Surviving long enough to win

Surviving long enough to win

What happens when a founder is offered $100 million and takes half on purpose? Deepak Thomas started PHILl 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 that matter most: price and convenience. In this conversation, Deepak talks about the capital discipline behind turning down $100m in funding in favor of taking half that amount, why character eats resume for lunch in early-stage hiring, how PHIL survived three distribution pivots before landing on enterprise sales, and why startups succeed through hermetic stress rather than hedging. This one is for founders optimizing for unit economics, not just the next financing round. About Deepak Deepak Thomas is the Founder and CEO of PHIL, a healthcare technology company modernizing how patients access prescription therapies. He founded PHIL more than a decade ago after seeing how fragmented, manual, and outdated the medication access experience remained for patients, providers, and pharmaceutical manufacturers. Today, PHIL partners with leading life sciences manufacturers to help millions of patients start and stay on therapy through a technology-driven, outcomes-based platform. Under Deepak’s leadership, the company has grown into a late-stage, fast-growing, profitable business in one of healthcare’s most complex categories. On CEO Pajama Time, Deepak shares lessons from building PHIL, navigating strategic inflection points, and turning long-held conviction into a scaled company. Presented by Aytza

The Midnight Pivot That Became Validic

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 infrastructure play, then later expanded into health systems and acquired a logistics business to own the full stack. Drew talks about the midnight conversation with Ryan where they realized they couldn't out-build Fitbit or MyFitnessPal and decided to solve a different burning market need of integrating data into them instead. He also talks about why he devotes a full day every month with his leadership team to talk about nothing but strategy, and how the Validic team rewrote the company's core values in 2018 without him in the room. This one is for founders building infrastructure businesses, navigating pivots, or trying to figure out when slower growth is the right call. About Drew Schiller Drew Schiller is the CEO and co-founder of Validic, the platform that connects data from wearables, in-home medical devices, and health apps into the healthcare system. He started the company in 2010 with his college best friend Ryan, and launched Validic in 2013 after a midnight pivot away from corporate wellness software. Today the platform normalizes data from over 700 sources into a single API used by health systems, health plans, and digital health companies. Presented by Aytza

Killing Growth to Build a Lasting Company: with Michelle Davey, CEO of Wheel

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 needed to change course despite it. About pivoting from SMBs to enterprise when every instinct said keep the revenue coming. About acquiring GoodRx's care platform and integrating it in only nine months. About over-hiring in 2021 and the dark days that followed when she had to unwind it. She also talks about her actual pajama time: blocking mornings for reading, then picking back up after the kids go to bed to catch up on what's happening in the market. As Michelle puts it: "A lot of people get into being a founder because it seems glamorous. It is not." In this episode: * From Enzyme to Wheel: the three horizons of building virtual-first care infrastructure * The board meeting where she stopped chasing SMB growth * Acquiring GoodRx's care platform and building an EMR she said she'd never build * Horizon 3: An AI-native platform powering programs like weight management, menopause, and longevity * Her biggest mistake: over-hiring in 2021 and the layoffs that followed * Hot take: "GLP-1s are going to be more disruptive to healthcare than AI" * The signal she's watching: stagnation in large payer market values About Michelle Davey Michelle Davey is the CEO and founder of Wheel, the infrastructure platform powering virtual-first care for enterprise healthcare companies. She started the company in 2018 after spending 15 years undiagnosed with an autoimmune condition in rural Texas. That experience drove her into healthcare, but the perverse incentives drove her out and into tech, where she built her career across startups and gig economy marketplaces before finding her way back to telehealth in 2016. Today, Wheel’s AI-native Horizon platform is on track to power 3 to 4 million patient visits this year for enterprises including retailers, pharmaceutical companies, and digital health brands. Presented by Aytza

Two Acquisitions in 60 Days: What Scaling That Fast Actually Looks Like with Taylor Justice

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 say he was wrong. He also talks about the reality of scaling fast. Tripling headcount. Two acquisitions in 60 days. And what it took to stay the course when everything is moving at once. As Justice puts it: “This sh*t is hard. And you definitely cry sometimes." In this episode: * Building for veterans, then pivoting into healthcare before knowing the landscape * The first product they built (and why it was wrong) * Realities of scaling fast: 300 to 900 people, two acquisitions, and trying to stay focused * 12 years with a co-founder, and what it's like now that he's gone * Myth bust: "Stealth mode is the biggest waste of time" Taylor Justice Taylor Justice is the CEO and co-founder of Unite Us, a software company connecting healthcare, government, and community organizations to coordinate care around health-related non-medical needs like food, housing, and transportation. A former U.S. Army infantry officer, Taylor was medically discharged and built Unite Us out of his own experience navigating the VA system and the gaps he saw for veterans without a network. Thirteen years later, Unite Us operates throughout the United States and has raised over $250 million to transform how human services are delivered.

Jen Goldsack’s Journey from Olympian to CEO, Declining a 20x Offer to Stay True to the Mission, and Leading Through Cancer

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 crying with her dog, knowing she'd just made everything harder. Or the org structure she championed for two years that wasn't working. And the courage it took to acknowledge it and rebuild. This year, she's been navigating all of it while fighting late-stage colon cancer. She talks about the brutal self-talk that preceded her diagnosis, what being a patient has taught her about the system she's trying to fix, and why the work feels more urgent than ever. In this episode: * Turning down $4M to protect DiMe's positioning as "expert generalists" * The org structure shortcomings she wishes she'd caught sooner * What it's like to navigate the healthcare system as a patient after 20 years working in it * Hot take: Why longevity tech investment is "incredibly gratuitous" * The signal she's watching: direct-to-patient pharma pathways About Jen: Jen Goldsack founded and leads DiMe, a nonprofit working to ensure digital technologies actually improve health, healthcare, and research. Her path to healthcare leadership started unexpectedly. She landed in the field during the 2008 financial crisis after competing in the Beijing Olympics as an elite athlete. Before DiMe, she built experience across two digital health startups (one successful exit), led digital initiatives at a Duke-FDA partnership, and conducted research at Penn. Today she sits on the boards of the Coalition for Health AI and Sage Bionetworks, and contributes to the National Academies' Roundtable on Genomics and Precision Health. She holds three graduate degrees: chemistry from Oxford, history and sociology of medicine from Penn, and an MBA from George Washington. Beyond her professional credentials, Jen is a Pan American Games champion, former world record holder, and World Championship silver medalist. Resources & Links: Digital Medicine Society (DiMe) - https://dimesociety.org/ [https://dimesociety.org/] Follow Jen Goldstack - https://www.linkedin.com/in/jgoldsack [https://www.linkedin.com/in/jgoldsack] Presented by Aytza https://www.aytza.com/ [https://www.aytza.com/]