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Meet the team

Our name implies our approach to life. We’re founders, just like you, and we operate with that same entrepreneurial creativity and passion.

Our Story

As serially successful entrepreneurs, Freestyle has been backing market leaders for the past 10 years. 

Dave and Josh originally teamed up in 1997, after meeting at a tech conference at the Fairmont. That year they launched Spinner, the first multichannel Internet music service, and in 2014 Grouper (now Crackle), one of the first Internet video networks. Both companies were acquired in less than three years and sold for $320 million and $65 million, respectively. After taking a few years off, Josh and Dave joined forces again in early 2009 to found Freestyle. Their goal was to fill the current void of VC’s who were simply writing checks, and be investors that offered real-world, real-time operational advice. Jenny joined the Freestyle tribe in 2014, a serial entrepreneur herself, she dropped out of Stanford before it was cool, to found – the first aggregated gift registry. She joined Freestyle because she shares the same fundamental beliefs about investing, but adds a new voice and perspective. In the summer of 2020, Josh stepped down as full time GP to focus on helping companies that help the earth.

Freestyle has a common goal: to be brutally honest mentors and share strategic and operational experience as you grow your company. We are an extension of your management team, not just a VC writing a check. We are sector agnostic, so as long as you are a tech company, we’re here with open ears. We are most at home as your funding lead, so we will work 24×7 and deliver whatever you need to win.

Team Freestyle

We are all serially successful entrepreneurs with a startup addiction. 

Dave Samuel


Jenny Lefcourt


Josh Gilbert


David Bill


Molly Gunderson

Director of Operations

Josh Felser

Board Partner

“You can’t ask for better seed investors than Dave and Josh. They bring to the table excitement for your vision, experience as real founders, and high respect from the investment community. And best of all, with Freestyle, you’re more than likely to have fun along the way.”

— Howie Liu, Founder Airtable

“Josh is always there for me when I go seeking advice. He always takes two different perspectives on things: what’s best for the company and what’s best for us personally. I appreciate that perspective.”

— John Esrey, Founder Juvo

“Jenny is the rarest of investors: she balances being your biggest champion with pushing you exactly when you need it most. She is crazy smart and intuitive, but gives founders the room to build their companies in an authentic way. Jenny is the best investor I’ve ever met, and I’m so proud to build our company together.”

— Sahil Mansuri, Founder, Bravado



Work with our Companies

Want to be a part of something extraordinary?
Find your new home with one of our portfolio companies.