Earn Your Leisure Podcast: “CEO Made $120 Million From Healthcare”

Hosted by Rashad Bilal & Troy Millings | Guest: Tommy Duncan
Release Date: January 1, 2026

Episode Overview

In this deep-dive episode, hosts Rashad Bilal and Troy Millings sit down with Tommy Duncan, serial healthcare entrepreneur and founder of JetDoc. Tommy shares his extraordinary journey: from growing up in a Black-owned healthcare family in Detroit, through dramatic wins and losses, to building and selling businesses for over $120 million. The conversation gives behind-the-scenes financial views, breaks down healthcare business models, and offers actionable advice for entrepreneurs. They also discuss the critical political and community dynamics shaping the healthcare industry.

Key Discussion Points & Insights

1. The True Scale and Nature of the Healthcare Business

• Healthcare is the “biggest business in the world” (08:51), comprising 24% of the American budget—larger than even the military.
• The industry is recession-proof and “everything proof,” because healthcare needs persist regardless of economic cycles.

“People don’t necessarily think of healthcare as a business. It is a business. The biggest business.”
— Rashad Bilal (08:51)

• Tommy highlights that significant wealth in seemingly unrelated scenes, like Paris Fashion Week, often traces back to healthcare earnings.

“The folks with the money that's actually spending, they in healthcare.”
— Tommy Duncan (11:50)

2. Early Exposure: Family in Black-Owned Healthcare

• Tommy’s mother (academic) and stepfather (entrepreneurial) bought United Community Hospital in Detroit, making it one of the last Black for-profit hospitals (13:01).
• As a child, Tommy was on the “sales team,” knocking on doors to sign people up for Medicaid, learning business by osmosis.
• At its peak, the family business had $40M/year revenue but lost it all due to over-investment and lack of separation between personal and business assets (15:49).

“They had the biggest house in Detroit; they literally put it up trying to save the hospital...they lost everything.”
— Tommy Duncan (15:48)

• Key lesson: Don’t get emotionally attached to the business; don’t risk everything for one venture.

3. Early Ventures and Entrepreneurial Trials

• Tommy tries ice cream trucks and sandwich shops as a student but finds he doesn’t love the business, ultimately failing and returning to healthcare.
• Importance of aligning business with personal passion and unique expertise.

“Even though I could grow the business because I could sell, I didn’t like...the business itself. So ultimately, all failed.”
— Tommy Duncan (19:13)

4. Game-Changing Healthcare Model: Medicaid Managed Care

• Tommy explains the government pays a set fee per Medicaid member to insurance companies (“managed care”), who assume risk for all member healthcare costs.
• He describes winning a contract for 30,000 members, generating $12 million/month in revenue (26:27).
• The industry average profit margin is ~2%, but Tommy achieved over 10% by deeply studying data and targeting highest-cost members (29:57).

“Big companies are built with mediocre people...I own 40% of my company. So if I make 20 million, eight million is coming to Tommy Duncan’s pocket.”
— Tommy Duncan (28:23)

5. Data-Driven Community Impact: Reducing Costs by Addressing Homelessness

• Tommy discovers that homeless members’ healthcare costs are 5x higher than the average. By building outreach programs and housing initiatives, he reduced homelessness by 50% and massively increased profitability (30:22).
• Example of “doing well by doing good": Improving community health directly improves the bottom line.

“The only metric we needed to focus on was getting folks that were homeless into housing...Cost came down at 50% and our profitability went up.”
— Tommy Duncan (29:57)

6. Scaling, Exits, and Major Deals

• Tommy details buying and selling a health plan from Tenet (for $13M, sold for $22.5M), then building and later selling another Medicaid insurance company for $120M (44:59, 54:01).
• Discusses how to value companies: healthcare services (~8x EBITDA), tech companies (up to 20x+ revenue).
• Stresses the necessity of understanding political dynamics in governmental contracting—contracts often hinge on relationships at the governor level (33:25 – 36:11).

“Go to where the opportunity is...the environment has a big impact on your opportunity.”
— Tommy Duncan (33:25)

7. The Harsh Realities of “Wolf of Healthcare”

• Tommy recounts business battles, investor power struggles, and surviving losing $1M+/month after a deal gone wrong—but ultimately negotiating, restructuring, and selling for major profit anyway (50:01 – 53:22).
• Reveals the emotional/financial hazards of attaching personal identity to business, advocating for rational deal-making and exit strategy.

8. Entering Health Tech: JetDoc & the Future

• After exiting, Tommy quickly founded JetDoc, a telehealth platform, but struggled with direct-to-consumer traction. He pivots to a B2B and government licensing model, using relationships and recurring tech contracts for scalable growth (63:12, 67:05).

