Episode 5: Jenny Lefcourt

October 29, 2020
updated on

In this episode, I’m speaking with Freestyle.VC Partner, Jenny Lefcourt. We grew up together in Miami, Florida, and it’s been fun to watch her professional life evolve into what it is today.

After graduating from the University of Pennsylvania, Jenny became a CPA at Arthur Andersen-where she discovered public accounting wasn’t for her. After a couple of years working for a startup in Silicon Valley, she attended the Stanford Graduate School of Business, before dropping out to start her own company.

We talk about how-after an initial bumpy start-she discovered her true passion and became the co-founder of two successful startups, eventually leading to her current role as a venture capitalist.

Favorite Moments

  • (5:40) – Growing up in Miami
  • (20:52) – Moving to the suburbs
  • (25:16) – Becoming a CPA
  • (38:46) – Becoming a co-founder
  • (43:27) – Entrepreneur vs. VC
  • (58:42) – Favorite investment

About Jenny Lefcourt

Jenny Lefcourt brings 20+ years of startup experience to her role as general partner at Freestyle, a $100M seed stage fund in San Francisco. Freestyle has led investments in companies such as Airtable, Intercom, BetterUp, Digit, and Patreon. Jenny is a founding member of All Raise, a non-profit dedicated to diversity in funders and founders.

Prior to working at Freestyle, Jenny co-founded (sold: XOXO) and Bella Pictures (sold: CPI). She angel invested in many technology companies, including Discord, MainStreetHub, and Minted.

Jenny earned her B.S. in economics from The Wharton School at the University of Pennsylvania and attended Stanford’s Graduate School of Business. She lives in Marin, California with her husband and three children.

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