Freestyle

Overview

Freestyle is an early-stage venture capital firm based in San Francisco that invests in technology companies, typically making 10-12 investments per year with check sizes of $1.5-3 million.¹⁶ It manages over $565 million in assets across multiple funds and has backed over 130 companies, including Airtable, Intercom, Patreon, and BetterUp.³⁶ The firm is led by general partners who are former serial entrepreneurs, emphasizing founder support and diversity in venture capital.³

History

Freestyle was founded in 2009 by Dave Samuel and Josh Felser, both of whom previously built and sold Spinner to AOL for $320 million in 1999 and Grouper (later Crackle) to Sony for $65 million in 2006.¹ The firm raised its first formal fund of $27 million in 2011, followed by a $40 million second fund in 2013 and a $60 million third fund in 2015; Jenny Lefcourt joined toward the end of Fund II and became an equal partner with Fund III.¹ It has since closed additional funds up to Fund VI in 2022 and remains active, with its latest investment on December 1, 2025.³⁵

Notable Products

• Freestyle Capital Fund VI - Latest closed fund from March 2022 focused on early-stage venture investments.⁵
• Airtable investment - Investment in cloud-based relational database platform.³⁶
• Intercom investment - Investment in business-customer communication tools.¹⁶
• Patreon investment - Investment in membership platform for creators.¹⁶
• BetterUp investment - Investment in employee coaching and learning platform.¹⁶

Reputation

Freestyle is perceived as a founder-friendly VC firm due to its general partners' entrepreneurial backgrounds, providing operational support to portfolio companies.³⁴ It has gained recognition for promoting diversity in venture capital and maintaining a consistent investment pace in early-stage tech.³ With over 130 investments and multiple funds raised, it holds a solid position among seed-stage investors, though specific criticisms are not detailed in available sources.³