The Five Mile Difference

Episode 5: Stephanie Strong – Transforming Addiction Treatment With Boulder Care

In this episode of The Five Mile Difference, I sit down with Stephanie Strong, founder and CEO of Boulder Care, to talk about what it takes to reimagine addiction treatment in America.  Stephanie shares her journey from shaping health policy in D.C. to venture investing to founding Boulder, which has now cared for more than 30,000 patients through a fully virtual model. We explore her decision to focus on Medicaid, the unique challenges of payer contracting, and the values that guide Boulder through industry uncertainty. We discuss: * How early policy work shaped her founder journey * Why focusing on Medicaid patients creates the most impact * The importance of advocacy in shaping telehealth rules * Lessons from building patient-first culture at scale * How Boulder proved virtual addiction care can outperform in-person Stephanie holds degrees from Duke and has dedicated her career to the intersection of health policy, innovation, and care delivery. Today, she leads Boulder Care from Oregon, expanding access to life-saving treatment nationwide.

Episode 4: Tim Barry – Lessons from $5.7B Healthcare Outcome

In this episode of The Five Mile Difference, I sit down with Tim Barry, former CEO and Co-Founder of VillageMD, for a conversation on what it takes to truly transform healthcare delivery in America. We explore Tim’s journey from his early entrepreneurial ventures to building one of the nation’s fastest-growing primary care providers, serving millions of patients through Village Medical, Summit Health, CityMD, and Village Medical at Home. Tim shares lessons from his first startup, Evo Knowledge, the resilience needed after failure, and the vision behind VillageMD’s integrated, outcomes-driven care model. We discuss: 1. Why healthcare delivery must focus on outcomes, not just processes 2. How investing in primary care improves patient health and lowers costs 3. The importance of resilience in overcoming setbacks 4. Building strong physician relationships as the foundation for growth 5. Navigating the shift from idea to scaled impact Tim earned his undergraduate degree in agricultural economics from Cornell University and a graduate degree from Michigan State University. He lives in the Chicago area with his wife and family.

Episode 3: Roy Rosin – Driving Innovation in Healthcare

The importance of behavioral economics, rapid experimentation, and the role of policy in driving healthcare innovation. Description: In this episode of The Five Mile Difference, host Joe Kitonga sits down with Roy Rosin, Board Partner at First Round Capital and former VP of Innovation at Intuit and Chief Innovation Officer at Penn Medicine, for a compelling conversation on what it really takes to move the needle in healthcare. They explore the "Five Mile Difference" in life expectancy in Philadelphia and unpack Roy’s journey from leading innovation in tech to transforming healthcare delivery at Penn Medicine. Roy shares lessons learned, common pitfalls in healthcare innovation, and where he sees the most promise, especially as AI, behavioral economics, and telehealth continue to evolve. This episode dives deep into the structural, behavioral, and systemic levers that can drive meaningful change, with an emphasis on collaboration, empathy, and persistence. We cover: * Why healthcare innovation requires a mission-driven mindset * How behavioral economics can improve outcomes * The rising potential of disruptive innovation powered by AI * How telehealth is evolving beyond just digitizing care * The importance of cross-sector collaboration * How regulation can unlock new opportunities * Addressing social determinants of health for equity * The role of rapid experimentation in finding what works * Why empathy and storytelling matter in stakeholder engagement * The need for relentless persistence in this complex industry About our guest: Roy Rosin is a seasoned innovation leader with a track record of building and scaling impactful programs. He spends most of his time at First Round in the healthcare space, drawing from his experience as Chief Innovation Officer at Penn Medicine. During his 12-year tenure, his team designed, tested, and implemented 150 technology-enabled interventions across care delivery. These novel solutions decreased readmission rates, ER utilization, morbidity, hospital stays, and clinician burden while increasing adherence, screening, patient engagement, quality of life, and use of high-value sites of care. Earlier in his career, Roy built and led the innovation program at Intuit, where he spent 18 years. Starting as the product manager of Quicken, he helped grow it into the top-selling consumer software application with 14 million consumers. After five years of redesigning entrepreneurial practices, which were also applied to existing businesses, Intuit delivered shareholder returns 33x the S&P 500. Throughout his career, Roy has learned from some of the best, including Scott Cook, Bill Campbell, and Brad Smith at Intuit, as well as leading behavioral scientists at Penn, and remarkable founders who showed him how hard things could become possible. He received his MBA from Stanford and graduated with honors from Harvard College as a John Harvard Scholar.