“If you’re in tech, it’s like...you get a couple contracts, now you’re 40 million—and you’re just doing tech.”
— Tommy Duncan (69:05)

• JetDoc’s innovation: Integrates remote patient monitoring devices, aiming to disrupt managed care by targeting the highest-cost problems (e.g., chronic illness, homelessness).

9. System Flaws and Solutions: Fixing Medicaid and Medicare

• Tommy’s book, “The Trillion Dollar Medicaid Monster,” argues that mandatory “medical loss ratio” (requiring 85% of funds go to care costs) disincentivizes innovation and cost control (78:03).
• He proposes that removing such requirements and incentivizing cost reduction would foster real healthcare efficiency and improved outcomes.

“The only way to really get cost down in healthcare is to get people healthier...If I can get my costs lower, I should get more business.”
— Tommy Duncan (78:56, 84:33)

10. Advice for Entrepreneurs

• Emphasizes doing deep industry research, calculating risk before jumping into business, understanding failure rates, and knowing what “upside” you’re pursuing: lifestyle income vs. value creation and big exits (87:37).
• Celebrate the era of entrepreneurial disruption: social media has removed traditional resource barriers—“every industry is up for disruption” (91:28).

“I just really advise people, do their homework, calculate risk—but take risk...If you want more, you gotta do more.”
— Tommy Duncan (90:14)

Notable Quotes & Moments (with Timestamps)

• On the size of healthcare as a business:
  “Healthcare is the biggest business in the world... Recession proof, everything proof.”
  — Rashad Bilal (08:51)

• On growing up in Black-owned healthcare:
  “I grew up selling people on health insurance for low income. By osmosis, I learned the business.”
  — Tommy Duncan (13:13)

• On learning from setbacks:
  “What happens for us...is we are met with failure. But that’s where the wisdom is.”
  — Tommy Duncan (14:39)

• On the power of government contracting:
  “Go to where the opportunity is...the environment has a big impact on your opportunity.”
  — Tommy Duncan (33:25)

• On maximizing profit through community impact:
  “Out of all the metrics and data in healthcare, the only metric we needed to focus on was getting folks that were homeless into housing... Our profitability went up directly.”
  — Tommy Duncan (29:57)

• On when it’s time to be rational about selling:
  “There’s no emotional attachment to business. You have to look at it from a very rational standpoint.”
  — Rashad Bilal (60:59)

• On company valuation (tech vs. services):
  “If you’re in tech, it’s like...you get 10, 15x [top-line revenue]; you get a couple contracts, now you’re 40 million.”
  — Tommy Duncan (68:56 – 69:05)

• On the future of entrepreneurial opportunity:
  “Because of social media, every industry is up for disruption...it’s the first time in history that’s the case.”
  — Tommy Duncan (91:28)

Key Segments & Timestamps

• Why Healthcare is Big Business: 08:51 – 11:10
• Duncan’s Family History in Healthcare: 12:01 – 15:48
• Early Entrepreneurial Failures & Lessons: 18:40 – 21:12
• Getting Into Medicaid Managed Care: 25:04 – 27:02
• How Data & Focus on Homelessness Boosted Profits: 29:57 – 31:50
• Government Contracts and Political Realities: 33:25 – 38:27
• Winning, Losing, and Selling Health Plans: 44:59 – 53:47
• Valuing and Selling a Company, Private Equity: 54:01 – 57:57
• Founding JetDoc, Telehealth Innovation: 63:12 – 67:47
• Solving Health System Flaws, Medicaid Book: 77:43 – 85:17
• Advice for Entrepreneurs and Final Reflections: 87:37 – 90:58
• The Age of Disruption: 91:28 – 93:12

Memorable Moments

• The Balmain Paris story: How most true “ballers” at Paris Fashion Week weren’t celebrities or entertainers—they were healthcare executives (11:10).
• “Wolf of Healthcare”: Dame Dash calls Tommy Duncan “the Wolf of Healthcare”, equivalent to the Wolf of Wall Street but for the medical business (93:33).
• Surviving a million-a-month loss: Tommy’s story of clawing his company back from the brink after unexpected financial disaster (50:01 – 53:22).
• Mentorship and Black entrepreneurship: A recurring theme—how mentorship and relationships are essential but often lacking in Black business communities (14:39, 38:27, 87:37).

Closing Advice & Contact

• Calculated risk, deep homework, leveraging disruption:
  “Do your research on your business... Calculate your risk... take risk.”
• Tommy’s social handles:
  • IG: @Tommy2Duncan
  • JetDoc: @myJetDoc | JetDoc.com
  • Movie: Prince of Detroit Film

Summary

This episode is a must-listen (or read) for anyone interested in how big money really moves in healthcare, the intersections of community impact and business, and the realities of entrepreneurship at the highest level. Tommy Duncan’s story is one of resilience, data-driven innovation, calculated risk, and social disruption. Whether you’re an aspiring entrepreneur, a healthcare professional, or just someone fascinated by the business of America, his lessons and candor are invaluable.