Langley Steinert

Founder & Executive Chair, CarGurus; former cofounder, TripAdvisor

What I found so refreshing about Tuck and why I think it is such a special place is its size. You know everyone in your class and you build very close bonds.

Langley Steinert T’91 tells a story about giving a talk at his kids’ school about TripAdvisor, the travel review and referral company he co-founded in 2000 and sold four years later for $210 million.

“I told them how the company worked and about being an entrepreneur,” Steinert recalls, “and this seventh grader in the back of the room blurts out, ‘So did you make a lot of money?’

“I started to laugh, because I’ve done well but that’s not the reason I do it. I do it because I love it,” says Steinert, who followed his TripAdvisor debut with an even bigger entrepreneurial encore, founding CarGurus in 2006 and building it into the second-largest and fastest-growing car-shopping site in the United States.

Steinert no longer speaks at middle-school career days but from time to time he gives talks about entrepreneurship at Dartmouth and Tuck, and there he delivers the same wisdom he shared with that precocious seventh-grader.

“I tell college and business school students, if you’re starting a company because you want to be the next Mark Zuckerberg and make a ton of money, you’re going to fail,” says Steinert, who is a long-time and dedicated supporter of entrepreneurship education at both Dartmouth and Tuck. “My number one rule is do it because you’re passionate about it, not for the money.”

Steinert learned that lesson early on, going straight from Georgetown University to a leveraged buyout shop on Wall Street. It was 1985, the height of an era novelist Tom Wolfe would chronicle in his satirical masterpiece The Bonfire of the Vanities. As a young investment banker, Steinert toiled in the industry’s metaphorical boiler room, feeding reams of analysis into an insatiable profit engine. He lasted three and a half years.

My number one rule is do it because you’re passionate about it, not for the money.

“I had less than zero work-life balance. In my first year I worked—and I’m not joking—seven days a week until one in the morning,” says Steinert, who plotted an escape route through Tuck to the burgeoning software industry. He was immediately taken with Tuck’s collegial atmosphere and culture of mutual support.

“What I found so refreshing about Tuck and why I think it is such a special place is its size. You know everyone in your class and you build very close bonds,” says Steinert, whose classmates impressed him with their diversity of background and business experience.

“To my right was a guy who was a submarine captain from the Naval Academy, and to my left was a woman who had been a very senior person in the NOLS [National Outdoor Leadership School] program out in Wyoming,” Steinert says. “It was a very interesting, eclectic class. Coming from an investment banking world where it tends to be a little more homogeneous, it was really refreshing to get into a classroom and hear all these different perspectives.”

By his own admission, Steinert, too, was a bit out of the mainstream. “I’d say 98 percent of my classmates not only had a job lined up when they graduated, but a really well-paying job at Goldman Sachs, or McKinsey, or Frito-Lay,” he says. “But when I graduated, I didn’t have a job.”

Plenty of companies would have leaped at the chance to hire someone with Steinert’s mix of education and experience, but he was determined to go into software, and only two companies at that time could provide the learning experience he sought—Microsoft in Seattle and Lotus in Boston. Steinert, who grew up in Manchester, MA, wanted to stay close to home. Lotus didn’t have the head count for a full-time MBA, so Steinert started there as a consultant.

“I took a part-time job at meager pay without benefits, because I really wanted to learn the industry,” says Steinert, who credits those hellish years on Wall Street for the determination, and the financial security, to stick to his guns.

“It was not fun and I didn’t enjoy it, but I learned how to be really good at modeling and spreadsheet analysis and to stay up all night if I have to—I think I worked 48 hours straight on one deal.” He was also well compensated, and the bonuses he socked away allowed him to finish Tuck with no debt and a modest nest egg. That gave him the freedom to take risks, he says. “So my time in investment banking did have its rewards.”

Between his first and second years at Tuck, Steinert interned with a software company, and the CEO there told him to resist the urge to start a company right away, and instead spend a few years making mistakes on somebody else’s dime. Steinert spent three years learning the software ropes as a product manager at Lotus, and four more at early-stage startups in Boston. He was one of the first executives at Papyrus, which produced NASCAR Racing, the best-selling CD-ROM game in America, and later joined Viaweb as the fifth employee. The founders were four Harvard PhDs who created a product that allowed small merchants to open an online store using nothing but a web browser—a revolutionary idea in 1998, when Yahoo purchased the company for $49 million.

Steinert found himself at a crossroads. “I didn’t know what I wanted to do with my life at that point, so I did a year and a half as a partner at a venture capital firm in Cambridge, and that’s how I came to know Steve Kaufer.” The duo founded TripAdvisor with $4 million in 2000 and sold it to Expedia/IAC four years later for $210 million.

