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

phil.berry@northwindhealth.com

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/