Most Agents Advise.
I've Actually
Done it.

My name is Dylan McDonald. I'm a REALTOR® based in Winston-Salem, and a Brooklyn native who didn't think he'd ever leave New York — until he did.

For ten years I worked as a Director of Operations, overseeing logistics, inventory, fulfillment, and people for a multi-million-dollar high-end bicycle company. I started there as a stock hand who didn't even know how to ride a bike. Don't worry, I do now.

Outside of that, I've spent the last five-plus years building my own real estate portfolio — buying, renting, and selling properties. When I'm not working on a deal, I'm hiking, lifting, or on a road trip with my wife to somewhere we haven't been.

Why North Carolina?

I was born and raised in Brooklyn, and even at a young age I never really felt at home there. I felt more at home visiting my grandfather upstate, where he was surrounded by woods and had acres of land between himself and his neighbors.

Don't get me wrong — New York is great. The food scene is infinite, the public transit makes life without a car genuinely possible, and the bagels are undisputedly the best. But aside from that, it didn't have what I needed.

I honestly never thought I'd leave. It's all I'd ever known. But as I got older, it became a necessity. My wife and I visited North Carolina just to see what it was about. We didn't think we'd move.

It took one visit to know. I found what I'd always been looking for: a slower pace, strangers who say good morning, a place where building a community feels effortless. People talk about the cost-of-living advantage, which is real, but that's not why we chose it. We chose it for peace, for the people, and for the version of life we'd been chasing.

Why Winston-Salem?

When my wife and I were figuring out where in NC we wanted to be, everyone told us about Raleigh, Greensboro, Asheville. Not once did Winston come up.

I came across it doing my own research and added it to the list. We visited all of those places and loved each of them for their own reasons — but when we got to Winston, we just knew. I remember sitting downtown in the car, turning to my wife and asking what she thought. Without skipping a beat, she said this was where she wanted to move. We knew instantly, without saying a word to each other.

Winston is unique because it's considered a big city, but it's the smallest of the big cities here. That's exactly what we loved about it. It wasn't trying to be Raleigh, New York, Boston, or Houston. It was authentic to itself. It embraced its history while still innovating and reimagining its downtown. There's something rare about a city that doesn't feel the need to be anything other than what it is.

I got into real estate as a wealth-building strategy — not as a sales career. I never planned on getting my license.

I didn't want to work for someone else until I retired at 65, and the majority of wealthy people I'd read about built their wealth through real estate. So I figured I'd give it a shot.

While my peers were out partying or taking vacations, I was studying and researching, trying to figure out how to get my foot in the door. After years of working, saving, and preparing, I bought a multifamily property and rented it out. It put me through the ringer, to put it lightly. Ask me about it sometime — I love talking about it. It gave me real-world experience that no amount of research could have prepared me for.

So why become an agent?

Honestly? I never planned on it.

I wanted to be an investor — build wealth through ownership, not sales. I got my license initially to save on commissions if I purchased more properties, and to help any family or friends who eventually fell in love with NC the way I did.

But I enjoy connecting with people. Hearing their stories, their dreams, their motivations. And I genuinely love helping others. Having the opportunity to guide someone through one of the scariest, highest-stakes decisions of their life is a responsibility I take on wholeheartedly.

I'm able to empathize and see it from your perspective because I've been there. But I'm also able to help you move through that fear using data and logic rather than emotions. The commission is the cherry on top — but at the forefront, it's getting to help make someone else's dream happen.

I chose the name because it works on a few levels.

As a buyer or seller, it represents what's ahead of you — whatever path you're on. It's scary, but it's also exciting and invigorating. It's about starting fresh and embracing the possibility that the grass actually can be greener.

It's also an ode to all that I've personally gone through to become the person I am today. It's about moving forward and not getting stuck looking back — the past is a reference key, not the whole story.

It's having hope that no matter the adversity you're facing — whether it's a real estate transaction, problems within your career, or anything else we face as human beings — there is always potential for better days. And they start here.

My personal real estate portfolio — three properties, the lessons learned the hard way, and the reasons I think personal experience changes the kind of agent you become — written out plainly on its own page.

Read: My Portfolio →

The first conversation, how I communicate, what buyers and sellers can expect from me at each step, and the things I won't do — written out plainly on its own page.

Read: What to expect →