Host Michael Sonnenfeldt concludes Season 1 with a retail legend and world-changing philanthropist, TIGER 21 Member David Jaffe. David’s mother Roslyn founded Dressbarn in 1962. David joined the family business in 1992. As CEO, David took the company from $1 billion in sales all the way to $7 billion as Ascena Retail Group, Inc., a Fortune 500 retailer with eight distinct brands including Ann Taylor, Loft, Lane Bryant, Catherines, and Justice, with over 4,500 stores across the U.S. and Canada, employing 65,000 associates.

In 2019, David transitioned out of Ascena. Today, he's a philanthropist on a quest for social change, leading two different nonprofits. David shares insights on family business succession, integrating philanthropy, and his advice for those transitioning out of their primary careers. Key topics include the evolution of Dressbarn, strategies for successful acquisitions, and the importance of aligning career choices with personal passions.

Video clips:

The 10-Year Rule for Family Business

"After My Exit, I Became the Wrong Kind of Investor"

Topics:

(00:00) Podcast announcement (Season 1 finale)

(00:31) Introduction to David Jaffe  

(01:00) Early career 

(02:27) Philanthropy and social change  

(03:13) Family business dynamics  

(04:28) Career transition  

(19:58) Lessons from leadership and mentorship  

(23:12) End of an era at Ascena

(25:50) The day after retirement  

(27:46) Exploring new opportunities  

(28:40) Advanced Leadership Initiative at Harvard  

(29:13) Combining passions: education and environment  

(30:21) Advice for post-career transitions  

(31:09) Investment lessons learned by Michael Sonnenfeldt and David Jaffe 

(34:04) Philanthropic ventures: FARE and Subject to Climate

(35:50) Balancing nonprofit and personal life  

(38:30) Partnerships

(40:40) Impact and future goals  

(46:27) Personal reflections and advice  

(49:37) Tip Jar

About:

TIGER 21 is the premier peer membership organization for ultra successful entrepreneurs, investors, and executives.

Tip Jar:

Dad’s Ten Rules

Salman Khan: "Brave New Words"

Merrily We Roll Along

Stereophonic

Links:

tiger21.com

Michael Sonnenfeldt - LinkedIn | @mwsonnenfeldt

FARE foodallergy.org

Subject to Climate subjecttoclimate.org

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