My first stop: a conversation with Carey Armstrong, who has glimpsed the Grail! She's been at Zillow, built a mortgage company, and is one of the few people I know who's seen this from every angle. I needed someone I trust to help me map the whole landscape before I start digging into the specifics. What we found: the Holy Grail has always been about profit, not consumers. The executives pitching it have probably never processed a loan. And the real unlock might not be price or convenience — it might be confidence that your deal will actually close. I didn't expect that going in.

I'm starting something new. This is the first episode of an investigative series — The Search for the Holy Grail of Real Estate. I'm going into the field, talking to the smartest people I can find, and piecing the evidence together as I go. In this episode, I lay out what the Holy Grail is, why companies keep chasing it, who's tried and failed, and why I think now is the time to figure out what's real and what's a myth. I don't have a destination in mind, just a direction. Come along for the ride!

Jun Choo, Chief Operating Officer of Zillow, and I discuss the launch that agents hated (and the lessons it taught about empathy), why Zillow Home Loans is really a trust business, how Zillow allocates resources, why the 10% revenue share with listing agents on Zillow Preview is such a big deal, why AI search is real but some of the predictions are hype, what Zillow Pro and the My Agent feature mean for the CRM play, and the fortune cookie advice he'd send his past self: you don't have to have all the answers.