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.

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.

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.

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.

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.

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.

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 all over again.

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 between the brokerages and agents thriving, including eXp’s recruiting flywheel, Compass’s communications machine, various new business models, and the overlooked importance of emotional value and culture.3. How we’d build it from scratch -- a focused brokerage designed for the top 20%: lean, selective, efficient, culture-rich, and boringly effective.The themes that emerge again and again: focus, clarity, culture, recruitment, and communication. If you want to understand where brokerage is heading -- and what it really takes to compete where you can win -- this is for you!

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 podcast again.

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 with some timeless lessons learned.Among other things, we talk about:The vision behind the employee-agent modelWhy Redfin never really scaled profitablyThe consumer site everyone loved — but didn’t monetizeBig bets on rentals and mortgage that didn’t pay offAnd what happens when you try to do everything at onceThis is the first long-form podcast I've done. Let me know what you think!

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 companies to innovate.

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 Consumer Revenue Stream

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 needs, the Homes.com ad strategy, and a great case study in defining Pacaso’s brand.

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 you missed it, check out my interview with Joe from February 2024.

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.

Tamir Poleg, co-founder and CEO of Real, and I discuss work days beginning at 3pm, how agents are underserved, growing from 800 to 22,000 agents in four years, what he would do as CEO of an incumbent, how everyone failed with tech, the one stop shop graveyard, replacing 90% of agent tasks with AI, and the most important thing he does as CEO.

Wendy Forsythe, CMO at eXp Realty, and I discuss why the industry is so slow to change, tech that’s moving the needle, the last mile solution, what agents really want, the power of scale, international network effects, how to talk to human beings, corporate bingo, and rate the job performance of eXp’s CEO.

Jeremy Wacksman, CEO of Zillow, and I talk about taking big swings, celebrating failure through learning, constructive feedback from customers, why clear cooperation is such a big deal, extending the Zillow brand, the changing value of a lead, solving the last mile problem, making less people cry, and what the CEO of Zillow actually does.

Mark McLaughlin, interim president at Compass, and I discuss the 9x Pacific Union turnaround, downsizing until someone screams, either growing your market share or slowly going out of business, the hardest part of getting acquired, brainstorming without financial constraints, his greatest recruiting tool, the key post-acquisition message, the cost of low performers, and leading with confidence.

Chris Heller, president of Movoto and former CEO of Keller Williams, and I talk about the importance of making decisions fast, learning from mistakes, how consumer behavior is changing, agent natural selection, operating in an industry without logic, building real relationships, and there being no bad leads, just bad follow-up.

Gene Millman, most recently the CEO of REcolorado, and I discuss the nuts and bolts of MLSs, if they are still relevant in 2024, consolidation, reinvention, how to run an MLS like a business, why disruptors need MLSs, their top threat, the biggest tech pain point, and the critical importance of agility.

Greg Schwartz, CEO of Tomo and former Zillow president, and I discuss cold showers, the durable real estate agent model, what's changing fast and slow, turning the lights off, why portal traffic isn't real, the birth of Tomo on a train platform in Tokyo, making mistakes quickly, and Greg's goat expertise.

Hari Krishnan, CEO of Southeast Asia's PropertyGuru, and I discuss the demographics of emerging markets, an emerging middle class fueling housing growth, the benefits and challenges of operating in multiple markets, building trust and transparency, SE Asia's data opportunity, responding to AI's existential threat to property portals, the business case for staying calm, Vietnam's optimistic energy, and the power of industry connections.

Court Cunningham, CEO of Orchard, and I discuss sunrises, the job of a CEO, six years of learnings, the land of 1,000 edge cases, wasteful spending, knowing what not to do, being too good to be true, the Orchard pitch to agents, why the salaried agent model doesn't work, being impaled on CAC, learning velocity, and putting "Super App" in quotes.

Megan Meyer Toolson, Opendoor's President of Sell Direct & Services, and I talk about the typical Opendoor customer, the trust equation, celebrating progress, navigating a changing market, early arrogance, the $2 trillion question, rationally slow adoption, learning from customers, Opendoor's superpower, the self-serve strategy, and learning from this podcast.

Leo Pareja, Chief Strategy Officer at eXp Realty, and I discuss time compression, why the industry is slow to change, busting NAR settlement hype, buyer agents not going away, treating your buyers like your sellers, the rise of the super team, pain killers vs. vitamins, and never being qualified.

