Tripadvisor Co-Founder: Why He Left and What He’s Building Now
EP 107 of The Logan Bartlett Show: Untold stories from tech's inner circle
Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He shares his greatest wisdom from getting acquired and spun out from IAC, becoming a public company CEO, and operating a fast-growing company over a decades-long journey. Steve also shares behind-the-scenes insights of his new venture, Give Freely, and reflects on his entrepreneurial path.
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✉️ Episode Memo
→ Tripadvisor didn’t work until attempt #5
Tripadvisor went through four failed business models before finding the one that worked. At a critical juncture, they had just six months of runway remaining. Steve credits their success to their swift decision-making and ability to pivot rapidly. Without these quick shifts, the company wouldn’t have made it.
→ Will AI take over travel recommendations?
For simple queries like flight information, AI is fabulous. However, for more personal decisions that require an opinion (like finding a restaurant or hotel that fits exactly the vibe you’re looking for), human reviews may feel more trustworthy. Thus, Steve predicts legacy review platforms like Tripadvisor, OpenTable, and Yelp will remain valuable through the age of AI. When making a decision, people will likely trust a brand putting its name behind a recommendation above an AI agent with no reputation to uphold.
→ Speed wins
Steve hung a sign on his door that says "Speed Wins" to remind everyone of his core philosophy. He believes in the principle of "disagree and commit," emphasizing action over endless debates and meetings about how to make decisions. As a CEO, Steve is highly risk-tolerant and believes that if you're not making mistakes, you're not pushing hard enough. For him, it's better to get things done, even if it means occasionally making errors along the way.
More wisdom from Steve’s experience in the full episode.
⭐ Trailer
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