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Stephen Kaufer
Former President & Chief Executive Officer, TRIPADVISOR INC

Steve Kaufer Sharing His Biggest Learnings As The CEO Of Tripadvisor

🎥 May 20, 2025 📺 Everything Marketplaces ⏱ 5m 👁 145 views
Highlight clip from the Everything Marketplaces Group Chat #165 (7/16) with Steve Kaufer, who's the Co-founder & former CEO of Tripadvisor. Tripadvisor is an early travel marketplace that’s scaled to now being one of the largest with over 1 billion reviews on their platform. Tripadvisor was acquired by IAC, merged with Expedia, and went on to IPO, which Steve led as the CEO until 2022.‍ Group chat recording:    • Starting & Scaling Tripadvisor With Steve ...   Steve on Twitter:   / kaufer   Tripadvisor: https://www.tripadvisor.com Give Freely: https://www.givefreely.com Mike (Yoroomie) on Tw...
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About Stephen Kaufer

In a recent interview, Stephen Kaufer discussed the early challenges of building Tripadvisor. He recalled that the company initially had a "failed business model" and described the travel industry as being "in total disarray" at the time. Kaufer also reflected on a difficult financial decision the company faced, stating that while it was "a crazy bad decision" financially, it was "absolutely the right decision" given the risks and the life-changing experience it provided for the company's employees. Kaufer also recounted the origin of the Tripadvisor idea in 1998, which came after he spent a significant amount of time online trying to research a resort in Mexico. He described the early business model of sending users to Expedia for bookings, noting that the company was not initially aware of how many of those users actually completed a booking.

Source: AI-verified profile updated from Stephen Kaufer's recent appearances. Browse all interviews →

Transcript (6 segments)
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Interviewer0:00
I wanted to learn a little bit more about the difference, primarily from the role of a CEO, kind of pre-IPO to if we fast forward to the later stages. What would you say are some of the biggest differences between those two different stages, and then maybe even looking back now?
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Stephen Kaufer0:18
Yeah, it's nice to be out of the public eye. You just have more flexibility again, depending on who your parent company is or your ownership structure.
I
Interviewer0:32
Is the word on the street in terms of, oh, it's miserable being a public company CEO?
S
Stephen Kaufer0:38
No, it wasn't. I don't think it was bad at all.
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Interviewer0:41
Oh, you have to be on the road all the time talking to your investors?
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Stephen Kaufer0:45
No, you don't. I am existing proof point that says nope. I would do a Boston investor conference, sometimes a New York investor conference, was kind of it. I sent my CFO to do those. And I won't say I enjoyed the earnings calls, but they were a great quarterly opportunity to take stock of your business, to think about the questions that kind of your customers as a public company, your investors are going to ask, really get down and dig into. Hey, they're going to ask about, hey, is it domestic or international? Where's this off? This, like, we should have a better answer to that because I'm not really sure. And we would dig ahead of time so that I could understand that. So I, you know, I didn't ever have to deal with a hostile takeover, that sort of thing. And I very carefully and deliberately shared with the people inside the company that we were not going to be a company that was going to pay any attention to quarterly earnings and hitting quarterly numbers. We're going to miss some, we're going to exceed some. I accept an annual report card, like how did we do? But if we feel we have an investment that we want to make that will hurt our earnings and pay off, and we're confident about that, where it's good odds on the risk, I will go to the board and make that claim. And I did several times. The board said we agree, go, or they said we agree, let's test it this way and then, you know, spend the real dollars. And I've been on several boards and like that's the way many boards operate. I'm well aware that there are other boards that are like, like you'll keep your job if you hit your quarterly number. But if you're the CEO creating a board and then deciding to go public, hey, you're calling the shots. You can create the board that you want, usually. And like employees did not like it when stock price went down after a bad quarter, and I addressed it the next company meeting, but that was it. Just didn't give it more airtime. And those companies that, but those people that were really there to make sure their equity went up, they probably weren't joining TripAdvisor in the first place, which was fine with me. And that's kind of how I dealt with that aspect as a public company. You know, you have the stock to play with. If you spend your cash, if it's not a lot, Wall Street doesn't even notice. So that's another reason to do an acquisition. Like literally, I could grow by spending $10 million to buy a company that I thought had a product that could generate a couple million or more in the following years. If it was break-even, like super, I could spend the money and no outside investor would give a damn. Truly, if they were losing money, I, you know what, I would have to report that EBITDA loss on a consolidated basis. What are a company doing a couple hundred million if they were losing 1 million? It just didn't matter to me. They were losing 10, it did matter to me. So like, as a startup, try not to lose money. Company can be bought when they are losing a lot of money, not a strategy I recommend. But yeah, like I'm thumbs up on being a public company if you have the background to get there.