Touchstone Talks: Ep. 8 - Protecting What You’ve Built: Estate Planning Insights for Business Owners
In this episode, trust and estate attorney Michael Clear, Partner of Wiggin and Dana discusses how thoughtful estate planning can help business owners preserve and protect the wealth created through a lifetime of work. He explains the strategic use of trusts—revocable and irrevocable—to minimize estate taxes, provide asset protection, and ensure family continuity. Clear emphasizes the importance of starting planning well before a sale—ideally two or more years in advance—to take advantage of valuation discounts and tax benefits. With a counselor’s mindset, he guides clients through not just the technical but also the personal aspects of planning, helping families clarify goals, communicate effectively, and set up structures that reflect their values and future aspirations.
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Creators and Guests
Host
Deborah Agrafojo
Deborah has influenced and directed strategic and owner-operator mergers and acquisitions in many different fields. She believes strongly that assisting a business to grow and develop strong practices is the best way to create a company that is poised for exit planning or gaining an equity growth partner.
Producer
David Chmielewski
At the end of 2013 David founded DirectLine Media, a video production company that specializes in creating memorable and compelling video content for businesses. Admired for his unique and creative visual story telling, David continues to work with small to large businesses and nonprofit organizations.
Guest
Michael T. Clear
Michael, Partner at Wiggin and Dana, is Chair of the firm’s Private Client Services Department, leading a team of more than 30 lawyers and allied professionals. He advises clients on estate planning, trust and estate administration, probate litigation, and business succession planning, combining legal expertise with a counselor’s understanding of family dynamics. Known for his empathy and good humor, Michael helps clients make sound decisions and hopefully resolve disputes before litigation arises. His practice includes tax-efficient estate and gift planning, trust and estate administration, and business succession planning, including entity formation, shareholder and buy-sell agreements, and facilitating business transfers. A Fellow of the American College of Trust and Estate Counsel, Michael frequently speaks on trust and estate strategies and is active in professional organizations, including the Connecticut Bar Association and the Exit Planning Exchange (CT XPX). He earned his J.D. magna cum laude from Quinnipiac University School of Law, where he was Executive Managing Editor of the Quinnipiac Probate Law Journal, and holds a B.A. in political science from the University of Richmond and an M.Ed. from the University of Maryland. A former Division I baseball player, he lives in Fairfield, Connecticut with his wife, Melissa, and their three children, and remains active in local youth sports.
Guest
Sean Healy
Sean Healy currently serves as a Vice President of Business Development at Keswick. Sean is responsible for sourcing new investment opportunities, business development, and conducting preliminary financial, operational, and competitive diligence for potential investments. Prior to joining Keswick, Sean was head of origination for a family office, led his own search fund, and also served in various strategy and management consulting-related roles for companies spanning all stages of the business lifecycle from startup to corporate stalwart (Lowe’s and Home Depot, among them). Prior to entering the private sector, Sean served as a Combat Engineer Officer in the US Army. He later served as a Joint Operational Strategist for the Navy and Marine Corps before transitioning into the Reserve Force of the US Army, where he remains a Lieutenant Colonel today.
Editor
Stefania Sassano
Known for being determined and focused, Stefania is often the first to memorize lines and dedicates significant effort to each role. She excels in both comedic and dramatic performances, embracing the motto by Mark Twain, "Find a job you enjoy doing, and you will never have to work a day in your life," making every project both a professional commitment and a joy.