Context with Mike DelPrete

I begin by tracking the number of mortgage loan originators at the big players — which tells me who's really investing in the search for the Grail. Then I sit down with Ryan Dibble, one of the Flyhomes co-founders. Flyhomes is a power buyer that stumbled on the Holy Grail with mortgage attach rates around 80%, and then pivoted away from it. Turns out finding the Holy Grail and making the Holy Grail business work are two very different things. One insight: an object in motion stays in motion, meaning consumers will stay in an ecosystem unless there's a reason to leave. That changes how I’ve been thinking about the whole system.
Check out the companion site for this podcast series at ⁠holygrail.mikedp.com⁠. It's a case file — the evidence I've gathered, the theories I'm testing, the questions I'm chasing, and a place to drop intel if you're seeing patterns from the field.

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.
Check out the companion site for this podcast series at holygrail.mikedp.com. It's a case file — the evidence I've gathered, the theories I'm testing, the questions I'm chasing, and a place to drop intel if you're seeing patterns from the field.

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.

Rory Golod, President of Growth at Compass International Holdings, and I discuss what it's like to go from 20 agents to 340,000 across 120 countries, why the Rocket/Redfin partnership is about shifting the balance of power back to agents, not holding grudges against former adversaries, what he would do if he found $20 million in a briefcase, pre-marketing as a pricing tool (and the Halloween costume analogy), why being on the front lines is how you actually learn, the addictive habit of focus, and what really motivates Robert Reffkin.