Context with Mike DelPrete Mike DelPrete

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.