Challenges in Real Estate Financing and Strategy

Let’s try something new. I’m joined by Carey Armstrong for a deep dive on Redfin — the business, the model, and the legacy. With Redfin’s acquisition by Rocket, one chapter closes and another begins, so let’s see what we can learn.

Over an hour and forty minutes, we unpack Redfin’s history, do a deep dive into the business model(s), discuss key challenges and structural issues, and wrap it all up with some timeless lessons learned.

Among other things, we talk about:

• The vision behind the employee-agent model
• Why Redfin never really scaled profitably
• The consumer site everyone loved — but didn’t monetize
• Big bets on rentals and mortgage that didn’t pay off
• And what happens when you try to do everything at once

This is the first long-form podcast I've done. Let me know what you think!