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. The board meeting where he quoted Yeats and Colonel Jessup from A Few Good Men. The walk with a Greylock partner that reset his entire relationship with his board. The rentals acquisition he financed with debt in 2021, right before the music stopped. Rewriting a single email 83 times because he could not figure out how to disagree with his new parent company's CEO.

Jeff and Jessica bring two decades of executive search experience to the hiring question Glenn admits he never fully solved, including the advice from Jeff that gave Glenn permission to walk away from a candidate he had already taken to dinner, drinks, and references.

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TOPICS COVERED

FINDING THE WORK
→ Why writing alone in a room made him depressed, and why business is just being creative with other people
→ Working for three founders barely older than him and realising he could do it too
→ Picking the big idea over the small one, and why ambition makes recruiting easier
→ His brother's addiction, the ER doctors, and the decision to do something good inside business

HIRING AND JUDGEMENT
→ Jeff's method: go in looking for every reason the person is wrong
→ Never hiring someone you are not genuinely excited about, even when you have come too far to stop
→ What negotiating severance reveals about a candidate before they start
→ Why subjectivity is a feature, not a bug, and the Peter Chernin story behind it

BOARDS AND CEO GROWTH
→ How a fraught, adversarial board became one of his greatest assets
→ Blaming the board when the real problem is the product
→ The one question that turns a board meeting from a performance into a working session
→ Why $50M seed rounds at $400M valuations have made honest board conversations harder

LEADERSHIP AND THE HARD CONVERSATION
→ Being too kind for too long, and the cost of hints instead of clarity
→ Writing down what you need to say, then throwing the paper away and saying it anyway
→ Getting nearly fired at Plumtree in a 30-second conversation, and the turnaround that followed
→ Why founder mode has a real insight buried inside a bad excuse
→ Making the call people disagree with, then calling them afterwards to replay their argument back

WHAT HE ACTUALLY LEARNED
→ Working 15-hour days when four or five one-minute decisions created more value than all of them
→ Why he stopped trying to be the smartest person in the room
→ Real estate agents, a sea of love, and how they changed how he sees business
→ His closing gift to listeners: if people feel the love, they will forgive almost anything

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