TripIt’s Short Trip to a $120M Exit: A Travelogue from CEO Gregg Brockway

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help businesses understand where their travelers are and what they’re spending. I’m guessing that two or three years out, the enterprise side of TripIt will be as big or bigger than the consumer-facing side. [Author’s reminder: this was all before the Concur acquisition.]

X: Backing up even more—can you talk about how you founded the business, and what the fundraising process was like for you?

GB: I’ve been doing travel-related projects for over 10 years. I was a co-founder of a discount travel site, Hotwire, that we started at the end of 1999. It was very successful and got acquired by an IAC company, Expedia, and it’s still doing great as one of the brands in the Expedia network. I stayed with Expedia for a few years after the acquisition ran another company they acquired in the luxury travel space. But I am a product person, and I like thinking about people and what they actually do on a daily basis and how technology can solve problems. [TripIt] all started as a casual conversation between two friends, myself and Scott Hintz, who was also an early person at Hotwire. We got excited about trying to solve some of the problems in travel, but neither one of us is an engineer; we came across our third co-founder, Andy Denmark, who is an incredibly bright engineer and helped us understand how to take this opportunity and turn it into a prototype.

Once we proved that you could actually extract meaning from e-mail and use it in an interesting way, we decided to make it a full-time thing. We self-funded for the first six or seven months, at which point we raised some money from a local early-stage venture firm, Tim O’Reilly’s AlphaTech. We have raised three rounds of funding now, not quite $13 million total.

The neat thing about our product is, people understand it. It’s never been a very hard sell, in terms of bringing people on board. It’s one of those things where they look at our product and say, ‘Wow, I can see myself using that.’

X: It seems like there was a big change in the travel industry back in the initial dot-com wave, when it became possible to book everything yourself online, but then that’s where it stopped—there wasn’t a lot of innovation, in terms of the actual mechanics of travel planning, after that. Today things are perhaps even more confusing than before.

GB: I totally agree. There was this initial wave of innovation, which was really empowering for people. They could do what previously they had to rely on a travel agent to do. But then the choices multiplied and became overwhelming. There is this interesting theory about the paradox of choice, which says a little choice is a good thing but too much actually makes people unhappy. We have gone through the happy phase and we’re on the back side of the curve, where there is too much information and too many places [to shop for travel deals] and none of them have the level of trust and competence you’d like, so nobody is happy about the state of online travel. There was an interesting article in USA Today just today about how people seem to be going back to travel agents, because they help simplify choices.

X: So is there still a place for travel agents?

GB: Travel agents excel when it’s a more complicated trip—not when you need to fly from San Francisco to Boston but when you’re planning a 10-day trip to Southeast Asia. They can add a lot of value and save you a ton of time and money. We are not trying to take the travel agent out of the equation—we are trying to help people keep track of all that information, and our hope is that … Next Page »

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Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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6 responses to “TripIt’s Short Trip to a $120M Exit: A Travelogue from CEO Gregg Brockway”

  1. At least as he is reflected in this interview, I like the way Gregg Brockway thinks. I am a pretty new Tripit user, and considering upgrading to the Pro Account. It really works beautifully (except for the lack of Priceline integration–which is not debilitating, just a little annoying).

    Two pieces of info he shared (among many) that really made sense:

    1) “A lot of people, in the old days, had personal assistants to do this work for them. In today’s economy, people are working more independently, and TripIt can act in many ways as a personal assistant to do all of this for you”

    2) Travel agents are making a comeback, in an era of info overload and too many choices.

    Exactly. Exactly why Tripit is needed and timely. Gregg really thinks like a terrific product and consumer person. I’d like to meet him and trade observations some day.

    Congrats to Gregg, his co-founders, the investors and the whole team who created this great product.