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Artwork for Context

Context with Mike DelPrete

Mike DelPrete
Real Estate
Zillow
Redfin
Technology In Real Estate
Mortgage Industry
Real Estate Technology
Market Trends
Brokerage Models
Compass
Customer Experience
Real Estate Industry
Technology
Real Estate Agents
Real Estate Market
Exp Realty
MLS
Pacaso
Recruitment Strategies
Aalto
Emotional Dynamics

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

PublishesWeeklyEpisodes56Founded3 years ago
Number of ListenersCategory
Business

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Artwork for Context

Latest Episodes

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 stum... more

YouTube

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 la... more

YouTube

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 e... more

YouTube

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 listin... more

YouTube

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Recent Guests

Ryan Dibble
Co-founder of Flyhomes
Flyhomes
Episode: Holy Grail 03: The Power Buyer Clue
Carey Armstrong
Former Zillow, Tomo, and TruList executive; mortgage and real estate operations expert
Former Zillow/Tomo/TruList
Episode: Holy Grail 02: Surveying the Landscape
Jun Choo
Chief Operating Officer of Zillow
Zillow
Episode: Jun Choo: Customer Problems First
Rory Golod
President of Growth at Compass International Holdings
Compass International Holdings
Episode: Rory Golod: Balance of Power
Guy Gal
CEO and co-founder of Side
Side
Episode: Guy Gal: Coming Soon Stratagems
Joe Rath
Head of Industry Relations at Rocket (formerly Redfin)
Rocket (formerly Redfin)
Episode: Deep Dive: The Redfin & Compass Deal
Scott Bond
VP of Brokerage North America at Renny, with extensive experience in real estate portals.
Renny
Episode: Deep Dive: The Portal Wars
Nick Narodny
PropTech entrepreneur and founder of Aalto
Episode: What Didn't Work: Aalto
Austin Allison
Co-founder and CEO of Pacaso
Pacaso
Episode: Austin Allison: Bucking the Status Quo

Host

Mike DelPrete
Host of Context with Mike DelPrete

Reviews

5.0 out of 5 stars from 59 ratings
  • Solid conversations

    Always appreciate learning Mike’s perspective and nice to hear the conversations. Thanks.

    Apple Podcasts
    5
    EvanSage
    Canada3 years ago
  • Must-listen for anyone in real estate

    Mike asks the important questions that reveal the insights we all love to hear. From hard data to opinions and commentary on marketplace events, he always brings the best conversation to the stage. Mike’s analysis on all aspects of real estate business is second to none and provides compelling content and much to ponder. Thanks, Mike for delivering an easy way to ingest your content via this pod. Keep up the stellar work!

    Apple Podcasts
    5
    Brookelindsay
    United States3 years ago
  • Love Ally

    Super smart

    Apple Podcasts
    5
    sassygirl10
    United States3 years ago
  • Amazing

    Great podcast. One of the most important minds in real estate today.

    Apple Podcasts
    5
    Coach71
    United States3 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise the host's deep dives and data-driven insights into market dynamics.
Guests are seen as high-caliber experts providing real-world perspectives on complex topics.
The show is consistently described as one of the best sources for understanding real estate technology today.
Thoughtful breakdowns of real estate tech trends that help inform strategy for partnerships and sponsorships.

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Talking Points

Recent interactions between the hosts and their guests.

Holy Grail 03: The Power Buyer Clue
Q: What makes a company best positioned to succeed in achieving the Holy Grail?
A company needs strong boots-on-the-ground presence with tight integration between the real estate agent, mortgage product, and localized service, ensuring a differentiated consumer experience that actually moves the needle in terms of outcomes and trust.
Holy Grail 03: The Power Buyer Clue
Q: Do you think the Holy Grail is a myth, or is there real differentiation that could justify the model?
The guest argues it's not a myth but insists there must be genuine differentiation—something beyond funnel placement and tech improvements, like true value for the consumer that keeps them within the ecosystem due to clear advantages and savings.
Holy Grail 03: The Power Buyer Clue
Q: What was the role of mortgage attach in Flyhomes' strategy and why did it matter for customers?
Mortgag attach served as a differentiator by turning financing into a trusted, integrated experience that helped customers win offers, with the mortgage products delivered through Flyhomes' own mortgage operations, making it easier for customers to stay within the ecosystem.
Holy Grail 03: The Power Buyer Clue
Q: When did Flyhomes start exploring the idea of a one-stop shop and what problem were you trying to solve for customers in hot real estate markets?
The guest explains they began by solving customer problems in hot markets, testing a path toward a seamless, insured financing process, and ultimately forming a long-term mortgage integration after proving the real estate experience could be streamlined.
What Didn't Work: Aalto
Q: What is the biggest learning you can take away from that five, six year experience?
We did not properly account for the emotion that goes into a real estate purchase or sale.

Audience Metrics

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Listeners per Episode
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Frequently Asked Questions About Context

What is Context about and what kind of topics does it cover?

A data-forward show that collects insights from real estate tech leaders and industry observers to explore how end-to-end platforms, agent incentives, and consumer trust shape the housing market. Across recent conversations, the core theme is the pursuit of a seamless, one-stop real estate experience — blending search, brokerage, mortgage, and title services — and the tensions between scale, high-touch service, and compliance. Episodes frequently probe how incumbents and startups are attempting to align incentives among agents, lenders, and buyers, reveal practical lessons from landmark launches, and speculate on which models can deliver tangible value to consumers without sacrificing margins. A notable thread is the exploration of portals,... more

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Which podcasts are similar to Context?

These podcasts share a similar audience with Context:

1. HousingWire Daily
2. All-In with Chamath, Jason, Sacks & Friedberg
3. The Brian Buffini Show
4. The Bill Simmons Podcast
5. Industry Relations

How many episodes of Context are there?

Context launched 3 years ago and published 56 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Context?

Recent guests on Context include:

1. Ryan Dibble
2. Carey Armstrong
3. Jun Choo
4. Rory Golod
5. Guy Gal
6. Joe Rath
7. Scott Bond
8. Nick Narodny

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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