Does MBA spell entrepreneur? Part, I

Bambi Francisco Roizen · June 22, 2010 · Short URL:

Tripit co-founder Gregg Brockway: MBAs have an outsized estimation of what they think they can do

Tonight, I'm moderating a panel titled MBA Entrepreneurs in the Valley.

The discussion will be on whether an MBA helps entrepeneurship. Most successful entrepreneurs don't have MBA's, so why bother getting one if entrepreneurship is your career choice? And, if you have one, how do you position it in the Valley? That's the topic of discussion. On the panel will be some great entrepreneurs, such as Pete Slosberg, the founder of Pete's Brewing, which went public in 1995, Sami Inkinen, co-founder of Trulia, Jack Kloster, co-founder of Yardbarker, and Gregg Brockway, co-founder of Tripit, and co-founder of Hotwire, which was sold to IAC for some $650 million. I decided to publish my pre-interviews with these entrepreneurs, starting with Gregg.

Gregg Brockway is president and co-founder of Tripit, a provider of travel intelligence for business travelers and road warriors. Tripit has raised $13 million in venture funding, with the most recent round of $7 million, led by Azure Capital Partners. Gregg became an entrepreneur after first having a stint as an investment banker. He felt constantly pulled to enter the operational side of a company, as opposed to just the advisory work that’s done as a banker.  In 1998, 1999, he went to a garage startup, which turned out to be a “complete failure.” Like a true entrepreneur, he learned from his experience and brought them to a company he eventually co-founded in 1999, called Hotwire, an online travel company which was sold to IAC for $665 million in 2003.  Gregg graduated from Harvard Business School in 1995.

Here’s our interview, partly edited.

Does having an MBA help you as an entrepreneur?

Gregg: On balance, I think it’s a good thing. A lot of MBAs don’t leave business school with a good understanding of what they don’t know. They have some outsized estimation of what they think they can do. But experience counts for a lot. When we do hire MBA’s, it’s because of what they’ve done. Yes, the MBA adds something, but it’s more about who you are and what you can contribute. As for positioning the degree in Silicon Valley, I would position it as an interesting experience. Hopefully, it’s not the most interesting experience the person has to offer. I would not hire someone because of an MBA. An MBA plus the other things I’m looking for make a good combination.

Why did you become an entrepreneur?

Gregg: I thought it would be fun. And, I also thought I might be good at it. I started a small advertising business in college, which I loved doing. After business school and several years of private equity, it seemed like the people having the most fun were my friends doing Internet projects, so I jumped in too. The first was a bomb, but the second was Hotwire, and that worked out pretty well.

What are some lessons you learned as an entrepreneur? 

Gregg: The first startup I joined was a complete failure. I jumped in with both feet before I understood. But you learn more from your failures. The two things I learned from that experience was that entrepreneurship is not an individual sport.  It’s not an individual pursuit, and you don’t appreciate how important that is. It took me far too long in my career to realize that success for companies is all about the team. I’m still digesting this. The team is important. You have to attract A players and start with them because A players attract A players. Then once you have them on the team, you have to make sure they all work well together and whether they understand roles and responsibilities, and the team has to have a good sense of who’s doing what.

What lessons did you apply from this experience working at a startup that failed to the company you eventually co-founded, Hotwire?

Gregg: We had a lot more money at Hotwire. So, the first thing was we tried hard to get the best people.  We did attract great people. But that was where I learned that it’s not just about getting the right team. It’s about spending time outlining goals/objectives, which change over time.  I wasn’t wired to be an organizational leader. It’s a muscle you have to develop. Unlike skiing, where you spend the hours getting better, in entrepreneurship, you have to spend the hours helping the team to get better.

How close to your business plan is your current business? Are business plans worth spending time on?

