HeyJaredCEO Pajama Time
CEO Pajama Time takes you inside the after-hour decisions and toughest strategic choices made by founders as they scale.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 10, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 9, 2026
Latest episodes
In the Business of Reinvention (opens the original)
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What do you do when you’ve built a product that works, solved the technical hurdles, landed major customers, and then realize you’ve built it for the wrong decision maker? Oron Afek is the co-founder and CEO of Vim, a collaborative healthcare system that brings innovation directly into clinical workflows. In this conversation, Oron walks through Vim’s eleven-year journey, starting with its first incarnation as BookMD, a marketplace designed to steer patients toward more cost-effective healthcare
The Morning After the Exit (opens the original)
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What does it take to sell the company you spent 16 years building, and how does it feel the morning after? Drew Schiller returns to CEO Pajama Time, this time from the other side of an exit. In June 2026, Validic, the platform he co-founded in 2010 to connect data from wearables and in-home medical devices into the healthcare system, was acquired by ChartSpan. In this conversation, Drew walks through the full arc of the sale, from the work his leadership team did to map the acquirer landscape 18
Beware the Red Herring: A Founder’s Balancing Act (opens the original)
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What do you do when you've built the ideal care model and realize it won't scale? Tara Raffi is the founder and CEO of Almond OB-GYN, a functional OB-GYN practice built on the belief that women should be living more healthy years, and that much of the solution to our health problems is found in lifestyle: sleep, stress, diet, exercise, metabolism, gut, and pelvic and vaginal health. Tara’s mission was to build a hybrid in person and virtual functional clinic for the $200 billion OB-GYN market in
Pivoting in public: Building a business that sustains the mission (opens the original)
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What do you do when the model you spent years building isn’t working economically, and the only way forward is to drastically change the shape of the business? Naomi Allen is the co-founder of Brightline, a pediatric mental health company. She previously held leadership positions at Castlight and Livongo. In this conversation, Naomi talks about leading through profound uncertainty as both a parent and a CEO, especially in the early days of building Brightline during COVID. She shares the "art an
Built on trust: Category creation in women’s health (opens the original)
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How do you convince investors, patients, and the healthcare system that a new category in women's health needs to exist? Joanna Strober is the founder and CEO of Midi Health, the telehealth company providing insurance-covered primary care for women navigating perimenopause, menopause, and beyond. Joanna started Midi in 2021 after her own frustrating search for menopause care, following an earlier career as a venture capitalist and as health tech founder. In this conversation, Joanna talks about
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