A lot of team leaders are trying to grow right now, but very few know how to scale without burning out, losing culture, or drowning in problems that show up the moment the business gets bigger. That tension is exactly where Lindsay Stevens built her strength. And the way she talks about these challenges will make every real estate leader stop and think.

On this episode of the GRIT Podcast, Brian Charlesworth sits down with Lindsay, co-owner and team leader of Stevens Real Estate, to uncover how she went from overwhelmed agent to running one of the fastest-growing teams in her market. 

The twist is that none of it came from perfect planning. It came from saying yes to uncomfortable moments, including being thrown onto a five-thousand-person stage with one week to prepare. She also breaks down the discipline required to survive New York’s long 120-day transaction cycle. It is the kind of cycle that forces leaders to either master their systems or get buried by them.

Lindsay talks about the seasons she had to fight through distractions, doubt, and long days that made her question whether she was even built for leadership. She shares a simple line that keeps her centered. "Life is hard. Real estate is hard. But the sun comes up tomorrow." It is the kind of line that hits differently when you hear the story behind it.

Brian and Lindsay also break down a moment that shifted their entire operation. Dialing in their Sisu stages, statuses, and tagging finally removed the chaos inside New York’s long transaction cycle, and it changed the way their agents performed. As she puts it, "You do not rise to the level of your goals. You fall to the level of your systems."

Top Takeaways:

(2:23) Saying yes to a 5000-person stage

(9:51) Breakthroughs after wanting to quit

(12:02) CEO vs. team leader roles in a business

(14:21) How Sisu rebuilt transaction flow

(21:08) The power of proximity and fast execution

(32:19) Scaling with leverage and a new COO

(32:12) Working on the business, not in the business

(37:58) Why systems come before 20 agents

(38:28) Micro commitments and predictable wins in Sisu

(42:21) AI as a business partner and coach

(45:00) Why AI will not replace relationships in real estate

If you want an honest look at growth, leadership, and the real work behind building a strong team, this episode with Lindsay will pull you in from the first few minutes.

About Lindsay Stevens

Lindsay Stevens is a Hudson Valley native and co-founder of Stevens Realty Group, featured on HGTV’s House Hunters. She led New Paltz as the top sales agent in 2017, 2018, and 2019 while growing the firm into a multi-million dollar real estate and property management company. With a background in Legal Studies and Business from UMass Amherst, she has worked in sales, marketing, and communications with companies like Edelman and Morgan Stanley. Lindsay is also a mother of two and an active runner who has deep roots in the Hudson Valley community.

Connect with Lindsay:

LinkedIn

What does it take to go from solo agent to community leader? For Sandee Payne, the answer came from a single moment of saying yes before she was ready. A military spouse turned interior designer, Sandee spent years helping families feel at home across the world. That love for creating spaces eventually led her to real estate, where she built a thriving business centered on listings and design-driven marketing.

Early in her real estate career, Sandee noticed that agents often worked hard but lacked structure. Determined to change that, she tracked everything and shared what she learned. Her natural ability to teach became a foundation for coaching others. “I realized if I could do it, anyone could,” she said.

Her defining moment came on stage at a Tom Ferry event, when she was dared to sign 100 listings in 10 months. With 8,000 people watching, she accepted. The challenge forced her to focus, simplify, and prove what was possible through consistent effort. “I had to believe it before I could see it,” she recalled. Ten months later, she reached 103 listings.

That accomplishment sparked something bigger. Sandee created a Facebook group that grew into thousands of agents following her strategies. What started as one bet evolved into a full accountability platform, showing others how to set measurable goals and follow through.

In this episode, Brian Charlesworth talks with Sandee about turning pressure into performance, the power of public accountability, and how her Zero to 100 Listing Challenge is helping agents shift from reaction to intention. They also explore why systems, mindset, and community are now the backbone of her business. 

