Playmakers with Andrew Flachner

Playmakers gets inside the minds—and moves—of the people shaping the future of real estate. Hosted by Andrew Flachner, co-founder of RealScout and a trusted interviewer of top industry leaders, the show features unfiltered conversations with the executives, entrepreneurs, and dealmakers behind real estate’s biggest shifts.

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Episodes

Redfin CEO on AI, Rocket Acquisition, Vertical Integration, and Housing’s Next Era

For nearly two decades, Glenn Kelman has led Redfin’s push to merge cutting-edge tech with full-service brokerage, reshaping how homes are bought and sold. Now, following its multi-billion-dollar acquisition by Rocket Companies, he’s setting his sights on an AI-powered, vertically integrated future. In this candid conversation with Andrew Flachner, Glenn shares lessons from Redfin’s early missteps, insights on making housing more transparent and liquid, and why he believes housing is “the ultima...

Aug 14, 2025•34 min•Ep. 5

How a $5.7B Real Estate Leader Stays Disciplined in Tough Markets

Sue Yannaccone is the CEO and President of Anywhere Brands, overseeing iconic real estate brands such as Coldwell Banker, Century 21, Sotheby's International Realty, Corcoran, Better Homes and Gardens Real Estate, and ERA. Under her leadership, Anywhere completed more real estate transactions than any other company last year. Andrew Flachner leads RealScout, a rapidly scaling real estate technology platform that powers agents, teams, and brokerages nationwide. In this episode of Playmakers, we e...

Jul 23, 2025•41 min•Ep. 4

$315B Founder on What AI Means for Real Estate Agents

Joe Lonsdale is the co-founder of Palantir (the #1 top-performing stock in the S&P 500) and General Partner at 8VC, where he’s helped shape some of the most influential AI and infrastructure companies of the last two decades. In this episode of Playmakers, we explore what the rise of AI means for real estate agents, the future of knowledge work, and how autonomous systems—from flying taxis to AI-driven construction—could reshape housing itself. We also dig into: – What AI will automate vs. a...

Jul 09, 2025•27 min•Ep. 3

Buyer Market Predictions, Private Equity at KW, Why Agents Can’t Pitch Their Value — with Gary Keller

RealScout CEO Andrew Flachner sits down with Gary Keller, founder of Keller Williams Realty and one of the most influential thinkers in real estate/business. Gary opens up about what it really takes to succeed in today’s market—and why most agents still can’t clearly articulate their value. He also shares his prediction for when the buyer market returns and what private equity’s growing role means for brokerages like KW. We also dive into: – KW’s new partnership with Stone Point Capital – Gary’s...

Jun 10, 2025•54 min•Ep. 2

Why Gino Blefari Stepped Down, Real Estate Leadership Burnout, CCP, Warren Buffet, and more

In this inaugural episode of the Playmakers Podcast, RealScout CEO Andrew Flachner sits down with Gino Blefari, former CEO of HomeServices of America and Berkshire Hathaway HomeServices, for an unfiltered, 45-minute conversation. Gino opens up about his decision to step down, what’s changed in real estate leadership, and why he believes it’s still a great market for agents—even if it’s “no longer fun” for many at the top. We also dive into: – The impact Warren Buffett had on Gino’s career – His ...

May 28, 2025•41 min•Ep. 1

Coming Soon: Playmakers with Andrew Flachner

Playmakers: Inside the Minds—and Moves—of Real Estate’s Power Players is a new podcast featuring real conversations with the executives, entrepreneurs, and dealmakers shaping the future of real estate. No fluff. No self-promotion. Just sharp insights into the strategies and decisions driving the industry forward. Subscribe now to get inside access to the conversations shaping what’s next.

Apr 27, 2025•13 sec

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