Answer extracted from The Boulos Beat: A Commercial Real Estate Podcast — listen to the full episode below.
How did the competitive bidding for 82 Running Hill Road lead to a landmark 13-year leaseback arrangement?
In 2017, George Cacoulidis purchased 82 Running Hill Road in South Portland in a competitive bidding situation against several interested parties, buying the office building from Dead River Company and securing a 13-year leaseback arrangement that created a sale-leaseback structure. The property was originally built by his brother and occupied by Fairchild, positioning the investment in a region experiencing robust business growth at the time.
The acquisition of 82 Running Hill Road represented a strategic moment for Grand Metro Properties' expansion into southern Maine. The competitive nature of the deal required Cacoulidis to move decisively against rival bidders who recognized the property's value in the strengthening South Portland and Portland market. The building's heritage—built within the family's own construction background—added institutional knowledge to the purchase decision.
The sale-leaseback structure created with Dead River Company proved to be an effective capital deployment strategy. As Cacoulidis details in this episode of The Boulos Beat, the 13-year leaseback term provided stability and predictable cash flow while allowing the seller to continue occupying the space—a common structure in commercial real estate that aligns incentives between buyer and tenant.
The timing of the acquisition proved significant in retrospect. South Portland and Portland were in the midst of business expansion in 2017, creating favorable conditions for commercial property investment. However, the portfolio would face a major test three years later when the COVID-19 pandemic reshaped commercial real estate fundamentals across New England, forcing investors to adapt to unforeseen market conditions.
"Don't fall in love with the building. Fall in love with the money—how is the cash flow, how is this asset performing."
George Cacoulidis — CEO of Grand Metro Properties. Cacoulidis is the second-generation leader of the company founded by his father John in 1985. After building a 20-year career in corporate transactional law—including work with motorsports clients—he returned to Grand Metro as COO in 2015 and assumed full leadership, guiding the company's expansion across Maine and New York with a disciplined, metrics-driven approach to acquisitions.
The principle Cacoulidis articulates reveals why the 82 Running Hill Road deal succeeded where others might have faltered. Cash flow fundamentals drove the acquisition logic, not emotional attachment to the building's location or history. The 13-year leaseback with an established tenant like Dead River Company locked in reliable revenue, making the financial case clear and defensible in the competitive bidding process.
Understanding how this specific transaction unfolded—from the initial bidding competition to the final leaseback terms—provides a window into Cacoulidis's investment philosophy and how he navigates Maine's commercial real estate market, a topic explored in greater depth during the full episode.
See also
How did acquiring Hope Island in Casco Bay represent a family's first entry into Maine real estate investment?
George's parents purchased Hope Island in Casco Bay as their first Maine property because his mother wanted to return to her roots growing up on a farm, marking the family's initial foothold in Maine real estate.
What was the visionary but controversial proposal for a 60-acre former Irving Oil property in South Portland?
In the early 1990s, George's father purchased 60 acres of land formerly owned by Al Glickman (known as Bug Light) and envisioned building two or three major developments on the site, though the proposal faced community resistance.
Why did a historic 1970s Yankee Stadium renovation project require burying equipment in the outfield?
George's father, who renovated the old Yankee Stadium in the 1970s during Mayor Beam's administration, needed to show rapid progress to justify continued investment in the large-scale restoration project.