CEO who used ChatGPT to talk to business icons: “The advice was so good”

Joanna Stober, CEO and co-founder of Midi Health, has never had the opportunity to execute her business plans past legendary venture capital investor John Doerr, chairman of Kleiner Perkins. But that didn’t stop her from asking Doerr in an AI version for advice on developing her startup, a virtual clinic that offers health care to middle-aged women.

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

Strober, a former venture capitalist herself, 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 launched testosterone hormone therapy. Midi counts Amy Schumer and Tory Burch among its investors and reports annual revenue of $150 million.

Strober was named to the 2025 CNBC Changemakers list.

As Strober laid out the milestones for her startup’s next phase of growth, advice and mentorship from successful business leaders – through AI input – became an important and surprising part of her process.

During a recent plane ride, Strober said she “talked to John Doerr for eight hours” and got 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 again on the OKRs I came up with,” Strober said. “He finally liked them and it was very nice.”

An extensive trove of Doerr’s public work allows the AI ​​chatbot to emulate his leadership. 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 in podcasts, speeches, videos and interviews over the past few decades. This wealth of content, Strober says, gave her a remarkably lifelike Doerr to interact with.

“It’s really fun. You can have a ‘nice John Doerr’ or say, ‘Be a strict John Doerr,’ and then the feedback you get changes,” she said.

Although she 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 on YouTube. Wojcicki, an early Google employee and later CEO of YouTube, died of lung cancer in August 2024 at the age of 56. Strober says her close friendship with Wojcicki and Susan’s business success helped motivate her to start Midi.

“I kept showing up at Susan’s house and asking her questions, and I miss her very much,” Strober said.

As Strober sat on the same plane refining her business strategy and texting with her husband, he suggested pursuing business goals beyond an AI-generated version of Wojcicki, which he did. “Your advice was so good,” she said. “I was very emotional on the plane when she said, ‘These are pretty good, but I could think about it and change that.'”

“It was really valuable that she gave me advice,” Strober added.

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