Real Estate Team OS

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 welcome
1:50 Clarity within leadership and resilience within team members
4:41 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 model
9:44 How working with Tony Robbins and Deepak Chopra helped Brett unlock agent and team growth
12:24 Where to go next after nearly 10x sales in three years
15:06 The motivation and plan to grow through acquisitions to $4B and 600 agents
19:34 How peer accountability helped create more than a dozen $1M GCI producers
21:52 Two characteristics of a well-aligned acquisition target
28:06 Why agents and staff need a bigger “why” than money alone - and how to deliver
31:38 How to create your own peer accountability pods and why Brett’s betting big on them
35:16 How to increase participation in the optional pod program
38:33 Why self-discipline and self-actualization are the next iteration of conscious business
42:13 The next steps for the Good Vibe Tribe movement

44:56 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.com

Connect with Real Estate Team OS
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/

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 welcome
1:47 The balance of a clear, big-picture vision and efficient, ground-level operations
4:39 The role of education and simplification in growing from a 3-person team to 250 agents in 10 markets
6:56 What the “Uber-fication” of real estate actually looks like - and what it requires of you
9:10 How Jon partnered with Works Real Estate over the past decade
14:01 The power of a 150-page manual (and the mantra "scale thyself")
16:44 Why agents never graduate off their lead programs
19:50 Three stages of business maturity and what each requires
22:52 A vision for the death of ego and setting swords down across the industry to best serve consumers
26:23 The key to differentiating Works Real Estate 
28:33 Top projects for 2026, including unifying the front and back of house
36:36 The challenge and opportunity of supply-side affordability solutions

49:09 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/

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 welcome
1:42 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 assistant
7:17 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 for
17:27 Why referring out excess business is a good first step toward a team
20:10 How to find your first assistant
22:49 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 Gibbs

39:05 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/

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 welcome
2:19 Why community is so desirable and powerful right now
4:05 How principles scale and why personality doesn’t
6:04 His four core principles, his eight core values, and the difference between them
8:34 The three ways to get people to take action
14:39 The two ways to give people attention and why fear holds team leaders back from both
21:29 Why 90% of team leaders shouldn’t be team leaders and four criteria to help you know for your yourself
29:41 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 sales

46:03 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, contribution

Eight values Jon lives by:
→ Fun, love, dignity, respect, humility, vulnerability, transparency, volunteerism

Mentioned 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=PLCJiXNo93cVqQmwl4tTOQYebBkBoL6ipz

Connect 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/

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 welcome
2:28 The value of getting clear on your purpose
4:36 How she developed an expertise in lead sources and lead conversion, one small step at a time
6:48 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 Estate
20:43 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 size
25:15 Specific tech for retargeting, texting, database, and accountability by team size
32:40 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 business

48:08 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-kVacpWjvAm

Connect with Lauren Bowen:
→ Email: Lauren.Bowen at LPT dot com
→ Call or text: (352) 843 3434

Connect with Real Estate Team OS:
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/

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 HILLER
Finding 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 team
• Specific things his Director of Operations did to set them up to double agent count without adding any additional cost
• How they successfully integrated 8 VAs into their organization and how they’re tasked
• Why quarter-to-quarter planning makes more sense for his team than annual planning
• How he preserved profit while losing 100 transactions as the housing market halted back in 2022
• A 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 COLEMAN
Opt 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” means
• Who’s successful in the Opt system
• The transformative nature of FUB’s open API and how tools like Sisu, Rokrbox, StackWrap, and HouseWhisper help
• The value of in-house and offshore talent
• What they walk agents through for annual business planning
• An AI solution they’re working on for 2026
• A 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/bot

Connect with Mark Hiller:
→ https://www.instagram.com/markhillerfl

Connect with Drew Coleman:
→ https://www.instagram.com/drewcoleman
→ (503) 351 3739

Connect with Real Estate Team OS
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/

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 NICKLEY
Alexis 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 production
• The division of labor between husband-and-wife, co-team leaders
• Why their recruiter’s job is so challenging
• The 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 2026
• A 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 STAUTER
Jen 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 her
• How they structure their mentorship program and one of its unique qualities
• Which changes the EOS process (the VTO, specifically) forced them to make
• Keys to successful recruiting en route to 50 agents
• A 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/

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 time

This 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 assistants

At 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/followupbosscommunity

Connect with Matt Croteau:
→ Email: Matt at MattSellsOC dot com

Connect with Real Estate Team OS
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/

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 accountability
• The path from a degree and career in architecture to a Director of Operations role
• Transitioning from real estate team to independent, family-owned brokerage
• How the Director of Operations role was shaped from scratch and what it brought to the team
• A prioritized list of projects and SOPs to set up the business to scale successfully
• The vital role of constructive criticism and three questions to ask every staff member and agent to help draw it out
• The specific pieces of their tech stack
• How they carved out distinct, aligned roles between Director of Operations, Team Founder and Partner, and Broker Owner and Partner
• Specific recruiting tactics as they look to double agent count in the year ahead
• How to find your own Director of Operations

At 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/

What if your biggest mistakes became the blueprint for your next business?

That’s exactly what Marissa Canario is doing with Apex Realty Group, which she’s building from Milwaukee, Wisconsin. 

After building a 7th-level insurance agency and after opening 168 markets (yes 168!) as a real estate leader on a national expansion team, Marissa’s now taking lessons learned to build again - with deeper obsession and a clearer value prop.

She shares the key to improving both agent experience and client experience. She details her segmented approach to onboarding (and re-onboarding) agents. She explains the pitfalls to avoid in market expansion and when to know if you’re ready. And she shares a vision of teams getting larger and larger in the years ahead through mergers and acquisitions.

Watch or listen for Marissa’s insights into:

• Why obsession with agent experience and client experience drives success
• What was required and what was learned by opening 168 markets in a real estate team expansion
• How to improve communication and get more done by meeting people where they are
• How to turn past mistakes into a tighter, more focused model with a clearer value proposition
• How Marissa’s segmenting and improving “one of the most important factors of your entire foundation and one of the most difficult to get correct” … agent onboarding
• Why to celebrate more (and more specific) agent milestones
• AI and ISAs as new leverage points for real estate teams
• Ways to make technology amplify rather than replace real estate agents (and what that means they should focus on)
• How self-awareness, network strength, and sufficient capital set you up for market expansion success
• Why mergers and acquisitions will drive larger teams and what your participation in that growth might look like

At the end, learn about the value of integrity, the ends of toilet paper rolls, the bottoms of shampoo and ketchup bottles, and fewer business books.

Episodes mentioned:
→ AI Voice and Texting with Kyle Draper and Tiffany Gelzinis
→ Redefining the Role of the Real Estate Team Leader with Keith Anderson
→The Roll-Up Strategy for Business Growth with Sam Khorramian

Connect with Marissa Canario:
→ https://www.instagram.com/marissacanario/

Connect with Real Estate Team OS:

→ https://www.realestateteamos.com

→ https://linktr.ee/realestateteamos

→ https://www.instagram.com/realestateteamos/