Skift Take
Ask anyone who the most successful investor in travel is, and they'll talk about Joel Cutler of General Catalyst Partners. But, when it comes to individual investors, this gang of five has a lot of experience and is pretty good. None are infallible, of course, but this is where a lot of the smart money is.
Erik Blachford, a former CEO of Expedia, was traveling to Seattle for a board meeting of Zillow, the real estate marketplace co-founded by his good friend Rich Barton, who founded Expedia for Microsoft and was the online travel agency's first CEO. Blachford, a Zillow investor, booked his hotel stay through Sam Shank's Hotel Tonight, and wanted to have some fun with his entrepreneurial and investor buddies.
"I then used Room 77 [founded by Brad Gerstner] to get a bead on the relative quality of my room in hopes of giving Sam a hard time, but of course it turned out to be just fine," Blachford says.
Blachford, Barton, Gerstner, Shank and Hugh Crean, the former CEO of Farecast, make up what you might call a Fab Five group of angel investors in travel. You see their names pop up a lot in launch announcements: They invest at times in each others' companies, and their investments in other companies frequently overlap.
Ties that bind
For example, all five are involved as a founder, investor, or board member in Room 77 and Hotel Tonight; Barton, Gerstner and Shank have collaborated with TravelPost and Duetto Research; Crean, Blachford, Shank and Gerstner are investors in Russia online travel agency Ostrovok, and Blachford and Barton were early investors in Hipmunk.
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If you have founded a travel startup, are seeking advice and a seed round, and then land one of the Fab Five as an investor, your success won't be assured -- but your new business will instantly get some credibility in the travel industry.
You want to get these guys on speed-dial.
The informal group doesn't conduct any secret meetings, and there are no gang signs that they covertly display to one another that we know of. The scope of their personal and business relationships, and the extent of their common investments vary
