I’ve asked myself this question a thousand times since I started property management in 2020. It might sound crazy to have jumped into the industry in the middle of a global pandemic—but, of course, I didn’t know a pandemic was coming when I started. Looking back, it’s actually a wild story.

I had launched my company, Milestone Premier Properties, in April of 2018. And when I say “launched,” I mean I had an LLC, a website, and a vision. By all legal measures, Milestone was officially born on April 19, 2018, per the Secretary of State.

I was obsessed with the idea of my company—yes, the idea of it. I hadn’t yet gained the wisdom I have now. In my mind, I envisioned a high-end real estate brokerage with top-producing agents dressed in sharp suits, selling multi-million-dollar properties. You know… Selling Sunset style.

Reality, however, had different plans. Instead of selling luxury homes, I found myself renting $600 leases to residents barely scraping by.

My goal when I entered real estate was simple: I wanted to find clients who were constantly buying and selling. The traditional real estate model—buying leads, sitting in an office hoping the phone would ring, or paying high referral fees to a brokerage in exchange for leads—never felt right to me. I tried it, learned a lot, and ultimately realized that wasn’t the path I wanted. I needed to build something different.

So, I did.

I started my own company. And I did it without the support of many people I cared about. My decision confused and even upset some—after all, who starts a real estate brokerage with less than a year of experience?

But I knew something they didn’t.

I wasn’t just a new real estate agent. I came with the experience of owning a bookkeeping business. I understood what it took to run a successful operation: how to structure a business, obtain proper licensing, manage finances, develop efficient systems, and market a brand. I wasn’t simply opening a brokerage—I was building a business I knew could thrive.

And it did.

Between 2018 and 2020, I closed over 230 transactions. My strategy? I built relationships with builders who let me list their properties—for a crazy low fee of $500 per listing. It wasn’t about the money. It was about experience. The average agent sells 10 homes a year; in three years, I gained what most would take two decades to achieve.

Then, at the end of 2019, a client asked if I would manage a few warehouses. I had no clue about property management, but the idea intrigued me—long-term client relationships, recurring revenue, and a break from the commission-only grind. After some research, I was sold.

Of course, I had no idea what I was getting into. But that’s never stopped me before.

If something feels right, I go for it. If it doesn’t, I walk away. That gut instinct has been my guide through business and life, and it hasn’t failed me yet.

So, property management began.

At first, I only managed a handful of properties. The extra income was nice, and overhead was minimal. I purchased a subscription for a property management software, got the necessary insurance, opened bank accounts, and created a spreadsheet. That was it. Everything else? I figured it out as I went.

And truthfully… I still feel like I’m figuring it out.

Only now, we manage nearly 300 properties.

I say we because I had to build a team. I managed the first 100 doors alone—wearing every hat: property manager, assistant, bookkeeper, maintenance coordinator, marketing director, salesperson, and even the bank funding my own crazy dream. It was insane. Looking back, I have to give props to my 28-year-old self for jumping in headfirst.

It was exhausting. It was thrilling.

I dove deep into the right circles, never stopped learning, and juggled an insane workload—helping clients buy and sell 70+ properties a year, managing 100+ rental doors, running a bookkeeping business, and flipping properties for capital. It was a lot.

And every step of the way, I questioned myself.

“Why am I doing this?”
“Is this really worth it?”
“What if I just walked away?”

But right alongside that doubt was something else—gratitude.

Because as overwhelming as this business is, I also feel blessed every day to do it.

Property management is one of the toughest, most thankless industries out there. People complain about everything. The costs to operate are high, the margins are thin, and no matter how hard you try, you will upset someone. The liability is staggering, and lawsuits are always a possibility. The work consumes your mind, strains relationships, and sometimes takes a toll on your mental health.

But it’s also one of the most humbling careers you can have.

You see people at their best and their worst. You witness real-life struggles—families losing jobs, residents desperately trying to make rent, owners panicking over unexpected repairs. And as much as you want to be compassionate, you also have a job to do: protect your client’s asset. Sometimes, that means evicting a good family who just fell on hard times.

It’s a brutal contradiction.

This business creates connections in ways you’d never expect. You have the privilege of helping someone secure their future home and the opportunity to build lasting trust with investors who count on you to protect their assets. You navigate important conversations—guiding owners on pricing strategies to get their properties rented or advising them on necessary improvements to maintain their investment’s value. Along the way, you sharpen your communication skills, strengthen relationships, solve problems with confidence, and continuously refine your processes to grow and improve.

You’re challenged every single day—by owners, residents, vendors, staff, and the market itself.

But you survive.

And when you take a step back and see all the lives impacted by what you do, it clicks.

This is why I do property management.

Because I make a difference—whether it’s for a family finding a home, an investor building wealth, or a team growing within a business that supports them.

Because I am the linchpin.

And because now that I’ve come this far… I have to see how far I can go.