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 employe...
Jul 02, 2025•1 hr 41 min
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.
Jun 24, 2025•28 min
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.
Jun 20, 2025•27 min
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.
May 05, 2025•28 min
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...
Apr 22, 2025•28 min
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.
Apr 09, 2025•34 min
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.
Feb 10, 2025•27 min
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.
Jan 09, 2025•35 min
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.”
Nov 19, 2024•28 min
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....
Nov 08, 2024•28 min
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.
Oct 31, 2024•31 min
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.
Oct 25, 2024•29 min
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.
Oct 21, 2024•33 min
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.
Oct 17, 2024•32 min
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.
Sep 30, 2024•29 min
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.
Sep 20, 2024•26 min
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.
Sep 13, 2024•29 min
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.
Jun 03, 2024•31 min
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.
Apr 29, 2024•29 min
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.
Apr 21, 2024•30 min
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.
Mar 26, 2024•28 min
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.
Mar 22, 2024•30 min
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.
Mar 12, 2024•31 min
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.
Mar 04, 2024•30 min
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.
Feb 29, 2024•27 min
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.
Feb 26, 2024•32 min
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.
Feb 19, 2024•30 min
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.
Feb 12, 2024•28 min•Season 2Ep. 3
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.
Feb 05, 2024•28 min•Season 2Ep. 2
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.
Jan 29, 2024•28 min•Season 2Ep. 1
