Real Estate Insiders Unfiltered

What happens when a former Zillow exec jumps back into production and builds one of the most successful teams in Northern California—from scratch? You get Colby Culbertson, founder and CEO of Culbertson & Gray Group at eXp. In this episode, James and Keith dive deep with Colby on: How he grew from 6 to 185 agents in 5 years Why he starts every recruiting call trying to talk people out of joining T...

What if "not for sale" didn't mean "not interested"? In this episode, James and Keith sit down with Katie Hill, founder and CEO of Unlisted, a startup turning heads and headlines by unlocking the hidden inventory between "just browsing" and "for sale." Katie's background in direct mail, digital marketing, and startup advising uniquely positioned her to spot a massive opportunity in the market: hom...

NYC real estate is not for the faint of heart. In this episode, James and Keith sit down with Scott Hustis, co-founder of Paradigm Advisory at Compass, to talk about how he built one of New York's top-performing real estate teams; one relationship at a time. Scott shares why he runs his team more like a wealth advisory firm than a brokerage, how he built a repeat-and-referral machine in one of the...

From the U.S. Marine Corps to running one of California's largest brokerages, Michele Harrington's leadership journey is anything but typical. Alongside Lauren Henss, a marketing powerhouse with a Chanel-to-Compass résumé, these two leaders are redefining what it means to build a modern, human-first brokerage. In this episode, James and Keith sit down with Michele (CEO) and Lauren (VP of Marketing...

You can care too much and it can break you. That's one of the many leadership lessons Matt Delhougne shares in this episode. From police officer to running a 70-agent team in St. Louis closing nearly 1,000 deals a year, Matt has seen it all and survived it. James and Keith sit down with the Chief Vision Officer of DRG at eXp to unpack everything from burnout and broker models to MLS politics, Goog...

What happens when you hand the mic to the audience? You get an hour of raw, unfiltered, sometimes hilarious, sometimes profound truth from James and Keith. In this special "Ask Us Anything" episode, we answer your biggest—and weirdest—questions. From the future of AI and Zillow to team building, associations, pricing strategy, personal regrets, and the emotional toll of leadership, no topic is off...

Cleve Gaddis didn't just build a real estate business, he built a legacy. From selling vacuums door-to-door to creating a trademarked, systemized team model in Atlanta, Cleve's story is packed with practical wisdom, hard-won lessons, and big laughs (yes, he brings a sword). In this episode, James and Keith sit down with Cleve to unpack how he's structured a sellable, scalable real estate business,...

You're not going to lose your job to AI. But is someone using AI better than you? That's a different story. In this episode, James and Keith sit down with Biju Ashokan, CEO of Radius Agent, for one of the most thought-provoking AI conversations we've had yet. Biju brings a deep tech background (Carnegie Mellon grad, by the way) and a bold vision for how artificial intelligence will reshape real es...

There's no magic in real estate, just discipline, standards, and execution. In this episode, James and Keith sit down with East Coast powerhouse Tom Toole to talk about what really drives success in today's market. From building a 50+ agent team to running a hyper-efficient operation with a deep focus on agent development, Tom breaks down exactly how he's scaled, where most team leaders go wrong,...

What if you could search for homes the same way you live your life? In this mind-bending episode, James and Keith sit down with Andrew Flachner (Co-Founder & CEO of RealScout) and Anthony Sosso (VP of Engineering) to explore the revolutionary AI product shaking up how agents—and eventually consumers—search for homes. You'll hear how RealScout is flipping the script on property search by: Using nat...

Scott Poe has lived a few lives—cable box repo man, nail tech, and now one of the fastest-scaling team leaders in real estate. In this outrageous and inspiring episode, James and Keith sit down with Scott to talk about how he built a 50-agent team and a mortgage company in under three years, landed partnerships with Realtor.com and Zillow, and has his sights set on a billion-dollar business. Scott...

When lawsuits and legal risk threaten to derail an entire industry, what happens next? In this episode, James and Keith sit down with Jon Waclawski, General Counsel and SVP of Legal at the National Association of REALTORS®, for an unfiltered, inside look at how NAR is rebuilding from the inside out. You'll learn what "de-risking" really means, how governance may change going forward, what's being...

