Meet the team

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 WeddingChannel.com – 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 invest in 12 companies each year so you get the time and attention you deserve. Since our founding, we have invested in a total of 106 companies and have $247M AUM across our funds. Our sweet spot is $1.25M – $1.75M checks for 12-18%. We are also 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 24x7 and deliver whatever you need to win. 

Team Freestyle

We are all serially successful entrepreneurs with a startup addiction.