Thomas Matthew Juster

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.

James Shannon is a CFA® charterholder with 11 years of industry experience. He is the sole advisor at Shannon Investment Management, an independent firm based in Falmouth, MA. Prior to founding his firm, he has been affiliated with SoFi Securities LLC and Social Finance, Inc. since 2012. Shannon Investment Management provides fee-only, discretionary investment management and ongoing investment guidance to individuals, families, trusts, businesses, and nonprofit entities. The firm primarily utilizes passively managed exchange-traded funds, applying principles from modern portfolio theory and market-efficiency research to build diversified portfolios with strategic and tactical asset allocation.

Daniel Seidman is the sole advisor at Seidman Investment Portfolios in Vineyard Haven, MA, holding a Series 63 designation with 33 years of industry experience. He has led his independent firm since 1988. Outside of advisory services, he is also a licensed insurance agent and owner of an insurance agency. Seidman Investment Portfolios offers tailored portfolio management and comprehensive financial planning to individual investors, including high-net-worth clients, as well as institutional clients such as pension plans, endowments, and charitable organizations. The firm combines a long-term, low turnover investment philosophy with active tactical management, utilizing research from public and subscription sources and conducting regular account reviews.

I’m T.J. van Gerven, founder of Memento Financial Planning—a virtual, fee-only firm helping high-earning couples in their 30s and 40s align their money with what matters most. Most of my clients are navigating complex financial lives: managing equity comp, balancing student loans and child care, investing excess cash, and trying to figure out when enough is enough. I help them make smart, tax-efficient decisions while building toward a life of financial flexibility—where work becomes a choice, not a necessity. My planning process combines technical expertise with deeper conversations around values and purpose. Because financial planning isn’t just about growing net worth—it’s about using your resources to live more intentionally. When I’m not reviewing tax returns or modeling equity strategies, I’m probably road tripping with my partner, wandering a farmer’s market, or listening to a philosophy podcast.

Victor Kester, Jr. is an advisor with Essex Private Wealth Management LLC and holds Series 63 and Series 66 designations. He has three years of industry experience, with prior roles at firms including Deloitte and Mass Mutual Investors Services. Outside of financial services, he is also active in real estate sales as a licensed salesperson with Keller Williams. Essex Private Wealth Management serves individuals, high-net-worth clients, trusts, estates, retirement plans, and charitable organizations, managing approximately $330.5 million across 216 clients. The firm employs a combination of fundamental and technical analysis to construct portfolios primarily with mutual funds and ETFs, offering discretionary and non-discretionary investment management along with comprehensive wealth and retirement-plan advisory services.

Jeffrey Cutter is a financial advisor with Cutter Financial Group LLC in Falmouth, MA, holding the PFS™ and Series 66 designations and having 19 years of industry experience. He has worked at Cutter Financial Group since 2006 and Precision Capital Management since 2015. Outside of advisory roles, he is involved in insurance and financial product sales through independent contracting arrangements. Cutter Financial Group provides investment advisory and planning services to individuals, high net worth clients, trusts, estates, and charitable organizations. The firm employs a risk-first investment approach focused on retirement income needs and offers portfolio management primarily through mutual funds, with additional services including income, legacy, risk management, and advanced tax planning.