Context with Mike DelPrete

I hit the road and spend a day with Rocket in Detroit. I want to walk the floors and see the biggest company chasing the Holy Grail for myself. I went in skeptical. Redfin's posting a 50% attach rate since the acquisition and I didn't believe it — they were at 27% before. How? Turns out the magic is that the loan officers and the agents just like each other. Bundles work when the partners...

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...

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 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...

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 me...

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 c...

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...

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 p...

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 cooperat...

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 t...

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 t...

Austin Allison, CEO and co-founder of Pacaso (and dotloop), and I discuss what makes a real estate startup successful, the advantage of raising money from retail investors, why you need agents on your side, why we’re all resistant to change, surviving the past two years, listening to constructive feedback, skepticism as a validator of new ideas, and what he would do differently if he had to do it...

If I were to start a real estate brokerage   today , what would it look like? In this long-form conversation, I sit down with Austin broker-owner Eric Bramlett to answer that question. We cover: 1. What’s broken in brokerage today  -- from “masses of asses” recruiting and misaligned incentives to the flood of part-time agents and industry noise. 2. What’s actually working  -- the common threads be...

Garth Graham, Senior Partner at Stratmor Group, and I chat about the biggest problem in mortgage, the cost of origination ($12k), optimizing the consumer experience, being worse than you think, spending bad money after good, the loan officer compensation issue, training AI models, what consumers really hate (the 7 deadly sins), what makes a great loan officer, and why Garth will never be on my pod...

Let’s try something new. I’m joined by Carey Armstrong for a deep dive on Redfin — the business, the model, and the legacy. With Redfin’s acquisition by Rocket, one chapter closes and another begins, so let’s see what we can learn. Over an hour and forty minutes, we unpack Redfin’s history, do a deep dive into the business model(s), discuss key challenges and structural issues, and wrap it all up...

Varun Krishna, CEO of Rocket, and I discuss when to pick up your phone in the morning, being a newcomer to the housing industry, what he wishes he knew when he joined Rocket, the industry’s adversarial dynamic, AI as the removal of experience, why he got the top job, structuring the org chart to match strategy, different vs. better, the art of customer-driven innovation, and how to get big compani...

Levent Künzi, CEO at Switzerland’s Properti, and I discuss disruption and data limitations in European markets, sustainable growth, going against the grain of an end-to-end ecosystem, moving faster with more focus, international inspiration, permanently improving yourself, generating seller leads, why brand is so important, and exclusive listings in the Swiss portal landscape.

Lisa Farrar, COO at Sweden’s leading real estate portal Hemnet, and I discuss starting your day with a forest run and swim, the importance of clarity in strategy, Hemnet’s top KPIs, balancing demands of different customer groups, partnering with agents, balancing a portal’s role in exclusive listings, copying with pride, a specific product f*ck up, and moving fast vs. moving perfectly.

Lukas Rose, CEO of Germany’s ProperBird, and I discuss the exclusive inventory power dynamics across Europe, how it encourages competition, the U.S. being the exception and not the rule, how to monetize home seekers, why tech adoption is so slow, killing new ideas, and why an agent’s top lead sources are his dog, his kids, and firefighters. Here's the research I mention: Scout24: Growing a New...

Rory Golod, president of Growth and Communications at Compass, and I discuss his 10 year journey at Compass, focus as a luxury, building boring products, being a lightening rod in the industry, companies as confusion machines, the inventory strategy and its momentum, outworking your competitors, a 2019 fortune cookie, and the lack of brokerage innovation.

With $7.3B in mortgage origination volume in 2024, Justin Messer, CEO of Prosperity Home Mortgage, and I discuss being affiliated with Berkshire Hathaway, why attach rates top out at 25%, where tech is having an impact, why being on the road is a winning formula, powering a 15 minute pre-approval, starting a mortgage company from scratch, lead source durability, and why mortgage is so hard.

Steve Sanders, with deep brand and marketing experience from working with Zillow and Pacaso (and fellow CU Boulder professor), and I chat about key learnings from iBuyer consumer research, the power and limits of Zillow’s brand, the importance of differentiation, which iBuyer is getting it right, what consumers really want from their agent, how to do real estate branding wrong, understanding unmet...

Damian Eales, CEO of realtor.com, and I talk about the necessity of disciplined focus, the origin of the flat white, turning negatives into opportunities, partnering with your closest competitor, leveraging News Corp assets, doing the right things in the down cycle, why everything starts with audience, scheduling think time, investing in MLS relationships, and “debate, decide, deliver.”

Joe Rath interviews me! We discuss trends in real estate tech, what’s surprised me, the impact of AI, the best product not winning, great ways to incinerate millions of dollars, the only thing that matters to portals, the “perfect house” fallacy, the decreasing value of a lead, psychological bulwarks, news vs. entertainment, strategic planning advice, and competing where you can win. And in case y...

Sean Soderstrom, CEO and co-founder of Courted, and I discuss goat yoga, working in a sauna, motivation vs. inspiration, predicting agent migration, solving actual problems, strategic mistakes, unbundling the brokerage business model, recruiting innovation at Compass, the value of the Hub, making data easily actionable, and trusting your instincts.