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

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appreciate how these little things make a difference, like simply having your confirmation code when they can’t find your hotel room at check-in. 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. It saves time and money and just makes the travel experience better.

X: How much does today’s TripIt resemble what you set out to build in 2006, and in what ways has your business model changed as we’ve gone through this economic upheaval?

GB: It’s more or less the same idea. There have been twists and turns along the way. The original idea was that there are lots of places for people to book travel, but really no place that helps you after you book. For most places that would just be a cost center, a customer-service expense, since after the customer has bought something there’s no way to make any additional money on them.

When we started off, we weren’t sure if this was going to be more of a business service or a leisure-travel service. It’s become very clear that it’s for business travelers. It should have been obvious in retrospect, but they’re 80 percent of our customers today. It wasn’t clear at the time, four years ago, how incredibly important mobile platforms and mobile apps were going to be for our success. The iPhone didn’t exist then—it was a watershed event for pretty much everybody. Also, when we started this, we had a lot of ideas around how we might make money, and we narrowed the focus to two or three. So our business model has evolved quite a bit.

X: How so?

GB: When we started TripIt, the business model was going to be, someone sends us an airline ticket, and we will try to pick the perfect hotel for that person. There was a lot of money in hotel lead generation, so we wanted it to be a lead-generation and advertising-driven business. And there is money there. But the scale you need to get to become profitable and was so large—and this was the end of 2008, when the world was falling apart—that we thought we’d better have a Plan B.

We figured out that if we could just get a couple percent of our users to pay us some money, we would have a profitable business and could survive whatever the economy was going to throw at us. So we pivoted the revenue model to launch a premium subscription service, which has been very successful, and today accounts for more of our revenue than advertising and lead generation. It was in large part driven out of necessity, which is always a great way to focus the mind.

X: What else have you learned along the way?

GB: We’ve discovered a lot of things. In focusing on solving problems for individual business people, we essentially stumbled on a really neat opportunity to solve problems for companies. So today, we have TripIt and TripIt Pro for individuals but we’re in the process of launching a service called TripIt for Business. The first couple pieces are live. It’s a really unique way to … 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.