Lee Generous
Wealth Advisor, Wealth Management / Tax Advisory
Lee Generous is the founder of Generous Wealth Management, a virtual financial advisory firm based in Massachusetts. With over 15 years of experience in financial planning, tax strategy, and investment management, he has built a practice focused on providing clarity and structure to clients’ financial lives. Lee holds several professional designations, including Chartered Financial Consultant (ChFC), Enrolled Agent (EA), and Dope CFO Certified Advisor. His firm combines traditional wealth management with forward-thinking strategies, helping individuals, families, and business owners achieve long-term financial success through coordination and discipline.
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Early Life and the Foundation of Discipline
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Born in Dorchester and raised in Marshfield, Massachusetts, Lee’s early life significantly shaped his outlook and work ethic. Diagnosed with type 1 diabetes as a toddler, he learned from a young age the importance of routine, consistency, and responsibility. These lessons became the foundation for his approach to financial planning, careful analysis, long-term thinking, and constant adaptability.
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Lee’s curiosity about money and investing began in childhood. As a boy, he saved earnings from his paper route and purchased his first mutual fund, discovering the power of financial independence. This early experience inspired a lifelong passion for helping others make informed financial decisions that align with their goals and values.
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Education and Early Career Development
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Lee Michael Generous attended the University of Massachusetts Amherst, graduating in 2004 with dual bachelor’s degrees in Economics and Political Science. While pursuing his studies, he launched a small business to help pay for tuition, gaining first-hand experience in entrepreneurship, budgeting, and business planning.
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After completing his undergraduate studies, he continued to expand his financial knowledge. Lee earned a Certificate in Financial Planning from Boston University’s Center for Professional Education and completed the Chartered Financial Consultant (ChFC) program through The American College of Financial Services. His Enrolled Agent (EA) designation from the IRS allows him to represent clients in all tax-related matters, including audits and appeals. This blend of education and professional certification has given him a unique perspective on integrating investment management with tax and estate strategy.
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Expanding Horizons in Independent Advising
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In 2015, Lee transitioned to an independent advisory firm affiliated with LPL Financial in Braintree, Massachusetts, where he served as a Wealth Advisor. Over nearly seven years, he managed a substantial portion of the firm’s client base, overseeing customized planning across investments, estate, retirement, and tax strategies. His structured, process-oriented approach helped streamline client management systems and improve service delivery. Under his leadership, the firm’s assets under management doubled.
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The Creation of Generous Wealth Management
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In 2021, Lee Generous realized his vision of independence by founding Generous Wealth Management, which was officially approved by the Massachusetts Securities Division in 2022. The firm delivers a family office-style experience to clients through an integrated framework that includes investment management, tax planning, and legacy strategy.
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Lee's personal journey influenced the creation of the firm. After supporting his wife through her successful battle with cancer and managing his own health challenges during the COVID-19 pandemic, he developed an even deeper appreciation for preparation and resilience. Those experiences reinforced his belief that financial planning should not only focus on wealth growth but also on stability and peace of mind.
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Specialized Expertise in Cannabis and Hemp Advisory
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Lee’s work extends into specialized industries, most notably cannabis and hemp. As a Dope CFO Certified Advisor and co-founder of Dope CFO Wealth Management, he assists cannabis business owners across the United States with accounting, tax, and financial strategy. His understanding of cannabis taxation, including IRS Section 280E, has made him a sought-after resource for entrepreneurs navigating this highly regulated market.
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In addition, he serves on the National Cannabis Industry Association’s Banking and Finance Committee, where he contributes to financial policy, compliance education, and advocacy. His goal is to help legitimize and strengthen the economic infrastructure of this emerging industry through sound, ethical financial practices.
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Community Engagement and Personal Interests
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Outside of his professional achievements, Lee remains actively involved in his community. He volunteers at the Boston Pine Street Inn, supports the Juvenile Diabetes Research Foundation (JDRF), and participates in the Eversource Walk for Boston Children’s Hospital. His community work reflects his lifelong commitment to helping others and giving back.
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Lee enjoys outdoor activities, coaching youth sports, and studying economic and financial trends when not working. His curiosity and dedication to personal growth mirror the same qualities he brings to his clients—balance, focus, and a drive for continuous improvement.
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A Legacy of Clarity and Trust
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Through Generous Wealth Management, Lee Generous continues to redefine what it means to be a modern wealth advisor. His career is a testament to the power of discipline, empathy, and knowledge in guiding others toward financial stability. Each client relationship he builds reflects his belief that true wealth is about accumulation and understanding, planning, and living confidently in every stage of life.
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Learn more:
Generous Wealth Management LLC
NCIA’s 13th Annual Cannabis Industry Lobby Days & National Stakeholder Summit