Discipline, Development, and Deal Flow

Q: You transitioned from a high-volume investment sales role in Manhattan to a leadership position in Chicago in 2023. What was it about Matthews™ that made you want to join the company?

A: It felt like I was seeing Matthews™ everywhere I looked, online and in conversations with people in the business. I’ve always aspired to be a Market Leader, and when the chance to step into that role at the firm came up, it felt like the logical next step. I was really inspired by the Matthews™ growth mindset, it aligned perfectly with where I wanted to take my career.

 

Q: You are known for being in the office by 6:30 a.m. to set the daily tone. Beyond just the early start, what are the daily habits you believe are essential for anyone looking to reach the next level in this business?

A: As Market Leader of the Chicago office, leading by example is crucial. It sounds cliché, but it’s the truth. If I’m in early, prepared, and consistent, it sets the tone for the day and reinforces expectations across the office.

 

For a young agent, success is built on a consistent, non-negotiable routine. That starts at 6:30 AM, ensuring you’ve done the necessary prep work to win before you even pick up the phone.

 

From there, it’s about mastering the daily habits that move the needle: hitting your conversation targets, prepping your call lists, and over-preparing for every meeting and pitch. There is no shortcut—it’s about being the most prepared person in the room.

 

Q: In a competitive industry like commercial real estate, why is it important for you to maintain an open-door policy and stay accessible to both new and senior agents?

A: As a new agent, following a proven game plan is everything. At Matthews™, we’ve cultivated a culture that reinforces that roadmap at every level, ensuring that no one is just handed a manual and left to figure it out alone.

 

Both new and veteran agents know that my door is always open, but I tailor my leadership to meet them where they are.

 

As a new agent, you must really follow the gameplan, which we absolutely have at Matthews, and it is proven to work. Both new and veteran agents know that my door is always open. However, managing new vs. Veteran agents is different. With a new agent, they do not know much, if anything, so you really have to spend tons of time with them to show them the correct way to do the business. With an older or veteran agent, it’s all about how I can best support their business.

 

Q: What are the top things you look for in a recruit that can’t be taught in a training manual?

A: Grit, coachability, accountability, and sacrifice. If a new agent does not have these things, it will be an uphill battle to make it in this ultra-competitive business.

 

Q: What advice do you give your mentees about staying resilient when the market gets unpredictable?

A: Unpredictability is a part of every business. Commercial real estate brokerage is a cyclical business and always will be. It’s all about how you handle both the ups and downs of the market. How you respond is the biggest indicator of whether someone will be successful.

 

Q: The Chicago office has become a major hub for Matthews™ under your leadership. What is your primary focus for the office as we move through 2026?

A: There are a lot of focuses for 2026. As always, growth is at the forefront of what we are doing as a company right now, continuing to recruit at a high level and fill seats in my office remains the top priority.

 

But the real work starts once they’re in those seats. I’m focused on cultivating a culture for new agents taking the next step in theri careers and helping them develop the tabits of top-producers. My goal is to “home grow” as many new agents into senior agents as quickly and productively as possible.

 

Q: What types of sellers are coming to market in Chicago right now, strategic exits, maturities/refis, partnerships unwinding, and how is that shaping deal flow?

A: Multifamily is still the leader of transactional volume, but across multifamily and industrial, refinancing activity often dictates whether owners list or hold, thus creating periodic waves of inventory. Industrial provides a steady baseline of deal flow, often with sellers recycling to newer cores. Refinancing pressures and loan maturities are key drivers of current listings, sometimes more so than distress itself.

 

Office is different. Maturities without viable refinance options are pushing some assets into special servicing, note sales, or recap situations before you ever see a clean equity sale. As a result, office deal flow is still lagging and skewing toward opportunistic buyers and strategic sellers, rather than broad institutional accumulation.

 

Beyond maturity-driven sellers, we’re also seeing selective partnership unwind activity that is often handled off-market, so it doesn’t always show up as visible inventory.

 

Q: As more loan maturities hit, where do you expect distress or motivated selling to show up first in Chicago, it at all?

A: Office will likely be the first place where distress or motivated selling shows up, particularly downtown towers and secondary assets facing near-term maturities. Hotel properties with weaker occupancy or rate growth are another area to watch, especially where debt was structured aggressively.

 

In multifamily and retail, distress is likely to be more selective. Assets where cash flow can’t support today’s higher refinancing costs may come to market, but it’s less immediate. Overall, a significant portion of loans are already matured or approaching maturity, which is putting pressure on owners to either sell, recapitalize, or renegotiate.

 

Q: Are you noticing a widening gap between best-in-class assets and non-core products?

A: Yes—there’s a clear and widening gap between best-in-class core assets and non-core or undifferentiated products, and it’s showing up across most asset classes. The divergence is being driven by a combination of higher cost of capital, greater risk selectivity, and structurally slower growth.

 

We’ve moved from a ‘rising tide’ market to a ‘prove-it’ market. Best-in-class assets are being treated as safe havens, while non-core products are being repriced for complexity, capital intensity, and uncertainty.

 

Q: Who is driving the market right now? Are we seeing more ‘motivated’ sellers facing 2026 maturities, or strategic owners who finally feel the bid-ask gap has closed through to exit?

A: In the CRE market right now, both motivated sellers (especially those facing 2026 maturities) and strategic, long-term owners who feel the bid/ask gap is closing are active. The balance between them depends on the asset class, financing profile, and investor type.

 

Sellers with looming maturities and refinancing stress are increasingly willing to negotiate on price and terms, narrowing the traditional bid–ask spread. At the same time, strategic, well-capitalized players are stepping in. This isn’t just forced sales—owners who see valuations reconverging toward fundamentals are also willing to transact, especially where growth prospects or repositioning opportunities exist.