10 Questions: Gregg Brockway from TripIt.com

I’ve been playing with, and fascinated by the new travel site, TripIt.com for a while now. It’s helping me wrangle my large collection of travel itineraries, mostly via email (rather than mass input in a Web form). I reached out to Gregg Brockway, co-founder and president of TripIt and he was nice enough to answer a few questions:

1. Tell me about TripIt – what does it do, who’s it for, and why is it cool?
TripIt was started to make travel easier by helping travelers organize their travel plans and stay connected to their friends and colleagues. It’s cool because it’s incredibly easy and does much of the work automatically. You just forward all your travel confirmation emails to plans@tripit.com and TripIt automatically creates a master travel itinerary with your bookings plus maps, weather and more.

2. Travel is an interesting space. It feels like there’s nothing more to innovate for the amount of activity we see in the space, yet there has been little innovation for years. What interested the team in going after a market like this?
Although there are some very big companies in the online travel world, that doesn’t mean there isn’t any room left to innovate.  I’ve been part of this evolving industry since 1999 when I co-founded Hotwire and the majority of our team has online travel experience.  Travel is now the largest e-commerce category, but you won’t find many people saying it’s easy to plan and book a trip.  On the contrary, organizing a trip is confusing and time-consuming for many travelers, and that’s what we’re trying to address. We don’t care where travelers book, we just help them organize their travel plans.  Until I hear travelers saying travel is easy, I think there is plenty of room for disruptive innovation.

3. How do you find a balance between making travel and travel planning easier, and also providing appropriate rich content around that travel and travel planning?
I can’t envision a time when there will be a “one stop shop” for all things travel.  Our focus is helping people organize their travel plans regardless of where they choose to research or book their trip.  We are developing foundational tools and service that can help you regardless of what type of trip you are taking, business or leisure, solo or group, budget or luxury.  We’ll let our users tell us how much content they want us to provide, how much they want to get from other sites and how much they want to get from each other.

4. What’s been the biggest challenge in building this service?
Keeping it simple and focusing on what people really need.

5. From the way the site focuses on the email-to-site function, I’m guessing you’re building and positioning much of the experience around this function? Why do think that so few web services have taken advantage of email in this way?
Yes, the TripIt user experience is part-email, part-web site which I think is one of our core strengths and seems to be working very well. It’s certainly more challenging to develop in this hybrid model, but ultimately we think better for busy travelers. There is another “part” to what we’re doing which is to push our service beyond the browser and make the information in TripIt available to users in the applications and formats they user most.  Some early examples of this are how we support iCalendar format to you can see your TripIt information in your Google calendar or Outlook 2007 as well as our new TripIt To Me mobile service.  You will see more coming along these lines.

6. We’ve seen several attempts to “socialize” the travel process, yet nothing has really kicked into mass usage mode. Why do you think that is?
Most travel social networks focus on sharing trip experiences and advice, but that can be time consuming work for many people. With our TripIt Friends network, we’re focusing on really practical and useful stuff that’s easy for anyone to participate in. For example, we make it easy to share travel info with your spouse, or see where all your friends and colleagues are traveling at any time. I guess you could say that our social network is focused more on utility than entertainment.

7. How well are you being “accepted” by the big guns of the industry, players you want to slurp data easily in order to power your site?
Because travelers send us their information directly, we’re not dependent on industry partnerships for information.  That isn’t to say we’re not interested, but having done this before, we know we’ll be old and grey before we as a start-up could move the big industry players.  Behind TripIt is a sophisticated technology that we’ve named the Itinerator that is able to understand email from nearly 80 of the top travel sites.  We’re adding more as we see interest from our travelers.  We’re very focused on being an open platform that works no matter where you book.  Going forward, there are lots of interesting partnership opportunities for TripIt to support the industry “big guns.”

8. TripIt uses connections to other web resources such as Flickr and (my new favorite site) SeatGuru. Do you ever worry about building your business in conjunction with services and APIs that could possibly change or disappear at a moment’s notice?
The strength of TripIt is being an open platform, both for supporting travel websites and other website resources. We’ve designed this support using standards that enable us to quickly add and modify the websites that we access. So we can adapt very quickly to new resources that our users want to see in their itineraries, like SeatGuru which is one of our favorites too.  With so many great resources available in travel, we don’t feel overly dependent on any one source.

9. Every Web app has it’s hidden gems, or under-utilized features… what are they for TripIt?
There are some cool features in the Itinerary that are quite useful, like checking in for flights, adding maps/directions, etc. and the power of TripIt Friends sharing and calendars if very helpful, but the hidden gem is probably TripIt To Me which we just released on 10/18. It enables a user to email TripIt a command like “get trip” and TripIt automatically emails back the info from their itinerary. It’s a simple idea but huge for road warriors or anyone in the middle of a trip who has forgotten their flight, hotel or rental car details.

10. What question does nobody ask you, but you’re dying to answer?
How much do we charge?   We’re free and plan to stay that way. We expect to make money next year by helping our users add the missing pieces to their itineraries.