From Rural Doc to AI Entrepreneur Ep 38 : How Tod Stillson Built Autonomy on His Own Terms
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From Rural Doc to AI Entrepreneur Ep 38 : How Tod Stillson Built Autonomy on His Own Terms
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☕ Coffee Playdate Podcast with Dr. Tod Stillson
In this episode, I sit down with Dr. Tod Stillson — rural family physician, bestselling author of Doctor Incorporated, founder of the Physician Entrepreneur Academy, and creator of ChatRx.
We talk about what it really looks like to stop being an employee and start thinking (and operating) like an owner. Tod shares how 30 years of rural medicine shaped his engineering mindset, why he built an AI-powered asynchronous urgent care platform that answers the two questions patients ask him everywhere he goes, and the simple mindset shift that changes everything: ownership over employment.
You’ll hear practical wisdom on:
- Why most doctors never realize they can ask for a 1099 contract
- How to design a medical career that fits your life instead of the other way around
- The power of creating value first (instead of extracting it)
- Why identity work comes before business strategy
- Advice he would whisper to his younger self
This conversation is equal parts practical and freeing — especially if you’re a physician who wants more autonomy without burning out or walking away from medicine entirely.
Timelines / Chapters
00:25 – Welcome + coffee talk
02:56 – Rapid Fire questions
03:34 – Take a Sip game
05:02 – Tod’s journey: rural family medicine to independent contractor
06:47 – The origin story of ChatRx
12:09 – Why AI triage matters (and why most chatbots fail at it)
16:25 – Designing your life on your own terms
20:35 – The ownership mindset shift every doctor needs
26:38 – Biggest challenges physicians face when starting a business
29:56 – Advice to younger Tod
33:24 – Book recommendation: The Go-Giver
35:08 – Closing thoughts + gratitude
Want to learn more about Dr. Tod Stillson?
Check out his AI-powered on-demand urgent care platform ChatRx at https://www.chatrx.md/ and the Physician Entrepreneur Academy at https://www.simplimd.com/. His book Doctor Incorporated is available on Amazon.
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✨ — Dr. Olga Deengar, Coach Olga MD © 2026 Coach Olga MD. All rights reserved.