Matthews™ celebrates emerging leaders in commercial real estate

Introducing Edward DeSimone

Edward DeSimone

First Vice President & Director

Years with company/firm: 6.8

Years in field: 6.8

Years in real estate industry: 7.2

Real estate organizations/affiliations: ICSC

What is your most notable project, deal, or transaction?

One transaction that stands out is the $37.1 million sale of a 14-property Jiffy Lube portfolio across Georgia and South Carolina. The client was a quick lube operator looking to acquire both the business and the real estate simultaneously, a complex structure made even more challenging by a high cost-of-capital environment. To make the deal work, we executed a simultaneous sale-leaseback at closing, which effectively funded the business acquisition and eliminated the need for a large bank loan at a higher interest rate. It was a creative capital solution that required all parties working in lockstep, and getting it across the finish line was one of the most rewarding deals of my career.

Who or what has been the strongest influence in your career?

The colleagues around me have shaped me more than anything else. In this business, you are only as good as the people you surround yourself with, and I have been fortunate to work alongside some truly driven and knowledgeable professionals throughout my career. Matthews™ has a culture that attracts a certain type of person, someone who is hungry, competitive, and genuinely passionate about the work. That energy is contagious.

Whether it was learning how to structure a complex deal, navigate a difficult negotiation, or simply carry myself with clients, so much of what I know came from watching and working alongside the people around me. Commercial real estate is not an industry you can learn from a textbook. You learn it by doing, and you learn it faster when the people around you hold a high standard. That culture at Matthews has pushed me to continually improve and set the bar for what I expect of myself every day.

Tell us how and when you began your career in the profession you are in today and why you chose the field/profession you are in today?

I graduated from the University of Colorado at Boulder in 2019 with a degree in finance and initially set my sights on a traditional Wall Street path. But I quickly realized I wanted something more personal, something where I could see the direct impact of my work and build real relationships along the way. Real estate gave me that.

I joined Matthews in 2019 out of the firm’s El Segundo office and have not looked back since. In 2023, when Matthews opened its first New York office, I moved back to my home state of New Jersey and have focused on growing the firm’s presence in the Northeast ever since. What drew me to this business and keeps me here is the combination of capital markets, entrepreneurship, and relationship-building, all under one roof. Every deal is different, every client has a unique situation, and that variety keeps me engaged and motivated every single day.

What challenges and/or obstacles do you feel you needed to overcome to become as successful as you are today?

Learning to handle rejection and building the discipline to show up consistently regardless of outcomes. In investment sales, you can do everything right and still lose a deal. Early on, that was hard to accept. But I came to understand that rejection is part of the process, not a reflection of your ability. My approach has always been about volume and consistency rather than waiting around for the perfect deal.

Closing a high number of transactions every year requires a certain discipline and mental toughness that takes time to develop. The brokers who last in this business are the ones who maintain their standard of effort, whether the market is hot or cold, and building that consistency was probably the most important thing I did early in my career.

What was the most defining moment for you?

Honestly, it has not happened yet, and I mean that as a source of motivation rather than uncertainty. I am still early in my career, and I believe my best work is ahead of me. Nearly 200 transactions closed, totaling over $300 million, and I still feel like I am just getting started. Every deal I close and every relationship I build is laying the groundwork for something larger. The goal is to become a dominant player in Northeast retail investment over the next five years, and when that comes to fruition, that will be the defining moment. Until then, I keep my head down and keep working.

Who do you feel was most influential in your life when choosing this profession? At the end of the day, it comes down to betting on yourself. I left a traditional finance career and pivoted into something completely unfamiliar, and the only way to make it work was to fully commit and take ownership of every outcome. I think that is true for many people who find success in this business. At some point, you have to stop waiting for the right moment and just go for it. That decision to trust myself has shaped everything that came after.

What outside activities do you enjoy during your free time?

Outside of the office, I make it a priority to stay active and recharge. I enjoy exercising, traveling, and exploring new restaurants and live music whenever I can. Having those outlets keeps me grounded and allows me to show up at my best every day.

What inspiring word of advice would you give to a young executive graduating from college?

Work hard and may success attend your efforts.

This industry rewards people who show up every day, put in the effort, and play the long game. Early in your career, it can be tempting to measure success by how quickly things are moving, but the foundation you build in those first few years matters more than any single deal or milestone. Be consistent, be coachable, and do not be afraid to bet on yourself.