Sam Silberstein

I bring over a decade of experience spanning financial planning, tax strategy, and investment management. Before joining Chicory Wealth as a Tax Advisor, I served as an advisor at Motley Fool Wealth Management and held prior roles at TIAA, Vanguard, and SLP Wealth. That background gave me a deep understanding of how tax decisions influence nearly every aspect of a financial plan, from investment management and retirement income planning to estate and legacy planning.

As a CERTIFIED FINANCIAL PLANNER™ practitioner (CFP®), Chartered Financial Analyst® (CFA®), and Enrolled Agent (EA), I bring a multidisciplinary perspective that combines financial planning, investment analysis, and tax expertise. I believe some of the most valuable planning opportunities exist at the intersection of these disciplines, where thoughtful tax planning can meaningfully impact long-term outcomes.

I earned my undergraduate degree in Economics from Temple University. Financial education remains a passion of mine, and I enjoy making complex topics, particularly those related to taxation, investing, and retirement planning, more accessible and engaging. In addition to my work at Chicory Wealth, I teach CFP® education and review courses for aspiring financial planners.

My grandmother, a CPA, liked to joke that good money habits and knowledge were genetic. More importantly, she also believed money should be discussed openly rather than avoided. Growing up, she encouraged conversations about finances, how money works, and the opportunities thoughtful planning can create. Those early discussions sparked my lifelong interest in personal finance, and ultimately led me to this career where I have the privilege of helping people confidently navigate their financial decisions.

I live in Philadelphia with my partner. Outside of work, I enjoy exploring the city on foot, practicing Spanish, planning future travel adventures, and cheering on the Phillies, an activity that often requires equal parts optimism and emotional resilience. I also spent part of my college years as an amateur breakdancer. While I still occasionally think about getting back into it, my knees tend to have other plans.