The Second Act Power Play

Midi Health's CEO on ambition in midlife.

Me (left) and Joanna Strober (right) in Montana, where we talked about weightlifting, menopause and starting a company in her 50s.

At an age when the world often tells women to wind down, Joanna Strober is hitting her stride.

The longtime venture capitalist, now 56 years old, started her career at Bessemer Venture Partners, and invested in multiple consumer internet and software startups, including Blue Nile and BabyCenter. Seven years heading venture capital and private equity at Silicon Valley investment firm Sterling Stamos led Joanna to become an entrepreneur. In 2014, she founded Kurbo Health (a digital platform for childhood obesity), led the company as CEO for four years, and sold it to Weight Watchers.

She launched Midi Health—a virtual care platform for women navigating perimenopause and menopause—at 52. The move was more than just a career pivot. It was visionary.

“I had more time and energy than I ever had,” Strober says of that stage of life. “My kids had left the house. The opportunity was so obvious.”

I met Strober in Montana at the annual Kickoff Retreat for JOURNEY, a women’s leadership organization where she’s a fellow. "During Covid,” Strober recalls, “I went for a walk with my best friend, Susan Wojcicki [the former CEO of YouTube, who passed away from cancer in 2024] and talked to her about the idea for Midi. I said, ‘I really think this could be a big company.’ She believed in me. That mattered."

Founded in 2021, Midi Health offers insurance-covered telehealth visits designed specifically for women over 40—a demographic that, despite being half the population, has been chronically underserved by the healthcare system. Midi is now one of the fastest-growing companies in women’s health, helping tens of thousands of women each month access trained clinicians and personalized hormone care from the privacy of home.

For Strober, it’s about closing a care gap she was shocked to discover still exists.