Tag Archives: CelebrityEstate

69. Vince McMahon Sr. and the Evolution Of Generational Values



Vince McMahon Sr. is best known for founding the company that eventually became World Wrestling Entertainment. In a family business, which the WWE very much is, passing down core values can be a struggle as future generations look to create their own paths.

In this episode, David Lenok is joined by Kelley Wolfington, Senior Wealth Strategist at SEI Private Wealth Management, in dissecting the idea of inheriting values. She reveals the importance of creating conversations between generations to develop an effective plan for the future.

Kelley discusses:

  • How the generational divide impacts personal values;
  • The importance of introducing commonalities between generations; 
  • Where the financial advisor fits within the conversation;
  • How to have open conversations with advisors with your family members around;
  • And more!

Editor’s Note: This episode was recorded before the recent allegations against Vince McMahon Jr. came to light.

Connect With Kelley Wolfington:

Connect With David Lenok:

About Our Guest:

Kelley Wolfington provides holistic advice in the areas of trust and estate planning, wealth transfer, philanthropy, succession planning, tax planning and family communications strategies for ultra-high net worth and high net worth individuals and families. Her responsibilities include collaborating with internal and external colleagues and partners to craft and deliver such advice as well as develop strategies, techniques, tools and materials related to these advisory areas. She helps facilitate a perpetual process to improve her clients’ condition by working with them to navigate goals, values and visions for themselves, their families and their communities.




Ep 57 – Prince: Planning for Intellectual Property With Matthew Erskine



From his home and liquid possessions to his image and royalty rights, settling Prince’s estate would have been a complex process, even with a will. But Prince did not have a will, and this led to one of the largest and most complex estate battles in Minnesota and even American history. 

However, the most mysterious part of Prince’s estate is the bank vault with a code that even Prince himself forgot.

In this episode, David Lenok is joined by Matthew Erskine of Erskine and Erskine revisiting the topic of Prince. Focusing on the sealed vault filled with unpublished songs and recordings, David and Matthew discuss the relevance of protecting your intellectual property (IP) regardless of your celebrity status. They reveal the potential ramifications of posting content online and why the importance of understanding your collection for future heirs.

Matthew and David discuss:

  • How the internet has immortalized intellectual property
  • The ramifications of self-selling when it comes to IP ownership
  • The impact of fan-made creations on the original creators
  • Why you should categorize your collection for you heirs
  • And more

Connect With Matthew Erskine:

Connect With David Lenok:

About Our Guest:

Matthew Erskine is the managing partner of this fourth generation law firm. He focuses his estate planning and trust services practice on serving business owners, professionals, individuals, families, collectors, and inheritors of significant assets. Helping his clients and their families achieve their goals by providing customized solutions. Matt carries on his family’s tradition of integrity, continuity, and service.

Matt has a particular expertise in the stewardship of special assets that few other estate planning and trust attorneys can match. Working with collectors of art, jewelry, heirlooms, and other valuable assets, as well as owners of real estate and family businesses, Matt brings his and his family’s generations of experience and intimate knowledge of unique areas of the law to help clients achieve their desired investment and personal goals.

The Erskine family has been counsel to client families since 1876, overseeing litigation, estate and income taxation planning, residential and commercial real estate conveyances, close corporations, nonprofit corporations, personal trusts, dynasty trusts, private foundations, and family offices. Matt is also active in numerous community organizations in the Worcester, Massachusetts area, including the American Antiquarian Society, the Council on Foreign Relations Worcester Committee, Inc., the Worcester Economics Club, and the John J. Kittredge Numismatic Foundation.

Matt is an active member of Wealthcounsel, Wealthcounsel Advisors, Vistage, the American Bar Association and several other professional organizations.

After graduating from Lawrence Academy, Matt received his B.A. in Medieval History from Carleton College and his J.D. from Suffolk University Law School.