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CEO who used ChatGPT to talk to AI clones of business icons: ‘Advice was so good’

Robert Frost by Robert Frost
December 2, 2025
in Industries
CEO who used ChatGPT to talk to AI clones of business icons: ‘Advice was so good’
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Joanna Stober, Midi Health CEO and co-founder, has never had an opportunity to run her business plans past legendary venture capital investor John Doerr, chairman at Kleiner Perkins. But that didn’t stop her from tapping Doerr, in an AI version, for advice on growing her startup, a virtual clinic offering midlife health care for women.

“He is basically accessible to you on ChatGPT,” Strober told CNBC’s Julia Boorstin in the latest episode of the “CNBC Changemakers and Power Players” podcast.

A former venture capitalist herself, Strober co-founded Midi Health in 2021. Today, the company has a network of 400 women’s health specialists, has served more than 200,000 patients and recently introduced testosterone hormone therapy. Midi counts Amy Schumer and Tory Burch among its investors and reports an annual revenue run rate of $150 million.

Strober was named to the 2025 CNBC Changemakers list.

As Strober was laying out the milestones for her startup’s next phase of growth, getting guidance and mentorship from successful business leaders — through AI prompts — became a key, surprising part of her process.

During a recent plane ride, Strober says she “talked to John Doerr for eight hours,” gathering feedback on her ideas for Midi’s ‘Objectives and Key Results’ (OKRs), a framework Doerr has championed to help companies and organizations set and achieve ambitious goals.

“I got feedback over and over and over again on the OKRs that I came up with,” Strober said. “Finally, he liked them, and it was very nice.”

A vast trove of Doerr’s public work enables the AI chatbot to emulate his guidance. Doerr is the author of “Measure What Matters” — a guide to the OKR system adopted by Google, the Gates Foundation, and Bono — and has shared his approach across podcasts, speeches, videos and interviews over the the past several decades. That rich body of content, Strober says, gave her a remarkably lifelike Doerr to interact with.

“This is actually really fun. You can have a ‘nice John Doerr,’ or you can say ‘be a harsh John Doerr’ and then it changes the feedback that it gives you,” she said.

Though she has never received advice directly from the real Doerr, Strober’s closest friend growing up in Silicon Valley was the late Susan Wojcicki, who is featured in Doerr’s book for the OKRs she developed at YouTube. Wojcicki, who was an early Google employee and later became the CEO of YouTube, died of lung cancer at age 56 in August 2024. Strober says her close friendship with Wojcicki, and Susan’s success in business, helped motivate her to start Midi.

“I used to show up at Susan’s house all the time asking her questions, and I miss her a lot,” Strober said.

As Strober sat on that same plane ride refining her business strategy, and texting with her husband, he suggested running the business goals past an AI-generated version of Wojcicki, which he did. “Her advice was so good,” she said. “I was very emotional on the plane when she said, ‘these are pretty good, but I might think about this, and I might change this.'”

“It was actually very valuable to have her giving me advice,” Strober added.

Follow and listen to this and every episode of the “CNBC Changemakers and Power Players” podcast on Apple and Spotify.

CNBC is accepting nominations for the third CNBC Changemakers: Women Transforming Business list. The unranked list will recognize a distinguished group of women whose accomplishments have left a mark on the business world and who are paving a path forward.



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