Tim Wentworth, Retired CEO of Walgreens : From Parking Lots to Boardrooms - Leadership Lessons running multi billion dollar companies

On this 3d long-form edition of #TheShot of #DigitalHealth Therapy, Jim Joyce and I had the privilege of sitting down for an unforgettable deep dive with Tim Wentworth, the candid, thoughtful, fiercely grounded and recently retired CEO of Walgreens (previously CEO of Evernorth Health Services). Tim’s story reads like a masterclass in leadership and life itself - from sweeping parking lots in Rochester to leading global healthcare giants like Cigna’s Evernorth and Walgreens. Across nearly two hours (and honestly, we could’ve gone four), Tim brought raw honesty, wisdom, and humor to every story - from his early scholarship thanks to a teacher who believed in him, to leading multi-billion dollar companies but always defining what it means to lead with heart. This is not just a leadership interview - it’s a living case study in resilience, humility, and purpose. 🧠 Key Takeaways 🔥 From parking lots to the C-suite 🏢 The birth, growth, and controversy of PBMs 💊 Merck - Medco, and the spin-off that changed healthcare 💼 Crisis leadership 101 💰 Cigna, Evernorth, and the end of rebates? 🏪 Walgreens, reinvention, and going private 💡 The power of asking for help 🎯 Leadership as legacy Fun mentions as always: Shaine Borukhovich Jay Parkinson, MD, MPH Dr Jack Kreindler Roberto Ascione Mark Cuban Robert Pellegrini Glen Stettin, MD David Snow Kenny Klepper David Benshoof Klein Richard Lungen Frank Sheehy David Cordani Neal Sample Per Lofberg 00:00 — Cold open: Parking-lot beginnings & the teacher who changed Tim’s life 06:20 — Early career: Music industry, Pepsi, Mary Kay, discovering healthcare 13:40 — Joining Medco: First exposure to healthcare operations 21:10 — PBM history: Why PBMs exist, why pharma once owned them, and why that broke 31:55 — Merck → Medco spinout: Fixing the original conflict of interest 41:12 — Express Scripts: Crisis moments, lawsuits, leadership under fire 50:28 — Cigna acquisition: Building Evernorth and changing the role of services 01:02:00 — The “no more rebates” move: What it means and why it matters 01:15:45 — Why Tim came out of retirement to lead Walgreens 01:20:50 — Was he brought in to take Walgreens private? 01:29:30 — Running a 300,000-person company vs. running a PBM 01:38:40 — The future of community pharmacy & neighborhood care 01:46:10 — Startups, AI, and what founders keep getting wrong 01:54:50 — Leadership legacy & advice to his younger self