Ronald C. Lipof

Ron is a Partner in AAFCPAs’ Transaction Advisory Practice, where he provides strategic guidance to start-up, emerging growth, middle-market, and pre-IPO companies navigating mergers, acquisitions, and other complex transactions in a variety of industries nationwide. He has more than 30 years of experience in highly regulated and nascent industries, including cannabis, finance, and emerging growth sectors. Ron helps business leaders strengthen organizational readiness, streamline operations, restructure/turnaround, and position for long-term growth and value creation. He works closely with AAFCPAs’ tax, assurance, advisory, outsourced accounting, and wealth management professionals to ensure each transaction strategy aligns with broader financial, succession, and governance objectives.

Ron is also a leader in AAFCPAs’ Cannabis practice. He facilitates transactions between buyers and sellers involving cannabis licenses and operating businesses, offering expertise in buyer/seller matchmaking, deal structuring, due diligence, and post-transaction integration. Ron works with operators to navigate the complex application and licensing processes, remain compliant with evolving regulations, and establish foundational business practices. This includes end-to-end support, including business planning, license application drafting, community and municipal engagement, compliance documentation, inspection readiness, and development of policies for security, quality control, and operations.

Ron is recognized for his extensive experience in business lifecycle management—from formation and business development through exit—and his ability to guide organizations through regulatory, financial, and reputational challenges. He collaborates with entrepreneurs and management teams nationwide to develop business plans, model financial outcomes, structure deals, build strategic alliances, and coordinate due diligence. By integrating financial, strategic, and operational insight, he ensures clients are prepared to respond to opportunities and challenges at every stage of growth, capital raise, or sale.

Ron has served as an Economic Development Commissioner for the City of Newton, Massachusetts and as a member of the Duke Children’s Hospital National Board of Advisors. Ron was recognized as one of Boston’s community leaders in “Boston” by Bill Brett, received the Boston Celtics Heroes Among Us Award, and was named to The Boston Business Journal 40 Under 40. Ron has a bachelor’s degree in government with a focus on government relations and political strategy from Boston University. He is active in civic and philanthropic initiatives, including his long-standing leadership of Cancer Awareness Day with the Boston Red Sox in partnership with Dana-Farber Cancer Institute, which engages hundreds of families affected by childhood cancer and raises awareness in the community. Ron and his wife have helped numerous entrepreneurs hone their business pitches for appearances on Shark Tank, drawing on their real-world experience to prepare contestants for the spotlight.

Education

• Boston University – Bachelor of Arts, Government

Publications

• CANNACurious: Fundamentals of the Legal Cannabis Industry
• Entrance to Exit: The Entrepreneurial Path
• The Virtual ISP: Crossing the Chasm

Service

• MassChallenge Start-up Accelerator — Finalist (2012), Mentor, and Judge
• National Cannabis Industry Association (NCIA) — Past Member, State Regulations Committee
• Cancer Awareness Day with the Boston Red Sox – Founder