This week, Jamie talks with a man who needs no introduction: Ashton Kutcher. Ashton is an A-list celebrity with a long career in film and television. Today, he is a serial investor, garnering equally as much media attention from his investment choices as he does from acting. On his hit list of early investments are Skype, Pinterest, Houzz, Uber, and Airbnb.

Ashton grew up in Iowa in a lower middle class working family. Having experienced the effect of a recession on his family, his worldview was shaped by always being a bit behind the curve of where his family wanted to be socioeconomically.

Though he knew he wanted to go into acting, there weren’t many opportunities in Iowa. After a couple of years working and going to school, he moved to New York and then to LA to pursue acting and modeling.

During his downtime between shoots, he started producing content and investing in companies that were taking content online. That’s what really catalyzed his work in investments.

In this episode, Ashton talks about his life, his investments, and the future. More specifically, he dives into his story and the lens through which he views the world, why he invests the way he does, and what he sees for the future of startups and investments.

Special thanks also to Ron Carson, our CEO, for joining us on this episode.

“I don’t just have to live in the world that everybody else creates. I can be a part of that narrative they’re living. That leaves a real imprint. It’s why I’m so attracted to entrepreneurs that are building things and I get so excited because it is the very essence of the human spirit. ~ @aplusk

Main Takeaways

  • The world was built by people no smarter than yourself. You can participate in the economy and add value just as well as anyone else.
  • Ashton’s key investing strategies include understanding the following:
    • Many startups fulfill wants, not needs. You need to look at the underlying industry and figure out a need that your investment will help.
    • A counterintuitive thesis can be a  sign of a good investment because skepticism of the mission allows for massive growth by that company (i.e. Uber, Airbnb).
    • A passionate founder and a mission-based company are critical to long-term success.
  • There are two ways to look at investing in technology: 1) look for the disruptive technology and then put it into a business or 2) look for businesses that happen to have disruptive technology.

Links and Important Mentions

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Jamie Hopkins

Managing Director, Carson Coaching
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