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

Context with Mike DelPrete
Claim This Podcastby Mike DelPrete
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Podcast Overview
Conversations with industry leaders about the businesses and technologies changing real estate.
Language
🇺🇲
Publishing Since
9/10/2023
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Recent Episodes

April 26, 2026
Holy Grail 03: The Power Buyer Clue
<p>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.</p><p>Check out the companion site for this podcast series at <a href="https://holygrail.mikedp.com">holygrail.mikedp.com</a>. 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.</p>

April 15, 2026
Holy Grail 02: Surveying the Landscape
<p>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.</p><p>Check out the companion site for this podcast series at <a href="https://holygrail.mikedp.com" target="_blank" rel="noopener noreferer">holygrail.mikedp.com</a>. 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.</p>

April 15, 2026
Holy Grail 01: The Search Begins
<p>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!</p>
56 total episodes available
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Frequently asked questions
Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.
- What is Context with Mike DelPrete?
- How often does this podcast release new episodes?
This podcast updates bi-weekly.
- Where can I listen to this podcast?
This podcast is available on 7 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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