Navigating the Deal Cycle: Legal Insights from Real Estate Attorney Michael Webb
Join host Matthew Wallace on this episode of The Matthews Podcast as he sits down with Michael Webb, a seasoned real estate attorney with over a decade of experience in handling complex and high-value commercial transactions. In this insightful conversation, Michael shares his journey into real estate law, his diverse portfolio of deals across various asset classes, and his perspective on the current macroeconomic environment impacting the real estate market. They discuss the importance of managing client expectations, the impact of AI in the legal profession, and trends to watch for in the future of commercial real estate. This episode is packed with valuable insights for investors, developers, and any commercial real estate professional looking to navigate the evolving landscape of the industry.
From Urban Curiosity to Real Estate Law
Michael Webb’s journey into real estate law began with childhood trips into Manhattan from Long Island. “I always really loved the architecture, the buzz in the city, the pace,” Webb recalls. That early fascination led him to study Urban Studies at Queens College, a program that sharpened his interest in how space is used and planned. After law school, he dove headfirst into transactional real estate law, drawn to its dynamic, tangible nature. “You can look at projects you’ve worked on, you can touch them. You can feel them.”
A Practice Rooted in Breadth and Depth
Now entrenched in a practice that spans the entire deal lifecycle, Webb describes himself as a “dirt attorney”—someone who helps clients use, own, operate, and finance real estate. Whether working with regional developers, institutional clients, or municipal bodies, Webb thrives on structuring and guiding deals from term sheet to shovel in the ground. “I like to say I run the checklist. I don’t get run over by the checklist,” he quips.
From middle-market leasing deals to high-stakes closings, his practice ranges from financing and acquisitions to entitlements and economic development incentives. Recent highlights include a $265 million Hollywood refinancing, an $11 million nonprofit office acquisition in Garden City, and the relocation of a global financial firm to the Spiral at Hudson Yards.
Inside the Deals: High Stakes, High Precision
Discussing the Hollywood refinancing, Webb emphasizes that geography doesn’t change the fundamentals of getting a deal done. “The principles remain the same—responsiveness, attentiveness, managing expectations,” he explains. Serving as a “quarterback” for a cross-country legal team, Webb ensured every moving piece aligned for a seamless closing.
The Hudson Yards lease was another standout transaction. “It’s one of the newest, prime Class A spaces,” he notes, describing the process of securing an entire floor for a financial services firm. The key, he says, was weekly collaboration across brokers, attorneys, and design professionals. “Everyone was deal-oriented, solution-oriented. We worked over hurdles instead of letting them trip the deal.”
Building Relationships, Not Just Contracts
In a field as competitive as law and brokerage, relationships matter. “You have to be someone people trust,” says Webb. His business development strategy is grounded in community involvement, philanthropy, and consistent visibility—whether that’s attending charity events or sharing wins on LinkedIn. “If you’re not talking about it, publicizing it, people don’t know what you’re doing.”
But business development is a balancing act. “You always need to make sure you have that next deal coming in the door, but you need to close the one that’s in front of you,” Webb says. His old-school productivity system? A legal pad marked with blue and red pens for daily task tracking.
Legal Trends: Guarantees, Financing, and Slow Closes
Webb highlights a notable shift in financing negotiations, especially around non-recourse carve-outs. “That line is getting blurred,” he cautions, referring to increasingly aggressive lender terms. Meanwhile, underwriting remains cautious, and financing timelines are elongated. “Everything just drags out,” he says, a trend exacerbated by market uncertainty and lower transaction volumes.
Market Outlook: Uncertainty with a Side of Optimism
When asked about the macroeconomic outlook, Webb doesn’t shy away from complexity. “There’s a lot of powder on the sidelines,” he says, pointing to developers waiting for stable interest rates and clearer policies before ramping up activity. Still, he’s optimistic: “Once we know the rules, people are going to be able to play the game.”
He sees multifamily housing as a crucial growth area, especially in suburban markets where population growth is stalled by lack of housing. “You can build the greatest open-air retail center, but if no one lives nearby, what’s the point?”
On office real estate, Webb expects bifurcation. “Class A space will perform. Class B and C are going to continue to struggle—just like we saw with malls a decade ago.”
AI and the Legal Frontier: Cautious Optimism
No 2025 podcast would be complete without a discussion on AI. While intrigued by AI’s potential in diligence and lease abstraction, Webb remains cautious. “The nuance isn’t quite there,” he warns, citing a deal where AI misread a lease’s core requirements. “I’m not against adopting it, but I want a more standardized adoption before I do.”
Looking Ahead: Building the Future, One Deal at a Time
For Webb, the real reward lies in shaping the communities where he lives and works. He cites a transit-oriented development in Long Island as a prime example. “To see it go from a dilapidated building to a 63-unit residential hub is exciting,” he says.
As the market heads into the latter half of 2025, Webb remains “bullish and hopeful.” Leasing activity is up, dealmakers are engaged, and despite headwinds, the foundations of commercial real estate remain strong.
Stay tuned for more insights from top professionals on The Matthews Podcast as we continue to navigate the ever-evolving landscape of commercial real estate.
