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 services. After more than a year navigating enterprise relationships and building around entrenched infrastructure, the team discovered that patients weren’t actually making the decisions they had designed the product around. Oron shares how that failure pushed Vim from patient-facing to provider-facing, and eventually from a point solution into the platform it is today.

He talks about using design partners without becoming a custom dev shop, what it takes to keep reinventing a company over more than a decade, and the difficult process of rebuilding Vim to become AI-native while still supporting a large existing business. He also makes the case that AI is changing an old startup assumption: building something bespoke for one customer may no longer be a bad thing.

About Oron

Oron Afek is the co-founder and CEO of Vim, a collaborative healthcare system that brings innovation directly into clinical workflows. Vim's proprietary integration layer sits securely on top of the electronic health record and, through a single JavaScript SDK (VimOS.js), standardizes clinical workflow events and data across otherwise incompatible EHRs — so any developer can build once and deploy everywhere, in-workflow, with bi-directional data exchange and no new logins or systems. On that foundation, partners deliver point-of-care experiences like insights, referrals, and documentation directly to care teams.

Presented by Aytza

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 the United States.

In this conversation, Tara talks about running clinical operations with a ruthless focus on profitability, reaching sustainable margins on a hybrid insurance-plus-membership model, and why she believes you need both a strategic vision and the discipline to watch every dollar. She opens up about the brick-and-mortar "red herring" that distracted her: she was crushing build-out efficiency, but the real problems were inefficiency of marketing dollars and the partnerships a single location couldn't unlock. She walks through the excruciating decision to shut the clinic, the early-2025 shift to a telehealth-only subscription that opened new horizons, and what she'd do differently. She digs into building a better filter as a founder, reading a venture-funded market where growth can mask what's really happening under the hood, and building the muscle to absorb the constant sting of setbacks without buying into the "die trying" mythology. Finally, she shares where Almond is headed: unlocking one of the largest functional women's health data sets.

About Tara

Tara Raffi is the Founder & CEO of Almond OB-GYN, reimagining women's health as proactive and personalized. A UC Berkeley, McKinsey, and Y Combinator alum, Tara believes in a world where women's bodies are studied and understood, and where they get true healthcare before cues become crises.

Presented by Aytza

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 months prior, to the inbound offer that set things in motion, and the nitty gritty of managing an exit.

Drew talks about both the mechanics and the emotional reality of a strategic sale and shares advice for other founders. He explains why you can never tip your hand that you're a seller without losing all your leverage, why the conversations that went furthest came from prior relationships, and why lining up the right value proposition with the right executive at the right time is the hardest part. Drew talks through surviving an earlier near-exit that didn't close, and the roughly 75/25 split between running the sale and running the company, and how to successfully get through a diligence.

Then there's the morning after the close, when Drew says he felt 5,000 pounds lighter and realized just how much weight founders carry the whole way through.

About Drew

Drew Schiller is the Chief Development Officer & Board Director at ChartSpan. Prior to that he was the CEO and co-founder of Validic (founded in 2010 with his co-founder Ryan), a platform that connects data from wearables, in-home medical devices, and health apps into the healthcare system, which was acquired by ChartSpan in 2026.

Presented by Aytza

Resources

Bought not sold: positioning your company for exit optionality

M&A Is Hard to Get Right