From Law to Real Estate: How Matt Silvers Mastered the Art of Deal Making and Opportunity Recognition

In the competitive world of real estate deal making, success often comes down to more than just market knowledge, it requires perception, persistence, and empathy. Matt Silvers, a self-described "professional purveyor of opportunity," has built a remarkable career by mastering these soft skills while navigating multiple industry transformations. From environmental law to scaling a national entertainment concept, his journey offers valuable insights for anyone looking to excel in real estate transactions and business development.

The Unexpected Path from Law to Real Estate

Breaking Away from Traditional Legal Practice

Matt Silvers' entry into real estate wasn't planned. After being encouraged to pursue law school by his future father-in-law, he spent eight and a half years practicing environmental and transactional law. The pivotal moment came during a deal closing when he realized he should be the client, not just the attorney facilitating the transaction.

"I realized as we completed the deal that I actually should be the client and not the scrivener of the deal, the guy putting the deal together and closing the deal."

This realization led him to transition into Brownfield deals, real estate transactions involving environmentally compromised properties, where his legal background provided a unique advantage in understanding complex regulatory requirements and deal structures.

Leveraging Legal Skills in Real Estate Brokerage

When Silvers obtained his broker's license in Illinois, he discovered that his legal training gave him a significant competitive edge. While other brokers struggled with follow-through, his attorney background instilled a clock-based urgency and systematic approach to deal management.

His legal experience enabled him to see and understand deal structures that others missed, while his pacing and follow-through capabilities impressed clients who appreciated the accelerated timeline and thorough attention to detail.

The Great Recession: A Phoenix Rising Moment

Learning from Financial Devastation

The 2008-2009 recession brutally impacted Silvers' real estate business, creating what he describes as a "horrible mess" both professionally and personally. However, this setback became a catalyst for reinvention rather than retreat.

Rather than abandoning real estate, Silvers used this crisis as an opportunity to refine his focus within the industry. He recognized his strengths in strategic thinking and brand development, skills that would prove crucial in his next venture.

Scaling Flicks Brewhouse: A National Success Story

The recession's aftermath led to one of Silvers' most significant opportunities: joining an upstart movie theater company in Austin, Texas, as Chief Development Officer. This role perfectly aligned his real estate expertise with his passion for brand development.

"When I joined the company was one location, and when Covid reared its ugly head, we were up to 13 locations and had built a very nice run rate. It was a very large at that point profitable multimillion dollar business."

The Flicks Brewhouse expansion demonstrates how combining real estate acumen with brand strategy can drive exponential growth. Silvers utilized all his professional skills simultaneously, legal knowledge, deal-making expertise, and brand development, to scale the business from a single location to a profitable national chain.

Current Role: Advisory Services and Development Management

Transitioning to Consultative Approach

Following the pandemic's impact on the entertainment industry, Silvers joined Project Management Advisors as a partner, heading their Advisory Services division. This role focuses on pre-development activities including due diligence, site selection, highest and best use analysis, and market analysis.

The transition from principal to advisor represents a mature phase in his career, where he applies decades of experience to help others navigate complex real estate decisions. This consultative approach allows him to remain close to deals while providing objective perspective, something that principals often lack when evaluating their own projects.

The Three Pillars of Real Estate Success

Core Skills for Deal Making

When asked to identify his most important skills, Silvers emphasizes three critical attributes:

1. Perception - The ability to see opportunities and understand market dynamics

2. Persistence - Following through on commitments and maintaining momentum

3. Empathy - Understanding client needs and market psychology

These soft skills often prove more valuable than technical knowledge in complex real estate transactions.

Understanding ROI Drivers

Silvers identifies three fundamental factors that drive real estate returns:

• People and demand patterns - Where people want to live, work, shop, and access services

• Cost of money - Interest rates and financing availability

• Regulatory environment - Zoning, permitting, and policy stability

Successful real estate professionals must understand how these factors interact and influence investment decisions.

The Art of Creating New Markets

Placemaking and Node Development

One of Silvers' most significant experiences involved representing Forest City (now part of Brookfield), a developer known for creating entirely new places rather than just filling existing demand. This work included transforming Denver's old Stapleton Airport into a complete community with residential, commercial, and office components.

"They were not shopping centers, they were places to live, places to shop, places to work. They were small cities."

Creating new nodes requires substantial capital, long-term vision, and tolerance for risk. Most developers prefer to locate near existing demand centers, but those willing to create new places can achieve exceptional returns with proper execution and patience.

The Role of Design in Value Creation

Silvers uses a "cake and icing" analogy to explain design's importance in real estate value creation. While the underlying real estate fundamentals represent the cake, aesthetic design serves as the icing that attracts initial interest and influences purchasing decisions.

Humans are visual creatures who respond to environmental cues both consciously and subconsciously. Whether developing residential, retail, or office projects, thoughtful design investment can significantly impact occupancy rates and rental premiums.

The key lies in finding the optimal balance between design investment and budget constraints, spending enough to reach the "sweet spot" where aesthetics positively influence decision, making without exceeding financial parameters.

Market Insights and Industry Trends

Understanding Real Estate Cycles

Real estate markets are inherently cyclical, moving through periods of growth and contraction. Successful professionals must anticipate these cycles and position themselves accordingly. The most profitable opportunities often occur during the "shoulder" periods before peaks and valleys, requiring careful timing and market analysis.

The Importance of Specialization

For those entering real estate, Silvers emphasizes the critical importance of specialization. Attempting to be a generalist, a "Jack of all trades", rarely leads to success in real estate. Instead, professionals should:

• Identify a specific niche or market segment

• Develop deep expertise in that area

• Build a reputation for specialization

• Consistently promote themselves within that niche

Key Takeaways for Real Estate Professionals

The conversation with Matt Silvers reveals several crucial insights for anyone involved in real estate deal making:

Leverage transferable skills - Legal, financial, or other professional backgrounds can provide significant advantages in real estate transactions when properly applied.

Embrace reinvention - Market downturns and setbacks often create opportunities for those willing to adapt and evolve their approach.

Focus on relationships - Success in real estate depends heavily on building trust and understanding client needs through empathy and consistent follow-through.

Understand the fundamentals - While market conditions change, the core drivers of real estate value remain consistent across cycles.

Invest in presentation - Design and aesthetics significantly influence human behavior and can justify premium pricing when executed thoughtfully.

Conclusion and Call to Action

Matt Silvers' journey from reluctant law student to successful real estate deal facilitator demonstrates that career transitions can lead to extraordinary success when approached with strategic thinking and persistence. His emphasis on soft skills, specialization, and long-term relationship building offers a roadmap for anyone looking to excel in real estate transactions.

Whether you're just entering real estate or looking to elevate your current practice, the principles Silvers shares, perception, persistence, and empathy, combined with deep market knowledge and strategic thinking, can help you identify and capitalize on opportunities others might miss.

Ready to dive deeper into real estate deal making strategies? Listen to the full ROI Masterclass podcast episode with Matt Silvers to hear more insights on scaling businesses, navigating market cycles, and building lasting success in real estate. Don't forget to subscribe for more conversations with industry innovators and share your own deal-making experiences in the comments below.

Connect with Matt Silvers on LinkedIn for ongoing insights and industry updates from this experienced deal facilitator and strategic advisor.

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