Former President & Chief Executive Officer, Tripadvisor
Search every verified Stephen Kaufer interview, podcast appearance, and on-the-record quote — each transcript cross-checked by AI and human review to confirm speaker identity. 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.
“We looked at this and said massive sigh. We got a massive problem ahead of us cuz travel industry is in total disarray. We have, you know, just a there's no other way to say it. We just had a failed business model.”
“I'm like, 'Well, financially it was a crazy bad decision.' But given everything I knew at the time with the risks you outlined before, the fact that it was kind of a life-changing experience for everyone at the company was absolutely the right decision.”
“I think absolutely transformational. A friend of mine said uh oh my god I went to GPT. I put in give me a 5day itinerary for Paris and I got this amazing list. I'm like yes Arthur Fromer did that before I was born. Right. That's not the impressive AI that I think is really coming.”
“We're trying to get the price point below what you're going to pay your credit card processor, right? A tenth of what you'd pay the OTAAS in the same situ.”
“I would never short booking or Expedia now. They're going to do just fine. We think direct bookers really has the opportunity to help the individual hoteliers, to help the chains with this brand new technology that no one really knows where it's going to go.”
“We got an offer for $200 million cash in 2004. And then IC spun out all of their travel asset into a group called Expedia, Inc. And then we continued to grow and grow as a pure media company under Expedia.”
“It was a combo of money and risk. So that none of the founders were kind of independently wealthy. The notion of venture buying out x% of founder shares wasn't common back then. It was more seen as oh founders becoming risk adverse or founder isn't all in if they've sold some of their shares. Truly ridiculous. Glad tha...”
“Trip Advisor Plus was uh was our uh co invention. Okay. Uh as the political saying goes, never let a good crisis go to waste. Uh we were able to secure enough uh you know bank loans to go through you know like Trip Advisor was profitable since that very first uh quarter in 2002 uh every quarter until COVID where revenu...”
“I put a sign on the door to my office that said speed wins because anyone coming in to talk to me about anything would have to see that sign. I want to drive home with every single person in the company that we value going fast.”
“I'm not going to slap you if you miss a deadline. I used to be an engineering manager for many, many years when I would miss a deadline I'd get penalized. So I got used to padding my deadlines so I wouldn't miss them. Then I was a hero. Everyone optimizes for being a hero. So therefore like, oh, can't you pull that sch...”
“The number one job is to not let those people in the company. Your number one job is not having a great performance system that gets the people out. Your number two job is to make sure they don't get in the company in the first place. It just breeds the mediocrity.”
“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 f...”
“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, I could spend the money and no outside investor would give a [__] truly if they were losing money. I know what I would have to report that loss co...”
“Trip Advisor raised 1.2 million in a seed round in February of 2000. By summer of 2000, we were offered another 2 million because travel was picking up. Our investors got more excited about what we were doing and the risk that I would assemble a terrible team because they invested just in me. One co-founder was address...”
“If the company sold for $100 million and your share was $30 million or your share was $30 million less 20%, is that going to change your life? Like no, not at all. Okay, if the company runs out of money and you have to start over, is that an impact on your life? Oh yeah, good. So let's optimize for what will prevent th...”
Steve Kaufer got the idea for Tripadvisor in 1998 after spending way too many hours online, trying to figure out if a resort in Mexico ...
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How did Tripadvisor become every traveler’s starting point? Steve Kaufer joins Joubin Mirzadegan on Grit to break down how Tripadvisor became the internet’s trusted travel companion, built on over a billion reviews and decades of trust. He also shares why early personalization fell short and how AI is finally doing what travel agents once did by understanding the traveler, but faster, smarter, and at scale. Guest: Steve Kaufer, co-founder of TripAdvisor Chapters: (00:00) Trailer (00:45) Introduction (01:32) Early days of Tripadvisor (08:14) Catching the startup bug (18:42) Luck and timing (…
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…
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…
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…
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…
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…
Recording of the Everything Marketplaces Group Chat #165 (7/16) with Steve Kaufer, who's the Co-founder & former CEO of ...
Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path. (00:00) Intro (01:00) Steve Kaufer's Journey with Tripadvisor (03:18) Handling Negative Reviews and Legal Issues (05:24) Psychology of Reviews and User Behavior (10:01) Impact of AI on Review Platforms (15:02) Graduation Speech and Key Lessons (16:3…
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