Scaling a Real Estate Business: Insights from Steve Montgomery on Systems, Consistency, and Grit

Success in real estate isn’t just about selling homes. It’s about building sustainable systems, maintaining consistency, and developing a disciplined work ethic. Whether you're a new agent or a seasoned professional, the right strategies can make all the difference.

This week on Real Estate on the Up, I sat down with Steve Montgomery, a top-producing agent and owner of Kavu at eXp Realty, who has closed nearly 650 sales in his 11-year career. His journey from being a reading education teacher to a thriving real estate entrepreneur is nothing short of inspiring. We talked about the power of systems, the importance of consistency, and how he built a referral-based business that continues to grow year after year.

From Teaching to Real Estate: A Leap of Faith

Steve didn’t always sell homes. In fact, he spent 15 years as a reading education teacher. He loved teaching, but the reality of low pay and job instability left him in a tough financial spot. Things came to a head when he had heart surgery and was left with $40,000 in medical debt. That same week, he was pink-slipped from his teaching job—again.

With no financial safety net and a growing family, Steve had a choice: stay in a cycle of low pay and uncertainty or take a leap into something new. Real estate offered a quick entry point and unlimited potential, so he went all in.

The Relentless Hustle of a New Agent

Starting out wasn’t easy. Steve had no salary, no fallback plan, and a mortgage to pay. He threw himself into prospecting seven days a week, making calls, knocking on doors, and doing everything possible to generate business.

• The first 30 days? Nothing.

• By month two? He started closing deals.

• The key? Consistency and discipline.

Steve adopted a “burn the ships” mentality—there was no plan B. He worked tirelessly to ensure his business would succeed, and his persistence paid off.

Building a Scalable Real Estate Business

Fast forward 11 years, and Steve now leads a successful team of eight agents with two virtual assistants (VAs) and a transaction coordination team. But despite the growth, one thing hasn’t changed—his work ethic. He still:

• Starts his day at 8 AM with prospecting calls

• Holds open houses on weekends

• Works six days a week (instead of seven!)

What’s the secret? Systems.

The Power of Systems: What Every Agent Needs

Steve credits his success to structured systems that eliminate busywork and allow him to focus on what matters—generating business. The first system every agent should implement? A Transaction Coordinator (TC).

• Cost: $350–$400 per file

• Value: Ensures compliance and smooth transactions

• Benefit: Allows agents to focus on lead generation, not paperwork

Many agents waste time on admin work when they should be focusing on revenue-generating activities. Steve’s advice? Outsource early so you can scale faster.

Lead Generation Strategies that Work

Generating consistent business isn’t magic—it’s about leveraging your network and staying top-of-mind. Here’s how Steve does it:

1. Sphere of Influence (SOI)

• Calls past clients, friends, and family using the DTD2 system (calls contacts by last name on a set schedule)

• Sends weekly emails every Thursday at noon

• Engages on social media

• Hosts client appreciation events (e.g., delivering pies to past clients—this alone generates 8–10 deals annually!)

• Sends fun, personal gifts (e.g., Ninja Turtle Valentine’s cards with Fun Dip—small gestures that keep him memorable!)

• Works closely with a mortgage broker to ensure clients have access to the best financing options available.

2. Agent-to-Agent Referrals

Steve doesn’t just network with clients—he builds relationships with top-producing agents nationwide. His referral strategy includes:

• Attending four real estate conferences per year

• Connecting with high-volume agents ($20M+ in annual sales)

• Receiving 50+ referrals annually, closing at least 25 deals per year from agent referrals alone

His mindset? Instead of farming neighborhoods, he “farms” top agents across the U.S. for referrals. This has become a major pillar of his business.

Navigating Market Challenges: High Inventory & Interest Rates

The real estate market is always shifting, and Orlando is no exception. Right now, Steve is seeing high inventory in certain areas, making it harder for sellers to move properties.

• Areas like St. Cloud and Davenport have an oversupply of homes, requiring sellers to price competitively and offer concessions.

• Luxury markets ($600K–$1M+) remain strong, while mid-priced homes are moving slower.

• Interest rates are affecting buyer demand, with some waiting for rates to drop.

The takeaway? Real estate is hyper-local. A well-priced home in one area may sit for months, while a similar home in another neighborhood sells in days. Steve emphasizes setting realistic seller expectations based on both micro (neighborhood) and macro (city-wide) market trends.

Setting Seller Expectations the Right Way

One of the hardest parts of real estate is managing seller expectations. Many sellers overestimate their home’s value and resist pricing adjustments. Steve’s approach?

• Tell the truth, not what they want to hear.

• Use data to back up pricing recommendations.

• If a seller is unrealistic, be willing to walk away.

His honesty builds trust and long-term relationships. As he puts it:

Some sellers want the perfect deal, but Steve believes in telling them the truth—even if it means losing the listing. He focuses on setting realistic expectations and ensuring clients understand the market dynamics rather than giving them false hopes.

Tune in to Real Estate On the Up and Master Success Today

Sitting down with Steve Montgomery has been an eye-opening experience. This episode of Real Estate on the Up wasn’t just about his success—it was about the systems, strategies, and mindset that any agent can use to thrive in the industry. Beyond that, it reinforced the importance of learning from experts, whether through direct mentorship or by listening to real estate podcasts that provide valuable industry insights.

And if you’re looking for more expert insights, subscribe to Real Estate on the Up for weekly deep dives into the world of real estate. Until next time—stay consistent, stay accountable, and keep moving up in the world of real estate!