Real Estate Insiders Unfiltered

What if the biggest thing standing between your client and homeownership… is you? In this episode, James Dwiggins and Keith Robinson sit down with Rob Chrane (CEO of Down Payment Resource) and Mosi Gatling (SVP at New American Funding) to expose one of the most overlooked problems in real estate: agents not talking about down payment programs. There are over 2,600 programs available, but most buye...

Zillow Pro is changing how agents manage relationships and most agents don't realize what it means yet. In this episode of Real Estate Insiders Unfiltered, James and Keith sit down with Zillow COO Jun Choo to break down Zillow Pro, My Agent Connection, and how Zillow is rethinking the agent-consumer relationship. The big idea? "If you're already married, we stop offering you dates." Instead of con...

What if the biggest mistake you're making in real estate… is who you're listening to? In this episode, James and Keith sit down with Michael Hellickson, CEO of Club Wealth and one of the highest-producing agents in the country, for a conversation that challenges how agents think about coaching, growth, and success. From becoming the top listing agent in his office at 18 to building one of the top...

What happens when data, technology, and power start consolidating in real estate? In this episode, James and Keith sit down with Pierre Calzadilla, co-founder and CEO of Upfront, to break down one of the biggest shifts happening in the industry right now. From his early days at Trulia to building multiple proptech companies, Pierre shares a unique perspective on how mergers, data control, and AI a...

Are "coming soon" listings putting the real estate industry at risk?   In this episode, James Dwiggins and Keith Robinson sit down with Art Carter, CEO of CRMLS, and Ed Zorn, VP and General Counsel, to unpack one of the most heated and misunderstood topics in real estate right now.   From "coming soon" listings to private listings, MLS rules, and seller choice, this conversation breaks down what's...

What if everything agents are worried about right now… doesn't actually matter? In this episode, James and Keith sit down with Danny Brown, a top-producing Los Angeles agent with over 25 years in the business, to break down what actually drives success in real estate. From MLS debates and private listings to luxury real estate and industry shifts, Danny brings a grounded perspective: the agents wh...

What if the biggest misunderstanding in real estate is when the agent's job actually begins? In this episode, James and Keith sit down with Sheila Reddy, Founder and CEO of Mosaik, to challenge one of the most common assumptions in the industry that agents step in after the home search. Drawing from her experience as a buyer, seller, investor, and operator, Sheila breaks down why the real value of...

Who actually survives when the real estate market slows down? In this episode, James Dwiggins and Keith Robinson sit down with Jack Miller for a wide-ranging conversation about the forces shaping the next phase of residential real estate. Drawing on research analyzing the top 1,000 brokerages, Jack shares what the strongest companies do differently and why market downturns tend to separate durable...

What separates agents who build real businesses from those who stay stuck selling just a few homes each year? In this episode, James and Keith sit down with Lisa Chinatti, broker-owner of Chinatti Realty Group, to unpack the mindset and systems that helped her go from selling a handful of homes per year to closing 82 transactions as a solo agent and eventually building a brokerage with over 100 ag...

What does real estate actually look like without an MLS? In this episode, James Dwiggins and Keith Robinson sit down with Todd Cutter, broker-owner of 2Costa Rica Real Estate, to explore how real estate works in a country where agents operate without centralized listing data, standardized addresses, or a shared marketplace. Todd shares what it's like building a successful brokerage in Costa Rica,...

What happens when the MLS collides with Big Tech? In this episode, James Dwiggins and Keith Robinson sit down with Amit Kulkarni (formerly Realtor.com and Bright MLS) to unpack the power struggle shaping real estate right now; platforms, MLS organizations, brokerages, and Wall Street-backed players all fighting for leverage. They break down the Compass–Rocket–Redfin move, why data, not just listin...

What happens when you mix 26 years of experience, private property rights, and zero tolerance for nonsense? You get Leigh Brown unfiltered. In this episode, Leigh dives into the real history of the MLS, why cooperation matters more than ever, and what newer agents are missing about how this industry was built. She breaks down universal cooperation, the danger of fragmentation, and why forgetting o...

What happens when a Marine-turned-software-engineer builds a flat-fee MLS company in 36 states… and then says AI might replace most white-collar jobs?   You get one of the most philosophical and heated conversations we've had on this show.   Jon Minerick, CEO of homecoin.com, joins James and Keith to unpack his a la carte real estate model, why most flat-fee companies fail, and how AI could fundam...