TripAdvisor’s original strategy was to market a deep database of travel information to online booking firms like Expedia and Travelocity. It didn’t take. Next, Steinert and Kaufer hired editors to comb the Internet for great travel articles to link to. Again, crickets. Finally, as an afterthought, they added a feature that allowed travelers to leave their own reviews. Almost overnight, the website came alive. The next step was to monetize referrals by charging advertisers for each click-through. That combination—consumer-generated content coupled with advertising revenues and per-click commissions—revolutionized online business, not just in the travel space but a host of other industries as well.

Steinert launched CarGurus from the same playbook. Here it’s worth noting that the guy who turned the American car market on its head is not an automobile enthusiast. Steinert was simply looking for an opportunity outside the travel space because he’d signed “a big fat non-compete.” The product and business model changed many times before Steinert found the winning combination. CarGurus uses algorithms and deep-data analytics to take the mystery out of purchasing a car. If you’re wondering whether $62,000 is a good price for a 2017 Land Rover Discovery HSE Td6 with less than 4,000 miles on the clock, CarGurus will assure you it’s a great deal—more than $5,000 under market—and provide a link to contact the dealer. This data-rich approach has made CarGurus wildly popular with consumers and advertisers alike. From a cold start 11 years ago, the company has become the second-largest car buying site in the United States, with a dealer network of more than 40,000 dealers, more than 5.4 million car listings, and 28.6 million monthly unique users. It’s the fastest-growing business in the space, and has recently expanded into Canada, the U.K., and Germany.

In entrepreneurship, you live it 7-24. Ironically there’s no day off because you’re constantly thinking about it, but it’s something I love thinking about. I love what I do.

The big takeaway for other entrepreneurs, Steinert says, is to be flexible in your original business plan and product approach. “Both in the case of TripAdvisor and CarGurus, our first year and a half we were pursuing the wrong product plan and the wrong revenue model and so in both cases we had to pretty much scrap what we had been doing,” he says. “A lot of entrepreneurs aren’t willing to do that.”

A related lesson, which goes counter to startup culture, is to not raise more money than you need. TripAdvisor launched with $4 million, and Steinert started CarGurus with $5 million. “When we started TripAdvisor one of the running jokes was that Steve wouldn’t let us buy a laser printer for the longest time,” Steinert says.

That economy allowed the founders the time they needed to find and implement a winning strategy. Steinert took that philosophy to CarGurus, which for the first three years consisted of Steinert and six developers in a Harvard Square townhouse.

“The benefit of that is twofold. Number one, when we did screw up as most startups do, we could live to see another day. And the related benefit is that we were able to retain in both cases a ton of equity in the hands of the employees and the founders,” says Steinert, who kept a controlling interest in CarGurus when he took it public in October 2017. Share prices spiked 72 percent in the first day of trading, and CarGurus now has a market capitalization of about $3.9 billion.

So to answer that bold seventh-grader’s question, yes. Langley Steinert has made a lot of money. But more importantly, he has retained control of his company and balance in his life. An avid cyclist, he can step out his front door and ride 60 miles at a clip, and he never misses his teenagers’ sporting events. “It’s one of the highlights of my life, and if my kids have a lacrosse game ’m out of here,” he says. That flexibility is a far cry from the Wall Street grind he experienced as a young man, but Steinert is quick to note that he pays back the time.

“In entrepreneurship, you live it 7-24. Ironically there’s no day off because you’re constantly thinking about it, but it’s something I love thinking about,” Steinert says, coming back to his first rule of entrepreneurship: follow your passion. “I love the intellectual curiosity, I love working with software developers and I love creating new and interesting products,” he says. “I love what I do.”

Continue Reading

Related Stories

The Strategic Operator

Much of what Michael Aragon T’01, former CEO of MIRROR and lululemon digital fitness, has learned during his accomplished career is captured in his “operator’s manual,” a running guide of leadership lessons, insights, and advice. 

Read More

The Resilient Founder: Sarah Ketterer T’87, CEO of Causeway Capital

As Sarah Ketterer T’87, CEO of Causeway Capital Management, will attest, weathering the inevitable storms that arise in global financial markets requires ample grit, teamwork, and humility. 

Read More

The Decisive Risk-Taker: Meet King Arthur Baking Co. CEO Karen Colberg T’91

Beginning early in her career, King Arthur Baking CEO Karen Colberg T’91 realized how important it was to embrace the long view and take some calculated risks.

