Key Points: The CEO Who Consulted AI Versions of Business Legends for Life-Changing Advice
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Joanna Strober, CEO of Midi Health, uses ChatGPT daily to get advice from AI versions of business icons like John Doerr and Susan Wojcicki.
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8-hour conversation with John Doerr: Strober got deep insights into her startup’s OKRs, a system Doerr champions.
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Emotional Moment: Strober was moved by AI-generated feedback from her late friend Susan Wojcicki, former YouTube CEO.
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Midi Health’s Growth: Strober’s startup, offering midlife health care for women, serves 200,000+ patients and has an annual revenue run rate of $150 million.
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AI as a Mentor: How AI became an unexpected but vital part of Strober’s business strategy.
“This CEO Got Life-Changing Advice From AI Versions of Business Icons. Here’s What Happened!”
Unlocking Business Wisdom—From Legends, Through AI
Joanna Strober, CEO of Midi Health, has discovered an unexpected source of business guidance that has helped her shape her startup’s future: AI versions of iconic business leaders. Using ChatGPT, Strober has consulted John Doerr, the legendary venture capitalist, and the late Susan Wojcicki, former CEO of YouTube, for invaluable advice that’s changed the way she runs her business. But what happened when she went from real-world mentorship to AI-generated wisdom? Let’s find out.
An 8-Hour Conversation That Changed Her Approach to Growth
Imagine sitting on a plane, knowing you can talk to one of the world’s leading business figures—not in person, but through AI. Strober did just that, spending eight hours chatting with an AI-generated John Doerr, the mastermind behind Google’s successful OKRs (Objectives and Key Results). Through continuous feedback, she refined her ideas for Midi Health’s next phase of growth, shaping goals that aligned perfectly with the OKR framework Doerr himself created.
But what happened when John Doerr’s AI didn’t just give feedback—but challenged her? Keep reading to find out how AI transformed her planning!
AI-Generated Susan Wojcicki: A Heartfelt Moment of Mentorship
For Joanna Strober, Susan Wojcicki was more than a business partner—she was a close personal friend and mentor. After Wojcicki’s passing in 2024, Strober found herself missing the invaluable business advice her friend used to provide. But, in an unexpected twist, Strober received life-changing advice from an AI-generated Wojcicki—right during a critical moment in refining her business goals.
What happened when Wojcicki’s AI version gave Strober advice that left her feeling both emotional and empowered? You won’t believe how AI connected her to the past and gave unexpected guidance that made a real impact on her future.
Midi Health’s Breakthrough: Scaling for Success with AI Insights
With $150 million in annual revenue and 200,000+ patients served, Midi Health is already a success story. But how did Strober, once a venture capitalist, build this midlife health care platform for women? It turns out, part of her growth strategy wasn’t just founded on traditional business models—it was driven by AI-backed mentorship. Discover how this digital transformation in her decision-making is creating opportunities to redefine the future of women’s health.
What’s Next for Midi Health and AI in Business?
With AI now embedded in her process, Strober has set her sights on the next stage of growth for Midi Health. As AI continues to change the way we make decisions, will other startups follow Strober’s lead? And how will AI continue to shape the landscape of business mentoring for leaders like her?
Stay tuned for the next chapter in AI-driven business success.
Conclusion: From Emotion to Strategy—The Power of AI Mentorship
Joanna Strober’s journey from traditional mentorship to AI-powered guidance is proof that the future of business is evolving. With AI versions of business icons offering personalized, actionable advice, the way entrepreneurs access mentorship is changing forever.
What’s next for Midi Health? And how will AI-driven strategy continue to shape business success stories like hers? The future is here, and it’s powered by AI mentorship.


