I start this episode sharing a personal message about my high school football coach, Bob Gregg. He died last Sunday (October 24, 2021). He was 88 years old. Coach Gregg had as big of an impact on me as any person in the world outside of my immediate family. I am so grateful that I got to play on his team for four years. Coach Gregg won 301 games and will go down in history as one of the greatest high school football coaches of all time. He was inducted into the Ohio High School Football Coaches Hall of Fame in 1996 and the Wilmington College Hall of Fame in 1998. He retired from Centerville after the 1999 season.

In 2005, Rebecca Minkoff designed her first handbag, which she dubbed the “Morning After Bag. This iconic bag ignited Rebecca’s career as a handbag designer and inspired the brands’ expansion into a lifestyle brand in the years to come. Actress Jenna Elfman wore her “I Heart New York” shirt on The Tonight Show with Jay Leno. Today, Rebecca Minkoff is a global brand with a wide range of apparel, handbags, footwear, jewelry, timepieces, eyewear, and fragrance. In September of 2018, she established the Female Founder Collective, a network of businesses led by women who invest in women’s financial power across a socioeconomic spectrum by enabling and empowering female-owned businesses.

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The Learning Leader Show

  • When Rebecca was 8 years old, she wanted her mom to buy her a dress. Her mom said, “no, but I’ll teach you to sew.” From that point, Rebecca was fascinated with the idea of buying things for herself.
  • Rebecca doesn’t love the word “mentor.” She was forced to learn by doing.
  • She moved at age 18. Became an intern and then a designer. Eventually, she started her own business.
  • When Jenna Elfman wore her I heart NYC shirt on Jay Leno’s show, it got her foot in the door.
  • “When Jenna asked if I could make her a handbag, I lied and said I could do it.”
  • “I think everyone should get cozy with failure.”
  • Self Care: “Work can be self-care, too.” She’s particularly resistant to the notion that self-care can solve burnout — the feeling of acute exhaustion that has gained more attention recently. “There is no scented candle in the world that will make that feeling go away.” Self-reflection cures burnout, she argues, not self-care.
  • “You don’t need to ask for permission. Don’t seek permission. Just go for it.”
  • Rebecca learned from her mom to be genuinely herself. “I learned to be tough, resilient, and fight back from my mom.”
  • “Don’t get scared to lead with strength.”
    • “Trying hard is not good enough. You must get results.”
  • Advice for future generations? “There are no shortcuts.”
  • “Failure is like a muscle. Sometimes you win, sometimes you learn.”
  • “Success is the ability to keep going.”
  • “The definition of happiness is overcoming barriers towards your goal.”
  • Apply to be part of my Leadership Circle


More Learning:

Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon

Episode 216: Jim Collins — How To Go From Good To Great

Episode #300: AJ & Keith Hawk – How To Instill Work Ethic & Curiosity In Your Children

Episode #303General Stanley McChrystal – The New Definition Of Leadership