From Lawyer to $18 5B Healthcare Deal — How Lee Shapiro Made the Leap

What does it really take to build and scale a healthcare company? In this episode of Boombostic Health, Bradley Bostic sits down with Lee Shapiro—Managing Partner at 7wire Ventures, former President of Allscripts, and co-founder of Livongo—to talk about his journey from “recovering lawyer” to building one of the most successful companies in digital health. Lee shares how he and Glenn Tullman grew Livongo into a public company and ultimately merged with Teladoc in a landmark $18.5 billion deal. He breaks down why healthcare innovation is never an overnight success, how to spot “Uber moments” in healthtech, and why solving consumer hassles is the future of care. Whether you’re an entrepreneur, investor, or operator, this conversation offers a masterclass on building meaningful healthcare businesses that last. Key Moments 00:00 – Intro: Bradley Bostic welcomes Lee Shapiro of 7wire Ventures 01:40 – From lawyer to entrepreneur: Why Lee left law to build companies 05:20 – Allscripts and the early days of digital health 10:30 – The Livongo story: 6-year grind to IPO and $18.5B Teladoc merger 13:50 – The B2B2C model in healthcare explained 15:20 – Consumer hassle mapping: Finding healthcare’s “Uber moments” 17:20 – Value-based care & empowering the patient 19:40 – Scaling through M\&A: The $620M Accolade–Transcarent deal 25:30 – How 7wire Ventures supports portfolio founders beyond capital 29:20 – Doing well by doing good: Investing with purpose in healthcare 31:10 – Cubs or Sox? Lee’s Chicago roots and final thoughts Key Topics Digital health entrepreneurship Venture capital in healthcare How Livongo scaled to an $18.5B deal with Teladoc The future of value-based care Consumer hassle mapping and patient empowerment Healthcare M&A and scaling strategies Connect: 🎙️ Subscribe to Boombostic Health:    / @boombostichealth   📩 Subscribe on LinkedIn https://www.linkedin.com/build-relati... 🔗 Follow Bradley Bostic on LinkedIn:   / bradleybostic   🌐 Learn more about 7wire Ventures: https://www.7wireventures.com/ #DigitalHealth #HealthcareInnovation #VentureCapital #Livongo #Teladoc #BoombosticHealth