Leo Connolly

With over 18 years of experience in financial planning, estate management, and investment advisory services, I founded Vineyard Wealth Group to help families, individuals, and non-profits navigate their financial journeys with confidence. My approach combines personalized planning, trusted advice, and innovative strategies tailored to each client’s unique goals and values, with a particular emphasis on Social Security analysis and decision-making as a cornerstone of financial success. Prior to starting Vineyard Wealth Group, I spent nearly 14 years at Charles Schwab, managing a $15 billion complex with over 30 employees, and served as a Senior Financial Advisor at Martha's Vineyard Investment Advisors. These experiences honed my ability to deliver comprehensive and collaborative wealth management solutions. As a CERTIFIED FINANCIAL PLANNER® professional, I bring advanced expertise in asset management, estate planning, tax strategies, and Social Security planning, along with credentials as an Accredited Asset Management Specialist® and Chartered Mutual Fund Counselor®. My Six Sigma Black Belt certification further reflects my commitment to efficiency and excellence in service delivery. Beyond the numbers, I’m deeply invested in my community. I serve on the board of the Martha’s Vineyard YMCA, actively support local initiatives, and completed the 2023 Boston Marathon, raising over $8,000 for the Doug Flutie Jr. Autism Foundation. Let’s connect and explore how I can help you achieve financial clarity, optimize your Social Security decisions, and enjoy lasting peace of mind.

Mary Sanchez is a Senior Financial Advisor at Merrill Lynch Wealth Management. She works closely with her family members, including her mother, father, and uncle, focusing on serving divorced individuals, business owners, and highly compensated executives. The team operates out of South Florida, including Miami and Marco Island, as well as Wellesley, Massachusetts. The McKee Group, with over 70 years of combined experience, specializes in wealth management services that encompass retirement income planning, college education planning, wealth preservation, tax minimization strategies, risk management, and liability management. Mary and her team employ sophisticated modeling tools to develop financial strategies tailored to the creation, preservation, and transfer of wealth, emphasizing enduring client relationships and comprehensive personal assistance. Mary holds a Bachelor's Degree from Connecticut College and maintains the Personal Investment Advisor (PIA) designation. She is an active member of the Junior League of Miami and serves as Co-Chair of the Women Who Make A Difference fundraiser for the organization. Outside of her professional commitments, Mary enjoys biking, boating, golfing, racquetball, scuba diving, skiing, swimming, tennis, yoga, and spending time with her family.

James Simpkins is a Wealth Management Advisor at Merrill Lynch Wealth Management. With 20 years of experience on the floor of the New York Stock Exchange and a decade at Merrill, he utilizes his extensive industry background to help clients navigate financial markets and pursue their long-term goals. His areas of expertise include legacy planning, liquidity management, retirement income, portfolio management, and values-based investing, among others. James works closely with clients to develop personalized financial strategies based on their individual objectives, risk tolerance, and liquidity needs. James holds a Bachelor's Degree from Colgate University and maintains professional designations including CERTIFIED FINANCIAL PLANNER (CFP) and Personal Investment Advisor (PIA). Beyond his professional work, he is involved with the Marthas Vineyard Boys and Girls Club and enjoys golfing, skiing, and spending time with his family.

Beth Fratalia is a Wealth Management Planning Consultant at Fidelity Investments, where she collaborates with clients on their daily financial planning and service needs. She aims to be a trusted point of contact to ensure positive experiences in every interaction with Fidelity's team. Beth has been with Fidelity Investments since 2020, initially serving as a Relationship Manager before taking on her current role as a Planning Consultant. Prior to joining Fidelity, she worked as a Marketing Analyst at F.L. Putnam Investment Management Company from 2019 to 2020 and was a Wealth Advisor Associate at Morgan Stanley from 2014 to 2019.

Olivia Pearsall is a Planning Consultant at Fidelity Investments, a position she has held since 2025. She has been with Fidelity Investments since 2020, progressing through roles including Financial Consultant, Planning Consultant, Relationship Manager, and Intern. In her current role, Olivia collaborates with clients to understand their short-term and long-term financial goals, co-creating personalized financial plans and developing customized investment strategies. Her professional experience encompasses various aspects of financial consulting and client relationship management within Fidelity Investments.

Gina Costa is a Wealth Management Planning Consultant at Fidelity Investments, a role she has held since 2019. In this capacity, she collaborates with clients to identify strategies across all aspects of their financial lives, providing continuous and accessible service alongside her team. Her experience with Fidelity Investments spans multiple roles, including Private Client Group Relationship Manager from 2011 to 2014, Investments Consultant from 2008 to 2011, and Financial Representative from 2006 to 2008. This progression reflects her extensive background in wealth management and client relationship development. Outside of her professional work, Gina enjoys activities such as barre, beach outings, board games, cooking and baking, family activities, and fitness.