Gregg: We’re about a year behind schedule. When the world was melting down in 2009, we stopped hiring, which slowed down our product development and growth. We’re back after it now, and very excited about the future. You need a business plan. But it isn’t a long word document. It’s something simple that outlines what you do, who needs it, how you attract customers and how you will make money. And, you need to be ready to pivot as you see how the plan foots to reality, or not. At Hotwire, we didn’t pivot that much. That’s one of the reasons we survived relatively unscathed during the dot-com explosion. We stayed focus and didn’t get too distracted. Priceline was our competitor. They were expanding well beyond travel, and going international, as well as going after gasoline and groceries. We felt we were letting own the market and one Board member was adamant, saying that we were moving too slowly. Ultimately, Priceline shut down all those endeavors.

Have you made any pivots at Tripit?

Gregg: While we’re still focused on the same problem, we’ve made adjustments. Back in the fall 2008, I saw the writing on the wall that money would be hard to come by. Instead of focusing on scale, we focused on a monetization plan. That got us through. And, that got us to launch a premium service.

(Do you have an MBA and like to be interviewed for this series? Email

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Bambi Francisco Roizen

Founder and CEO of Vator, a media and research firm for entrepreneurs and investors; Managing Director of Vator Health Fund; Co-Founder of Invent Health; Author and award-winning journalist.

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About TripIt

TripIt, the trip management company, helps people organize and share their travel plans no matter where they book. Travelers simply forward their travel confirmation emails from over 1,000 sites to TripIt automatically creates a master itinerary that combines all their travel plans plus weather, maps, restaurants and more.

With TripIt it’s easy to share and collaborate on trips with friends and colleagues in social networks. TripIt itineraries can be accessed via online, mobile device, free Android, BlackBerry and iPhone apps, personal calendars and social networking sites including the free LinkedIn travel app.

TripIt is an open itinerary platform that works with a growing eco-system of travel and mobile partners. The new TripIt Pro premium service for frequent travelers automatically monitors travel itineraries, providing mobile alerts, alternate flight options, frequent traveler point tracking and automated trip sharing. 


TripIt Founders

TripIt was founded in San Francisco in October 2006 and launched in September 2007. The company has raised $13.1 million from investors that include O’Reilly AlphaTech Ventures (OATV) and Azure Capital Partners. The TripIt co-founders are an experienced team of travel and technology executives:

Gregg Brockway, President – Former president of Classic Vacations (an Expedia company), and co-founder and chief product officer at Hotwire

Scott Hintz, VP Business Development– Former senior vice president of product at Hotwire, and strategy consultant at Accenture.

Andrew Denmark, VP Engineering – Former engineering director at Opsware, and chief technology officer at


TripIt Technology

At the heart of TripIt is the Itinerator, which automatically creates structured trip itineraries from the unstructured data in travel confirmation emails. It also aggregates related data from other websites to provide useful travel information, like weather, maps and directions. The Itinerator is an open technology platform that works with all major travel websites and all major email systems. TripIt's goal is to provide one place for all travel information, accessible whenever travelers need it. 

TripIt has also been architected for social networking and includes many options for trip sharing and collaboration. Travelers can share trips with people inside and outside their TripIt Network, and post plans on social networks like Facebook, Twitter and LinkedIn. Closeness alerts tell travleers when their trips overlap with other people in their TripIt network. TripIt Company Groups tracks and shares the dates and locations of employee business travel, and TripIt for Google Apps has Company Groups and a several Google gadgets to help organizations and individual travelers manage their business trips.

TripIt has an open API that powers My Travel on LinkedIn and TripIt for Facebook Connect. Additionally, hundreds of developers use the API to intergrate TripIt with their web services and mobile apps. 



Gregg Brockway

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Gregg is a serial entrepreneur, angel investor and travel industry survivor. Co-founder of two successful companies, TripIt and Hotwire, Gregg has failed a couple times too.

Sami Inkinen

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Sami Inkinen is the CEO & Founder of San Francisco-based Virta Health. Previously, Sami was a co-founder, COO and President of Trulia. He is an investor in companies advancing human health and performance as an angel investor and at Obvious Ventures.

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