Context with Mike DelPrete

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.