Context with Mike DelPrete

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 op...

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...

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.