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From Appointment-Fed to Well-Rounded Agents with Ryan Crighton and Danny Rinaldi | Ep 114
Jun 2, 2026
53m 42s
30% Net Profit from a Real Estate Team That Runs Without You with Nathan Clark | Ep 113
May 19, 2026
1h 00m 52s
Why Fast Growth Breaks Real Estate Team Culture with Brittany Gibbs | Ep 112
May 12, 2026
50m 19s
The Real Estate Team Bottleneck That AI Now Solves with Christopher Watters | Ep 111
May 5, 2026
51m 19s
How Leadership Training Becomes a Market Expansion Engine with Keegan Siegfried | Ep 110
Apr 28, 2026
54m 27s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/2/26 | ![]() From Appointment-Fed to Well-Rounded Agents with Ryan Crighton and Danny Rinaldi | Ep 114 | Many real estate teams try to build an appointment-fed model with ISAs serving agents ready-to-go opportunities. This can work - it can create efficient production.But when Ryan Crighton and Danny Rinaldi tried it, they discovered it wasn’t building agents who were as strong and well-rounded as they wanted.Learn how the shift from appointment-fed to well-rounded happened, including what prompted it, what it took, and what it produced for their 23-agent team serving clients in Las Vegas, Henderson, and Boulder City.Learn the accountability structure that’s enforced more by the environment than by team leaders and the vibe-first recruiting approach that attracts new agents who exceed performance standards before anyone asks them to.And learn how Danny evolved from ISA to coach to sales manager, what that role looks like day to day, and how he and Ryan complement each other in a partnership that lets each of them operate in their strongest area.Watch or listen for Danny's and Ryan's insights into:0:00 Intro and welcome1:22 Being in the weeds as the must-have characteristic — and why agents watch what you do more than they ask what to do2:08 The difference between vibe and culture — and why vibe is what actually drives performance and retention4:11 How Ryan built from REO listings in the 2008 downturn to a 23-agent brokerage team, and how Danny went from Brooklyn phone sales to Las Vegas sales manager10:00 Why new agents book appointments before they know anything about real estate — and why knowledge without attitude slows them down16:17 Why Danny leads recruiting conversations with vibe, not accountability — and how accountability reveals itself before the agent ever joins17:34 How the Creighton Rinaldi accountability system enforces itself. No manager required.19:06 How the peer accountability pod model (inspired by Brett Jennings, Ep 98) turned Danny into a facilitator — with agents coaching each other for most of the hour26:59 Why Danny makes phone calls side-by-side with every new agent within 24 hours of joining — and what that did to prospecting adoption29:32 How Nevada's two-month gap between passing the real estate exam and receiving a license became a training opportunity32:37 Why handing agents ready-made appointments produced weaker agents — and what happened when they stopped37:25 Why too much focus on market stats gives agents an excuse not to prospect — especially in one of the most volatile real estate markets in the U.S.40:23 Why the team model is the only structure built to meet what today's real estate clients actually expect41:51 At the end, Danny gives an impossible-to-follow team story and a sought-after spreadsheet and Ryan reveals a frivolous ride and a timely sports team.Related episodes→ Peer Accountability Pods with Brett Jennings→ Leadership Structure with Ryan Rodenbeck and Johnny McCarthyBook mentioned in this episode→ The War of Art by Steven PressfieldConnect with The Crighton Rinaldi Team→ Ryan at CRHomeTeam dot com / 702 217-1048→ Danny at CRHomeTeam dot com / 347 598-0913→ https://www.instagram.com/dannyrinaldi/→ https://www.instagram.com/crightonrinalditeam/→ https://www.crightonrinalditeam.com/team-pageConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 53m 42s | ||||||
| 5/19/26 | ![]() 30% Net Profit from a Real Estate Team That Runs Without You with Nathan Clark | Ep 113 | Most real estate teams are built around their leader. And at some level, most team leaders know it. Nathan Clark identified that problem early, named it clearly, and spent 20 years solving it. The result is a 600-plus transaction, 24-agent, 5-ISA, and 7-staff real estate team in Rhode Island that generates 30 to 35% net profit annually and genuinely runs without him: 15 to 20 hours of work per week, five race cars, and a full year away from the business when his family needed him. The team kept running.You'll learn how Nathan structures the financial model that makes that possible, starting with the COGS ceiling most teams quietly violate and the full P&L benchmark he reviews weekly.You'll learn why he charges sellers $2,000 and buyers $1,000 before showing a single home, how that generates $40,000 to $50,000 per month in working capital, and how that revenue funds better advertising and a better agent income on a lower split.You'll also learn when to step out of production, the ideal ISA:agent ratio, what team size has been most profitable for them, how to grow revenue per client instead of chasing transaction count, and what Nathan believes the team model will look like when AI is fully in the