Top Takeaways:

(3:48) Life as a military spouse and constant change

(6:28) From interior design to real estate

(8:58) Focusing on listings and early success

(10:49) How technology reshaped the industry

(14:07) Standing out through creative marketing

(15:58) The $10,000 bet that changed everything

(18:50) Bringing others along through accountability

(22:24) The power of focus and belief

(26:09) A $10,000 story of luck and persistence

(28:17) Visualizing success before it happens

(30:47) Why listing agents hold the leverage

(32:56) Building tools and community for agents

(34:43) The Zero to 100 Listing Challenge explained

Tune in now to hear how one bold yes turned into a movement that’s changing the way agents think about accountability. 

Registration for the Zero to 100 Listing Challenge is officially live! Visit www.02100listingchallenge.com to join the 10-month race kicking off January 1, 2026.

About Sandee Payne

Sandee Payne is a Broker Associate and the founder of the Designed 2 Sell Real Estate Group in Central Texas. After 18 years as a Texas resident and military spouse, she combines her real estate expertise with decades of experience in interior design and home styling. Sandee began her career with Centex Homes in 2007 and has since helped countless families find and create their ideal homes. Her design work has been featured in major publications and on HGTV’s House Hunters Renovations.

Connect with Sandee:

Website

Many teams in real estate are struggling with how to grow without overspending on leads or losing control of profitability. At the same time, leaders are facing shifting interest rates, limited inventory, and the challenge of keeping agents productive in a competitive market.

On this episode of the GRIT podcast, Brian Charlesworth sits down with Robert Conway from the Jeremy Orton Group in Idaho. Robert leads both operations and sales, giving him a unique view of how to scale while keeping systems and people aligned.

Robert shares how he approached cutting lead costs, building a referral-based business, and using Sisu’s predictive models to forecast closings with precision. He explains why accountability is central to the culture of their team. “Accountability is the highest form of love,” he says.

With a team of 12 agents today and a goal to grow further, Robert talks about what it takes to bring new people into production quickly and why referrals remain their strongest growth channel. “It’s not the quantity of leads, it’s the quality and how you work it,” he adds.

Top Takeaways:

(4:40) Cutting lead costs without losing closings

(7:05) Using Sisu to forecast team growth

(10:39) Industry consolidation and AI ecosystems

(15:36) Explaining rates with “marry the house, date the rate”

(21:12) Will the U.S. hit 5M home sales again?

(26:03) Data, Sisu, and building accountability into culture

(28:37) Netting 18 agents before expansion

(33:46) How the team staggers new agent onboarding

(37:01) Fixing cracks in systems before they become canyons

If you are trying to figure out how to balance growth with profitability, and what to expect as the market shifts again, this conversation will give you practical insights you can apply to your own business. Tune in now to catch the full episode.

About Robert Conway

Robert Conway is the Director of Sales and Business Development at the Jeremy Orton Real Estate Group in Twin Falls, Idaho. He oversees both operations and sales for the team, which currently has 12 agents and is aiming to grow to 20. Robert has more than 15 years of management experience, with degrees in psychology, business, and human resources. He moved into real estate over three years ago to bring more flexibility to his life while driving the group’s growth and systems.

Connect with Robert:

LinkedIn

Real estate is an industry where the market can change overnight, making it harder for agents to know how to stay consistent. Some try to solve this by chasing more leads or working longer hours, but that often leads to burnout instead of growth. What if there was a way to build a predictable business no matter what the market does?

(0:55) From local brokerage to joining eXp

(4:32) Zoocasa’s surprising tech origins

(8:32) Why real estate success is always local

(14:55) From 2% to 7% conversion growth

(19:43) Daily huddles that keep agents aligned

(21:16) Monday focus on objections and wins

(24:08) Doing the hard things every day

(30:36) Staying connected during tough times

(33:39) Comparing the US and Canadian markets

(35:29) Creating a culture of accountability

You will also hear how their daily huddles keep agents connected across different markets, how they build accountability without micromanaging, and why their approach works even when transactions are down nationally.

LinkedIn

LinkedIn

Many agents are feeling the pressure as deals get harder to close and the market shifts. Some are waiting for things to improve, while others are putting in the work now to get ahead. The difference comes down to skills, systems, and long-term planning.

