E182: Lessons from 17 Years at Menlo Ventures and Accel w/Tyler Sosin
How I Invest with David Weisburd
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
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E182: Lessons from 17 Years at Menlo Ventures and Accel w/Tyler Sosin

E182 • Jul 2, 2025 • 52 mins

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.”

Highlights:

  • The power of vertical software and markets that start small but grow big
  • Characteristics Tyler looks for in early-stage founders
  • Misconceptions around TAM and the overlooked upside in niche markets
  • Why customer lock-in and annuity-like business models matter
  • Thoughts on growth at all costs vs. compounding sensibly
  • Lessons from past investments like Flywire, Carta, and Indio
  • What venture gets wrong about market sizing and competition
  • How Villain balances elements of both VC and growth equity
  • The underestimated strength of founders who’ve been burned before

-- 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.

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-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Tyler Sosin: https://www.linkedin.com/in/tylersosin/

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

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