picture.Watch or listen for Nathan’s insights into:0:00 Intro and welcome 1:43 Why speed, going all in, and staying focused would make more leaders successful 6:57 What "runs without you" actually looks like 10:36 Specific lessons learned between 200 and 600 transactions, including the right ISA:agent ratio 17:34 Starting with the end in mind and making your team or brokerage more valuable 21:49 Why your cost of sale should be 40%, what that means for your splits, and how your agents can still get ahead 27:20 Raising your commission when everyone else is cutting it 29:06 Getting paid three times on each transaction, including upfront (and what he's doing with the $40-50k/month in working capital that generates) 36:36 Why they were most profitable at 20-25 agents and when you should be able to leave sales production 39:34 Why growing GCI by 50% doesn't require 50% more agents and 50% more closings 43:35 The weekly or monthly meeting you must have, even if it's just with yourself 44:36 The P&L benchmarks: 40% COGS max, 15% advertising, 14-15% payroll (including yourself), 1-3% rent, 25% base profit, up to 35% with add-ons 48:24 Why teams modeled after enterprises will continue to take market share and how AI can empower a 600-transaction team to scale to 2-3k 51:37 At the end, learn about the underdog and the goat, an addiction that runs fast and costs a fortune, and a personal crisis that proved his business was worth every hour he put into it over the years.Mentioned in this episode:→ Mike Schumm “The Hidden Curve That Kills Real Estate Team Profit”→ Andy Mulholland “Mastering Real Estate Business Financials”→ Anthwon Thomas “Preserving Your Profit Margins”Connect with Nathan Clark:→ Nathan at NathanClarkTeam dot comLearn about the systems Nathan runs on:→ https://hs.yhsgr.com/maibConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 1h 00m 52s | ||||||
| 5/12/26 | ![]() Why Fast Growth Breaks Real Estate Team Culture with Brittany Gibbs | Ep 112 | Most real estate team leaders assume more is better. More agents, more channels, more tech, more systems, more growth, more quickly.Brittany Gibbs built her brokerage on the opposite premise. When she opened Move Real Estate the day she got her principal broker's license, she made a deliberate choice to do less and focus more: fewer agents added at a time, simpler systems, one channel done well instead of ten done poorly. That philosophy has protected something most fast-growing teams eventually lose - the culture that made the business worth building.Brittany Gibbs founded Move Real Estate in Portland, Oregon, growing it over 12 years to 60 agents serving Portland Metro. She recently expanded to Seattle, adding 15 agents, and runs both markets with 6 total staff. She still sells real estate herself, closing 60 homes in what she calls a bad year.In this conversation, you’ll learn how Brittany thinks about growth and why she limits herself to roughly one new agent a quarter after 12 years of building, as well as what happened to her culture during a period of mass hiring, why she'll never do it again, and how slowing down in hiring, in systems, and in what she asks agents to focus on has produced better agents and a more sustainable business. Watch or listen for her mentor-based integration model, the production-tiered coaching structure that serves four different agent groups with four different conversations, and the simplicity philosophy that cuts through the noise of everything real estate teams are told they need to do.Watch or listen for Brittany's insights into:0:00 Intro and welcome 2:25 Why making changes too slowly or too late early in her career was her most expensive way to learn it 4:06 Starting a team in year one and a brokerage at year three 7:29 What the broker-owner role actually costs in time, compliance, and liability that nobody warns you about 8:14 Why she didn't name the brokerage after herself and how her reputation in Portland preceded her all the way into Seattle 17:36 The mass hiring lesson: 10-15 agents added to meet demand, immediate culture shift, never again. She now adds one agent a quarter. 20:13 How to protect culture during growth: clear vision, intentional hiring, and a mentor paired to each new agent by personality fit 23:04 The simplicity philosophy: CRM mastery and talking to people outperform social media, AI tools, and other distractions 27:58 60 solo deals in her worst year, not working weekends, done at 4:30 or 5pm every day — and trying to figure out how to leave production completely 33:22 The value prop and what leverage is provided to agents 36:25 The Thursday all-hands mastermind where new agents and veterans solve problems together 38:20 Who gets hired and who doesn't: personality and mindset over experience, and why "I got into real estate for my schedule" is an automatic no 40:06 The 4-group Tuesday coaching model segmented by production level (baseline, brokerage leads, transitioning, and heavy hitters)43:19 Where the team model is heading and what it will take to succeed 44:23 At the end, Brittany reveals she's a fully invested sports mom, holds more cheapskate habits than she needs to, and recharges by finding passion in whatever she's doing — from a 100-acre farm where no neighbors are visible.Connect with Brittany Gibbs:→ https://moverealestate.orgConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 50m 19s | ||||||
