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:

https://givefreely.com/ 

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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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.