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PODCAST

Real Estate Insiders Unfiltered

Real Estate Insiders Unfiltered

You talk about it privately - We talk about it publicly. This is the Real Estate Insiders Unfiltered Podcast. Running a real estate business is challenging, but understanding the industry, the players, and who"s affecting change can help you position your business for future success. Join us as we talk to industry leaders and influencers about the latest trends, strategies, and tactics for building a profitable and sustainable real estate business. This podcast is hosted by James Dwiggins and

business entrepreneurship

All Episodes

49:41

Agent Series 18: From Door-to-Door to Real Estate Empire

Real Estate Insiders Unfiltered ·

2025/12/29

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, why systems beat hustle, and how rejection actually made him stronger. He shares why he trademarked his

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46:00

How AI Will Transform Real Estate (Faster Than You...

Real Estate Insiders Unfiltered ·

2025/12/25

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 estate. From proactive assistants to fully automated client nurture, this isn't science fiction — it's

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51:45

Agent Series 17: Tom Toole's Real Estate Playbook:...

Real Estate Insiders Unfiltered ·

2025/12/22

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, and the boring-but-powerful habits that move the needle. You'll hear: The 4 things agents should do

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46:31

The Future of Real Estate Search: RealScout's AI...

Real Estate Insiders Unfiltered ·

2025/12/17

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 natural language prompts instead of checkboxes Deconstructing vague terms like "mid-century modern"

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50:55

Agent Series 16: From Cable Repo, Nail Tech to $50...

Real Estate Insiders Unfiltered ·

2025/12/15

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 doesn't hold back—about the pain, the hustle, and the real human side of building something that

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50:30

Inside NAR's Legal Strategy with Jon Waclawski

Real Estate Insiders Unfiltered ·

2025/12/10

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 done about buyer-side lawsuits, and why communication and transparency matter more than ever. Jon also

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49:06

Agent Series 15: How Jim Trueblood Built a $750M...

Real Estate Insiders Unfiltered ·

2025/12/08

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 to scale in today's market. You'll hear how he: Bought all the leads (and maxed every contract) Held

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53:24

Portals, CRMs & AI: The Future of Real Estate with...

Real Estate Insiders Unfiltered ·

2025/12/03

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 insights on where the business is headed—and what agents, brokers, and platforms need to do to stay relevant

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48:40

Agent Series 14: From Rockstar Agent to Real Estate...

Real Estate Insiders Unfiltered ·

2025/12/01

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 shift from closing deals to creating legacy, and how anyone (yes, anyone) can start growing their brand

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52:01

The Core of Massive Growth and Wealth

Real Estate Insiders Unfiltered ·

2025/11/26

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 core: money is the scoreboard of service to others. He offers unvarnished advice for anyone considering

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54:04

Agent Series 13: Cracking the Code on the Client's...

Real Estate Insiders Unfiltered ·

2025/11/24

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 adoption: if employees aren't using AI first, they are being "irresponsibly unproductive". Give your

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54:37

Agent Series 12: Why Unapologetic Authenticity Is...

Real Estate Insiders Unfiltered ·

2025/11/19

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 he made before finally publishing his content. His core advice: invest in finding a mentor who has

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55:56

Inside Nykia Wright's Master Plan to Fix NAR and...

Real Estate Insiders Unfiltered ·

2025/11/17

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 reactionary body to a proactive partner, demonstrating accountability down to the molecular project level. Follow

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47:05

Why 88% of Agent Conversations Never Make it to the CRM

Real Estate Insiders Unfiltered ·

2025/11/12

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" unless they master personalized outreach and transform their relationships into a sustainable differentiator

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54:30

Agent Series 11 - The Leads Don't Suck, You Suck: An...

Real Estate Insiders Unfiltered ·

2025/11/10

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, 2,200 transactions and reveal why agents must focus on becoming "findable on ChatGPT" to succeed in the

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58:55

The Blueprint for Authentic Social Media Storytelling

Real Estate Insiders Unfiltered ·

2025/11/06

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 and platforms to using their vulnerability and lived experience to attract clients. Connect with

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47:14

Agent Series 10: The Strategy to Save Canceled...

Real Estate Insiders Unfiltered ·

2025/11/04

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 canceled listings and stresses that consistent investment in self-development is the only way to sustain

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57:31

The Confederacy of Dunces: Why the Industry's...

Real Estate Insiders Unfiltered ·

2025/10/30

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 the Boston Celtics, and why agents must treat their work as a professional practice, not just a

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50:40

Agent Series 9: How Ryan O'Neill Leads the Top RE/MAX...

Real Estate Insiders Unfiltered ·

2025/10/28

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 as hustle. Ryan breaks down his tech stack, his approach to team structure, top lead sources, and the

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47:03

Real Estate Going Nuclear: An Unfiltered View on...

Real Estate Insiders Unfiltered ·

2025/10/23

Is organized real estate "going nuclear"? In this candid conversation, James and Keith sit down with Matt Widdows, Founder and Executive Chairman of HomeSmart, to talk about the seismic shifts reshaping the industry. From AI disruption and private listing wars to broker consolidation and MLS gridlock, this episode dives into what’s next—and what agents must do now to stay relevant. Widdows shares how he built HomeSmart to 26,000+ agents, why agents must lead the AI revolution, and how to stay

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205 results

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