Helping You Book Vacation Rentals: FlipKey CEO T. J. Mahoney (Part 1)

T.J. Mahoney is the founder and CEO of FlipKey, a leading vacation rental service with verified vacation guest reviews. Prior to founding Flipkey he worked at Compete.com, Zefer, and Accenture. He is a graduate of Macalester College.

SM: Can you take us back to the beginning of your story? Where do you come from?

TM: I was raised in Boulder, Colorado. I was recruited to play basketball at a small school in Minnesota called Macalester College. Once I graduated, I got into the world of the Web by working as a consultant at Accenture. I became disenchanted with large organizations, so I left Accenture and moved to Boston to work in various startups.

The most significant startup I worked at was Compete.com. I was one of the early members and was part of the small team that created Compete.com, which is now one of the largest competitive Web analytic services in the world. There I began to see how quickly an independent, open, honest, and transparent system could work. Things were going well, and I had earned the opportunity to buy my first house.

Although I was a first-time home buyer, I still had to travel a lot for Compete. I was seeing rather large mortgage bills for a condo that I was not sleeping in. I thought it would be more economical if I had the house rented out to other people who might be traveling to Boston. I listed my apartment on a vacation rental website and found that a lot of people were interested in renting my place. From that point on, whenever I would travel, I would rent my apartment to somebody else for about $1,200 a week.

I started to realize there was a tremendous marketplace for people to rent out their underutilized home assets to other people. There was only one issue I encountered while renting out my apartment. I found that people wanted to rent my home, but that they did not trust me. They wanted to make sure that I was a real person. I had to prove my employment, and they wanted testimonials from people who had stayed in my condo before. I would provide that, but it was very inefficient.

I felt that the Craigslist-like experience of listing vacation rental sites was insufficient for how prosperous and enjoyable the marketplace could be and a counter to how trustworthy the marketplace should be. I approached my colleague, Carl Query, who was the lead engineer on the Compete.com project. I basically told him that there was a huge opportunity to create a more trusted environment for vacation rentals. I indicated we could create a very specific guest review service to help market vacation homes, which I expected would really help bridge the trust gap and allow people to feel more comfortable staying in someone’s home.

SM: What year was this?

TM: This was in 2006.

SM: How long were you with Compete?

TM: I was there for five years. I joined in 2001 and I resigned in 2006.

SM: Is it fair to say that your experience in Boston was after the dot-com crash?

TM: It was before and after. I moved there in 2000 and joined Zefer. It was one of the largest Internet startup consultancies and grew from 5 to 500 employees in less than two years. Once I joined, it imploded within a year. I was definitely part of the buzz and the crash. I was unemployed for four months between Zefer and Compete. A Zefer co-founder had joined Compete as a chief marketing officer, and he brought me to Compete.

This segment is part 1 in the series : Helping You Book Vacation Rentals: FlipKey CEO T. J. Mahoney
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