| 5/5/26 | ![]() The Real Estate Team Bottleneck That AI Now Solves with Christopher Watters | Ep 111✨ | real estateAI in business+4 | Christopher Watters | The Million Dollar Real Estate Team | — | real estate teamsAI tools+3 | — | 51m 19s | |
| 4/28/26 | ![]() How Leadership Training Becomes a Market Expansion Engine with Keegan Siegfried | Ep 110✨ | leadership trainingagent retention+5 | Keegan Siegfried | Paramount Home GroupLPT Realty | TampaStuart+4 | leadership trainingagent retention+5 | — | 54m 27s | |
| 4/21/26 | ![]() How Commercial Agents Boost Team Revenue and Referrals with Grant Johnson | Ep 109✨ | commercial real estateteam management+3 | Grant Johnson | Twin Cities teamFollow Up Boss+1 | — | commercial divisionreal estate team+3 | — | 54m 42s | |
| 4/14/26 | ![]() Why This Real Estate Team Hired a Chef for Lead Generation with Cindi Featherston-Shields | Ep 108✨ | lead generationreal estate team+3 | Cindi Featherston-Shields | animal welfare nonprofitFollow Up Boss | — | lead generationreal estate+5 | — | 49m 59s | |
| 4/7/26 | ![]() Growing a Profitable Indie Brokerage Powered by Inbound Leads with Ryan Fitzgerald | Ep 107✨ | independent brokerageinbound leads+3 | Ryan Fitzgerald | Raleigh Realty | — | cold callingbrokerage+5 | — | 49m 55s | |
| 3/31/26 | ![]() Going All In with One Builder to Grow Your Real Estate Team with Kate Robinson | Ep 106✨ | new constructionreal estate partnerships+3 | Kate Robinson | Melnychuk Real Estate GroupCentury 21+1 | — | real estatenew homes+3 | — | 52m 15s | |
| 3/24/26 | ![]() Building a Real Estate Company That Works Without Your Production with Jason Mitchell | Ep 105✨ | real estatebusiness transition+4 | Jason Mitchell | JMGFollow Up Boss | America | real estate teamagent branding+6 | — | 41m 21s | |
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| 3/17/26 | ![]() Scaling a Real Estate Team to $6 Billion in Production with Jason Mitchell | Ep 104✨ | real estateteam building+4 | Jason Mitchell | JMGFollow Up Boss | United States | real estate teambusiness model+5 | — | 36m 35s | |
| 3/10/26 | ![]() How a Prospecting-First Team Became a Media-Driven Brokerage with Devin Tryan | Ep 103✨ | prospectingcontent creation+3 | Devin Tryan | Talk Realty | Hawaii | real estatebrokerage+3 | — | 54m 15s | |
| 3/3/26 | ![]() The Real Estate Sphere System Your Agents Actually Execute with Sadie Callegari | Ep 102✨ | sphere marketingreal estate coaching+3 | Sadie Callegari | The Perna TeamFollow Up Boss | — | sphere of influencereal estate agents+3 | — | 59m 29s | |
| 2/24/26 | ![]() Running Real Estate, Mortgage, and ISAs from a Single Playbook with Jordan Vreeland | Ep 101 | The Falcon system to deliver guidance and success.The tech hub to unify multiple lines of business.The merged calls to save deals.A mortgage expert who’s since grown a 100-person organization delivering integrated real estate services, Jordan Vreeland’s constantly building the playbook.Go inside his athletics-informed philosophy and approach to developing people, unifying teams, leveraging tech, and improving client experience.Watch or listen for Jordan’s insights into:0:00 Intro and welcome1:32 Two reminders and resets when you step onto the court4:18 Building winners, not just winning games6:49 When and why a mortgage expert started a now-70-agents real estate brokerage9:33 Getting turned onto tech, marketing, and lead generation12:47 Choosing to start independent rather than with another brand or brokerage14:34 The concepts behind their integrated tech stack16:03 Jordan’s role in the organization17:40 Example of solving a problem by creating a role that elevates team members21:07 What more real estate professionals should know about mortgage and how to get there27:59 How he built a team of overseas ISAs that’s become the defense system and the “lifeblood of the business,” and part of the family - with tips for you to do the same33:56 Enhanced client visibility and better client conversations with Zillow Pro43:56 Getting what you give and not falling prey to the sickness of chasing numbers45:57 At the end, learn about three winning basketball teams, lawless psychopaths, friends he’s never met, and family getaways.Connect with Vreeland Real Estate:→ https://www.instagram.com/vreelandrealestate/→ https://www.facebook.com/vreelandrealestate/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 53m 00s | ||||||
| 2/17/26 | ![]() The Hidden Math Behind Referral-Only Real Estate Growth with Carol Foderick | Ep 100 | More than 500 transactions last year - 100% by referral.Nearly $1B in sales over the past five years - working by referral only.Carol Foderick has built a 20-agent, 15-staff team that exclusively works by referral. Each agent owns their database and relies on the camaraderie of the team and the leverage of the staff. Go inside the structure of her team and get the numbers behind working by referral.How many marketing activities does it take to produce a referral? How many referrals does it take to produce a closed transaction? What is each outbound call or text worth? Carol can tell you - and she does in this episode!Watch or listen to Carol’s insights into:0:00 Intro and welcome1:42 The fuel for your real estate team (spoiler: it's lead gen)3:01 