Artwork for podcast Gravity
12. On the Cutting Edge: Having the Courage to Take Big Risks & Love Failure, with Chris Olsen
Episode 1224th February 2020 • Gravity • Brett Kaufman
00:00:00 01:26:22

Share Episode


Chris Olsen built a career investing in emerging technology and healthcare companies before founding Drive Capital, a Columbus based venture capital firm that believes the Midwest is the best place in the world to build great technology companies.

As a kid, Chris was always singular-minded—he wanted independence, his own bank account, everything. For him, money was freedom, and that was important. That drive to be free to express himself in whatever it was that he did has been his primary motivator through everything he has done.

What Brett asks:

  • [06:42] How did you learn to start expressing yourself through your work?
  • [13:30] Was your contrarian thinking shaped by your childhood or your DNA?
  • [18:30] What was your father’s role in shaping you?
  • [25:11] Where does your integrity come from?
  • [34:24] What was it about squash that got you so involved in it?
  • [46:31] When did you learn about what venture was and that you may want to do it?
  • [01:05:54] What was the impetus to start Drive?
  • [01:20:57] Where do you see the venture in the midwest?

To learn more about intentional living, and for the complete show notes, visit:


Gravity is a production of Crate Media