The Clapboard Hill Team

Thomas Pacilio
Senior Managing Partner

Tom, Clapboard Hill Private Wealth’s CEO/Founding Partner, has extensive experience and knowledge of wealth management business and the financial services industry. Initially as an investment advisor, then advancing into senior management roles at Merrill Lynch and Morgan Stanley.

Tom leveraged this experience, investment insight and client-centric focus to start his own independent wealth management firm, creating Clapboard Hill Private Wealth. Tom brings objectivity, transparency and passion into each individual and high net worth family that he works with.

Tom is very active in the Westport community, where he has resided for the past 26 years with his wife, Ann-Marie, raising their four children. Tom is a graduate of Adelphi University, where he majored in finance and has been at the forefront on many industry initiatives throughout his career to stay current and informed as the Private Wealth Management industry is constantly evolving.

Daniel Besse
Managing Partner CIMA®

Dan has always channeled his entrepreneurial spirit through not only the Wealth Management business, but also in charitable endeavors as well as mentorship programs. He had been involved in the strategy development and formation of a Multi-Family Office within an accounting firm. Dan is still actively involved and serves on the board of Summer Search, an education-based charity, funding at-risk student development. Additionally, Dan is a regular contributor to various high net worth and family office platforms including Family Office Exchange and Investment Managing Institutes. Additionally, in the past, he has written various investment related articles for Bloomberg. Dan also has regular involvement and mentorship with the Fairfield University Entrepreneurial Program, the StartUp Showcase. As a Managing Partner of Clapboard Hill Private Wealth, Dan is also committed to dedicated internship programs to help inspire the entrepreneurial spirit in local dynamic students. Dan has a Bachelor’s degree of Science from Fairfield University in Economics and Finance. He is also an active member of the Investment Management Consultants Agency and holds a Certified Investment Analyst Certification® (CIMA®).

Dan interests include golf, enjoying an active lifestyle and passionately supporting his Boston sports teams from enemy territory, alongside his young family in Easton, CT.

Kevin Looby
Managing Director – Private Wealth Advisor CFP®

With over 20 years of wealth management experience, Kevin’s focus is on helping clients plan, prepare, and achieve their best financial future.  Following an integrated wealth management process, he reviews and helps implement current and future planning needs such as investment management, tax planning, cash flow, insurance, and estate planning. As a fiduciary, Kevin works closely with accountants, estate attorney’s and insurance specialist to provide independent, unbiased advice in building or maintaining comprehensive financial plans for his clients.

Kevin is a CFP®. CERTIFIED FINANCIAL PLANNER™ certification is the standard of excellence in financial planning. CFP® professionals meet rigorous education, training, and ethical standards, and are committed to serving their clients’ best interests today to prepare them for a more secure tomorrow.

Prior to Clapboard Hill Private Wealth, LLC, Kevin held the titles of Director of Financial Planning and Vice President at local Registered Investment Advisor firms.  Kevin was also a Vice President, Regional Planning Consultant for Fidelity Investments in Manhattan, New York and several New Jersey branch locations where he garnered many awards and built a strong network of industry professionals.

Kevin enjoys golf, skiing and traveling with his family, as well as watching his kids enjoy lacrosse, soccer, and dance. Kevin, his wife Lori, and their two daughters reside in Madison, CT.

Walter Rich
Managing Director of Business Development 

Walter is the Managing Director of Business Development for Clapboard Hill Private Wealth. Walter is tasked with growing the practice through developing long-lasting, trusted, mutually beneficial relationships. Prior to joining Clapboard Hill, Walter spent over 10 years as the New England Regional Sales Manager for Sector SPDR exchange traded funds. He was instrumental in helping grow assets during his time at the firm.

Outside of the office, Walter is a proud veteran of 4 marathons, enjoys playing golf and watching his kids play hockey and lacrosse. Walter, his wife Cara, and their three children reside in Madison, CT. Mr. Rich received a Bachelor of Arts in History from Fordham University.

Brandon Pacilio
Business Strategist 

Brandon is a second generation member of the Clapboard Hill team.  Prior to Clapboard Hill Private Wealth he worked in Client Services at Bridgewater Associates. In addition, Brandon spent four years at SumRidge Partners a fixed income trading firm. At CHPW he focuses on client service, business strategy, and fixed income.  Brandon has a Bachelors of Arts in Economics from Middlebury College, where he also studied Italian. Brandon and his fiancé reside in Stamford and enjoy spending their time at Bromley Mountain in Vermont. 

Michael Blank
Investment Strategist 

Mike has worked in the private wealth management industry for over 7 years under the leadership of Tom & Dan in various capacities.  Currently as the team’s Investment Strategist, he oversees the investment platform including, but not limited to; market research and analysis, investment portfolio design, and trading and execution across various asset classes. His responsibilities also include providing customized portfolio reporting solutions, on client assets, both internal and external. He additionally contributes regular market commentary on behalf of Clapboard Hill Private Wealth. Mike is currently a CFA level III candidate.

Mike has a Bachelor’s degree of Science in Finance from Fairfield University’s Dolan School of Business. Outside of the office, Mike is charitably inclined as an active member of the community, is an avid NY sports fan and golf lover.

Stacey Williams
Senior Client Relationship Manager 

Stacey is the Senior Client Relationship Manager and specializes in making your client experience a memorable and easy journey. As the “director of first impressions,” Stacey heads up our client service platform, plays an integral role in the operations of the company, and works actively with our compliance and oversight teams. Stacey’s career spans 30 years in the banking and financial services industry. Additionally, Stacey lives locally, as she has her whole life, with her husband, son and beloved pets. Her interests include gardening and cooking in her spare time.