Jason Calacanis: Be Venture Worthy


Jason Calacanis is an entrepreneur, author, podcaster, and angel investor. He’s invested in more than 150 companies, including four multi-billion dollar “unicorns.” His story of investing in Uber is the stuff of investor legend. He’s also built and sold multiple companies for tens of millions of dollars and hosts the popular podcast “This Week in Startups” where he and a rotating group of guest experts bring you the weekly take on the best, worst, and interesting stories from the world of entrepreneurship.

As an entrepreneur turned successful angel investor himself, Jason knows how to spot a product that was crafted for growth. He’s had a front-row seat to the way that both startup investing and working for startups is evolving in light of COVID.

And he knows exactly what he needs from his founders – keeping him in the loop with regard to the health of your business is crucial. In today’s episode, he discusses why he’s eyeing a potential move outside of Silicon Valley, what it takes to make a truly remarkable product, why angel investors should ask for a board seat – contrary to what many people believe – and what types of companies to avoid if you’re just starting your investing journey.

Jason knows his game, so check out this episode to learn more about his thoughts on what’s happening with the current investment landscape, how to keep your investments close, and finding startups that are worth your investment.

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Some questions I ask:

  • How did you get started in angel investing, and what were you doing prior? (06:05)
  • What’s the one thing you look for in founders? (12:26)
  • At which stage do you like to invest? (14:04)
  • How many boards do you sit on? (23:23)
  • What do you think the future of crowdfunding is? (30:03)
  • If you look at the game-changing technology that’s coming on board these days, are there certain ones that you are most excited about? (41:45)

In this episode, you will learn:  

  • The changes the pandemic has brought in terms of doing business and closing deals. (02:27)
  • The story of Uber – what it was originally and how Jason ended up investing in it. (08:13)
  • How Airbnb was a unicorn that most people thought it was a bad idea. (10:46)
  • The types of companies you should avoid investing in if you’re a new angel investor. (14:36)
  • Jason’s four-bet strategy when he’s investing in a company. (16:18)
  • The importance of monthly monitoring of your portfolio of investments. (18:30)
  • The two things Jason requires founders in their term sheets: to receive monthly updates and to have the option of a board seat. (21:34)
  • How regular board meetings can help founders when they’re discussing with investors. (22:10)
  • The global trend around risk and the importance of investing no more than 20% of your income average in startups. (31:50)
  • The advantage of collaborating with an Angel Group. (40:13)
  • Jason’s advice for people who want to venture into the podcasting world. (45:06)

Connect with Jason


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