#219: Dale Wollschleger (ExactCare) — From Pharmacist to Building a Billion-Dollar Pharmacy Care Company

Dale Wollschleger is the Founder and former CEO of Cleveland-based ExactCare Pharmacy and the developer of the ExactPack™—a patient-specific medication packaging system designed to simplify complex medication regimens.

This conversation with Dale dives into the unlikely journey of a pharmacist-turned-entrepreneur who started in the back of a small Cleveland pharmacy and built a billion-dollar organization serving patients across the country.

ExactCare’s meteoric growth—from inception to a multi-hundred-million-dollar (revenue) business in under a decade—has earned it repeated recognition as an Inc. 5000 fastest-growing company; Dale himself was named an Ernst & Young Entrepreneur of the Year.

Ultimately, Dale’s remarkable journey stems from an observation he made as a pharmacist: that pharmacists have the opportunity to play a more integral role in clinical care—and that their responsibility doesn’t end when the patient leaves the store. Many patients could live healthier, more independent lives if only they took the right medications at the right times.

In our conversation, Dale shares how he navigated the many chapters of scaling a healthcare business: bringing in private equity and outside capital, evolving his leadership, and balancing high-growth expectations with a deep commitment to patient outcomes, company culture, family—and much more.

00:00 - The Journey of a Pharmacist Turned Entrepreneur
14:34 - Building ExactCare: Addressing Complex Patient Needs
24:18 - The Evolution and Vision of ExactCare
31:07 - Entrepreneurial Spirit in Pharmacy
38:59 - Understanding the Pharmacy Industry
43:24 - Pride in Building in Cleveland

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LINKS:
https://www.exactcarepharmacy.com/
https://www.linkedin.com/in/dale-wollschleger/

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Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.

Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.

Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.

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Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.

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