What lead generation looks like on her team5:02 How she became a team leader before she started her own team9:24 Who shouldn’t start a real estate team11:38 The structure and key roles in her company to support high per-agent productivity16:10 Why her agents’ databases have no value to her20:14 How to retain top producers on your team28:15 A systematic and measured process for working by referral (last year 226 actions drove two referrals and one closed transaction)32:47 A specific example that points to $300 or so as the value of each call34:15 Three main activities and five love languages for working by referral40:56 How to find agents who can work by referral43:06 Where we are in the "teamification" or "teamization" of the real estate industry49:12 At the end, learn about truth telling by the home team, expensive rocking chairs and cheap airplane seats, and the challenges of being perpetual.Connect with Carol Foderick:→ Carol at CarolFoderick dot com→ https://www.instagram.com/carolfoderickConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 57m 38s | ||||||
| 2/10/26 | ![]() How to Beat Sales Skepticism with Better Conversations with Nikki Pais | Ep 099 | Do you need an ISA? When? How do you comp them? What if they want to be agents? What if they’re overseas?Should your team follow scripts? How closely? Where are the non-negotiables and where do you find room to stay human?How do we uncover motivation and handle objections in a helpful way that improves client experience?Nikki Pais is here to address all that and more. She brings years of experience as an EA, ISA, and Director of Inside Sales, as well as years of experience coaching ISAs, agents, and team leaders across North America on better conversations, effective nurturing, and more closings.Watch or listen for Nikki’s insights into:0:00 Intro and welcome1:33 Why to apply what you learn without waiting, without tweaks, and without doubts8:35 The most common problem among the teams she’s coaching: exceptions (plus when to turn an exception into a tier)10:56 The difference between coaching and training - and how to figure out what you need15:19 Top signs that you’d benefit from an ISA17:28 Who makes a great ISA (domestic vs international, aspiring real estate agents, current agents)20:31 How to comp ISAs22:50 Managing handoffs and the division of labor between agents and ISAs27:39 Why to treat every new lead as a buyer (yes, even sellers)30:45 How to uncover motivation in a meaningful way33:53 The right way to use scripts35:34 The difference between objections and conditions - and how best to handle objections39:18 Taking notes vs relying on AI summaries41:33 Facing the challenge of sales skepticism43:47 Leveraging AI calls and texts for the right reasons45:03 At the end, learn about an inherited team, soaps you don’t like, well-traveled boxes, and 50 audiobooks for 50 ideas to apply immediately.Other episodes you’ll enjoy:→ More Deals from Your Database With (or Without) an ISA with Travis Halverson https://www.realestateteamos.com/episode/travis-halverson-deals-database-isa-inside-sales→ From ISA to Director of Opportunities with Lisa Ryan https://www.realestateteamos.com/episode/inside-sales-manager-isa-real-estate-opportunities-lisa-ryan→ How to Drive Per-Agent Productivity with Jonathan Campbell https://www.realestateteamos.com/episode/how-to-drive-per-agent-productivity-jonathan-campbellConnect with Nikki Pais:→ https://www.facebook.com/nikki.shanelle.pais→https://www.ezdials.com/shut-up-and-dialConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 54m 00s | ||||||
| 2/3/26 | ![]() How to Unlock Team Growth with Peer Accountability Pods with Brett Jennings | Ep 098 | Brett Jennings is making a big bet on peer accountability pods. A billion-dollar bet.The Owner and Founder of Real Estate Experts, Brett shares the details behind the nearly 10x growth of his hybrid teamerage (from $165M to $1.2B in sales) and the strategy to growth through acquisitions to $4B.Learn how purpose has made team agents, solo agents, and staff more productive (creating more than a dozen first-time $1M GCI producers in one year) and how purpose serves as a filter to find right-fit companies to acquire.Get proven strategies and simple tactics to grow revenue by growing your people (and why they might call themselves a Good Vibe Tribe).Watch or listen for Brett’s insights into:0:00 Intro and welcome1:50 Clarity within leadership and resilience within team members4:41 Two ways to test for agent grit and growth (including 1,000 calls in 10 days)7:14 What team agents and solo agents get in Brett’s hybrid brokerage model9:44 How working with Tony Robbins and Deepak Chopra helped Brett unlock agent and team growth12:24 Where to go next after nearly 10x sales in three years15:06 The motivation and plan to grow through acquisitions to $4B and 600 agents19:34 How peer accountability helped create more than a dozen $1M GCI producers21:52 Two characteristics of a well-aligned acquisition target28:06 Why agents and staff need a bigger “why” than money alone - and how to deliver31:38 How to create your own peer accountability pods and why Brett’s betting big on them35:16 How to increase participation in the optional pod program38:33 Why self-discipline and self-actualization are the next iteration of conscious business42:13 The next steps for the Good Vibe Tribe movement44:56 At the end, learn about expert advisors, luxury watches and refillable bottles, and two practices to revitalize your operating system.Free resources from Brett Jennings:→ https://goodvibetribeworldwide.com → https://bearealexpert.comConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 52m 03s | ||||||
