Three brochures offered Stephen Kaufer a choice, provided he could tell them apart. He was planning a holiday in Mexico. The resorts occupied different price brackets, but their promotional materials made each look like a very sensible place to spend money. Beautiful settings, persuasive photographs, a reassuring absence of anything unpleasant. The inexpensive option looked particularly tempting. He went online before committing.
Eventually, he found a personal webpage with a guest’s account and photographs. Here was information with a different purpose: someone describing the holiday they had actually taken. It changed his booking. He chose another resort. An ordinary act of consumer caution had exposed a problem that brochures, for all their sunshine, were poorly equipped to solve.
Kaufer’s wife, Caroline, encouraged him to turn the problem into a business. Tripadvisor followed in 2000. The neat version of the story ends there, with the discovery of an unmet need. The more interesting version begins with what happened next: a software engineer had noticed something useful, then had to work out who would pay for it.
Before the beach, the fencing strip
Long before travelers knew his company’s name, Kaufer was explaining a narrow defeat in a college newspaper. In December 1983, Harvard’s fencing team lost to Penn, 14-13. Harvard had led 11-7. Its captain, Stephen Kaufer, offered a diagnosis: “We are physically ready, but not mentally.” A close result evidently did not require a comforting explanation.
It is a pleasing early glimpse of someone later associated with numbers, decisions and the gap between preparation and performance. Fencing supplies an attractive metaphor for entrepreneurship, although the record does not require us to make him conduct a board meeting with an imaginary foil. He was a college athlete who also studied computer science. Both pursuits required his attention.
His first business career belonged to software development tools. He co-founded CenterLine Software and served as its vice president of engineering; later, he was president of CDS, another programming and testing tools business. Before he was helping people evaluate hotels, he was helping people build software. The travel business came with an engineer already attached.
The demonstration that became the business
The original Tripadvisor proposition was aimed at other companies. Kaufer and his colleagues would assemble travel information and supply search technology to websites that already served travelers. Langley Steinert was a co-founder. The consumer website was initially a demonstration of what their technology could do. Prospective customers could look at it and imagine buying the underlying service.
Unfortunately, imagining a customer and acquiring one are separate activities. The licensing plan failed to bring in the business they needed. The demonstration site, meanwhile, attracted visitors. The team had built something people wanted to use, alongside something companies were reluctant to buy. That distinction gave them a direction when their original plan was running short of road.
They tried advertising on the consumer site. Banner advertising disappointed; a model in which travel companies paid for clicks proved more useful. Reviews became central to the service. A traveler could read about a hotel and then follow a link toward making a booking. The opinion and the commercial opportunity sat close enough together for a business to form.
- 01License the searchSell travel information to other websites
- 02Follow the visitorsThe demonstration attracts an audience
- 03Connect the decisionReviews and paid referral clicks
The irony is modest but useful. A business that helped people choose between alternatives survived by reconsidering its own. The company’s first plan did not possess special authority merely because its founders had written it down. Travelers were already voting with their attention. Kaufer’s task was to notice where they were going and make the economics work around them.
Two signs, very little patience
By 2014, Kaufer had reduced part of his management philosophy to two handwritten signs on his office door. One read “Speed Wins.” The other read “If It’s Worth Doing, It’s Worth Measuring.” They make a compact pair: get moving, and establish whether the movement accomplished anything. A door can sometimes do the work of a rather expensive presentation.
“Speed Wins.”Stephen Kaufer’s office-door motto
He described challenging schedules that stretched a small software change across several months. What actually needed doing? Could the specification be written quickly? Could people comment by tomorrow? Breaking a project into its real steps made delay easier to question. He also preferred a direct conversation when an answer was needed, rather than an email exchange conducted across the same building.
There is a trap in celebrating speed: activity begins to look like achievement. His second sign supplied a useful brake. A percentage improvement means little without its starting point. He wanted measures connected to what travelers did and whether they had a worthwhile experience. The engineer’s interest in data survived the promotion to CEO.
His hiring questions tested a related habit: whether someone could reconsider their own work. In a 2024 interview, he described asking candidates about a successful project, then asking whether they would do it exactly the same way again. A polished account of a win could get someone only so far. He wanted evidence that the person had kept thinking after the applause.
