CEO Pajama Time

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...

What do you do when you haven’t yet reached scale, but market conditions have changed and runway is running out? Tori Lecomte founded Sesh in 2019 to bring the power of therapist-led group therapy to consumers. Not coming from a healthcare or CEO background, but convinced the modality was dramatically underutilized, she focused on making sure she had market validation, launching a revenue generati...

What do you do when lawyers tell you the thing you're building probably isn't possible? Demetri Karagas co-founded Thirty Madison in 2017 with no healthcare background, a consumer business playbook, and a conviction that a one-stop shop for telemedicine and prescriptions was obviously better for patients, even if the lawyers weren't sure it was possible. He and his cofounder had a vision for a pla...

Most founders get one shot at building something that matters. Glen Tullman has taken several, and he keeps going back for more. In this conversation, Glen traces the through-line of a career spent trying to fix a healthcare system that, in his words, still runs 50 years behind every other industry. From the early days of building Livongo into a category-defining chronic care company, to reenterin...

What happens when a founder is offered $100 million and takes half on purpose? Deepak Thomas started PHIL in 2015 after his own experience with chronic Lyme disease highlighted the gap between consumer-grade technology and how patients access medication. Phil now works with patients, prescribers, manufacturers, and pharmacies to make high-cost therapies accessible by solving for the two things tha...

Episode Description Most digital health companies of Validic's vintage have raised $100 million or more. Drew Schiller raised $35 million over 12 years, on purpose. Validic connects data from over 700 wearables, in-home medical devices, and health apps into the healthcare system. Drew started the company in 2010 with his college best friend Ryan, pivoted from corporate wellness into a data infrast...

Michelle Davey built Wheel from a bootstrapped clinician-matching service into the infrastructure behind virtual-first care for some of the largest healthcare enterprises in the country like Amazon Clinic. In this conversation, she gets honest about what that evolution actually looked like. She talks about walking into a board meeting with the investor hockey stick chart and telling them they need...

Taylor Justice spent 13 years building Unite Us from a veteran services startup into the infrastructure connecting healthcare, government, and community organizations across the country. In this conversation, he gets honest about what that actually looked like. He talks about the first thing they built being wrong. The investor who told him healthcare was a mistake, then wrote back a year later to...

Jen Goldsack has spent six and a half years building the Digital Medicine Society (DiMe) into a trusted voice for healthcare's digital transformation. In this conversation, she shares the inflection points that shaped the organization. And the real story behind them. Like the time a family office offered $4 million if DiMe would pivot to focus only on cancer. She said no. Then sat on the floor cry...

How Dan Vahdat Built Huma: The Platform Approach to Healthcare Innovation Enjoy this behind-the-scenes look at how bold vision, stubborn persistence, and platform thinking are revolutionizing healthcare, one disease, one regulation, one market at a time. Dan Vahdat, CEO of Huma, shares the story behind creating a platform that scales across diseases, regulations, and markets without losing sight o...

Most healthcare startups fail because founders chase every opportunity without knowing what to say no to. Kate Ryder built Maven into the first women's and family health unicorn by doing the opposite. In this conversation, Kate walks through the inflection points that shaped Maven: strong early signals, the decision to wind down Maven Campus when demand did not translate into a sustainable busines...

Welcome to CEO Pajama Time , the podcast that offers a candid look at the behind the scenes decisions and strategic turning points every founder faces. Host Sari Kaganoff, CEO and Founder of Aytza, sits down with healthtech leaders to explore the most difficult choices they made while scaling and the key inflection points that defined their journey.