Students at Hobart and William Smith Colleges will soon learn leadership lessons directly from some of the world’s most influential executives, artists, and entrepreneurs.
This spring, HWS will offer “MGMT 305: Leadership and Learning in Entrepreneurial Values,” a management course cotaught by Professor of Business and Entrepreneurship Tom Drennen and Chegg President and CEO Dan Rosensweig ’83.
The course is designed to feel less like a traditional lecture and more like a seat in the C-suite. Each week, students will engage with high-profile guest speakers who have led companies, shaped industries, or navigated major cultural shifts.
The guest list includes Sheryl Sandberg, former Twitter CEO Dick Costolo, producer Brad Falchuk ’93, rapper MC Hammer, investor Ashton Kutcher, singer-songwriter Jewel, climate entrepreneur Adam Met, and WNBA players Breanna Stewart, Napheesa Collier, Lexi Hull, and Cam Brink. Executives from companies such as ESPN, Nike, Meta, Verizon, Adobe, Eli Lilly, and Rent the Runway will also take part.
Rather than focusing only on theory, the course centers on real-world decision-making. Students will research each guest in advance, prepare questions, and reflect on how each conversation challenges their thinking.
“What has impressed me most about Dan’s preparation for this course is his discernment about what students can learn from each guest,” Drennen said.
Rosensweig brings decades of senior leadership experience from companies including Yahoo!, CNET, ZDNet, and Guitar Hero. He is a longtime supporter of HWS and a nationally recognized leader in the education technology space.
The course will culminate in a team-based venture pitch, where students develop and present a business idea inspired by lessons from the semester. Students will also complete a personal strategy statement outlining the values and principles they want to carry into their careers.
“It’s the advantage of a liberal arts education,” Drennen said. “Our course objectives prepare students to apply critical thinking, creativity, ethical reasoning and strategic problem-solving to challenges.”
College leaders say the class reflects HWS’s focus on experiential learning and preparing students to lead in complex, fast-changing environments shaped by technology, global markets, and artificial intelligence.

