Lists, Going through Grief, Crafting Life Missions, and Tim’s Greatest Penguin Impressions

What was your favourite quote or lesson from this episode? Please let me know within the feedback.



  • Join with Jason Calacanis:

Web site | Twitter


  • [05:39] Why is that this solely the primary time Jason’s been on the present?
  • [06:37] By no means underestimate the ability of checklists.
  • [08:56] How Jason’s younger life was steeped in blood and taxes.
  • [11:57] How Jason entered the world of entrepreneurship.
  • [29:32] What occurred when Jason bought fired from his personal firm.
  • [34:05] Orchestrating a comeback the very subsequent day.
  • [37:49] The Mercury Membership that by no means was.
  • [41:37] The origin of “Calacanis.”
  • [43:01] Constructing a running a blog empire.
  • [48:36] Discovering weblog writers.
  • [52:51] Planning occasions and making recollections.
  • [58:39] Friendship, loyalty, and collaboration with shut buddies.
  • [1:06:00] All-In: When a solo act will get tricked into becoming a member of a band.
  • [1:13:39] Memorable occasions All-In has gone off the rails.
  • [1:21:49] With drastically adopted podcasts comes nice accountability.
  • [1:27:38] MaintainingAll-In operating easily with 4 very completely different personalities.
  • [1:34:53] Expertise-wrangling methods.
  • [1:39:30] Invoice Maher’s moderation model.
  • [1:40:47] Pleasant rapport might be contagious.
  • [1:42:26] Are you able to see your consolation zone from the Overton window?
  • [1:45:44] Transfering expertise, constructing reputation, and co-existing with jet blockers.
  • [1:52:16] What occurs once you catch the automotive?
  • [1:55:15] Psychedelic remedy and a giant win in Colorado.
  • [2:01:28] Jason’s billboard and parting ideas.


“After I had no cash after which turned a millionaire, folks handled me in another way. Swiftly, I bought 30 extra IQ factors and I used to be two ft taller.”
— Jason Calacanis

“[On All-In], I’ve three companions and all three of my companions on it have by no means had a boss. So that you’ve actually bought 4 of essentially the most opinionated buddies who’ve by no means had a boss who’ve 4 completely different instructions they need to take it.”
— Jason Calacanis

“Have nice buddies; construct cool shit.”
— Jason Calacanis

“The system is very easy to win, and the system is ready up for entrepreneurs to win on this nation. Why on Earth would you cheat if it’s really easy to simply have a win by simply working arduous?”
— Jason Calacanis

“It’s vital to be, I feel, a very good, loyal good friend. I’ve been burned on this regard the place I’ve been extra loyal to sure folks they usually haven’t been loyal to me. And it’s very irritating for a number of the folks round me after they see that occur to me. And for me, I say that’s that particular person’s likelihood to discover ways to be a good friend, they simply haven’t gotten there but.”
— Jason Calacanis

“47 fucks given.”
— Jason Calacanis


The Tim Ferriss Present is one of the most well-liked podcasts on the planet with greater than 900 million downloads. It has been chosen for “Better of Apple Podcasts” 3 times, it’s usually the #1 interview podcast throughout all of Apple Podcasts, and it has been ranked #1 out of 400,000+ podcasts on many events. To take heed to any of the previous episodes without cost, try this web page.

I am Christian Nnakuzierem Alozie (Kris Kuzie Alozie). A native of Eziama Nneato in Umunneochi LGA, Abia State, Nigeria. I am an inspirational writer and a motivational speaker. And above all, a lover of charity.

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