Commercial Agency Contract Lawyers for Chicago, Illinois

A seasoned attorney with deep General Counsel experience and a flexible, business-minded approach to legal leadership. Skilled in collaborating with product, sales, operations, finance, and executive teams — not just to mitigate risk or ensure compliance, but to enable growth, innovation, and efficient deal execution. In my current practice at GCBench, I offer scalable, on-demand counsel tailored to organizations’ changing needs. Legal rigor is combined with operational sensibility, making guidance a facilitator rather than a hurdle. Whether structuring transactions, advising on regulatory matters, or shaping policies, legal strategy is aligned tightly with business objectives.

I am a solo-practitioner with a practice mostly consisting of serving as a fractional general counsel to growth stage companies. With a practical business background, I aim to bring real-world, economically driven solutions to my client's legal problems and pride myself on efficient yet effective work.

Experienced business advisor and in-house counsel with extensive litigation experience, representing parties in a variety of complex commercial disputes, including securities, financial fraud, contract, and antitrust litigation.

I provide practical, plain-English legal guidance to solopreneurs and small businesses who want to build strong foundations and make informed decisions with confidence. With 20+ years of experience—including 16 years in-house advising senior and executive leaders—I bring the insight of a trusted legal partner who understands how legal strategy supports long-term business growth. My clients walk away feeling supported, seen, and empowered. They know I genuinely care about their success and bring more than just legal knowledge—I bring a coach’s mindset, a problem-solver’s lens, and a commitment to helping them protect what they’ve worked hard to build. Whether you’re reviewing contracts, forming your business, protecting your brand, or need ongoing legal support, I’m here to deliver clear, actionable guidance and solutions that fit your business.

Michael has extensive experience advising companies from start-ups to established publicly-traded companies . He has represented businesses in a wide array of fields IT consulting, software solutions, web design/ development, financial services, SaaS, data storage, and others. Areas of expertise include contract drafting and negotiation, terms of use, business structuring and funding, company and employee policies, general transactional issues as well as licensing and regulatory compliance. His prior experience before entering private practice includes negotiating sales contracts for a Fortune 500 healthcare company, as well as regulatory compliance contracts for a publicly traded dental manufacturer. Mr. Brennan firmly believes that every business deserves a lawyer that is both responsive and dependable, and he strives to provide that type of service to every client.

Have over 40+ years of corporate and commercial law experience.

I am a business law attorney with over 15 years’ experience and a strong background in information technology. I am a graduate of the University of California Berkeley, a member of the Illinois bar, New York bar and a licensed lawyer (Solicitor) of England and Wales. I actively partner directly with my clients or indirectly, as Of Counsel, to boutique law firms to streamline business practices and manage legal risks by focusing on essentials such as - business contracts, corporate structure, employment/independent contractor agreements, website terms and policies, IP, technology, and commercial related agreements as well as business risk and compliance guidance.

My practice has involved a wide range of legal matters from commercial real estate, finance and international business transactions to litigation matters including commercial disputes, real estate, employment, and medical malpractice. Proficient in Spanish, I graduated from the University of Kentucky College of Law, the Patterson School of Diplomacy and International Commerce, and the University of Southern California. Prior to my legal career, I sought diverse professional experiences. After graduating from college, I orchestrated my own volunteering experience in southern Peru with a small non-profit organization. Later I gained valuable professional experience as part of a U.S. Senate campaign, and after that I joined the public policy team at Greater Louisville, Inc., Louisville's Chamber of Commerce affiliate. Prior to law school, I embarked on a month long excursion with the Northern Outdoor Leadership School in Alaska, which gave me a new found appreciation for sustainability.

Samantha has focused her career on developing and implementing customized compliance programs for SEC, CFTC, and FINRA regulated organizations. She has worked with over 100 investment advisers, alternative asset managers (private equity funds, hedge funds, real estate funds, venture capital funds, etc.), and broker-dealers, with assets under management ranging from several hundred million to several billion dollars. Samantha has held roles such as Chief Compliance Officer and Interim Chief Compliance Officer for SEC-registered investment advisory firms, “Of Counsel” for law firms, and has worked for various securities compliance consulting firms. Samantha founded Coast to Coast Compliance to make a meaningful impact on clients’ businesses overall, by enhancing or otherwise creating an exceptional and customized compliance program and cultivating a strong culture of compliance. Coast to Coast Compliance provides proactive, comprehensive, and independent compliance solutions, focusing primarily on project-based deliverables and various ongoing compliance pain points for investment advisers, broker-dealers, and other financial services firms.

Experienced General Counsel/Chief Legal Officer