Carl G. Shepherd is a semi-retired serial internet entrepreneur and active angel investor based in Austin, TX. See sector focus and contact routes.
Carl G. Shepherd is a semi-retired serial internet entrepreneur and active angel investor based in Austin, TX, who co-founded HomeAway in 2005 and served as its Chief Strategic and Development Officer from 2005 to 2015, architecting 22 acquisitions before the company’s sale to Expedia [1][4]. His investment thesis centers on early-stage businesses in the travel and sharing economy sectors, with a geographic focus on Austin-based privately held travel companies and international firms like Amsterdam’s @Leisure Group [1]. While his typical check size and lead/follow behavior are not publicly specified, he is noted to invest and serve on the boards of Turnkey Vacation Rentals, OnceThere.com, and @Leisure Group [1]. These three travel companies represent his notable portfolio, all aligned with his background in vacation rentals and online booking [1]. Shepherd holds a BA in Business Administration from Texas Christian University and an MBA in Finance from the University of Texas at Austin, which underpins his strategic approach [1]. He describes himself as an “Internet Travel Curmudgeur” and “sometimes investor,” reflecting a distinctive, candid public persona rather than formal publis
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