ADVISOR SPOTLIGHT: Jack Zamost

In this Q&A, Jack Zamost shares how his early exposure to a family-run real estate business shaped his path into multifamily investment sales and continues to influence his advisory approach today. With a focus on key Chicago neighborhoods like Andersonville, Edgewater, and Bucktown, Jack combines an ownership mindset with deep submarket expertise to help clients make informed, long-term investment decisions. His perspective highlights the importance of discipline, local knowledge, and understanding the fundamentals that drive value in today’s multifamily market.

Why were you interested in a career in real estate, and what led you to Triton Realty Group? 

Real estate has always been a natural path for me. My family has been in the business since 1996, when my father and his business partner started Aljack Investments, so I grew up around it, walking properties, talking deals, and seeing firsthand how real estate can create long-term value. It’s something that’s been ingrained in me from an early age, and over time it became clear this wasn’t just exposure, it's what I wanted to build my career around. 

I’ve always had the goal of growing something meaningful in the Chicago real estate market, ultimately building an empire of my own. What excites me is the ability to scale, create opportunities, and have a lasting impact on neighborhoods I know well. It’s a competitive market, but that’s part of what drives me. 

Triton Realty Group stood out to me because it aligns with that vision. Being part of a team that’s not just brokering deals but also actively investing was important. I wanted to be in an environment where I could learn from people who are actually in the trenches. It felt like the right place to accelerate my growth, sharpen my skill set, and continue building toward that long-term goal, especially with a mentor in Matt Fritzshall. 

What was your path to becoming a Advisor, and what experiences early in your career most shaped how you advise clients today?  

My path to becoming a Senior Advisor was pretty intentional from the start. Growing up around Aljack Investments, I had early exposure to how deals are structured, how properties are managed, and how long-term value is created. That foundation gave me a different perspective coming into the business. I wasn’t just focused on transactions, but on ownership and strategy. 

Early in my career, I made it a point to immerse myself in the day-to-day prospecting, underwriting deals, walking buildings, and having real conversations with owners. A lot of those early interactions didn’t lead to immediate deals, but they were invaluable in understanding how owners think, what actually drives their decisions, and how timing plays such a big role in this business. Being in the Chicago market, especially in neighborhoods I know well, helped me build credibility and a strong local perspective. 

Those experiences shaped how I advise clients today. I approach every situation from an ownership mindset, focusing on long-term value, risk, and opportunity, not just the transaction in front of us. I also put a big emphasis on being direct and transparent, because I’ve seen firsthand that trust is what ultimately drives repeat business and long-term relationships. 

In your work as a sub-market–driven advisor, how does focusing your scope on a handful of neighborhoods elevate the service you’re able to provide clients?   

Focusing on Andersonville, Edgewater, and Bucktown to name a few. allows me to operate with real depth instead of just surface-level knowledge. I’m tracking block-by-block activity sales, rents, zoning, and ownership patterns, which gives my clients a much clearer picture of the market. 

For sellers, that means more precise pricing and better buyer targeting. For buyers, it means uncovering opportunities others might miss, including off-market deals and value-add plays. 

Ultimately, that focus lets me be proactive and strategic, so my clients can make more informed decisions and get better long-term results. 

How would you describe the multifamily market today in Andersonville and Edgewater?  

I’d describe the multifamily market in Andersonville and Edgewater as very strong, driven by high demand and limited new supply. 

Both areas have tight vacancy and steady rent growth, especially for well-located 6+ unit buildings. Andersonville commands more premium pricing, while Edgewater offers a broader renter base. 

What really stands out is their resilience. In softer markets, these neighborhoods tend to outperform because of their location, amenities, and consistent renter demand, especially when you’re buying “main street on main street,” where retail corridors and transit access help anchor long-term value. 

From an investment standpoint, it’s a stable, landlord-favorable environment, but pricing is competitive, so being disciplined on your basis still matters. 

What advice would you give to someone considering their first multifamily investment? 

Focus on buying the right deal in the right location. Strong neighborhoods like Andersonville and Edgewater provide long-term stability, but understanding your numbers is critical. Be realistic about rents, expenses, and value-add potential—and think long-term. Discipline and fundamentals matter more than timing the market. 

To begin a conversation, contact Jack at jack@tritonrealtygroup.com or (847) 420-4616.