| 1/27/26 | ![]() Reducing the Structural Constraints on Your Growth with Works Real Estate | Ep 097 | No matter what stage of business maturity your real estate team or brokerage has achieved, you face growth constraints. Many are structural to your organization and to the industry - like affordability challenges, disconnected tools, siloed data, and even lead abundance.Learn to circle back to harden your foundation, identify and relieve stress points, and prepare for tomorrow’s market with Works Real Estate CEO Winston Murray and long-time collaborator Jon Boller, who are leading a 250-agent, 10-market operation into an AI-driven, Uberized future that requires more operational efficiency than ever.Get Winston’s vision for supply-side solutions to the affordability crisis - and steps you can take yourself.Learn how a 150-page manual about serving buyers and sellers connected them, supported team growth, got leveraged further with a new learning management system, and united the front and back of house within their independent brokerage.Discover an X-ray approach to agent success through data transparency.And see a consumer-focused vision of the future created through death of ego and setting swords down across the industry.Watch or listen for insights from Winston and Jon on:0:00 Intro and welcome1:47 The balance of a clear, big-picture vision and efficient, ground-level operations4:39 The role of education and simplification in growing from a 3-person team to 250 agents in 10 markets6:56 What the “Uber-fication” of real estate actually looks like - and what it requires of you9:10 How Jon partnered with Works Real Estate over the past decade14:01 The power of a 150-page manual (and the mantra "scale thyself")16:44 Why agents never graduate off their lead programs19:50 Three stages of business maturity and what each requires22:52 A vision for the death of ego and setting swords down across the industry to best serve consumers26:23 The key to differentiating Works Real Estate 28:33 Top projects for 2026, including unifying the front and back of house36:36 The challenge and opportunity of supply-side affordability solutions49:09 At the end, learn about a startup hockey team, an unexpected underdog, the benefits of style, and a zero-based social feed.Connect with Works Real Estate:→ https://worksrealestate.co/→ https://www.instagram.com/worksrealestateco/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 58m 42s | ||||||
| 1/20/26 | ![]() The Case for Small Real Estate Teams with Brian Buffini | Ep 096 | Brian Buffini started a real estate team before teams were a thing. Back in 1992. Back before brokerages had any idea what to do with a team.Today, Buffini & Company coaches and trains agents, team leaders, and broker owners around the world.All along, Brian’s viewed teams as “the future of real estate.” But team leadership isn’t for everyone and aspirations for a mega team aren’t necessary.Brian was kind enough to be a guest on our show as I was a guest at his Buffini Coaching live event to share decades of insights, experience, and influence.With a live audience of hundreds of real estate professionals, Brian sat down with me to share what it took to sell 100 homes in a year in the late 80s, why teams emerged, who should (and shouldn’t) build a team, what the main team models are, where “Death Valley” is for team leaders, what leaders must stay focused on and watch out for ... and much more!A HUGE thank you to Brian and his entire team for welcoming me into their community in such an open and sincere way!Watch or listen for Brian Buffini’s insights into:0:00 Intro and welcome1:42 Leading and managing yourself (in order to lead and manage others)4:11 What it took to sell 100 homes/year in the late 1980s with one assistant7:17 Why and how he started a team in the early 1990s (and why he struggled initially)14:42 Why he’s long viewed teams as “the future of real estate” and who teams are best for17:27 Why referring out excess business is a good first step toward a team20:10 How to find your first assistant22:49 What other stages of team maturity look like and the key to finding your right size (spoiler: 4-7 is a sweet spot)24:45 Why 80% of agents should keep selling (perhaps with a team to support them)30:00 What the hardest thing about real estate is (and what mistakes that leads to)32:09 How to restore connection with the people and relationships that matter most (your customers and your team)35:33 A leadership lesson from NFL and NASCAR champion Joe Gibbs39:05 At the end, learn about A and B teams, hotel soaps and sewing kits, and the power of ohana and the ocean.Connect with Brian Buffini:→ https://www.instagram.com/brian_buffini/→ https://www.instagram.com/buffiniandco→ https://www.buffini.com/solutions/realstrengths/→ https://www.buffini.com/solutions/blitz/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 46m 49s | ||||||
