David Jaffe: Ascena Retail Group CEO on Scaling Family Business, Investing, and His Next Chapter

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. Over 10 years of learning, then another 17 years as CEO, he took the company from $1 billion in sales all the way to $7 billion. 

David built Dressbarn into 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.

Hear career and investing lessons from David’s impressive journey strategically building Dressbarn into the Ascena Retail Group to his pivot to philanthropy focusing on food allergy research and climate change education. 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.

Dad’s Top 10 List

1. Be impeccable with your word and actions. Your word is your bond. 
2. Take responsibility for all your actions. Be an owner not a renter. 
3. Humility – don’t rely on recognition for your satisfaction. But, be proud of whatever you do. If not, do it again. 
4. Don’t take anything personally. Only you can make yourself feel bad. 
5. Listen before you speak. Be open and flexible to new and others’ ideas. 
6. Fulfill your potential. Be true to yourself. 
7. Leverage your resources. Make the most of what you have. 
8. Be here now. Focused and in the moment. 
9. Choose your attitude. 
10. Do your best and have fun! 

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NEXT with TIGER 21

Welcome to NEXT with TIGER 21, a podcast where paths to extraordinary success are highlighted by those who have travelled them, along with the direction where they are headed next. 

Join us as we explore the unique personal and professional journeys of some of the world’s most accomplished entrepreneurs and wealth creators. Each episode features a Member of TIGER 21’s exclusive peer network community, which is composed of ultra-high-net-worth individuals around the world who have made their mark and are eager to share the wisdom they have gained along the way.

In addition to recounting the pivotal moments that propelled them forward, they look beyond past achievements to discuss their visions for the future, what they see coming in the realms of innovation and enterprise, and what defines their next level of success. 

Tune in bi-weekly to gain exclusive access to the life lessons and forward-thinking ideas that can only come from those who have reached the pinnacle of achievement. Subscribe to NEXT with TIGER 21 and take the first step toward enriching your own path to success.

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