#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

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.


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!


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. LinkedIn
screens candidates for the hard and soft skills you’re looking
for and puts your job in front of candidates looking for job
opportunities that match what you have to offer.


Using LinkedIn’s active community of more than 800 million
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 also 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.


Listeners of The Tim Ferriss Show can use code
TIM20 to get 20% off all orders, plus free two-day shipping
across the US, UK, and African continent with the purchase of two
or more boxes!
Visit HouseOfMacadamias.com/Tim to
discover some of the most delicious and nutritious nuts on the
planet.


*


This episode is also brought to you
by Eight
Sleep! Eight
Sleep’s Pod Cover is
the easiest and fastest way to sleep at the perfect
temperature. It pairs dynamic cooling and heating with
biometric tracking to offer the most advanced (and user-friendly)
solution on the market. Simply add the Pod Cover to
your current mattress and start sleeping as cool as 55°F or as
hot as 110°F. It also splits your bed in half, so your partner
can choose a totally different temperature.


For a limited time, Eight Sleep is offering my listeners
up to $450 off their Sleep Fit Holiday Bundle, which includes my
personal favorite, the Pod 3 Cover. Go to
EightSleep.com/Tim to get the exclusive
holiday savings. Eight Sleep currently ships within the
USA, Canada, the UK, select countries in the EU, and Australia.
That’s EightSleep.com/Tim


*


[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.


*


For show notes and past guests
on The Tim Ferriss Show,
please
visit tim.blog/podcast.


For deals from sponsors of The Tim
Ferriss Show, please
visit tim.blog/podcast-sponsors


Sign up for Tim’s email newsletter (5-Bullet Friday)
at tim.blog/friday.


For transcripts of episodes, go
to tim.blog/transcripts.


Discover Tim’s
books: tim.blog/books.


Follow Tim:


Twitter: twitter.com/tferriss 


Instagram: instagram.com/timferriss


YouTube: youtube.com/timferriss


Facebook: facebook.com/timferriss 


LinkedIn: linkedin.com/in/timferriss


Past guests on The Tim Ferriss
Show include Jerry Seinfeld, Hugh
Jackman, Dr. Jane Goodall, LeBron James, Kevin
Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew
McConaughey, Esther Perel, Elizabeth
Gilbert, Terry Crews, Sia, Yuval Noah
Harari, Malcolm Gladwell, Madeleine
Albright, Cheryl Strayed, Jim Collins, Mary
Karr, Maria Popova, Sam Harris, Michael
Phelps, Bob Iger, Edward Norton, Arnold
Schwarzenegger, Neil Strauss, Ken Burns, Maria
Sharapova, Marc Andreessen, Neil Gaiman, Neil de
Grasse Tyson, Jocko Willink, Daniel Ek, Kelly
Slater, Dr. Peter Attia, Seth Godin, Howard
Marks, Dr. Brené Brown, Eric Schmidt, Michael
Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan
Peterson, Vince Vaughn, Brian Koppelman, Ramit
Sethi, Dax Shepard, Tony Robbins, Jim
Dethmer, Dan Harris, Ray Dalio, Naval
Ravikant, Vitalik Buterin, Elizabeth
Lesser, Amanda Palmer, Katie Haun, Sir Richard
Branson, Chuck Palahniuk, Arianna Huffington, Reid
Hoffman, Bill Burr, Whitney Cummings, Rick
Rubin, Dr. Vivek Murthy, Darren
Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter
Thiel, Dr. Gabor Maté, Anne Lamott, Sarah
Silverman, Dr. Andrew Huberman, and many more.


See Privacy Policy at https://art19.com/privacy and California
Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.