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We Study Billionaires - The Investor’s Podcast Network

TIP433: The Art and Science of Investing in Startups w/ Jason Calacanis

We Study Billionaires - The Investor’s Podcast Network

Stig Brodersen

Education, Investing, Business

4.63.6K Ratings

🗓️ 25 March 2022

⏱️ 60 minutes

🧾️ Download transcript

Summary

IN THIS EPISODE, YOU'LL LEARN:

  • 01:38 - The advantages of being an outsider.
  • 06:10 - The realities of running a startup.
  • 09:28 -What makes up a star founder and the ingredients for success.
  • 13:32 - Why so many startups fail and how to look for the signs.
  • 37:56 - Startup deal terms and syndicates.
  • 45:31 - Common traits of Jason's many billionaire friends and colleagues.
  • And a whole lot more!


*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.


BOOKS AND RESOURCES:

  • Angel Book.
  • This Week In Startups Podcast.
  • All In Podcast.
  • The Syndicate Website.
  • Inside Newsletter Website.
  • Jason Calacanis Twitter.
  • Trey Lockerbie Twitter.
  • Preston, Trey & Stig’s tool for picking stock winners and managing our portfolios: TIP Finance Tool.
  • New to the show? Check out our We Study Billionaires Starter Packs.
  • Get access to some of the most sought-after real estate in the U.S. with Crowdstreet.
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  • Learn more about how you can get started investing in some of the best cash flow markets today with Rent to Retirement.
  • Yieldstreet allows you to invest beyond the stock market with an evolving marketplace of alternative investments. Create your account today.
  • Find Pros & Fair Pricing for Any Home Project for Free with Angi.
  • Canada’s #1 employee benefits plan for small businesses! The Chambers Plan evolves with the way you work and live while keeping the rates stable. Opt for the simple, stable, and smart choice for your business.
  • Buy your own Bitcoin mining machines and host them with Blockware Solutions.
  • Be part of the solution by investing in companies that are actively engaged in integrating ESG practices with Desjardins.
  • Updating your wardrobe or just simply looking for a new fall flannel? Head to Mizzen+Main and use promo code WSB to receive $35 off an order of $125 or more!
  • Reclaim your health and arm your immune system with convenient, daily nutrition. Athletic Greens is going to give you a FREE 1 year supply of immune-supporting Vitamin D AND 5 FREE travel packs with your first purchase.
  • Live local in Melbourne and enjoy $0 Stamp Duty*!
  • Get the most from your bitcoin while holding your own keys with Unchained Capital. Begin the concierge onboarding process on their site. At the checkout, get $50 off with the promo code FUNDAMENTALS.
  • The interval fund, a breakthrough innovation. Only at Mackenzie.
  • Take advantage of a free mortgage review and learn about custom loans that can save you big money with American Financing.


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Transcript

Click on a timestamp to play from that location

0:00.0

You're listening to TI-P.

0:03.2

On today's show, we have Angel investing legend Jason Callacannis.

0:07.2

Jason is an entrepreneur who sold his second business web blogs to AOL for $30 million

0:11.9

back in 2005, and then he went on to found multiple other companies, and along the way, became

0:16.6

an angel investor in companies like Uber, Robin Hood, Calm, and 300 others give or take.

0:22.1

He's the author of Angel where he lays out his playbook for turning $100,000 into over

0:26.0

$100 million.

0:27.0

And you may also know Jason from the All-In podcast with Chimoth Paul Habatia, David

0:31.4

Sacks, and David Friedberg.

0:33.2

Or his other podcast this week in Start-ups.

0:35.8

In this episode, we discussed the advantages of being an outsider, what makes up a star

0:40.1

founder, and the ingredients for success, the realities of running a startup, why so many

0:44.9

startups fail and how to look for the signs, common traits of Jason's many billionaire friends

0:49.7

and colleagues, startup deal terms and syndicates, and a whole lot more.

0:54.4

He was a real thrill to learn about angel investing from one of the greats.

0:57.9

So I hope you enjoy this wide-ranging discussion with the multifaceted Jason Calicanas.

1:07.1

You are listening to the Investors podcast, where we study the financial markets and read

1:12.2

the books that influence self-made billionaires the most.

1:15.4

We keep you informed and prepared for the unexpected.

1:27.7

Welcome to the Investors podcast.

1:29.4

I'm your host, Tray Lockerby, and today I'm super excited to have with me on the show,

1:33.6

Jason Calicanas.

...

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