Jim Amen has lived through challenging markets before. He started in real estate during the 2008 housing crisis, first as an appraiser and later as a broker. What began as a small brokerage is now a 41-agent team in Sacramento. “You have to be willing to pivot when the market shifts,” Jim says.

In this episode, Jim talks with Brian Charlesworth about why his team has been able to grow year after year while so many others are falling behind. He explains the simple daily habits that drive results, including focused prospecting, clear expectations, and strong accountability.

Jim also shares how he built seven different revenue streams to protect his business and create new opportunities. From mortgage partnerships to flipping mobile homes, these extra businesses allow his team to scale without relying only on commissions.

They dig into how tools like Sisu and Battr help his team track data, hold agents accountable, and build a two-year pipeline instead of chasing short-term leads. “Building wealth comes from the work you do now, before the market turns,” Jim explains.

Top Takeaways:

(1:45) From marketing director to real estate team leader

(6:43) Growing while 71% of agents sell nothing

(7:53) Simple habits and expectations that drive success

(10:09) Taking market share before the shift hits

(12:56) Building wealth beyond just selling homes

(15:43) Lessons from losing $1M while scaling a team

(22:04) Why solo agents struggle to succeed today

(23:03) What joining a team really provides

(24:29) Turning client tracking into revenue with Sisu

(25:42) $150K in operations funded by TC fees

(27:09) Adding seven income streams to the business

(32:33) Four-step process to build a two-year pipeline

(34:58) Automating lead follow-up with Battr and AI

Listen in to learn how to prepare your team for the next big market shift and how to create a business that lasts.

About Jim Amen

Jim Amen is the CEO and Founder of Amen Real Estate, serving 14 counties across Northern California. With over 30 years of experience, including 20 years in real estate and 10 years in marketing, Jim brings a unique perspective to his work. He has completed over 4,000 home appraisals and has been part of multiple Realtor Associations for years. Jim also runs SOAR, a training company focused on coaching agents nationwide.

Connect with Jim:

Website

Some teams reach a point where the leader can step out of production without losing momentum. That usually takes years, but in under five, Brian Buckley grew his team from just a few agents to 35 and positioned himself to focus solely on building the business.

Top Takeaways:

(1:27) Sisu as a growth driver from day one

(4:22) Why experienced agents return to teams

(6:45) Cutting toxicity and building real teamwork

(8:34) Recruiting by sharing what works

(11:35) Controlling the process to close more deals

(16:26) Treating agents like partners

(17:34) Coaching agents into ownership

(19:36) Using automation to boost follow-up

(23:50) Lower costs, higher ROI with the right tools

(27:08) Turning “bad” leads into closings

(30:05) Winning deals with smart concessions

(31:51) Skiing adventures beyond real estate

Listen in to learn how to scale a real estate business with systems, protect culture as you grow, and free yourself from the day-to-day without losing momentum.

About Brian Buckley

Brian M. Buckley is with LoKation Real Estate in Pompano Beach, FL, and has worked in real estate for over 25 years across Georgia and South Florida. He studied Communications and Advertising at the University of Georgia before moving into residential home building and commercial real estate.

Connect with Brian:

LinkedIn

Some real estate teams are growing even in down markets. And that is not because they have doubled headcount or dumped money into leads, but because they have doubled down on data, service, and systems.

That is exactly what Courtney Gauchman, COO at Wilson Group in Massachusetts, has helped her team do. With a background in the beauty industry and over a decade of operational leadership, Courtney now leads the systems and strategy that have fueled the Wilson Group’s growth, despite navigating one of the toughest markets in recent years.

And what is her approach?

Track everything, but focus only on what moves the needle. From managing three full-time operations staff to building custom dashboards in Sisu, Courtney ensures every agent has clarity on where their business comes from and how to grow it. “We basically attribute the 88 percent growth during three of the hardest years in real estate to the fact that we use Sisu,” says Courtney.

