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David Lessner
Vice President, Wealth Advisor

Dave is a proud graduate of the University of Richmond, where he earned his degree in finance in 2004, laying the foundation for what would become a deeply rooted and client-focused career in wealth management. He began his professional journey by obtaining his licenses in 2006, working part-time alongside his father in the family business while simultaneously gaining valuable experience in software sales. This unique combination of financial expertise and business development skills helped shape Dave’s thoughtful, solutions-oriented approach to serving clients.

Driven by an entrepreneurial spirit and a passion for helping others achieve financial confidence, Dave took a significant step forward in 2013 by founding his own practice with Ameriprise Financial. His vision was to build a firm centered on long-term relationships, personalized advice, and comprehensive planning. That vision continued to evolve in 2017, when he merged his growing practice with Boston Harbor. At the same time, Dave began the meaningful process of acquiring his father’s business—bringing together years of family dedication with a modern, forward-thinking advisory approach and creating a seamless blend of legacy and innovation.

Dave holds both Series 7 and Series 66 licenses and is a firm believer in the power of holistic financial planning. He is passionate about helping clients navigate life’s financial complexities with clarity and confidence, taking into account every aspect of their financial lives. His approach goes beyond investments alone—integrating risk management, tax considerations, and estate planning into a cohesive, long-term strategy tailored to each client’s unique goals.

Continuing his commitment to growth and accessibility, Dave expanded his practice by acquiring another firm in Pittsfield, a location that holds personal significance due to its proximity to his family’s lake house. This expansion not only broadened his reach but also strengthened his ability to serve clients with the same level of care, attention, and personalized guidance that defines his practice.

At the heart of Dave’s work is a genuine dedication to building lasting relationships and helping individuals, families, and business owners create meaningful, well-structured financial futures. His thoughtful, comprehensive approach ensures that every client feels supported, informed, and confident in the path ahead.

David Lessner

I grew up in Northborough, Massachusetts, where I attended Algonquin Regional High School. My wife, Amy, is also from Northborough, and after reconnecting following college, we built our life together in Wellesley, where we now live with our six-and-a-half-year-old daughter, Abby.

Family is everything to me, and I love spending time outdoors—whether I’m on the golf course or chasing Abby around and making memories. I also enjoy getting down to Florida whenever I can to relax, recharge, and enjoy the sunshine.

Giving back is important to me as well. I serve on the President’s Council for the New England Center for Children and am passionate about supporting food shelters throughout the Greater Boston area.

At the end of the day, I’m all about family, community, and making the most of every moment.

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