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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:

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

Resources: