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:

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