Respect the Mic: What Freestyle Rapping Taught Me About Real Estate
Back in the early 2000s, when Nashville was my home, I made one of the most embarrassing mistakes of my life—and somehow, it taught me an important lesson about real estate. Nashville is not only home to Country Music, it's home to the contemporary christian music scene as well. A good friend and I went out on the town one crazy night in search of an adventure. Little did I know how this evening would make a lasting impact my career.
That evening, we decided to crash a Dove Awards after-party. For context, the Dove Awards are like the Grammys for Christian artists, and this particular party was hosted by a record label known for its rap and hip-hop acts. Fueled by a mix of youthful curiosity, liquid courage (in the form of a few PBRs), and the complete lack of venue security, my friend and I strolled right in without an invitation.
It wasn’t long before the DJ announced a freestyle rap competition. My friend turned to me with with the kind of misplaced confidence that only comes from peer pressure and beer, and with a a mischievous grin and said, “You should totally do that.” Now, let me be clear: I can’t sing, I can’t dance, and I certainly can’t rap. But for some reason, probably the three PBRs, I thought, Why not? With all the swagger of someone who has absolutely no business on a stage, I tilted my head, raised an eyebrow, and said, “Yeah, Boi!”
What happened next is basically like the movie 8 Mile —if 8 Mile was about a country kid bombing spectacularly in front of a room full of Christian music fans.
The first two rappers? Amazing. They worked the crowd like pros. Then it was my turn. The DJ handed me the mic, and I could feel the crowd’s energy. I took a deep breath, asked the DJ to drop a beat, and told the crowd, “Wave those hands from side to side!”
The crowd was with me, their hands in the air. For a split second, I actually felt I was about to settle the whole east coast west cost beef with some bars - strait out of Great Bend Kansas.
I was soaking it in. Then I dropped my first line: “My name is Justin Sterling, and I got something to tell ya.” something obvious, but the crowd is still with me... I’m now bending my knees with my arm extended above my head, then my brain locks up and I can’t quickly think of anything that rhymes with “tell ya”..
Fortunately for me there's a little time to come up with a brilliant lyric, and then as my arm has crossed my face with the beat like I'm a human metronome. I say “gonna take ya home, then I’m gonna smell ya”
Yes, you read that right. I said : "Smell ya." This wasn’t just a failed rhyme—it was an absolute catastrophe. In a room full of devout Christians, I had just made the most awkward, horrifying statement possible.
The music stops, and it's dead silence. The jaws are on the floor and those faithful followers of the Lord Jesus are staring at me like I just blasphemed Christ himself. I look at the DJ like “hey man, can we keep going?” Then he motions for me to give him back the microphone.
The DJ motioned for the mic, and I handed it over, defeated. Shoulders slumped, I slinked back to my friend, who couldn’t even make eye contact with me. “You want to leave?” he asked, eyes fixed somewhere far away.
“Yeah,” I said, trying to salvage a shred of dignity. “This party’s lame anyway.”
Lesson in Respect and Preparation
That night, I learned some things: First, I am not a rapper. And second, knowing your audience and being prepared is everything.
At the time, I wanted to pretend that night never happened. But over the years, that humiliating moment taught me something profound: whether you’re rapping on a stage or pitching a business idea, preparation is everything. You need to understand your audience, respect their expectations, and come ready to deliver—or risk silence and stares.
In my real estate career, I see this lesson play out all the time. Every week, I meet entrepreneurs full of enthusiasm, and some even sound like they’ve got everything together. But without a solid plan, they’re essentially stepping onto the mic with nothing prepared. and they want to lease a space for their big idea. Like the DJ handing me a microphone that night, we give them a platform. But if they don’t come prepared—with a solid business plan, clear goals, and a sense of direction—they’re just freestyling their way through it. And, unfortunately, freestyling in business doesn’t work.
The Cost of Freestyling
I’ll never forget one of my early experiences in real estate. I got a call from a guy who sounded confident on the phone. He wanted to open a restaurant and lease a space with a $100,000 annual rent. Intrigued, I drove an hour to meet him, showed him the space, and spent an hour discussing his vision.
At the end of the meeting, I asked, “What are you doing now?”
His response? “I work at Shoney’s.”
“Are you an owner?” No.“Manager?” No.“Franchisee?” No.“Have you studied culinary arts?” No.“Any hospitality experience?” No.
He had no experience, no savings, and no business plan. I had to apologize and tell him, “I should’ve done a better job preparing you for this meeting. This lease is over $100K a year and could cost you $200K in startup costs. How do you plan to pay for that?”
He had no answer.
Before he left, I told him my rap story. I explained that I wanted him to succeed, but without preparation, he’d end up on stage with nothing to say—and the consequences in business are far more serious than an awkward moment in front of a crowd.
How to Avoid Freestyling in Business
So, how can you prepare for your big moment? Whether you’re pitching a landlord, a banker, or an investor, here’s what you need to do:
Take Business Classes: Learn the basics of financial planning, marketing, and operations.
Start Small: Test your idea as a side hustle before going all-in.
Write a Business Plan: Understand your market, your expenses, and your path to profitability.
Gather Experience: Work in the industry you’re entering. Learn from others before you take the leap.
Ask for Responsibility Before Asking for a Raise: Build your credibility and skill set over time.
When a Landlord broker asks detailed questions about your finances, work experience, and the vision for your business, it's with a sense of responsibility towards the ultimate success of your Lease.
The Tenants preparation affects the banker who underwrites the loan, the insurance company who’s policy protects the property, and the Landlord who’s taken the risk in providing a platform for the Tenant to operate.
It won't feel like it, but when a bank, landlord or potential investor in your business say's no to your idea they probably doing you a favor - saving you precious time and money while you prepare yourself for greater success in the long run.
Prepare yourself for the person you are going to be every day and the cumulative effort will produce something you can be very proud of. Because no one wants to hear “smell ya” when they’re expecting a show.
Rock forth!

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