Kayak.com Founding Story

May 10, 2023 1:23 AM



This is my story of how Kayak.com was founded in 2004. When I was leaving GC, Joel Cutler saw me, and asked me if I would meet Steve Hafner. Steve and I then went down to Legal Seafoods in Harvard Square, where we had a few gin and tonics for lunch. At one point, we coined an internal mission statement "search with us, book with them". We went back upstairs to GC. Joel asked how it went. Steve said I now have a cofounder, and we're each putting in $1m to seed it tomorrow (somehow he neglected to mention this to me at our lunch), and now that there are two founders, the valuation should be higher. We had a good laugh at that. Recruiting Steve recruited Keith Melnick to join as VP of Business Development. I recruited Bill O'Donnell (chief architect), Paul Schwenk (VP Engineering), Jim Giza (VP Technology) and Jeff Rago (UI engineer extraordinaire). What is the company? A search engine for travel. Billo's initial reply was "They already made Orbitz and Travelocity, what's the point?" How much will you pay me? $100k. (He was probably making several times that at Intuit.) Plus notable equity as chief architect. Where will the company be located? I knew I needed billo on the team, and that my $100k salary offer was not compelling, so I said "anywhere you want it to be". Once we got the tech guys to sign up, we incorporated the company. Initially as "Travel Search Company, Inc" as we didn't know what we wanted to call it. We knew we wanted a brandable name, and we wanted to take the proper time to come up with the right name. (More on this below.) Offices Steve rented a cool office in Norwalk CT for the commercial team. For the early years, Steve would come to Boston once a week or I would go to Norwalk (or NYC as I preferred). Doing a startup based in Concord MA was a challenge, especially when we tried to recruit new college grads who did not have cars. But somehow we made it work. Company Name We hired a brand agency in NYC, Wolf Ollins, to help us come up with a name. The woman who ran the process was Carol Costello. She is the best brand strategist that I know, and we've since gotten to work together on other projects. When Steve and I went back to the board and said we're going to name the company Kayak, David Fialkow at GC said, and I quote, "you'll name this company kayak over my dead body - that is a terrible name". Being the good entrepreneurs that we were, and knowing the role of VC, we said "thanks for the input". The rest is history. Larry saw my badge (so geeky, parties with badges) and said "cool website". I said something like, "you don't use Kayak, you own your own plane" and rather than eliciting a laugh out of him, he quietly said "I use Kayak for hotels". Larry then tried to get me to tell him about our ad engine. I demurred, and tried to change the subject. At another point that night, I was introduced to Marissa Mayer. She gave me her sales pitch for what Kayak should build for our hotel product. I didn't like her ideas, and thought they were too geeky, and would only work for 1% of travelers. At one point she said "fine, we'll build it ourselves" and then she turned on her heels and walked away from me. A few times over the years, when Kayak was getting more and more press, I heard grumblings from engineers at ITA who felt that ITA had built the hard core technology, and Kayak was just a thin layer on top of their engine. When I heard this, it made me smile, because all I ever cared about was UI. See other founder stories.