Context with Mike DelPrete

Hosted by Mike DelPrete

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Episodes

Latest episode

Apr 2026

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EN-US

About the show

Conversations with industry leaders about the businesses and technologies changing real estate.

Listen to episodes

56 recent

April 26, 202645 min

Holy Grail 03: The Power Buyer Clue

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.

April 15, 202652 min

Holy Grail 02: Surveying the Landscape

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.

April 15, 202620 min

Holy Grail 01: The Search Begins

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!

April 8, 202635 min

Jun Choo: Customer Problems First

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.

April 2, 202643 min

Rory Golod: Balance of Power

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.

March 29, 202643 min

Guy Gal: Coming Soon Stratagems

Guy Gal, CEO and co-founder of Side, and I discuss why he was one of Zillow Preview's launch partners, the pre-marketing and iBuying parallel, why pre-marketing is a solution searching for a problem, the real problem nobody in the industry wants to address (too many part-time agents), how corporations extract value and small businesses create it, what the craft beer revolution teaches us about brokerage consolidation, why the gravity of real estate always pulls back to local, and why this is the last time he'll ever talk about pre-marketing.

March 11, 20261 hr 13 min

Deep Dive: The Redfin & Compass Deal

Rocket's Joe Rath and I unpack the recently announced Compass & Redfin partnership, that, among other things, will see Compass's exclusive listings appear on Redfin.We cover the specifics of the deal and the "why" behind it all -- from what Rocket is trying to accomplish, to why Compass, and what happens when someone clicks the button. Joe makes a strong claim -- Rocket is playing to win -- and then lays out their rationale for this deal and everything else they're doing in the real estate space.

January 21, 202631 min

Emily Girard: MLS Whack-A-Mole

Emily Girard, CEO of Unlock MLS and the Austin Board of Realtors, and I discuss morning dopamine hits, how I ruined her weekend, the Google listings fiasco, why she hates being reactionary, why an MLS exists, why no one can force private listings, the “what’s best for the consumer” fallacy, what needs to change in VOW and IDX feeds, and why she wishes the industry never launched the clear cooperation policy.

December 12, 20251 hr 52 min

Deep Dive: The Portal Wars

From deep inside the world of real estate portals, Scott Bond and I have an intelligent conversation about the past, present, and future of the Portal Wars.We look at the competitive landscape, how we got to today, why it’s trendy to hate Zillow, evaluate Homes.com’s strategy, look at the most important metric to track (trust), and sprinkle in international examples and learnings. We then shift to the two Power Plays that will shape the portal landscape for years to come: the end-to-end ecosystem and exclusive inventory. We talk about why it’s going to be an absolute grind, the challenge of selling mortgages, why I don’t do all my shopping at Target, and, yet again, why agents are absolutely indispensable.

October 5, 202547 min

What Didn't Work: Aalto

This is the first episode of a new series: What Didn't Work. I'm diving into the real estate companies and ideas that just didn't work out, unpack exactly why, and reveal the key lessons learned -- directly from the entrepreneurs involved.My first guest (who inspired this idea) is Nick Narodny, CEO and founder of Aalto, which just didn't work out. With over $50M raised from top tier VC firms, Aalto was a private listing marketplace and then pivoted to a "digital agent" once Clear Cooperation shut down their business. In the end, neither idea worked.Nick opened up about exactly what didn't work, why, and what he learned through the process. From navigating buyer emotions in real estate to product market fit suction to the three hurdles of fear, these are hard-fought learnings that I think everyone in the space should know!I'm doing this for two reasons. First, I want to reduce the stigma around talking about failure. Nick didn't fail. He tried and learned, and that should be celebrated. Second, I want to capture and publish these valuable learnings, which are really worth their weight in gold for other would-be proptech entrepreneurs in the space.Not everything is great all of the time. Sometimes things don't work out. Let's explore why, and get smarter together. Thanks for your vulnerability and openness, Nick.