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.

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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 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.

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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 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.

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Bought not sold: positioning your company for exit optionality

M&A Is Hard to Get Right

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 and science" of making big calls from incomplete data.

Naomi walks through the hardest chapter at Brightline: after building out a 50 state virtual model to support employers and scaling from nine customers to over 430 in under two years, she realized that the unit economics didn’t work. She got her team into gear, first running experiments and measuring impact week over week and then decided to drastically shift the model to focus on key locations, which led to a rapid four-week wind-down process. She opens up about the deeply personal side of a public pivot, and realizing that even while running a mission driven company you need to be financially viable to continue serving the mission.

About Naomi Allen

Naomi Allen is an entrepreneur and health care executive with more than 20 years of experience building high-growth health technology companies. She is the co-founder and executive chair of Brightline, an award-winning therapy and psychiatry practice that provides pediatric, teen, and parental mental health care to families and children up to age 18.

A mother of three, Naomi co-founded Brightline in 2019 after experiencing firsthand how difficult it can be for families to access timely, high-quality mental health care for children. Since then, Brightline has served hundreds of thousands of families with evidence-based mental health care and support. Today, Brightline serves families through virtual and in-person care across New York, New Jersey, Connecticut, Massachusetts, and Washington.

In addition to Brightline’s clinical services, the company offers BrightLife Kids, a CalHOPE program delivered in partnership with the California Department of Health Care Services. BrightLife Kids provides free online coaching, resources, and support for California families with children up to age 12.

Before Brightline, Naomi served as chief growth officer at Livongo, where she led strategic growth initiatives, including market expansions, acquisitions, and IPO preparation. She was a founding team member at Castlight Health, helping guide the company from startup through its public offering, and worked at McKinsey & Company’s Silicon Valley office, where she helped build the firm’s health care technology practice. Naomi earned an MBA from Stanford Graduate School of Business and a bachelor’s degree from the University of North Carolina at Chapel Hill.

Presented by Aytza

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 generating in person direct to consumer marketplace, before adding virtual services, expanding to b2b sales, and then ultimately selling the company in 2023.

In this conversation, Tori talks about the strategic choices and challenges of building Sesh, the marketplace conundrum at the start, the strategic pivot from consumer to employer sales, navigating a crowded mental health market, and being painted as a point solution. Tori shares the challenges she faced raising her next round of funding, how partnership conversations shifted to become acquisitions discussions, and what it felt like to exit before Sesh had hit the scale and impact she had hoped for. She shares what she'd do differently with hindsight and practical tips for founders who find themselves considering their options.

Tori also gets candid about myth-busting one of the most pervasive startup tropes, the idea that your business is your baby, and how she navigated having her first child at a pivotal time for the company.

About Tori

Vittoria (Tori) Lecomte is the founder of Domestic Futures, a project exploring how technology, markets, and institutions are changing the way we form families. Previously, she founded Sesh, a mental health company acquired by Caraway. She began her career as a technology investment banker at Barclays and later joined Blockchain.com as an early employee. She was named to Forbes 30 Under 30 for Social Impact.

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Bought note sold: positioning your company for exit optionality

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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 the early development of Midi, and how the model expanded based on patient need to offer the full scope of what Midi does today. She digs into how she raised venture capital for a category that didn't yet exist, and the economics of building an insurance-covered, clinician-led virtual specialty care model. Joanna also shares how she manages the business today, building a strong, trusted team so she can dive deep ("like a falcon") into new challenges as they emerge, and standing up the New Product Committee, which helps her turn her constant stream of ideas into disciplined, prioritized bets. Joanna also opens up about deliberately becoming a public figure, how she holds her confidence steady against critics, and how intertwined her personal life is with the business.

About Joanna Strober

Joanna Strober is the CEO and Co-founder of Midi Health, a virtual healthcare platform for women with a focus on perimenopause and menopause. Midi brings expert care, covered by insurance, to women nationwide. Previously, Joanna founded Kurbo, the first digital therapeutic for childhood obesity, which was acquired by Weight Watchers. Joanna also spent 20+ years in direct private equity and venture capital investing in health and consumer companies. She is also the author of the book Getting to 50/50, a primer on how women can succeed and thrive at work and home, and she was named to Forbes' 50 over 50 list of top Innovators, the CNBC Changemaker 2025, and Time 100 Healthcare Leaders.

Read up on Joanna & Midi here:

Midi Instagram

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Joanna’s Instagram

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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 platform of multiple deeply specialized brands of which “Project Samson” (the early working name for their flagship brand Keeps) was the first.

In this conversation, Demetri talks about early structural decisions, like which pieces of the value chain to own vs partner, why controlling that first patient touchpoint was worth a slower launch, and how Thirty Madison pioneered asynchronous telemedicine. Demetri opens up about the hubris trap after Keeps hit big, adding 20-30 people a week in early scaling days, and how they lost (and then regained) some of the rigor that made the first brand work.

Finally, he dives into being on both sides of M&A - acquiring two companies and then exiting via acquisition to get to scale. M&A can leapfrog years of organic growth, but integration is hard. Demetri shares how the team kept multiple paths open until the very end, including seriously considering another acquisition before deciding that selling was the right move.

About Demetri

Demetri Karagas is a New York City–based entrepreneur. He co-founded and led Thirty Madison, a digital health company that grew into one of the leading specialty care platforms in the United States. Founded in 2017, Thirty Madison served millions of patients through brands including Keeps, Nurx, and Cove before being acquired by Remedy Meds in 2025. Prior to Thirty Madison, Demetri founded Get Maid, an on-demand home services marketplace that was acquired by Homejoy. After Google acquired Homejoy, he spent a brief stint working on Search Ads before returning to startup life. Today, he's experimenting with new ideas across healthcare and consumer technology while trying to keep up with his 10-month-old son.

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Bought note sold: positioning your company for exit optionality

Presented by Aytza

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 reentering the startup space, the arc of his journey is less about any one company and more about making the healthcare system more affordable and accessible for all Americans.

Glen talks about what it looks like to lead at every stage, from building office furniture, rapid scaling, to IPO and beyond. He also shares the frameworks that have held across every chapter: make lists, measure what matters, attack ideas not people, and why not to invest in someone who has an exit strategy.

He talks about why he doesn't believe in work-life balance, instead focusing on working on things that matter and prioritizing family. And because Glen is Glen, he also built a 40,000-square-foot magic experience in Chicago to fulfill a childhood dream and bring people together.

About Glen Tullman

Glen Tullman is the Chief Executive Officer of Transcarent, the first comprehensive, consumer-directed health and care platform that makes it easy for people to access high-quality, affordable health and care. He is the former Executive Chairman, Chief Executive Officer, and Founder of Livongo Health. Glen led Livongo through the largest consumer digital health Initial Public Offering in history and the industry’s largest merger to date between Livongo and Teladoc Health.

A visionary leader and entrepreneur, Tullman previously ran two other public companies that changed the way health care is delivered: Allscripts, the leading provider of electronic prescribing, practice management, and electronic health records for physician practices and Enterprise Systems, the leading resource management systems for hospitals, which he also took public and then sold to McKesson/HBOC. Glen is also one of two Founding Partners at 7wireVentures, a leading healthtech venture fund. He is the author of On Our Terms: Empowering the New Health Consumer, in which he proposes new solutions to address the chronic condition epidemic facing our country. 

Resources & Links:

Bought note sold: positioning your company for exit optionality

Presented by Aytza