Tim Heyl, founder and CEO of Homeward, and I discuss morning clarity, eating the frog first, making 1,000 calls/day, magically attracting sellers, not moving too fast, hacking "buy before you sell," making hard decisions fast, what it would take for Homeward to fail, and giving more power to the consumer.

Jeremy Hofmann, Zillow's CFO, and I discuss making agents more efficient, Zillow's core insight, being a great coach, parenting advice, agents as the last mile, Zestimates, the super app vision, current AI applications, operational discipline, the key Zillow Offers learning, and my annoying research.

Sam Sawyer, founder and CEO of Pinnacle Realty Advisors, and I take time from the Hub event to chat about his subscription-based brokerage, the commission split gray area, selling his last company to Compass, building a brokerage app store, having a new school model with old school value, being a profitable unicorn, the real estate software arms race, and keeping your head out of the sand.

Joe Rath, Redfin's Senior Director of Brokerage Ops and Head of Industry Relations, and I chat about coffee subscriptions, the mother of all metrics, thinking small, the power of consistency, 100% tech adoption, the "your listing, your lead" counterfactual, the industry's most effective technology, issuing press releases when shutting down products, and being a good MLS partner.

Lacey Conway, CEO of Latter & Blum, and I discuss New Orleans coffee, incumbents going extinct, calculated gambles, acquiring a challenger brand, MLS innovation, power steering & lane assist, the fiefdoms of the status quo, and what she's learned from listening to this podcast.

Scott Trench, CEO of BiggerPockets, and I bust myths about the U.S. rental market and the prevalence of institutional investors, dig into the minds of 17 million mom-and-pop investors, and discuss dance parties, opportunity through inefficiency, investor demographics, why tech isn't adopted, opportunities for investor-friendly agents, and the financial benefits of house hacking.

Chris Kelly, EVP at HomeServices of America, and I discuss the challenge of incumbency, why attaching mortgage is hard, Homes.com vs. Zillow, how NAR can improve, leading with transparency, the benefits of not being a tech company, why real estate is like farming, and the unintended consequences of the commission lawsuits.

Orly and I discuss the upcoming Real Estate Innovation Hub, a new event I'm hosting in Boulder, CO. As an attendee, Orly discusses why she applied, the benefit of collaborating with nine other industry leaders, which business challenges she wants to unpack, the intersection of tech + humanity, how demographics are impacting her business, and why she would invite the goddess of war and strategy to be an attendee.

David Mele, president of Homes.com, and I discuss Dunkin Donuts coffee, post-acquisition growth, lead gen hell, the 97% opportunity, innovator's dilemma, exclusive content, strategic clarity, what's in Andy's head, and what he would do if he were Zillow's CEO.

Dan Duffy, CEO of United Real Estate Group, and I discuss United's quiet growth story, agent migration, fancy-pants MBAs, M&A breakage, the 3 attributes of a successful partner, cultural incongruity, CEO scar tissue, positive disruption, founder equity, Calvinball, and minding the value gap.

Glenn Sanford, CEO and founder of eXp Realty, and I discuss morning rituals, the push/pull of a down market, where ideas originate, game-changing tech, going against conventional wisdom, the power of pure-plays, overcoming a crisis of confidence, the sell-side pivot, and how to screw anything up.

Robert Reffkin, CEO and founder of Compass, and I discuss caffeination strategies, connectivity > productivity, how Compass became #1, learnings about building tech, 3 things agents care about most, what makes smart people stupid, sending messages back in time, and culture as a competitive advantage.

Steve “Capz” Capezza, president at Side and former SVP at Zillow, and I discuss brokerage learnings, the inertia of community, agent power, picking a funnel, full-contact leadership, what’s fueling Side’s best year, the future of brokerage, and the most impactful piece of tech in real estate.

Nick Boniakowski, head of agent partnerships at Opendoor, and I discuss what makes a perfect partnership, competitors + cooperators, agent realizations, what people don't know about Opendoor, why circumventing the agent is bad, going from a press release to a product, running towards new things, and being unpopular in a tough industry.

Nicole Reznik, a "Summer School" attendee, and I interview each other and discuss deflating idea balloons, insight immaculate conception, why Zillow is a reliable Honda, Napoleon's Peninsular War, and what gives me hope for the future.