Meet Riley Smith | President, Riley Smith Group at Compass

We had the good fortune of connecting with Riley Smith and we’ve shared our conversation below.

Hi Riley, how do you think about risk?
As a real estate professional, risk is just part of the DNA of this career. You’re constantly navigating market shifts, interest rate swings, policy changes: you name it. In my 25-plus years doing this, I’ve seen at least seven very distinct market cycles. And none of them looked the same. That unpredictability? That’s risk. But you learn early on that if you want to thrive in real estate, you can’t run from it. You have to lean into it.

When I first got into this business, I had no formal background in real estate. I bought a house from a friend, saw what he earned on the deal, and decided, “I can do that.” That was a risk. I had never worn a tie, never wanted a 9-to-5, but I jumped in. From there, I built my entire career around understanding the market, the city of Miami, and the community I grew up in, Coconut Grove.

So how do I think about risk? To me, it’s less about fear and more about preparation. Risk without a plan is gambling. But risk with preparation is strategy. I’m constantly preparing. My team and I work off a business plan. We have a clear marketing strategy. I’ve had coaches and mentors throughout the years who helped guide me through the uncertain times. That’s how you mitigate risk.

Every major leap in my career came from taking calculated risks. I doubled down on Coconut Grove when most agents were casting wide nets; and that local focus early on set me apart. I launched one of the first real estate blogs in South Florida before Zillow or social media were a thing, which made us a go-to online resource. And when the business was growing fast, I built a team that could function independently, so the business wouldn’t stop when I stepped away. Each risk was strategic and grounded in where I knew the market was going.

At the end of the day, this business isn’t for the risk-averse. You’ve got to bet on yourself… and if you’re truly prepared, those bets start to pay off.

What should our readers know about your business?
Over the years, we grew organically. First with one buyer’s agent, then a small team, and eventually a full business with in-house sales, marketing, and operations all working together. Today, I’m proud to say the Riley Smith Group runs like a real company, not just a group of agents under one name. And that has taken time, trust, and a lot of learning through testing and learning.

One of the things that really sets us apart is how seriously we study the Miami real estate market. I’ve always been fascinated by data: what it tells us, how it trends, and most importantly, how we can use it to guide our clients. Neighborhoods like Coconut Grove, Coral Gables, Key Biscayne, Pinecrest, South Miami, Shenandoah, Silver Bluff, and Palmetto Bay are only some of our specialties. We know the numbers inside and out, and we constantly track shifts so our clients are ahead of the curve. It’s about helping people prepare for what’s coming, not just reacting to it. That’s where the real value is.

One of the biggest lessons I’ve learned is the power of consistency. Whether it’s showing up for your clients, sticking to your niche, or creating content before it’s trendy, you have to play the long game. The other big one is that you should never try to do it alone. The only reason we’ve been able to scale the way we have is because I’ve surrounded myself with people who are better than me at a lot of things, and I let them do what they do best.

What I want the world to know about our brand is this: we’re not here to chase volume or flash. We’re here to give honest, knowledgeable guidance to people making one of the biggest decisions of their lives. We don’t take that lightly. Whether you’re buying your first home, investing, or selling a luxury property, we treat every client like they’re the most important one. Because to us, they are.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
If I had one day to show a friend the best of Miami, we’d kick it off with an early breakfast at Greenstreet Cafe in Coconut Grove: my regular morning spot for the past 20 years. A bowl of fresh fruit, cold iced tea, some good people-watching, and the perfect slow start to the day.

From there, we’d head straight to the boat. I love getting out on the water early, before the crowds. We’d cruise across the bay to Nixon Sandbar, drop anchor, maybe swim a little, and just enjoy the quiet. That’s my happy place. After that, we’d grab a casual lunch on the water or just eat on the boat, then head back to Coral Reef Yacht Club for drink with a bayfront view.

If there’s time, we’d swing by the dog park off Old Cutler near Matheson Hammock. It’s one of my favorite hidden gems, and it’s a great way to wind down the afternoon, especially if you want to take a nice stroll with your family and pups.

After cleaning up, we’d wrap the day with dinner at Michael’s Genuine in the Miami Design District, one of my all-time favorite restaurants. It’s one of Miami’s most famed restaurants and the perfect end to a relaxed Miami day done right.

Who else deserves some credit and recognition?
Honestly, I owe everything to my team. The Riley Smith Group has over 30 incredible real estate agents who know Miami inside and out. They’re not just great at what they do, they’re supportive, collaborative, and genuinely care about our clients and each other. That culture is what makes our Miami real estate business so special.

Behind the scenes, our operations, sales, and marketing teams keep the whole machine running. They handle the tough stuff most people never see, and they do it flawlessly. I couldn’t do what I do without them.

And above all, my wife, Kelly. She’s been by my side from the very beginning: helping shape our brand, writing blog posts every day when no one else in real estate was doing that, and supporting me and our family through every up and down. This has always been a team effort, and she’s been the heart of it.

Website: https://rileysmithgroup.com/

Instagram: https://www.instagram.com/rileysmithgroup/

Linkedin: https://www.linkedin.com/company/the-riley-smith-group/

Facebook: https://www.facebook.com/rileysmithgroup/

Youtube: https://www.youtube.com/channel/UCN-tgv7Zl2P839TEbhg31xA

Other: TikTok: https://www.tiktok.com/@rileysmithgroup
Google Business: https://g.co/kgs/4TnGzSW
Threads: https://www.threads.net/@rileysmithgroup

Image Credits
Mary Beth Koeth