In this episode, I speak with Tyler Sosin, founder of Villain Capital, a new fund focused on investing in vertical software businesses. Having grown up in the venture business for 17 years with storied firms Menlo Ventures and Accel Partners, Tyler brings a unique - and perhaps contrarian - perspective to venture investing. With Villain, Tyler's ambition is to help vertical focused founders efficiently scale their start-ups into dominant franchises that can compound their growth and relative market share over decades. The name of the firm, Villain, was inspired by a quote by Harvey Dent, a character in the Batman film The Dark Knight, who said to Batman, “You either die a hero or see yourself live long enough to become a villain.”

Guest Bio:

Tyler Sosin is the founding partner at Villain Capital and a board partner at Menlo Ventures. Tyler has a degree in International Relations from Stanford University and lives in New York City.

Stay Connected:

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David Weisburd: @dweisburd

David Weisburd: https://www.linkedin.com/in/dweisburd/

Tyler Sosin: https://www.linkedin.com/in/tylersosin/

Menlo Ventures: https://menlovc.com/team/tyler-sosin/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Episode preview

(1:37) Peter Thiel's perspective and the role of market power

(5:12) Identifying potential villain companies in early stages

(8:26) Successful strategies in product bundling and market control

(12:44) Venture capital approach to small markets

(19:11) Balancing growth and sustainability in startups

(24:56) Historical impact and profitability of tech giants

(27:37) The importance of collaborative thinking and networking in VC

(31:03) Herd behavior and innovation in fund management

(34:53) Vertical software companies: PE and growth equity interest

(37:23) Debunking market size myths in startup success

(42:36) Storytelling and scaling in startup growth

(44:15) Strategies for expanding market reach in growth companies

(48:56) Career advice from Tyler Sosin's perspective

(51:00) The Thiel fellowship's influence on young entrepreneurs

(51:40) Closing remarks