In this episode, Brian sits down with Courtney to talk about what it takes to run a referral-based real estate business, how to keep agents productive without burnout, and why they are starting to build an operations-as-a-service company for agents who do not want to manage staff. They also discuss how operational clarity impacts culture, conversion, and client experience!

Top Takeaways:

(1:38) From salon management to real estate ops 

(4:14) Why are salon pros thriving in real estate? 

(6:40) Building a business vs. slinging homes

(8:14) Growing 88% through post-sale follow-up

(9:26) Sisu dashboards built for ROI

(12:00) Deep conversations over cold calls 

(14:34) $70M+ in referral-based volume

(15:43) Setting the referral expectation early

(18:57) Building a referral system inside Sisu

(22:42) Custom accountability for agent success 

(26:43) Turning rental data into buyer leads

(31:41) Building an ops-as-a-service model from Sisu

(35:50)  Reviewing past data to guide marketing

If you are still guessing where your next deal will come from, this one is worth a listen.

About Courtney Gauchman

Courtney Gauchman is the COO of the Wilson Group, a Keller Williams team based in Massachusetts. She brings 12 years of operations experience and a background in real estate sales. At Wilson Group, she leads the development of systems that support both clients and agents. Outside of work, she enjoys family time, outdoor activities, and experimenting with espresso martinis.

Connect with Courtney:

Instagram

What happens when you stop building your real estate business the way everyone tells you to and start building it around who you really are?

(1:56) Listings sitting longer & seller strategy

(3:22) Pricing strategy that actually works

(7:26) Impact of interest rates dropping to 5%

(10:31) Lead gen strategy for every listing

(11:26) Sisu's new product “Battr”

(12:29) Tracking lead life from start to close

(18:24) Lead spending vs. accountability

(20:45) Training agents without scripts

(23:53) Using Sisu dashboards to coach agents

(28:05) Picky recruiting & low team turnover

(31:05) Builder partnerships through lead strategy

(33:58) Real estate and Porsche passions

(36:47) The 1% rule for long-term growth

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JD Reese - Instagram

The Genuine Group - Instagram

This week on GRIT: The Real Estate Growth Mindset, Brian Charlesworth is joined by Jace Gillies, team leader at Utah Life. They talk about growth, leadership, and building a team that performs with consistency. From closing 29 deals in his first year to now leading over 90 agents, Jace shares what it looks like to scale while keeping culture intact.

(4:16) Value of teams & shifting mindset

(9:35) Taking over the salt lake office 

(14:09) Mental shift in recruiting

(18:24) Tracking for predictable closings

(25:57) Sales contests & team culture

(29:50) Leading by example in real time

(33:26) Impact of sisu on everything

Connect with Jace:

LinkedIn

In this episode of GRIT: The Real Estate Growth Mindset, Brian Charlesworth sits down with Leo Pareja, CEO of eXp Realty, to talk about the journey from selling nearly 4,000 homes to leading one of the fastest-growing brokerages in the industry. Leo shares how he started in real estate at 19, thinking he would be an investor, and became one of the country's top agents.

Top Takeaways:

(1:53) Leo's real estate and tech journey

(6:22) Entering tech at the worst possible time

(8:32) The first big real estate win

(10:19) The two ways to scale in real estate

(11:27) Why should agents not copy top producers?

(13:38) The importance of relationships

(19:15) Why eXp changed everything

(20:49) Why franchises are dying

(21:53) What makes eXp 2.0 different?

(24:54) Real estate market growth predictions

(27:43) What agents should focus on now

(29:42) Adapting to change in business

(31:08) Controlling your own success

Leo Pareja started his real estate career at 19 and became the #1 Keller Williams Agent worldwide by 28. Over 15 years, he sold around 4,000 homes before co-founding Washington Capital Partners in 2012, which grew into one of the largest private lending firms on the East Coast. In 2016, he co-founded Remine, a real estate tech platform that reached 80% market share and over 1.1 million users. 

Connect with Leo:

Website

LinkedIn