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. 

Presented by Aytza

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

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