Tripadvisor Co-Founder: Why He Left and What He’s Building Now

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
(16:33) Speed Wins: The Importance of Agility
(22:46) Measuring Success and Embracing Change
(28:40) Hard Work and Personal Growth
(36:20) Management and Leadership Insights
(40:23) Setting Company Culture
(48:00) Adapting to Market Changes
(51:45) Hiring the Right People
(53:27) Identifying Red Flags in Interviews
(54:51) The Importance of Self-Improvement
(55:29) Curiosity and Adaptability in Candidates
(56:36) Managing Through Crises: 9/11 and COVID-19
(01:02:12) Lessons from Early Career and Centerline Software
(01:05:02) Founding Tripadvisor and Its Growth
(01:18:03) Tripadvisor's Acquisition and Integration with IAC
(01:25:23) Transitioning from Tripadvisor to Give Freely
(01:27:26) The Vision and Impact of Give Freely
(01:37:10) Conclusion and Final Thoughts
Show Notes:
givefreely.com/
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: / @redpointai
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.

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One go-to question he asks: What's the hardest project you've ever worked on? Kaufer said he listens for tendencies to blame others (a red flag) or an ability to empathize with coworkers (a green flag).
"That can often tell me, are they a team player?" he said. "It can tell me, are they ever taking responsibility for why something became difficult?"
This is totally dependant on level and circumstances. If you’re managing projects for executive level leaders and they’re making decisions without listening to the advice of the project manager and SMEs… the issue is the exec.
It’s completely unrealistic to think projects do not exist where people are the problem.