Jim Trueblood doesn't just run a brokerage—he runs the largest Zillow and Realtor.com partner in Indiana, and he's just getting started. In this episode, James and Keith dig into how Jim scaled from solo agent to leading 225 agents across Indiana and Kentucky, with $750M in production and a bold approach to growth. From tech stack precision to lead gen discipline, Jim shares what it really takes t...

Andrew Wild was Zillow's 60th employee. He spent 15 years helping build the portal giant before leading enterprise strategy at Tom Ferry, Final Offer, and now Lofty. In this unfiltered episode, James and Keith sit down with Andrew to unpack what he's learned across every corner of the real estate industry. From the evolution of portals to the rise of agentic AI, Andrew shares sharp, candid insight...

What happens when a top agent goes all-in on content? You get Ricky Carruth. In this episode, James and Keith catch up with one of the most followed real estate influencers online—and unpack exactly how he built his social empire.   Ricky shares the full playbook: from cold calls and a weekly email list to millions of views across Threads, Instagram, and Facebook. He opens up about the mindset shi...

Phillip Cantrell, founder of Benchmark Realty (2,000 agents with $5 billion in sales), shares his blueprint for building a massive fee-based brokerage from the ground up, starting with one desk in his living room. A self-professed "98% left brain" analytical thinker, he discusses overcoming a career-crushing failure in 2008, the crucial concept of "the power in the pause," and his philosophical co...

Amy Stockberger, CEO of Amy Stockberger Real Estate, shares her groundbreaking Lifetime Home Support (LHS) model, which generates repeat and referral business. She details how her team of "serverpreneurs" converted every cost center into a profit center, generating $385,000 annually from 110 vendor partners. Amy reveals the crucial flaw in her previous business and shares her firm's rule for AI ad...

Kris Lindahl, a three-time bestselling author and CEO, shares his inspiring journey from being a teacher to building a brokerage with billions in sales. He offers candid insights into how his early life trauma fuels his emotional intelligence and desire to give back. Kris reveals his secret to creating an "inescapable brand," starting with his infamous "hostage video" and the two months of excuses...

Nykia Wright, CEO of NAR, delivers a masterclass in organizational turnaround, detailing the newly approved strategic plan. She candidly discusses the past dysfunction, the challenge of replacing a third of the staff with "A players," and the three pillars of the roadmap: organizational health, external pressures, and stakeholder expectations. Nykia shares her goal of shifting NAR from a reactiona...

Dan Foody, CEO and co-founder of Cloze, dives deep into the data behind agent communication failures. He reveals that 88% of conversations never enter the CRM, leading to massive lost opportunities. Dan explains his vision for the future, where AI uses customer data to identify what's important to them in the moment. He warns that agents risk losing their sphere to the "Zillows of the world" unles...

Parker Pemberton and Liz Rein (former attorney) from Pemberton Real Estate share their vulnerable and inspiring journey of failure, comeback, and entrepreneurial bravery. They explain their unconventional decision to move from a massive team to an independent brokerage, breaking down their "elective services" model that keeps agents productive. They share their high-volume metrics $829 million, 2,...

Beverly W. Jackson, VP of Brand and Product Marketing at Zillow, joins the show to discuss her mastery of brand storytelling. She explains the critical difference between data and insights, and how Zillow uses culture and emotion, not just search, to connect with consumers. Beverly provides agents with a tactical, step-by-step guide to developing their personal brand, from selecting the right gear...

George Laughton, founder of The Laughton Team (200 agents, $900M+ volume), details his journey from a terrible investment start in 2006 to running one of the US's top teams. He shares his systems for anticipating market shifts, his philosophy of making friends with what he fears (like iBuyers), and the team's structure based on interdependence. He unveils his Reverse Offer Playbook for saving canc...

With nearly 50 years in the industry, including a stint as the CEO of realtor.com , Allan Dalton provides a rare, unfiltered masterclass on the power of language in real estate. He demolishes conventional wisdom, explaining why calling yourself a "listing agent" or using "comps" is killing your value. He also reveals the macro strategy behind the Zestimate, his personal experience being drafted by...

What does it take to lead the #1 RE/MAX team in Minnesota while staying kind, humble, and insanely effective? Ryan O'Neill joins James and Keith to share the story behind his 215-agent powerhouse team, doing over 1,600 sides and $621 million in volume in 2024. This conversation is a masterclass in servant leadership, attracting talent (instead of recruiting it), and why heart matters just as much...