76 minutes | Jan 4th 2021

Chris Sacca: Putting It All on the Line

Welcome to Season 2 of Betting On Yourself! We couldn’t think of a better way to kick off this season than with an amazing interview host Michael Redd did a couple of years ago with venture investor and entrepreneur, Chris Sacca.

Chris spoke at length with Michael about his road to success, times on his journey when he had to put it all on the line and bet on himself, and how he came to be one of the most successful venture investors ever.

“Startup investing is one of my things — but it’s not my everything.” – Chris Sacca

Chris is the Chairman of Lowercase Capital, and together with his wife Crystal, they’ve invested in over 70 early-stage companies that include heavy hitters like Twitter, Uber, Instagram, Twilio, Stripe, and Kickstarter, making Lowercase Capital one of the most successful funds ever.  

You might have seen Chris for a couple of seasons on Shark Tank making deals. But as of 2017, he’s stepped back from investing to focus on other efforts like rescuing democracy, healing the planet, promoting diversity within venture capital and technology, reforming our criminal justice system, and other endeavors.     

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In this episode Michael and Chris talked about:

  • Why you need to focus on each deal through the lens of a novice 
  • Lessons on going deep in the hole (like $4M in debt)
  • How Chris sent out 700+ resumes to the top 100 investors in tech … with no reply
  • Why success is about being ready for the right opportunities
  • The importance of finding balance in your life
  • How to create both impact and influence
  • And more!

To ask a question, read the transcript, or learn more, visit MichaelRedd.com.


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