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:

(3:21) Life as a military spouse and constant change

(6:07) From interior design to real estate

(8:46) Focusing on listings and early success

(10:58) How technology reshaped the industry

(14:22) Standing out through creative marketing

(16:16) The $10,000 bet that changed everything

(19:14) Bringing others along through accountability

(22:38) The power of focus and belief

(26:32) A $10,000 story of luck and persistence

(28:41) Visualizing success before it happens

(31:17) Why listing agents hold the leverage

(33:31) Building tools and community for agents

(35:26) 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