Ed on the Edge Ep 48 · Dan Rosensweig | Executive Chairman of Chegg
May 29, 2025
Dan Rosensweig, the Executive Chairman of Chegg and former CEO of Guitar Hero, shares his journey of transforming Chegg into a digital education powerhouse. He discusses the importance of prioritizing student needs and the role of AI in enhancing personalized learning. The conversation dives into his career transitions, including pivotal moments at Yahoo!, and how mentorship has shaped his path. They also explore the contrasting cultures of Silicon Valley and New York, emphasizing the unique influences each has on innovation and personal growth.
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Laid Off on First Day
- Dan was laid off from his first job the same day he started due to company changes.
- This unexpected event led him to a long career at Ziff Davis, beginning with selling computer magazines.
Personal Drive Behind Chegg Role
- Dan chose to join Chegg because of his daughters' college experience and desire to transform education.
- He found college outdated and saw opportunity to lower costs and help underserved students.
Chegg's Student-First Mission
- Chegg's North Star is to always put students first, helping them succeed and thrive.
- This mission originated from a personal encounter with a struggling student at the DMV in New York City.