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

Posted on Wednesday, Dec 23rd 2009

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, 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 I was one of the early members and was part of the small team that created, 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 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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Flip Key is very interesting, great site!

I also found this site to post your vacation rental reviews:

Tobias Randall Friday, January 14, 2011 at 8:03 PM PT