Lee Generous

high-net-worth families, business owners, and entrepreneurs through a coordinated approach that integrates financial, tax, and legacy planning under one roof.

Born in Dorchester and raised in Marshfield, Massachusetts, Lee’s early years reflected discipline and curiosity. Diagnosed with type 1 diabetes as a toddler, he developed a meticulous mindset that would later define his professional approach to financial planning. As a young boy, he was drawn to the world of finance, purchasing his first mutual fund with money earned from his paper route. This early experience ignited a lifelong interest in economics, analysis, and helping others make informed financial decisions.

Lee Michael Generous attended the University of Massachusetts Amherst, earning dual bachelor’s degrees in Economics and Political Science in 2004. During college, he founded a small business to help pay his tuition, combining his entrepreneurial spirit with practical financial skills. He later completed a Certificate in Financial Planning at Boston University’s Center for Professional Education to strengthen his technical foundation from 2011 to 2012. His dedication to professional growth continued with the Chartered Financial Consultant (ChFC) program at The American College of Financial Services and the Enrolled Agent (EA) designation from the IRS, which allows him to represent clients in complex tax matters.

His professional career began at Fidelity Investments in Boston in 2005, where he gained experience across several divisions, including pricing, cash management, and family office services. As an analyst, he handled global securities pricing and supported the firm’s communication with shareholders and financial systems. Later, as a lead analyst with Fidelity Family Office Services, he managed relationships with high-net-worth clients and helped build operational systems for emerging business units. His contributions were recognized with the prestigious Chairman's Shares Award. Lee became a Relationship Manager at Fidelity Personal Investments, guiding clients in creating structured strategies to achieve their long-term goals.

In 2015, Lee joined an independent LPL advisory firm in Braintree, Massachusetts, where he served as a Wealth Advisor for nearly seven years. Managing a significant portion of the firm’s clients, he provided personalized and comprehensive planning across investments, retirement, estate, and tax strategies. His focus on organization and client service led to greater efficiency and growth, doubling the firm’s managed assets during his tenure.

In November 2021, following his wife’s recovery from cancer and his own experience managing diabetes through the COVID-19 pandemic, Lee took a significant step by founding Generous Wealth Management. Officially registered in 2022, the firm reflects its belief that proper wealth management should simplify clients’ financial lives through thoughtful coordination and proactive planning. His goal is to bring the level of service once reserved for ultra-high-net-worth family offices to a broader range of successful families and business owners seeking clarity and long-term stability.

Beyond traditional financial advising, Lee Generous has become recognized for his work within the cannabis and hemp sectors. As a Dope CFO Certified Advisor and co-founder of Dope CFO Wealth Management, he helps cannabis entrepreneurs and investors navigate tax compliance, accounting, and business planning challenges. He also serves on the National Cannabis Industry Association’s Banking and Finance Committee, contributing insights on regulatory compliance and financial best practices.

Outside of his professional commitments, Lee is actively involved in his community. He volunteers with organizations such as the Boston Pine Street Inn, the Juvenile Diabetes Research Foundation (JDRF), and the Eversource Walk for Boston Children’s Hospital. Through his outreach and educational efforts, he promotes financial literacy and empowerment for individuals and small business owners.

In his personal life, Lee Generous enjoys outdoor recreation, coaching, and continuous learning. Whether reading about emerging trends in financial technology or exploring the outdoors with family, he approaches every endeavor with the same focus and dedication that define his career. His life’s work centers on helping others achieve financial confidence and peace of mind, which continues to guide Generous Wealth Management today.