Read More

How to Shake Up an Industry, with Tomo Cofounder Carey Schwaber Armstrong T’10

Carey Schwaber Armstrong T’10, cofounder of Tomo, is working to transform the homebuyer experience.

Read More

Bridging the Generational Divide: Meet Kinsome Cofounder Eben Pingree T’13

With his latest venture, Kinsome, cofounder Eben Pingree T’13 is helping deepen bonds between grandparents and their grandkids through an AI-powered social journaling app.

Read More

Less Waste, Longer Use: Meet Nike’s Peggy Reid T’98

Through profitable reuse and recycling programs like Nike Grind, Circular Economy Director Peggy Reid T’98 is helping eliminate waste and creating a longer life for Nike’s products. 

Read More

Closing the Financing Gap for Local Businesses: Meet Honeycomb Cofounder George Cook T’17

Honeycomb Credit works specifically with small businesses and allows consumers, nonprofits, and other organizations to loan small amounts of cash to a particular venture.

Read More

The Uber for Customer Support: Meet Chatdesk Cofounder Andrew Olaleye T’13

Contacting customer service feels like a chore to most consumers. But Chatdesk cofounder Andrew Olaleye T’13 says the exchange doesn’t need to feel dreadful.

Read More

Addressing the Opioid Crisis through the Power of Community: Meet Steve Kelly T’18

As cofounder of Boston-based Better Life Partners, Steve Kelly T’18 is focused on providing same-day treatment for opioid use disorder by tapping into a network of community organizations.

Read More

Making the Most of Time at the Laundromat: Meet Courtney Bragg T’18

For Courtney Bragg T’18, founder of Fabric Health, the key to helping the millions of low-income people across the country started in an unlikely place—the laundromat.

Read More

Building Solutions for the Childcare Crisis: Meet Shefali Shah T’09

Upfront cofounder Shefali Shah T’09 has long wanted to be a part of the solution for one of the country’s most pressing problems: increasing high-quality affordable childcare for all.

Read More

Meet Stemless Cofounder Koushi Sunder T’13

With Stemless, entrepreneur Koushi Sunder T’13 is offering solutions for the emerging cannabis industry.

Read More

Sweet Success: Meet Entrepreneur Sarah Bell T’14

A conversation with Sarah Bell T’14, cofounder of Spring & Mulberry, a plant-based, naturally-sweetened chocolate brand.

Read More

Building a Better Burrito: Meet Red’s Founder Mike Adair T’09

Mike Adair T’09, CEO of Red’s All Natural, credits his Tuck experience with helping him launch a leading brand in natural frozen foods. 

Read More

Walk of Faith: Meet Grain Management Founder David Grain T’89

“If you are pushing hard and facing an unusual amount of resistance, it’s probably not ‘go time’ yet,” says David J. Grain T’89, founder and CEO of Grain Management, LLC.

Read More

Entrepreneurial Spirit

Biochemistry and business are an optimal blend for founder and former CEO of High West Distillery David Perkins T’90.

Read More

Tuck Relationships Run Deep at .406 Ventures

Classmates and spouses So-June Min T’95 and Liam Donohue T’95 reflect on their winding path as co-founders of the Boston-based venture capital firm .406 Ventures.

Read More

Alex Jenny

It’s mind-boggling to think about how much work goes into making and shipping a pair of sneakers, even to Alex Jenny D’10, T’16, who’s been at Allbirds for several years.

Read More

Liz Nordlie

Nordlie has had a successful career that’s spanned the course of three decades, the majority of which she spent at General Mills, managing and integrating large acquisitions and spearheading turnarounds for well-known brands.

Read More

Hope Waldron

"When I moved from brand strategy to my current role at VF Corp., I had no supply chain experience, but the fact that I was able to make that move is a testament to the breadth of the knowledge I gained at Tuck." 

Read More

Sandy Chen Fedor

Fedor enrolled at Tuck with a keen interest in entrepreneurship, and she’s still using what she learned in her courses to this day, from negotiating with stakeholders to using competitive strategy when building a product.

Read More

Pandemic Lessons in Fashion

Fabletics COO Meera Bhatia T’04 on how technology and teamwork helped her address an increase in product demand and supply chain challenges during the pandemic.

Read More

Why We Need More Women Entrepreneurs—And Investors

A conversation with venture capitalist Elizabeth Davis T’20, an investor with the Anthemis Group’s Female Innovators Lab.

Read More

Blair Crichton

Meet Blair Crichton T’18, co-founder of Karana, a new whole-plant based meat company launched in Singapore.

