chegg
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Osman Rashid had the customers. Now he needed the books.
Chegg’s founding CEO learned to buy the textbooks after the orders arrived. From digital books to Pakistani classrooms, Osman Rashid has kept finding new ways to get an education into someone’s hands.
Irwin Liu and the talent a résumé leaves out
After leading education businesses at Chegg and Busuu, Irwin Liu took charge of Catalyte. His next assignment connects a familiar ambition - widening access to learning - with the harder business of getting people hired.
Marc Boxser Has Spent a Career Asking Technology the Awkward Question
From Charlie Rose to classrooms, Chegg and autonomous agents, Marc Boxser has made a profession of translating complicated technology into human consequences.
Gibson Biddle
Gibson Biddle is a product strategy teacher who ran product at Netflix from 2005 to 2010 and was Chief Product Officer at Chegg through its 2014 IPO. He now writes the 'Ask Gib' newsletter for 30,000+ product people, runs workshops, and gives talks built around his DHM model: delight customers in hard-to-copy, margin-enhancing ways. His career stretches from building video games at Electronic Arts to co-founding kids' software firm Creative Wonders to lecturing at Stanford.
Oren Zeev
Oren Zeev is an Israeli-American billionaire venture capitalist and the most successful solo general partner in VC history. Operating entirely alone from Cafe Venetia in Palo Alto - no partners, no office, no employees - he manages $2.5B+ in assets under management across 9 funds. His concentrated, conviction-driven approach has delivered ~100% IRR since 2008, with landmark investments in Navan (TripActions), Tipalti, Houzz, Chegg, and Next Insurance. His $50,000 'relationship check' in Navan's founders before they had even incorporated the company eventually became a $1B+ payday when Navan IPO'd in October 2025.