Legend! Part 2 of 2 Dame Stephanie Shirley R.I.P. Giving Away $100 Million and Become Wealthier

Part 2 of 2 of my conversation with a rare and iconic human, Dame Stephanie Shirley. 
Who the world lost in the summer of 2025

What is true resilience? 

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What if the very thing that almost broke you became the key to you in changing the world?

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Dame Stephanie Shirley is not just a tech pioneer, she is living proof that resilience is forged in fire. From a childhood escape on the Kindertransport, to founding the first all-women software company in 1962 (decades before anyone whispered “remote work”), to building a $3 billion empire that created 70 millionaires, her story reads like legend. But what makes her extraordinary is not her success, it is how she faced trauma, breakdown, and the raw reality of raising an autistic son—and turned it into fuel for innovation, compassion, and radical philanthropy.

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In this episode, we go deeper: how values-based hiring became her secret weapon, why Dame Shirley believes President Zelensky embodies the future of leadership, and how suffering, when confronted, can reveal who we truly are. If you think resilience means grinding harder, prepare to have that illusion shattered.

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This isn’t a feel-good tale of triumph. It’s a masterclass in what it really takes to lead, build, break, and rebuild—without losing your humanity.

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In this conversation, Dame Stephanie Shirley reveals:

• How trauma in childhood revealed her disruptive entrepreneurial DNA

• Why values, not skills, determine the fate of a business

• What Zelensky teaches us about the new face of leadership

• The brutal truth about resilience (and why most people misunderstand it)

• How breakdown became her turning point toward compassion and purpose

• The radical shift in how society views autism, and why neurodiversity is leadership’s untapped advantage

• Why philanthropy, done right, gives back far more than money ever could

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Dame Shirley’s story forces you to ask yourself: What parts of me have I disenfranchised in the name of fitting in, and what would happen if I brought them back?

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About Dame Stephanie Shirley

• Founder of Freelance Programmers, the world’s first all-women software company (1962)

• Scaled to 8,500 employees and a $3 billion valuation

• Transformed women’s opportunities in technology, creating 70 millionaires in the process

• Knighted as a Dame, awarded the Companion of Honour

• Pioneering philanthropist in autism research, education, and venture philanthropy

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