What if the secret to 100 transactions a year wasn't online leads… but real relationships?   In this raw and surprisingly vulnerable episode, James and Keith sit down with Montrose, Colorado broker Shawn Carroll, a 32-year industry veteran who averages 100 homes a year in a town of just 20,000 people.   But this isn't a "systems and funnels" conversation.   Shawn shares how he went from sleeping i...

After years of turbulence, lawsuits, and industry shakeups, the National Association of REALTORS is making a bold marketing reset. In this episode, James and Keith sit down with Bennett Richardson, Chief Marketing & Communications Officer at NAR, to unpack the strategy behind the new "More Than Opening Doors" campaign and what it signals about the future of the REALTOR brand. From rebuilding trust...

What happens when two founders challenge the entire brokerage model?   Guy Gal (Co-Founder & CEO of Side) and Hilary Saunders (Co-Founder & Chief Broker Officer) join James and Keith for a candid conversation about community, consolidation, private listings, and what it actually takes to scale a real estate business in today's market.   They unpack: Why consolidation cycles repeat themselves in re...

Kyle Whissel doesn't just lead one of the top real estate teams in the country—he's redefined what's possible with structure, systems, and relentless clarity.   In this episode, James and Keith dive deep with the CEO of Whissel Realty Group (now Whissel Beer Group) to talk about everything from EOS and business operating systems to letting go of control, finding balance, and why agents are already...

From making $18k his first year to building a real estate empire, Brandon Brittingham pulls zero punches in this brutally honest conversation about business, investing, and the power of mindset. James and Keith go deep with Brandon, CEO, national speaker, and bestselling author on everything from building multiple 8-figure companies under one roof to the hard truths agents need to hear about wealt...

Eric Bramlett isn't trying to be the flashiest brokerage in the country, just the best-run. In this episode, James and Keith sit down with the founder of Bramlett Partners to talk about the power of systems, the limits of online leads, and why "boring real estate" might just be the secret to building something scalable, profitable, and sustainable. Eric shares: How he scaled from solo producer to...

What's the real difference between a smart tool and an intelligent robot? In this special episode, AI futurist and author Steve Brown joins James and Keith to talk about the future of work, real estate, and humanity in an AI-powered world. They cover: Why agents won't be replaced—but do need to evolve The 4 waves of AI (generative, agentic, spatial, physical) The real threat (and opportunity) of h...

In one of the rawest and most inspiring episodes yet, James and Keith sit down with Jeffery Mcgonigle, co-founder of Power Real Estate Group. From crying in his car to closing 560 deals and leading a 160-agent team, Jeffery shares how grit, structure, and clarity fueled his rise—and why "feelings aren't real" might be your new mantra.   They go deep on: The 3-2-1 method that every agent should be...

Rajeev Sajja, SVP of Digital Marketing & Innovation at Berkshire Hathaway HomeServices Fox & Roach, joins James and Keith for one of the most forward-looking, practical, and real conversations about AI in real estate you'll ever hear. From replacing agents to empowering them, Rajeev explains where AI is actually delivering results today and where the hype still outweighs the help. This episode goe...

From a Craigslist ad to a 1,000-unit-a-year powerhouse, The Hogan Group's journey is anything but ordinary. In this episode, James and Keith sit down with Mike Hogan (Founder) and Alicia Pittman (Principal Broker & President) to unpack how they've scaled their Virginia-based team to 80 agents across multiple markets without sacrificing culture, accountability, or profitability. They break down: Wh...

Every January, James Dwiggins and Keith Robinson go on record and hold themselves accountable. In this annual "Predictions + Report Card" episode, the dynamic duo looks back at what they got right (and wrong) about 2025… and lays out bold predictions for the year ahead. This year's predictions episode covers: What the Compass/Anywhere merger signals for the future of brokerage Why big players like...

Damian Eales, CEO of Realtor.com, joins James and Keith for a no-punches-pulled conversation on the future of the MLS, the dangers of private listings, and why the real estate industry needs to stop the infighting and start serving the consumer. In this episode, Damian unpacks: The housing affordability crisis and why we're running out of first-time buyers How the new Realtor.com+ platform is resh...