Building a real estate business since 1998: lessons from the journey

When my twin brother Matt and I started Prestige Properties in 1998, we didn’t have a grand blueprint for what the company would become. We had a belief that real estate, owned well and managed carefully, could build something lasting. More than 25 years and more than 1,500 transactions later, I still believe that. But the path taught me a lot that I couldn’t have known at the start.

Personal input needed: one or two sentences on how and why you and Matt decided to start the company in 1998 (your first property, what drew you to real estate). This is the most valuable detail to add.

Markets move in cycles, and you have to plan for all of them

Anyone who has been in real estate for more than a decade has lived through good years and difficult ones. We started before the dot-com bust and have operated through the 2008 financial crisis, a global pandemic and sharp swings in interest rates. Each of those periods felt different while we were in it, but they shared one lesson: the decisions that hold up are the ones made with the bad years in mind.

That means conservative assumptions, financing you can live with if rents flatten, and enough reserves that you’re never forced to sell at the wrong time. It isn’t exciting, and in strong markets it can feel like leaving money on the table. Over a long career, though, discipline is what keeps you in the game.

Personal input needed: a specific example of how a market cycle (for instance 2008 or the 2022 rate increases) affected the company and what you learned.

Resilience is built before you need it

People often talk about resilience as something you summon in a hard moment. In my experience, it’s mostly built ahead of time: in the systems you put in place, the team you hire, the relationships you maintain and the habits you keep when things are going well. When a difficult stretch arrives, you fall back on what you’ve already built.

For us, that meant bringing more of the work in-house over time. Prestige Properties now handles acquisitions, property management, renovations and asset management under one roof. That structure gives us a clearer view of how every property is really performing, and it lets us respond faster when something changes.

Relationships compound like good investments

The most underrated asset in our business is the network of people we’ve worked with for years: lenders, brokers, sellers, contractors, employees and partners. Many of the best opportunities we’ve had came from someone who already trusted us to close when we said we would and to treat people fairly along the way.

Relationships, like real estate, reward long holding periods. Every transaction is also a chance to build or damage a reputation, and that reputation follows you into the next deal.

Working with my brother

Building a company with your twin is a unique experience. Matt and I share a lot, including values, work ethic and a long-term view, but we don’t always see every decision the same way. Over the years we’ve learned that a partnership works when both people care more about getting the decision right than about being right. Having someone you fully trust beside you through every market makes the hard years easier and the good years better.

Personal input needed: how you and Matt divide responsibilities today, if you’d like to share that publicly.

What I’d tell someone starting out

Be patient. Learn the fundamentals of every property you buy. Protect your downside before you think about upside. Treat people the way you’d want to be treated when you’re on the other side of the table. And think in decades, not quarters. Real estate rewards people who are still standing when the cycle turns.