TruthWorks · 2026-08-04 · 45 min
Glenn Kelman ran Redfin for 20 years. He says the most important thing he learned had nothing to do with software. Glenn joins Jessica Neal and co-host Jeff Markowitz on Truth Works for an unusually honest conversation about love, leadership, boards, and the handful of decisions that actually decide a company's fate. Glenn is not your typical tech CEO. At 21 he tried to write a novel, got nowhere, and his girlfriend broke up with him for being unemployed too long. He nearly went to medical school twice. He co-founded Plumtree Software in 1997 and took it public, then almost got fired from the company he started. He joined a nearly dead real estate website that a Seattle VC had put $500,000 into, and spent the next two decades turning it into Redfin, a business that saved consumers roughly a billion dollars in commissions before Rocket acquired it for $1.75 billion. In this episode, Glenn traces the whole thing back to his older brother's struggle with alcohol, the emergency room doctors who kept fighting for a patient any business person would have written off, and the moment he decided he wanted to be good like that. He is candid about the parts most CEOs edit out.
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