
Gary Benitt
Serial Entrepreneur, Venture Capitalist, Managing Partner at Social Leverage
San Diego, California
Joined January 2025
Network
5.4K connectionsCROMDS
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Summary
Gary Benitt is a highly experienced serial entrepreneur, having co-founded four technology companies. His entrepreneurial journey began in 1996 with eShare Communications, followed by eAssist Global Solutions, Goowy Media (acquired by AOL in 2008), and Assistly (acquired by Salesforce.com in 2011). He brings extensive operational experience from building and scaling businesses in both consumer and B2B sectors. socialleverage+2
Following a successful entrepreneurial career, Gary transitioned into venture capital, becoming a Managing Partner at Social Leverage LLC in late 2014. He also co-founded B Squared Ventures LLC in 2011 as an angel investor. In these roles, he actively invests in and advises early-stage tech companies, leveraging his deep understanding of startup growth, operations, and market strategies. His portfolio includes notable companies like Classy, Getaround, Gyft, and Gusto. socialleverage+2
Throughout his career, Gary has held various leadership positions focusing on technology and go-to-market strategies, including roles in business operations, customer service, client implementation and success, engineering, and quality assurance. Notably, he served as COO of Desk.com at Salesforce.com for three years after Assistly's acquisition. socialleverage+1
Work
Education
Writing
The Move from Entrepreneur to VC
December 1, 2014A reflection on his career transition from a lifelong entrepreneur to a venture capitalist, detailing his journey through four startups and his motivations for entering the VC world.
AOL Acquires Goowy!
February 1, 2008A blog post announcing the acquisition of Goowy Media, a company he co-founded, by AOL in early 2008, reflecting on the journey with his co-founders.
Notes
MMMatt Maurersaid
GBGary Benitt
has played a key role in major successful VC investments or exits they've seen.Oct 30, 2025
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