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 ultimate good.”

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• Apple Podcasts: https://apple.co/459lPWc

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We also dig into:

– How Redfin’s dual identity as a tech platform and brokerage became its superpower—and challenge

– Why AI’s biggest impact won’t be replacing agents, but freeing them to focus on high-value work

– The role of transparency in making housing more “liquid” and accessible

– How vertical integration can counter margin compression in a changing market

– Behind-the-scenes of the Rocket acquisition—and why Kelman believes they’re a perfect match

This is an unfiltered look at the moves shaping the future of real estate, straight from one of the industry’s most innovative and outspoken leaders.

00:00 — Intro

02:05 — The origin story: from map-based search to full-service brokerage

04:19 — Lessons from early missteps and finding the tech–service balance

06:33 — Stories from the field that shaped Redfin’s culture

08:18 — The challenge of being both a website and a brokerage

10:00 — Why data is AI’s real differentiator in real estate

11:00 — Current and future applications of AI at Redfin

13:38 — Why AI won’t replace agents in high-stakes transactions

14:24 — Making housing more transparent and liquid

15:57 — Why iBuying economics have changed

17:32— The push for integrated service models

20:50 — Standardization vs. personalization in brokerage

23:06 — Vertical integration as a path to profitability and better service

24:50 — How the Rocket deal came together

27:18 — The vision for Rocket Redfin

28:28 — Putting savings into mortgage rates where consumers feel it most

29:35 — Kelman’s future at Redfin and personal mission

31:38 — The impact Redfin has had on customers and agents

** Connect with Andrew Flachner on Social **

🔗 Instagram: https://www.instagram.com/aflachner/

🔗 Linkedin: https://www.linkedin.com/in/andrewflachner/

Produced by NOVA

Exodus 35 - 40; Leviticus 1; 16; 19