
Born in the 1960s to strong, resourceful working mothers, Kathleen Flynn and Mary Jo Kramer learned young that women could have it all—marriage, children and careers—fulfilling the traditional role while contributing financially to the family. Inspired by these role models, the girls filled with drive and dreams met and quickly became friends more than 40 years ago at an all-girls’ Catholic high school on the South side of Chicago.
Their friendship continued in college—studying, living and working together at the University of Illinois in Urbana-Champaign. In those days, they dreamt about their perfect jobs, Prince Charmings and everything in between. They stood up in each other’s weddings, watched their families grow and have been fortunate enough to work together at three different businesses.
In their 50’s, their fairytales fractured as both went through challenging divorces and most recently left (not by choice!) executive leadership teams with corporate severance packages. (Seriously, after years of corporate service, they were terminated from different companies within days of each other—you can’t make this up!)
Through it all, they have leaned on each other and shared both laughter and tears. They have shattered glass ceilings and still believe in happily ever afters. In this podcast, they will introduce you to other successful women who will share their own journeys and what they’ve learned along the way.
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Mary Jo Kramer spent 20 years championing marketing and communications in the direct selling industry with a primarily female target audience. After a few years as an independent consultant, she shifted gears to run marketing for a heating and air conditioning distribution company (definitely NOT a female-dominated field!!) When she started there, the company was at just over $100m in annual sales. When she left, it was an international success story with sales well over $1b. She’s moved from her fractured first marriage to a happily ever after with her husband, Keith. She has two adult children—one daughter and one son.
Kathleen Flynn spent over 35 years in the personalized gift industry, developing products to help people express themselves. With an eye for trends, she traveled the globe in search of the next “big idea!” From humble beginnings in the owner’s basement through multiple sales, the company had topped more than $200m when she stepped away from the corporate world in early 2025 (OK, maybe she was pushed). Today, she’s pursuing a career in residential real estate and utilizing that same creative intuition to market her clients’ homes or help them find the home of their dreams in the Chicago area. She is a mother of three adult children – one son and two daughters – and welcomed her first grandchild in February 2026.

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