| 1/13/26 | ![]() Why Most Real Estate Team Leaders Shouldn’t Be Team Leaders with Jon Cheplak | Ep 095 | What happens when you invest so deeply in your people that they could leave today and find success starting their own business?The most likely outcome: they stay and you continue growing together.But the more common path: a more transactional approach for fear they’ll leave you.Jon Cheplak returns to Real Estate Team OS to explain why he thinks 90% of real estate team leaders shouldn’t be team leaders and to share what the 10% have in common.Jon’s been in the seat himself and he and his partners coach top-performing team leaders and operations leaders (many you’ve met here on the show).Scaling on principles, rather than on personality.Pouring into people without fear, limitation, or calculation.Developing people first and businesses second.Walking the talk as the key to leadership.Improving your copywriting and storytelling.Jon shares all that and more in a great conversation to set you up for a successful year ahead.Watch or listen for Jon’s insights into:0:00 Intro and welcome2:19 Why community is so desirable and powerful right now4:05 How principles scale and why personality doesn’t6:04 His four core principles, his eight core values, and the difference between them8:34 The three ways to get people to take action14:39 The two ways to give people attention and why fear holds team leaders back from both21:29 Why 90% of team leaders shouldn’t be team leaders and four criteria to help you know for your yourself29:41 Two ways to find your operations leader and one way NOT to (spoiler: look inside your team)37:14 Why you’re already a better copywriter than you think, how and why to get better at it, plus the difference between marketing and sales46:03 At the end, learn about pitchforking manure and the risk and payoff of committing to a 375-acre ranch.Four principles Jon lives by:→ Personal responsibility, accountability, commitment, contributionEight values Jon lives by:→ Fun, love, dignity, respect, humility, vulnerability, transparency, volunteerismMentioned in this episode:→ FUBCON Session with Jon Cheplak https://www.realestateteamos.com/episode/jon-cheplak-real-estate-teams-traditional-brokerages→ 084 Living in the Leads with Lauren Bowen https://www.realestateteamos.com/episode/real-estate-leads-systems-tools-increase-conversion-lauren-bowen-lpt-realty→ 037 Prospecting for Listings with Greg Harrelson https://www.realestateteamos.com/episode/real-estate-prospecting-listings-greg-harrelson→ 082 Making Your First Operations Hire with Camila Rivera https://www.realestateteamos.com/episode/team-leader-guide-making-your-first-operations-hire-camila-rivera→ Inside Whissel Realty Group https://www.youtube.com/playlist?list=PLCJiXNo93cVqQmwl4tTOQYebBkBoL6ipzConnect with Jon Cheplak→ https://www.facebook.com/joncheplak/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 51m 47s | ||||||
| 1/6/26 | ![]() Living In The Leads: Systems and Tools To Increase Conversion with Lauren Bowen | Ep 094 | We’re kicking off the calendar year in a familiar way on Real Estate Team OS - with Lauren Bowen sharing practical tips on lead sources and lead conversion for the third year in a row!A thoughtful and generous expert on this topic, Lauren now serves as SVP of Lead Generation and Conversion for LPT Realty. In the role, she consults with teams of all sizes. In this episode, she shares what she’s learning and teaching!For 2026, Lauren delivers for you a simple process to improve lead conversion and ROI, the most common issues she sees in the databases of small, medium, and large sized teams, specific tech recommendations by team size, the what, who, why, and how of “living in the leads,” and other ways to drive big results with incremental improvements.Watch or listen for the Jon Cheplak-inspired mantra: tiny hinges swing big doors.Watch or listen for Lauren’s insights into:0:00 Intro and welcome2:28 The value of getting clear on your purpose4:36 How she developed an expertise in lead sources and lead conversion, one small step at a time6:48 A simple process to improve lead follow up (do this right now)9:55 Why and how she became SVP of Lead Generation and Conversion with LPT Realty after a decade with Robert Slack Real Estate20:43 The most common issue when she gets into a team leader’s CRM and database and how to solve it (note: the ROI of PPC)24:29 Primary issues team leaders and ops leaders face by team size25:15 Specific tech for retargeting, texting, database, and accountability by team size32:40 The what, who, how, and why of “living in the leads”42:55 What’s never changed about lead conversion in the decade she’s been in the business48:08 At the end, learn about Magic basketball, chicken frivolousness, and physical books.Mentioned in this episode:→ Ep 011 Lauren Bowen on 16 Lead Sources for 800 Agents https://www.realestateteamos.com/episode/lauren-bowen-robert-slack-coo-lead-sources-team-leaders → Ep 051 Lauren Bowen on Lead Quality vs Lead Quantity https://www.realestateteamos.com/episode/real-estate-lead-source-quality-quantity-lauren-bowen-robert-slack → Techtember and Julia O’Buckley: https://www.youtube.com/playlist?list=PLCJiXNo93cVoSlXhdFv_RC9V8G5tUw1QX → FUBCON Sessions and Jon Cheplak: https://www.youtube.com/playlist?list=PLCJiXNo93cVopyNz34nrcV-kVacpWjvAmConnect with Lauren Bowen:→ Email: Lauren.Bowen at LPT dot com→ Call or text: (352) 843 3434Connect with Real Estate Team OS:→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 54m 43s | ||||||
