How Phillip Berry Bootstrapped Northwind for 18 Years to Do What $500 Billion Giants Can't

In this episode, I sat down with Phil Berry, founder and CEO of Northwind Health, who has bootstrapped the company for nearly 18 years to over 100 people and close to $100M in revenue while taking on massive healthcare incumbents. We compare his early survival-mode years—keeping headcount lean, fearing payroll, and carrying the business himself—with his shift toward intentional growth, leadership hiring, and asking what the business is “called to do” beyond his personal identity. Phil shares how meaning emerged through employee wins and patient outcomes, shaped by his Catholic faith and a focus on human dignity, which he frames as serving “souls,” not “lives” or “belly buttons.” We also unpack why the healthcare system functions as “sick care,” why big players can’t structurally reduce costs, and how Northwind aims to scale high-touch, waste-removing, outcomes-driven care. 01:13 Founder Mindset Shifts 02:18 Early Hiring and Survival 06:24 Finding Meaning in Work 10:25 Planning Beyond Survival 13:10 Belief and Big Bets 14:42 Stewardship and Scaling 20:04 Separating Identity from Business 22:08 Is Growth Always Right 26:46 Leading in the Tension 30:06 Human Flourishing Thesis 34:01 Fixing Sick Care at Scale 39:14 Human Dignity in Healthcare 42:49 Defining a Human Soul Connect with Phillip:  • Northwind https://www.northwindhealth.com Personal website: https://www.phillipberry.com [email protected] Connect with Raul:  • Work with Raul: https://dogoodwork.io  • Free Growth Resources: https://dogoodwork.io/resources • Connect with Raul on LinkedIn (DMs open): https://www.linkedin.com/in/dogoodwork/