TIP433: THE ART AND SCIENCE OF INVESTING IN STARTUPS

W/ JASON CALACANIS

24 March 2022

On today’s show, Trey Lockerbie chats with Angel Investing legend, Jason Calacanis. Jason is an entrepreneur who sold his second business Weblogs to AOL for $30MM in 2005. Jason then founded multiple other companies and along the way, became an angel investor in companies like Uber, Robinhood, Calm and 300 others give or take. He’s the author of Angel, where he lays out his playbook for turning $100k into over $100MM. You may also know Jason from the All In Podcast with Chamath Palihapitiya, David Sacks and David Friedberg or his other podcast This Week in Startups.

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IN THIS EPISODE, YOU’LL LEARN:

  • The advantages of being an outsider.
  • What makes up a star founder and the ingredients for success.
  • The realities of running a startup.
  • Why so many startups fail and how to look for the signs.
  • Common traits of Jason’s many billionaire friends and colleagues.
  • Startup deal terms and syndicates.
  • And a whole lot more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Trey Lockerbie (00:03):
On today’s show, we have Angel Investing legend, Jason Calacanis. Jason is an entrepreneur who sold his second business, Weblogs, to AOL for $30 million back in 2005. And then he went on to found multiple other companies. And along the way, became an Angel Investor in companies like Uber, Robinhood, Calm, and 300 others, give or take. He’s the author of Angel, where he lays out his playbook for turning a hundred thousand into over a hundred million. And you may also know Jason from the All In Podcast with Chamath Palihapitiya, David Sacks, and David Friedberg. Or his other podcast, This Week in Startups.

Trey Lockerbie (00:35):
In this episode, we discuss the advantages of being an outsider, what makes up a star founder, and the ingredients for success. The realities of running a startup, why so many startups fail, and how to look for the signs. Common traits of Jason’s many billionaire friends and colleagues, startup deal terms and syndicates, and a whole lot more. It was a real thrill to learn about Angel Investing from one of the greats. So I hope you enjoy this wide ranging discussion with the multifaceted Jason Calacanis.

Intro (01:07):
You are listening to The Investor’s Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

Trey Lockerbie (01:27):
Welcome to The Investor’s Podcast. I’m your host, Trey Lockerbie. And today, I’m super excited to have with me on the show, Jason Calacanis. Welcome.

Jason Calacanis (01:35):
I’m super pumped to be here.

Trey Lockerbie (01:38):
Well, I’ve been loving all the stuff you’ve been putting out. The All In Podcast, especially, I think is just fantastic. And we recently had your bestie Chamath on our show, and we were talking about his background a little bit. And how he slowly realized his atypical background was an advantage, or could be an advantage. And I know that when I was reading your book, you described your humble upbringing in Brooklyn, and feeling like an outsider because of it. And so I’m curious, what was that like when you were first getting started? And the outsider feeling, was it still there even after you sold Weblogs to AOL?

Jason Calacanis (02:15):
So I have tried to cultivate my outsider status and maintain it. It’s a little hard to do as you become more successful, and your friends, who you’ve been friends with for a while, also become super successful. Then all of a sudden, people think you’re Illuminati. So in a way, I look at it like the hip-hop scene in New York. When I was growing up in the ’90s, there was this big hip-hop scene. And I used to play basketball, the Chelsea Piers, with a lot of the hip-hop guys. And they were just a group of guys doing business in the world, making art. And then, all of a sudden, they became Jay-Z and Diddy and DJ Clue, and all these other interesting cats.

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