Unlikely Entrepreneurs with Harvard Business School Professor Lou Shipley

Lou Shipley has led multiple startups to breakout growth ($100M+) and major acquisitions to companies like Citrix and Synopsys. He has taught some of the most in-demand sales and GTM courses at HBS and MIT. In this episode, we dig into the core traits behind Unlikely Entrepreneurs — the title of the new book he co-authored — and why unconventional founders so often win through curiosity, ambition, and determination. Lou breaks down “the problem with the problem,” why the sled only moves as fast as the lead dog, and the essential role founders play as keepers of culture. We explore the patterns he’s seen across high-growth companies, the misunderstood craft of sales, and what Fortune 500 innovators can learn from Unlikely Entrepreneurs.