Gracious Exit CEO And Founder Alison Winter On Preparing For The Most Important Exit Of Your Life (#032)

"Always be able to take care of yourself." - Alison Winter

Alison Winter is the Co-Fonder and CEO of Gracious Exit LLC, a web-based resource for individuals and families to prepare for the end of life.  

The workbooks and articles and resources provide the roadmap to navigate this last stage of one’s like, and do it in a way that is positive, eliminates a burden for those left behind, and leaves a full picture of one’s positive contributions.  

In 2006, Alison retired from Northern Trust Corporation, completing a markedly successful thirty-five year career, where she held leadership roles with increasing scope since 1987. She served on the Management Committee for the last five years of her tenure with Northern Trust.  When she retired, Ms. Winter was the founding President and CEO of Personal Financial Services-Northeast based in New York, where she established the Northern Trust’s presence in that highly attractive and competitive market.  Prior to that, she served as Co-President of Personal Financial Services for Northern Trust.   In all, she expanded the Northern Trust franchise as a leader in managing the wealth of the affluent in 20 new markets, on the West Coast, The Midwest and the Northeast.  Technology innovation, strategy, brand management and customer focus are hallmarks of her career.

In 2001, together with Susan S. Stautberg, they co-founded WomenCorporateDirectors (WCD), the only chapter-based international organization for women serving on Corporate Boards with over 3500 members serving on over 6000 Boards globally.  She established the framework for scaling up, domestically and internationally, and there are now 80+ chapters on six continents.  The organization has now been transitioned to Women Corporate Directors Foundation for Education and Research.  

Ms. Winter received her MBA from the University of Chicago Graduate School of Business, earned her Chartered Financial Analyst designation, and is a member of the CFA Institute. She holds a BA from San Francisco College for Women. Over her career, she served on dozens of charitable and civic organizations, including Los Angeles Metro YMCA, New York Metro YMCA, The Joffrey Ballet of both Los Angeles and Chicago, Steppenwolf Theatre, and    United Way Women’s Leadership Initiative. In 1998, she became the first woman to be Chair of the Los Angeles Area Chamber of Commerce in its 110 year history.

She lives in Pasadena with her husband, Joe.  Her daughter, Leigh, lives with her husband and three sons in Los Altos, CA, and her son, John, lives in Chicago, IL.


  • Alison's journey in the financial world
  • How Alison led the way and helped women in corporate America
  • The one question Alison asked her father that was the start of the Gracious Exit
  • Business owners plan for their business exit but overlook their life exit
  • The systematic process and journey Alison used to create the Gracious Exit
  • Why every family should have photo books to create a legacy
  • How a film about your family can help future generations
  • Tips on how to educate the younger generation about wealth, philanthropy, and planning
  • Alison's thoughts on when to speak to your parent's about their last wishes
  • Why withholding your wealth from your children can hurt them instead of protecting them
  • How the specific workbooks in the Gracious Exit save you time and give peace-of-mind
  • Alison walks through how to start preparing the information for your Gracious Exit
  • The importance of making your estate plan easy to understand through visual mapping
  • The power of having financial, medical, passcodes, and your last wishes in one place
  • How to ensure your jewelry, heirlooms, and antiques have significance for your kids
  • How to have a difficult conversation about last wishes with your parents or your family

This podcast is brought to you by Deep Wealth. Are you thinking about a liquidity event? You have one chance to get it right and you better make it count. Enterprise value is created from preparation, and not the event itself. Learn how the Deep Wealth Experience helps you maximize enterprise value. Master the same strategies our founders used to increase their company value 10X with a 9-figure exit. Click here to book your free exploratory call.

Enjoy the interview!


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