Drive Capital's Chris Olsen on Why Investing in the Mid-West is Better Than the Old West
Investors from the coasts can fall into the flyover trap, looking only for opportunities in larger coastal Metros like Silicon Valley or NYC, but our guest today Chris Olsen, Founding Partner of Drive Capital, threw conventional wisdom to the wind by leaving a job at Sequoia Capital and moving to Columbus, Ohio to raise a new fund and bet on founders in underserved geographies. Since then, Drive Capital has grown to $1.2B AUM and its portfolio includes Duolingo, Udacity, Lightstream, Root Insurance, and Comply360.
About Chris Olsen:
A native of Cincinnati, Chris is a Co-Founder and Partner of Drive Capital, a Columbus-based venture capital firm focused on investing in world-class technology companies outside of Silicon Valley. Prior to founding Drive, Chris was a Partner at Sequoia Capital for six years and helped launch the firm’s first growth fund. Chris’ first job out of school was on the professional squash circuit where he quickly learned he was better suited to work with entrepreneurs.
In this episode we discuss:
01:36 How Chris’ time at Sequoia Capital shaped him as an investor
04:52 Biggest winners and some of the lessons he took away
07:02 What he learned from the misses during that time
08:33 The importance of teams and iteration for early startups
10:03 The aha moments of when he saw the opportunities outside of Silicon Valley
14:32 The reality of being comfortable when you are starting something new
18:20 How he found his co-founders and why he moved before the fund had closed
23:52 Factors that Drive Capital looks at when investing in an underserved geography
25:35 How new ecosystems are made and how institutional dollars flow into new cities
27:58 Why Canada has been a focus of Drive’s recent investment
30:19 How Canada’s founders differ from US founders and why immigration is Canada’s secret weapon
32:42 Why Chris like founders to take big swings to create large enterprises
36:02 The culture of speed that Drive Captial has built and how founders should think about working with them
39:51 What Chris is excited about and nervous about in the current VC market
43:23 How Drive’s business model has evolved over the last 8 years
20 Minute VC
Tesla Model X
Growth of capital and companies outside of Silicon Valley
You’ve got to fail until you succeed.