| 12/29/25 | ![]() Your 2026 Game Plan with Mark Hiller and Drew Coleman | Ep 093 | This week, you’ve got two episodes in one! Both were recorded live on stage at Unlock by Zillow in November 2025. The first half takes you inside Hiller Group on Florida’s Emerald Coast and Opt Real Estate in Portland, Oregon.MARK HILLERFinding and empowering the right person allowed Mark to double production as a solo agent, start a real estate team, and set it up to scale. He shares lessons from that person and process, explains how he preserved profits as his housing market slowed to a halt, and gives you specific tips for working successfully with virtual assistants.Go inside Hiller Group, a 12-agent, 5-staff, 8-VA team in Niceville, Florida.Watch or listen for insights from Mark on:What allowed him to double his transaction count and start his teamSpecific things his Director of Operations did to set them up to double agent count without adding any additional costHow they successfully integrated 8 VAs into their organization and how they’re taskedWhy quarter-to-quarter planning makes more sense for his team than annual planningHow he preserved profit while losing 100 transactions as the housing market halted back in 2022A top takeaway for you: “You can’t scale chaos. Get your people aligned and watch the business become fun again.”His top takeaway from Unlock (standards!)DREW COLEMANOpt Real Estate is a 100-person company on pace to for 1,000 transactions and more than $500M in sales. But for Founder Drew Coleman, that’s not a goal - it’s an outcome of a dedication to “fabled service” for agents and their clients.Be sure to listen for a great Olympics metaphor that serves as an important reminder and even a caution about recruiting and retention!Watch or listen for insights from Drew on:His goal of becoming “the best brokerage that’s ever existed,” how it’s like a team, and what “best” meansWho’s successful in the Opt systemThe transformative nature of FUB’s open API and how tools like Sisu, Rokrbox, StackWrap, and HouseWhisper helpThe value of in-house and offshore talentWhat they walk agents through for annual business planningAn AI solution they’re working on for 2026A top takeaway for you: “Success requires two things: a path for agents to grow and a culture that fuels, not drains, their momentum.”His top takeaway from Unlock (Zillow Pro!)Team Bot (free, always on):→ https://realestateteamos.com/botConnect with Mark Hiller:→ https://www.instagram.com/markhillerflConnect with Drew Coleman:→ https://www.instagram.com/drewcoleman→ (503) 351 3739Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 41m 56s | ||||||
| 12/22/25 | ![]() Your 2026 Game Plan with Alexis and Tom Nickley and Jen Stauter | Ep 092 | This week, you’ve got two episodes in one! Both were recorded live on stage at Unlock by Zillow in November 2025. The first half takes you inside The Nickley Group in Florida and the second half takes you inside HomeTeam4U in Wisconsin.TOM AND ALEXIS NICKLEYAlexis and Tom Nickley, co-team leaders of The Nickley Group in Orlando, credit team culture with the growth and success of their 65-agent, 20-staff real estate team pacing for 900 transactions and $400M in sales. Learn two key roles, four core values, and three things they’re focused on in the year ahead!Watch or listen for insights from Alexis and Tom on:A bold decision to leave sales productionThe division of labor between husband-and-wife, co-team leadersWhy their recruiter’s job is so challengingThe purpose and role of the Director of Culture and Engagement (and specific tactics you can take for yourself)The purpose and role of their Director of Growth (it’s FAR bigger than recruiting)Three things they’re focusing on in 2026A key takeaway for you: “Keep the underdog mindset! At the end of the year, challenge your systems and processes to improve your client and agent experience.”Their key takeaway from Unlock (uniqueness and diversity!)JEN STAUTERJen Stauter serves as team leader of HomeTeam4U in Sun Prairie, Wisconsin. She walks you through the personality types that work within their 32-agent organization, how she plans to get to 50 agents, two specific ways the Agent Success Coordinator roles has helped her and the team, a unique quality of their mentorship program, and more!Watch or listen for insights from Jen on:Growing a team from 4 family members to 32 agents (and counting)The purpose and role of their Agent Success Coordinator, including two specific, high-value projects she took on and where they found herHow they structure their mentorship program and one of its unique qualitiesWhich changes the EOS process (the VTO, specifically) forced them to makeKeys to successful recruiting en route to 50 agentsA key takeaway for you: “You don’t need to do more. You just need someone who makes sure it happens.”A key takeaway from Unlock (recruiting!)Connect with The Nickley Group:→ https://www.instagram.com/thenickleygroup/Connect with Jen Stauter:→ https://www.instagram.com/jennifer_stauter_kornstedt/Connect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 45m 00s | ||||||