Episode 2: Dr. Kate Baron and Dr. Ash Shaub — A Safer Path to GLP-1s

Beyond prescriptions: A primary care-led path to long-term weight loss GLP-1 medications, such as semaglutide and tirzepatide, have seen a surge in popularity for weight loss, but behind the hype lies a growing concern: are we trading safety for convenience? With more and more programs offering prescriptions without proper evaluation or follow-up, many patients are left navigating powerful medications on their own. In this episode, we dig into what GLP-1s are, why they work, and what’s being missed in today’s one-size-fits-all approach. Host and Vitable CEO Joe Kitonga is joined by Dr. Kate Baron and Dr. Michael Ash Shaub of Vitable Health to talk about the risks of low-touch prescribing, the importance of primary care oversight, and how long-term success depends on more than just a shot. We cover: 💉 How GLP-1s work and why they’re so effective for weight loss ⚠️ The dangers of unsupervised use—from thyroid risk to nutritional deficiencies 🧠 Why behavioral support and lifestyle changes matter just as much as medication 🏥 The role of primary care in creating safer, more sustainable outcomes 📉 What happens when patients stop GLP-1s without a plan—and how to avoid it — About our guests: Dr. Kate Baron is Head of Medical at Vitable Health, where she oversees medical operations, ensures clinical excellence, and drives innovation in virtual care delivery. As a Board Certified Family Physician with experience scaling early-stage digital health companies, Dr. Baron’s work centers on expanding access to primary care, improving chronic disease management, and delivering patient-centered, high-quality care. Dr. Michael “Ash” Shaub is the Chief Clinical Officer at Vitable Health, where he oversees clinical strategy and clinical operations. With a background in both medicine and business, he’s passionate about building world-class comprehensive care models that improve access, outcomes, efficiency, and the patient experience - especially for working adults often left behind by traditional healthcare.

Episode 1: Tom Sondergeld — Bridging the Healthcare Gap

What causes a 20-year life expectancy gap between two zip codes just five miles apart? In the premiere episode of The Five Mile Difference, Joseph Kitonga, founder and CEO of Vitable Health, sits down with Tom Sondergeld, former VP of Global Benefits & Mobility at Walgreens Boots Alliance, the multinational company that owns Walgreens, to unpack one of healthcare’s most urgent challenges: closing the access gap for Americans. Drawing on his experience leading benefits for a workforce of over 250,000 employees and managing $2B a year in healthcare budget, Tom shares what it takes to design equitable health plans, what employers get wrong about engagement, and why the U.S. must shift from a sick-care system to one focused on prevention. The conversation spans the evolution of digital health, behavior change, the role of GLP-1s, and innovations like ICHRAs and level funding. About Tom Sondergeld Tom Sondergeld is a nationally recognized leader in healthcare and employee benefits strategy with over 30 years of experience driving transformation across Fortune 50 companies, startups, and global organizations. As the former Vice President of Global Benefits at Walgreens Boots Alliance, he led healthcare programs for one of the largest workforces in the world, delivering innovative solutions that saved hundreds of millions of dollars without raising costs for employees. Today, Sondergeld is the founder and Managing Partner of TS Consulting Services, where he advises startups, employer groups, transparent PBMs, and private equity-backed healthcare ventures. He also serves as a senior expert at McKinsey & Company, consulting with employers and payers on benefits design and delivery. Known for his deep industry relationships, strategic thinking, and operational excellence, Sondergeld is a trusted voice at the intersection of healthcare innovation, cost control, and access to care.