On the Cutting Edge: Having the Courage to Take Big Risks & Love Failure | with Chris Olsen

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. Founded in 2013, Drive now has over a billion dollars under management and has invested in more than 40 startups, including Root Insurance, Duolingo, Beam Dental, and Olive.

Chris was always a singular-minded kid — 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 everything and anything has been his primary motivator.

In college, Chris became obsessed with squash. There was a direct correlation to how much you played and how good you were — the more you played, the better you got — and there was something very satisfying about that. Following that path to its conclusion, he dropped out of college to play squash professionally. He found a group of professional players who would let him practice with him if he paid their rent, and he slept on their couch and trained with them.

His professional career didn’t really pan out, but he learned one of the most important lessons in his life: you can cold call almost anyone and be amazed at who calls you back. He took this lesson to heart as he pursued his back-up plan as a venture capitalist. While so much attention was being spent on Silicon Valley, Chris was convinced that the real opportunity was in emerging markets within the US — places like Ohio. This opportunity was a risk, but it could also be the opportunity of a lifetime. When he weighed the risk of staying with his current firm versus taking this leap, even if it meant failing, he had no doubt what he had to do. Even if he failed, it was worth the risk.

Our world is shaped by those who pursue their passions and take risks. Those are the people that are most successful in life, and they end up building things that nobody else would build. It’s not going to be easy, but life rarely is.

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?

Lessons for intentional living:

  • If you’ve got a passion that you’re excited about, you should give yourself the freedom and opportunity to pursue it. Whether or not that is what you end up doing, it nearly always leads to a fulfilling path in life.