There are not many startups that manage to sign a partnership agreement with a big brand before they even launch.

And there are perhaps even fewer new businesses that get details written into the same deal that include how an exit via an acquisition might look.

But that's what happened to Boston, U.S.-based FlipKey, when it secured a partnership with Tripadvisor to help get the vacation rental marketplace off the ground in 2007.

This wasn't because it was the wild west of private accommodation at the time (although for many other reasons, this was the state of the rental nation during that period), but because the then-senior vice president of corporate development at Expedia Group, Mark Okerstrom, structured the agreement and understood what might emerge.

Jeremy Gall, a former lawyer, was one of the co-founders of FlipKey and knows how important that first signing was for the company.

Tripadvisor eventually separated from Expedia Group (Okerstrom went on to become CEO from 2017 to 2019) and made good on the terms of the deal to buy FlipKey in 2012.

Gall, like his fellow co-founders, stayed on for around a year after the deal and has since launched and heads another startup in the shape of rental tech and services platform Breezeway.

He joins us as the latest guest on How I Got Here.

HIGH is a weekly show produced by PhocusWire and Mozio, aimed at getting the inside stories behind startups and innovation in travel and transportation.

It's hosted by PhocusWire's editor in chief, Kevin May, and Mozio co-founder and CEO David Litwak.

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