San Francisco — In a novel twist on entrepreneurial mentorship, Joanna Strober, CEO and co-founder of the virtual women's health startup Midi Health, is leveraging AI chatbots to receive strategic guidance from simulated versions of iconic business leaders like venture capitalist John Doerr.

Strober, a former VC herself who founded Midi in 2021, detailed on the CNBC "Changemakers" podcast how she recently spent an eight-hour flight iterating her company's growth objectives with an AI modeled on Doerr's public philosophy. "Finally, he liked them, and it was very nice," she recounted. The AI's feedback is based on the vast public record of Doerr's work, including his book "Measure What Matters" and decades of interviews.

Personalizing AI for Strategic and Emotional Counsel

The use of AI extends beyond professional frameworks into deeply personal territory. Strober's late childhood friend was Susan Wojcicki, the former YouTube CEO featured in Doerr's book. Strober's husband prompted an AI simulation of Wojcicki to review the same business plan. "Her advice was so good... I was very emotional on the plane," Strober said, highlighting the technology's capacity to emulate the strategic pivot and nuanced feedback of a lost mentor.

This practice allows for customized interaction styles. "You can have a 'nice John Doerr,' or you can say 'be a harsh John Doerr,'" Strober explained, suggesting founders can tailor the AI's tone to simulate different high-stakes advisory scenarios, a dynamic not unlike preparing for a critical negotiation or product launch.

A Tool for Scaling a Mission-Driven Business

Midi Health, which offers virtual care for midlife women and recently introduced testosterone therapy, reports an annual revenue run rate of $150 million. It has served over 200,000 patients with a network of 400 specialists and counts celebrities like Amy Schumer among its investors.

For Strober, AI mentorship is a practical tool for scaling. By repeatedly testing her "Objectives and Key Results" (OKRs) against the AI's simulation of Doerr's renowned methodology, she engaged in a form of intensive, on-demand strategic rehearsal. This process helps navigate the complex competitive ecosystem of digital health, where clear, measurable goals are paramount.

The New Frontier of Founder Support

Strober's experience points to an emerging trend where AI is used not just for operational tasks but for high-level strategic thinking and even emotional support during a founder's journey. It democratizes access to the distilled wisdom of top-tier mentors, allowing entrepreneurs to pressure-test ideas against legendary frameworks at any time.

While it cannot replace human connection—Strober deeply misses her real conversations with Wojcicki—this technology offers a unique, scalable supplement. It enables a continuous, iterative dialogue that helps founders like Strober refine their vision and strategy as they steer their companies through rapid growth, a challenging strategic maneuver in any market.