TripAdvisor Job – A Funny Thing Happened on My Way to World Domination

I announced recently that I was heading back into the corporate world. I will be a Director of Engineering at TripAdvisor.com in charge of SeatGuru.com and TripAdvisor.com/flights. As you can imagine, this has caused some mixed reaction among my nomadic travel blogging friends so i thought I would explain a bit more of the journey.

As those of you who follow the Amateur Traveler know, I left my job as the EVP of Engineering and Operations at LiveWorld to work on the Amateur Traveler full time on January 15th. To be honest, I thought it was a bit premature to try and make the Amateur Traveler into a company but:

• It was time for me to leave that job. I was there for 13 and a half years through all sorts of ups and downs (starting, going public, dot com bubble bursting, 10 rounds of layoffs, restarting). I still love the people there but I was ready for new challenges and both my boss Peter and I knew my heart was not in it any more. Peter offered to make a new position there for me for which I am grateful, but it was time to go.
• We had invested in a friends company called PayCycle which was bought by Intuit last Summer so we had some unexpected cash in the bank which is a good idea when you are leaving your job with two kids in college and a mortgage.

My plan was to do more traveling and working in a more location independent fashion. I could not just pick up and hit the road however because my wife recently started a brand new career that she loves. If she won the lottery she would still keep her job and frankly I enjoy, most of the time at least, traveling with her much more than traveling on my own. That was reinforced this year especially by my 2 week trip to New Zealand on my own. So I figured I would travel around California a lot and be back on weekends.

What I did not anticipate was that my wife’s mom (91) who took a fall last year would come and live with us, along with my wife’s niece and our niece’s dog. As it turned out it was a pretty good time for me to be home more, although not in the way I expected.

We were definitely living out of savings but we had not hit the magical number where I thought I would have to look for a new job.

In May I received a call from Bernie Bernstein who had been one of the founders of LiveWorld where we had worked together for 12 years in addition to a year or two at Apple. Bernie is one of those smart guys that it is a joy to work with. While he had worked for me at LiveWorld I would just as gladly work for him in different circumstances. Bernie worked at TripAdvisor and had just left the position that will be my new job to work on other projects. Bernie wanted to know if I was interested in moving to Boston to take his old job.

I like Boston and would consider moving there (even though the weather here in San Jose is better 3 seasons of the year), but with all the complications mentioned above this is not a good time for me to move. So that should have been the end of the discussion. Instead I said I would be glad to talk to Bryan his boss as long as everyone knew I could not move. And so we talked. I flew out to Boston after the TBEX conference in late June and then again in late July.

From the initial call with Bernie and the call with Bryan I was really surprised how interested I was in TripAdvisor. Remember, I was not looking for a job. While I was never one of those people who said they would never work for a company again, I was concentrating on trying to build a business.

As many people have pointed out TripAdvisor allows me to combine my love for travel with my love for creating cool websites (my favorite time at LiveWorld was when we ran our own website Talk City). And these TripAdvisor people are smart. At Amateur Traveler, where I was the company, I was always the smartest guy in the room, but TripAdvisor has people who know more about things like SEO than I do. I love to learn knew things. I love not being the smartest guy in the room. TripAdvisor has built a half a billion dollar company with a small fast moving team. That kind of thing makes me drool and laugh like a giddy school kid. It occurs to me that it may not be the secret dream of everyone in the travel space to have their hands on a meta search engine, but serious… I don’t see why not.

TripAdvisor, I think it is fair to say, was also a little surprised how interested they were in me. The whole idea of hiring a director who is not in Boston was something they really needed to think long and hard about but I am pleased that they have decided to take a chance on me. While I was waiting to hear back from them I did start sending other resumes out as I emotionally came to the place that this year has been a career break for me and not, at this time at least, a new career. But I have to admit that I sent out these resumes a bit halfheartedly. I saw positions that were a good match for my experience, but not that excited me in the same way.

So Wednesday I fly out to Boston where I will be spending most of the Fall. Add in a couple of trips I already had planned to Europe and Egypt and I won’t be home much. At times this will be difficult, but I had a dream the other night that I was in Bernie’s office and we were brainstorming a project at TripAdvisor. I woke up with familiar excitement of the joy of creating new things.

P.S. TripAdvisor is hiring. If you know a really smart software engineer who wants to live in Boston and is not afraid of a somewhat daunting interview process, have them drop me a line.