James Stark

James Stark is a seasoned business attorney with a proven entrepreneurial track record and deep understanding of corporate legal matters and best practices. He represents entrepreneurs, closely held and family-owned businesses, domestic and multinational companies, and non-profits across a wide range of transactional and litigation matters.

Prior to his legal career, James founded multiple businesses, including a carpentry firm, an apparel firm, a medical software firm, and a 501(c)(3) non-profit that provided education and mentoring services to underprivileged children in Chicagoland. His entrepreneurial background informs his legal approach, allowing him to understand his clients’ challenges and opportunities from a practical perspective.

James then transitioned to the legal field, serving as the Chief Legal Officer of C&H Financial Services, Inc. (CHFS), then a Chicago based start-up company. During his tenure, he played a pivotal role in expanding the company from one location to operations across six countries. In 2016, Inc. Magazine 500 recognized CHFS as the 21st fastest-growing private company in the U.S. and 3rd overall in the in the U.S. for the Financial Services segment. CHFS quickly became a top 50 financial services acquirer, processing billions of dollars annually. This experience further solidified his expertise in navigating the complexities of business growth, expansion, funding, and exit strategies.

James has extensive experience structuring, negotiating, drafting, and handling thousands of U.S. and international business transactions. He regularly develops comprehensive legal frameworks for business development programs, designs and implements growth and acquisition strategies, and serves as general outside counsel for clients. His expertise encompasses contract drafting and negotiation, mergers and acquisitions, investor transactions, employment law, licensing, regulatory compliance, and business succession planning. James serves businesses in diverse industries, including FinTech, healthcare, transportation, robotics, construction, professional sports, entertainment, retail, hospitality, manufacturing, brokering, private equity, and technology development.

Beyond his core work, James is championing a critical transportation industry initiative to reform the lease-purchase system overseen by the FMCSA and DOT. This effort aims to dismantle exploitative practices and empower truck drivers. He also champions social good through two non-profit boards. One fosters athletic opportunities for underprivileged youth, and the other is spearheading a national truck driver apprenticeship program in the vital tanker industry.

Outside of his professional life, James enjoys spending time with his family, engaging in outdoor activities, and supporting charitable causes, including the Special Olympics.