3min chapter

#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

The Tim Ferriss Show

notes

CHAPTER

Silicon Alley Reporter - How Did You End Up an Entrepreneur?

Sally Kohn: Having a dad who's an entrepreneur, it kind of puts it in you. She says she would look at people reading magazines and then go to cafes because of sort of pre-the web and mobile phones. "I was looking around going, well, who's that person getting out of that limousine? What's in that big tall building?" So something just clicked on my brain and I said, 'I want to be powerful'

00:00

Transcript

Episode notes

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.