| 12/16/25 | ![]() Simple Tech Systems Any Real Estate Team Can Use with Matt Croteau | Ep 091 | If you’re looking for ways to leverage AI, automations, and technology without losing sight of what matters most - relationships, culture, and client goals, then you’re in the right place!Best practices for AI voice and texting, including when and how to hand off to humans.Three things to set up for success in Follow Up Boss.A few under-used, high-value features of Follow Up Boss.Specific automations to increase lead engagement and conversion.A framework for better AI prompts and other prompting tips.Two Custom GPTs to save massive amounts of timeThis is just some of what you’ll get with Matt Croteau, team leader with The Fernandez Group in Orange, California.Get tech tips that honor the human touch and your client’s goals and that make AI your assistant, not your replacement. Learn Custom GPTs for on-the-fly coaching and real-time scripting. Hear automations that drive lead engagement and save time.Watch or listen for Matt’s insights into:- Ways to sustain a healthy culture even when agents aren’t in the office- The path from loan officer to real estate agent to team leader- Foundational pieces needed to start a productive partnership- The importance of staying focused on client goals- The role of AI and automation vs the role of the real estate agent- Best practices for AI voice and texting, including seamless handoffs to humans- Three specific ways to set up for success in Follow Up Boss- Specific automations to set up to improve lead engagement and lead conversion- The RELIC framework for better AI prompts and specific prompting tips for better output- The basics and benefits of Custom GPTs - with two time-saving examples- One way the Comet browser from Perplexity saves him time- What’s stayed the same and what’s changed for lead conversion over the past several years- Who to hire in-house and what to hire out to virtual assistantsAt the end, learn about a disappointing baseball season, overpriced robots, open skies, and quieter trails.Mentioned in this episode:→ Techtember on Real Estate Team OS https://www.youtube.com/playlist?list=PLCJiXNo93cVoSlXhdFv_RC9V8G5tUw1QX→ Follow Up Boss Success Community https://www.facebook.com/groups/followupbosscommunityConnect with Matt Croteau:→ Email: Matt at MattSellsOC dot comConnect with Real Estate Team OS→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 51m 36s | ||||||
| 12/9/25 | ![]() How to Architect a Director of Operations Role for Scale with Matteo Zingales | Ep 090 | After earning two degrees in architecture and starting your career with a design firm, you get into real estate operations.Your first task: turn a real estate team into an independent brokerage. Overnight, if possible.Your second task: expand and renovate the office to prepare for growth.Meanwhile: you need to get the systems and processes out of people’s heads, merge them together, get it documented, redesign onboarding, and teach it to agents.That’s just some of what you’ll get in this conversation with Matteo Zingales, Director of Operations at Team Zingales Realty, a family-owned, independent teamerage.How to create the role from scratch.Why to put observation before innovation.How to set up the tech stack for scale.Which three questions to ask to get constructive criticism from your business partners.Four years into his journey, Matteo shares these details and more!Watch or listen for insights into:The balance of clarity, alignment, and accountabilityThe path from a degree and career in architecture to a Director of Operations roleTransitioning from real estate team to independent, family-owned brokerageHow the Director of Operations role was shaped from scratch and what it brought to the teamA prioritized list of projects and SOPs to set up the business to scale successfullyThe vital role of constructive criticism and three questions to ask every staff member and agent to help draw it outThe specific pieces of their tech stackHow they carved out distinct, aligned roles between Director of Operations, Team Founder and Partner, and Broker Owner and PartnerSpecific recruiting tactics as they look to double agent count in the year aheadHow to find your own Director of OperationsAt the end, learn how Gillette Group, Wemert Group Realty, and SERHANT. Real Estate fuse brand, systems and performance, how luxury items can commemorate milestones, and which books have helped this Director of Operations.Mentioned in this episode:→ Camila Rivera https://www.realestateteamos.com/episode/team-leader-guide-making-your-first-operations-hire-camila-rivera→ Jenny Wemert https://www.realestateteamos.com/episode/jenny-wemert-group-realty-independent→ Emily Smith https://www.realestateteamos.com/episode/emily-smith-intrapreneur-entrepreneur-teamerage→ 10X is Easier Than 2X https://10xeasierbook.com/→ Rocket Fuel https://rocketfueluniversity.com/rocket-fuel-book/Connect with Matteo Zingales:→ https://www.instagram.com/matteoonops/→ https://www.linkedin.com/in/mzingales/→ https://www.tiktok.com/@team.zingales.realty→ https://teamzingales.com/team-zingales-difference/meet-our-team/Connect with Real Estate Team OS:→ https://www.realestateteamos.com→ https://linktr.ee/realestateteamos→ https://www.instagram.com/realestateteamos/ | 51m 12s | ||||||
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