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Tim Ferriss

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)

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“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 Music, or on your favorite podcast platform.

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, House of Macadamias delicious and nutritious nuts, and LinkedIn Jobs recruitment platform with 800M+ users.

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

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#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. ​Now, listeners of The Tim Ferriss Show podcast can use code TIM20 to get 20% off all orders and a free box of their best-selling Namibian sea-salted macadamia nuts worth $35!

This episode is brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. Using LinkedIn’s active community of more than 1 billion professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim.

This episode is brought to you by Eight Sleep. Temperature is one of the main causes of poor sleep, and heat is my personal nemesis. But a few years ago, I started using the Pod Cover, and it has transformed my sleep. Eight Sleep has launched their newest generation of the Pod: Pod 5 Ultra. It cools, it heats, and now it elevates, automatically. With the best temperature performance to date, Pod 5 Ultra ensures you and your partner stay cool in the heat and cozy warm in the cold. And now, listeners of The Tim Ferriss Show can get $400 off of the Pod 5 Ultra for a limited time! Click here to claim this deal and unlock your full potential through optimal sleep.

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.

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

  • Connect with Jason Calacanis:

Website | Twitter

SHOW NOTES

  • [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.

MORE JASON CALACANIS QUOTES FROM THE INTERVIEW

“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

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Rick
Rick
3 years ago

Two word impression of this episode: High energy. Loved catching the nuggets of insight scattered like tracer rounds throughout the machine gun barrage that is Jason Calacanis.

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