Matthew J. Youssef

Matthew J. Youssef is a seasoned litigator and strategic advisor to business professionals facing the most challenging problems of their career. In addition to helping people start new business ventures or sell their existing enterprise, he has extensive experience helping businesses navigate unexpected legal problems ranging from contractual disputes, infringement of intellectual property, allegations of wrongdoing, and personnel issues.

Matthew understands that business leaders need more than legal expertise; they need a trusted advisor who can navigate uncertainty, mitigate risk, and position their companies for growth. His approach combines deep legal knowledge with real-world business perspective to deliver results that align with his clients' strategic objectives. 

Business Transactions & Corporate Law 

Matthew guides clients through critical business decisions and transactions, from startup formation to major acquisitions. His transactional experience includes: 

Major Acquisitions & Strategic Deals: 

• Led the acquisition of a regional agribusiness, managing complex negotiations involving agricultural real estate and operational assets 
• Structured the acquisition of two waste and energy services companies through innovative asset purchase and lease-to-own arrangements 
• Represented buyers in commercial real estate acquisitions, including properties with national retail tenants 

Corporate Governance & Internal Matters: 

• Conducted confidential internal investigation for national nonprofit facing federal scrutiny 

• Negotiated executive severance agreement for Fortune 500 company senior executive which allowed transition to competitor unimpeded. 

• Managed complex business separations, including the buyout of a medical practice partnership involving restrictive covenants and patient continuity concerns 

Regulatory Compliance: 

• Advised national emergency services providers on multi-jurisdictional licensing requirements for security operations across multiple states. 
• Represented commercial property owners in administrative proceedings regarding permitting challenges. 

Commercial Litigation 

Matthew represents clients in state and federal courts throughout Maryland, Washington D.C.  and Virginia, handling complex commercial disputes that threaten business operations and value. 

Notable Cases: 

• Trademark Protection: Secured preliminary injunction for restaurant client against competitor using confusingly similar name, establishing common law trademark rights before securing trademark registration with the USPTO. 

• Executive Defense: Successfully defended multinational government contractor executive against employer replevin action, obtaining favorable trial judgment. 

• Real Estate Disputes: Managed multi-party commercial property disputes involving tenants, county inspectors, and administrative bodies attempting to block developer from obtaining necessary occupancy permits 

• Non-Compete Litigation: Achieved favorable settlement for real estate professional facing breach of contract and non-compete claims from former employer 

Startup & Emerging Company Counsel 

Matthew serves as outside general counsel for startups and emerging companies, helping entrepreneurs build scalable businesses from the ground up. He provides strategic guidance on business formation, intellectual property protection, equity allocation, financing strategies, and regulatory compliance—all with an understanding of resource constraints facing growing companies. 

His startup practice includes negotiating commercial leases, drafting equity agreements, structuring service contracts, preparing executive employment agreements, and developing Software-as-a-Service frameworks that position companies for sustainable growth. 

Intellectual Property Strategy 

Matthew helps businesses protect and monetize their most valuable intangible assets. His IP practice spans trademark registration and enforcement, trade secret protection, and brand development strategy. He has successfully litigated trademark infringement cases and negotiated IP disputes before they reach the courthouse. 

Clients across industries—from internet retailers to regional publications, restaurants, and emerging lifestyle brands—rely on Matthew's branding expertise to build and protect market position. 

Government Contracting & Procurement 

Matthew provides specialized counsel to government contractors navigating Maryland's procurement landscape. He represents federal and state contractors in contract disputes, bid protests, and appeals before the Maryland State Board of Contract Appeals, Baltimore City Board of Estimates, and Maryland Board of Estimates. 

His procurement practice includes strategic guidance during proposal development, pre-proposal protest analysis, and post-award debriefing strategies to position clients for future opportunities. 

Insurance Industry Representation 

Matthew maintains a sophisticated insurance practice, representing regional mutual insurance companies in property and real estate claims. His insurance expertise encompasses first-party and third-party litigation, coverage disputes, fraud investigations, subrogation matters, and regulatory proceedings before the Maryland Insurance Administration. 

Community Leadership 

Matthew serves on the boards of Hope Ignites, a residential program supporting at-risk students, and Open Works, a national leader in the maker space movement. He previously served as an AmeriCorps volunteer and achieved the rank of Eagle Scout. 

An avid athlete, Matthew is a competitive squash player, marathon runner, and former rugby player and competitive swimmer. He lives in Howard County with his wife.