David Thatcher, CFP®, is a CERTIFIED FINANCIAL PLANNER™ professional and a Partner and Senior Financial Advisor with Cypress Wealth Services. The CFP® certification requires rigorous education, a comprehensive examination, and a commitment to act as a fiduciary, placing clients’ interests first when providing financial advice. David works with high-net-worth families across the country whose financial lives have grown increasingly complex. Most are approaching retirement or already drawing on their wealth, and many are navigating a major transition: business owners preparing for or following a sale, families with significant real estate holdings, and executives with large single-stock or private-company stock positions, including at leading technology and aerospace companies.

David believes that meaningful wealth planning begins with understanding the people behind the assets. Before offering recommendations, he takes the time to learn what matters most to each client: the life they want to lead, the people they want to protect, the opportunities they want to create, and the values they hope to pass forward.

His clients often view him as the financial quarterback of their lives. David brings investments, taxes, retirement income, insurance, estate planning, charitable giving, and family priorities into one coordinated strategy, and he works closely with clients’ CPAs, estate-planning attorneys, and other professionals so that important decisions are considered together rather than in isolation.

Areas of Focus

David builds strategies that balance income, liquidity, risk, and taxes, including:

• Retirement income planning. Structuring tax-efficient withdrawals across accounts to create dependable income.
• Business and real estate transitions. Planning for liquidity events, reinvesting proceeds, and coordinating 1031 exchanges, trusts, and estate strategies with clients’ attorneys and CPAs.
• Concentrated stock and equity compensation. Managing stock options, RSUs, private-company shares, and single-stock risk through staged diversification, exchange funds, and charitable strategies.
• Direct indexing and tax-loss harvesting. Customized portfolios that harvest losses to offset gains from diversifying a stock position or selling a business or property.
• Lending against assets. Securities-based lines of credit that provide liquidity without triggering a taxable sale.

When much of a client’s wealth is tied to one company, one business, or one real estate portfolio, David helps them think beyond the immediate question of whether to hold or sell. Together, they consider how taxes, income needs, family security, and long-term goals fit within the client’s complete financial life. His role is not to predict what a company or market will do next, but to help clients make thoughtful decisions under uncertainty.

Preparing the Next Generation

Multigenerational planning is an especially meaningful part of David’s work. He often develops relationships not only with the individuals who created the family’s wealth, but also with their spouses, children, and grandchildren. By getting to know the entire family, David can help facilitate important conversations about estate plans, inheritance, financial responsibility, philanthropy, and the purpose of wealth.

These conversations extend well beyond transferring assets. David helps families consider how wealth can provide opportunity without diminishing ambition, and how heirs can be prepared for the responsibility that comes with it. Depending on the family, that can include family meetings, hands-on financial education, inviting adult children into planning conversations, staged gifting or starter investment accounts, trusts that release assets gradually or tie distributions to milestones, and family philanthropy, such as a donor-advised fund, where the next generation can practice making decisions together.

David’s Approach

David brings a thoughtful, personal, and highly involved approach to every relationship. He understands that the most important financial decisions are rarely financial alone. They can involve identity, family dynamics, career decisions, personal responsibility, and difficult tradeoffs between enjoying wealth today and preserving it for tomorrow. He helps clients slow those decisions down, understand their options, and move forward with greater clarity and confidence.

Background

David has worked in wealth management since 2008. Before joining Cypress Wealth Services, he served as Vice President and Senior Financial Advisor with The Cypress Group. He previously spent six years with Morgan Stanley and began his financial-advisory career at Merrill Lynch.

David and his wife previously lived and worked in New York City for ten years. Today, he enjoys spending time with his wife and four children, playing golf, and traveling whenever time permits.