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

Fast FavoritesPodcast20 Minute VC

Blog/NewletterThe Economist

Tech GadgetTesla Model X

New TrendGrowth of capital and companies outside of Silicon Valley

BookThe Old Man and The Sea

Life LessonYou’ve got to fail until you succeed.

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