Read More

Meet Allobee Chief Strategy Officer Anne Forsyth English T’08

Allobee is connecting business owners nationwide to an underutilized workforce of experienced, professional women—a mission that deeply resonates with Chief Strategy Officer Anne Forsyth English T’08.


Read More

Meet Military Veteran and Fitfighter CEO Sarah Apgar T’11

A commitment to public service is a current that runs through T’11 Sarah Apgar’s career and education.

Read More

Meet Peloton’s Chief Operating Officer Mariana Garavaglia T’08

At Peloton, Mariana Garavaglia T’08 is putting people, and culture, first.

Read More

Laura Scott

At Wayfair, Tuck alumna Laura Scott completely transformed the company’s operations. Now she’s dipping her toes into the startup world with Takeoff Tech.

Read More

Lincoln Spoor

Every December, Lincoln Spoor T’84, CEO of Feel Good Brands Corp, delivers a truckload of Popcornopolis popcorn to first-year students during final exams.

Read More

Juliet Horton

With Everly, Juliet Horton T’14 is changing how couples plan their wedding

Read More

How to Make a Successful Startup Pitch

In her seven years as a venture partner at LaunchCapital in Cambridge, Mass., Heather Onstott T’07 has heard about 1,000 pitches from startups.

Read More

Susan Hunt Stevens

In 2006 Susan Hunt Stevens T'98 started a blog as a "a guide to going green without going berserk." Years later the idea evolved into WeSpire, a platform that uses technology and social media to promote sustainable living.

Read More

Kinya Seto

CEO of Lixil Corporation Kinya Seto T'96 is leveraging his entrepreneurial smarts to tackle the global sanitation crisis.

Read More

Katrina Veerman

With PK Coffee in Stowe, Vermont, Katrina Veerman T’01 turned a passion into a livelihood.

Read More

Kristiana Helmick

Kristiana Helmick T’98 has had three very different jobs in the last decade. And all at a single company: Amazon.

Read More

Andrew Smith

Andrew Smith T'07 chose Tuck first because he was looking for a beautiful environment where he could spend time thinking about how to maximize his impact on big challenges in the world.

Read More

Tom Slosberg

Very few people can say that the shoe business is in their blood. Tom Slosberg D’90, T’99 is one of them.

Read More

Steve Voigt

How to breathe new life into one of the country’s oldest companies? During his twenty years at King Arthur Flour Company, former president Steve Voigt T'86 did it by embracing people’s love of something timeless: baking.

Read More

Tracy Sun

Poshmark co-founder Tracy Sun T’05 turned her love of fashion and psychology into a leading mobile commerce app. Shopping will never be the same.

Read More

Gibson “Gib” Biddle

NerdWallet's Gib Biddle T'91 came to Tuck as a marketer, but then realized he was more of a builder.

Read More

Bill McLaughlin

Bill McLaughlin D'78, T’81 is leading America’s oldest mail-order company into the digital future, while mentoring its next generation of leaders.

Read More

Rohit Dugar

Former investment banker Rohit Dugar T'07 is transforming his beer-brewing hobby into Hong Kong's first craft brewery—and using his Tuck experience to navigate the challenges of entrepreneurship.

Read More

Daniel Revers

The new Revers Center for Energy, made possible by Daniel Revers T'89, expands Tuck’s energy programming in the classroom and beyond.

Read More

Michelle Mooradian

Fluent in four languages and passionate about entrepreneurship, Michelle Mooradian D’95, T’04 went from her post-Tuck consulting job at Opera Solutions to spend almost five years working for McKinsey’s Rio de Janeiro office.

Read More

Jack O’Toole

For Jack O’Toole T’14, “building” and “contributing” are words to live by. As a Marine, he did both.

Read More

Roger McNamee

Investor. Philanthropist. Entrepreneur. Roger McNamee T’82 is all of these and more in a career that has taken him to the top of the tech world.

Read More

Barry Hume

After graduating from Tuck, Barry Hume T'95 joined PepsiCo’s Boston-area operations as finance director—a position that quickly provided the opportunity for advancement, but with a difficult choice to make.

Read More

Carly Rosenberg

Digital marketing was practically in the stone ages when Carly Rosenberg T'05 graduated from Tuck and went to work as a marketing manager at Saks Fifth Avenue.

Read More

Dennis Lasko

What's for dinner? Pantry, a new food retailer founded by Dennis Lasko T’08, has the answer.

Read More

Jeff Coleman

T’87 Jeff Coleman’s quest for better nutrition led him to a new, whole-food fuel for athletes and a surprising second act.

Read More