He also valued curiosity about new tools, including whether candidates had tried AI chatbots. The question made curiosity observable. Someone could describe themselves as interested in technology; experimenting with an unfamiliar product gave the conversation something concrete to examine. For a founder whose travel business had departed substantially from its original design, being willing to learn after an apparent success was a practical qualification.
A sale, a Passat, and another eighteen years
IAC bought Tripadvisor in 2004 for $210 million in cash. The business subsequently sat within Expedia, then became an independent public company in 2011. Kaufer remained CEO through those changes. Ownership changed more readily than the person responsible for the daily business. Selling the company had not exhausted his interest in running it.
His personal response to the sale included buying a Volkswagen Passat and setting aside money for his children’s education. As details of an internet windfall go, the Passat is refreshingly easy to park. It also fits the picture he gave of himself: someone attached to home in Newton, Massachusetts, without a consuming desire to travel constantly simply because he ran a travel company.
When he did stay in hotels, he said he tried to avoid special treatment and contributed reviews himself. His review carried the same weight as anyone else’s. That seems an appropriate rule for a founder whose product depended on the usefulness of ordinary guests. The executive could enter his own system, but the system did not owe him a better table.
2000Tripadvisor founded
2004Acquired by IAC
2011Independent public company
2022Kaufer leaves CEO role
Scale also brought arguments about who controlled the route to a traveler. Kaufer became a critic of Google’s practices in travel search. In a 2019 interview, he discussed both the competitive landscape and Tripadvisor’s partnership with Trip.com Group. A company built to make information accessible still had to contend with the businesses standing between that information and its audience.
His departure arrived in 2022. Tripadvisor announced Matt Goldberg as his successor, effective July 1. By then, the service counted more than a billion reviews and opinions. Twenty-two years is a long time to remain inside a company’s unfinished business: early experiments, new owners, a public listing, changing products, and an audience whose habits continued to move.
Putting the commission somewhere else
Kaufer did not leave with his next company already fully mapped out. He wanted room to consider work that would make him look forward to Monday morning. Affiliate marketing offered familiar material: retailers already paid commissions when another service sent them a customer. He began considering what would happen if those payments supported a charity chosen by the shopper.
Give Freely launched publicly in October 2023. Kaufer co-founded it with Brendan Buono, its chief technology officer, and funded the venture. Its shopping assistant finds coupons and directs commissions to charitable organizations. The shopper chooses a cause; the retailer supplies the money. Buying something becomes an occasion for giving without an additional payment from the buyer.
Chooses a charity→Retailer
Pays a commission→Charity
Receives the donation
Give Freely directs its commission to the selected cause. The shopper pays no extra donation.
The mechanism matters because the action is familiar. People already look for discounts. Stores already pay to attract purchases. Give Freely inserts a charitable destination into that existing exchange. It asks shoppers to make a small setup decision, then lets ordinary activity carry some of the work. A donation need not begin with another appeal arriving in the inbox.
The ambition is to combine many such actions. A single commission will seldom make an arresting headline. Repeated across a community, the amounts can accumulate. The connection with Tripadvisor is easy to see: one person’s contribution can be modest, useful, and worth collecting alongside other people’s. The new venture changes what gets passed along.
Still asking who gets the information
Travel remains part of his working life. DirectBooker identifies Kaufer as a board member and advisor, alongside former Google Travel leader Richard Holden. Its chief executive, Sanjay Vakil, has worked at both Google and Tripadvisor. The company aims to connect travelers with hotels directly as people increasingly use AI tools to plan trips.
At the 2025 Phocuswright conference, Kaufer joined Holden and Vakil in a discussion of that changing booking landscape. Hotels possess details about their properties, rates and benefits that they want travelers to see. Decades after a frustrating search for a Mexican resort, he is still involved in the question of how information reaches someone deciding where to stay.
There is continuity in these projects without a need to pretend they were inevitable. A disappointing search led to experiments. Experiments led to a business. A later departure created room for another one. Kaufer keeps finding work in the space between a person’s ordinary action and its possible usefulness to someone else. The brochure remains beautiful. He would still like another opinion.