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David Wolfe

Smart Money RatingBased on the data VC Catalog holds.

Smart Money Rating: 71 out of 100

Senior Advisor — Multiple Founder, Expert Direct to Consumer Marketing, Greenwood AND Cavalier

Firm
Greenwood AND Cavalier
Title
Senior Advisor — Multiple Founder, Expert Direct to Consumer Marketing
Role
Advisor
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Record updated 1 October 2026

About

A multiple-time Founder, proven money maker for investors, and global expert in direct to consumer (DTC) marketing. David has uncovered and invested in more than 50 entrepreneurial tech startups. Part of the strong funnel of investment opportunities flowing from Greenwood & Cavalier is a direct result of follow on investment options from Mr. Wolfe. After earning his MBA at the London Business School, he started his career in strategy consulting in London before moving to Virginia to be Co-Founder and President of The Vacation Store that was sold to America West Airlines. Co-Founder at Leesa Sleep, the online mattress company. David led his team to achieve sales of $128m in year four. Co-Founder and Member of Investment Committee at Envest Ventures, with three funds fully invested. Recently, he has been Founder and CEO at The Fascination, an innovative new online marketplace. It was acquired by StackCommerce.

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