Ep. 39  ·  June 9, 2026

$343 a Month for a Family of 5 The Health Insurance Play Founders Don’t Know

Mike Bledsoe paid $80,000 for a hernia surgery. His friend paid $8,000 cash.

1h 0m

Listen on

Mike Bledsoe paid $80,000 for a hernia surgery. His friend got the same surgery for $8,000 in cash. That’s the entire game.
Michael Caz, founder of ShareWise and producer at Virtuous Benefits, walks Mike and Ted through what most operator-founders don’t know about US health insurance, and the alternative that costs a family of five $343 a month.
The conversation goes deep on why insurance companies want prices to go up, what a “Charge Master price” actually is, why United Healthcare’s denial rate is 33% and CrowdHealth’s is less than 1%, how Pharmacy Benefit Managers hide 40% of Big Insurance’s profits, and the 100x markup on drugs like Ozempic.
If you’re a self-employed founder, a business owner running 6 to 7 figures, or a W-2 employee staying at a job you hate just for the benefits, this one’s for you.
Key insights from this episode:
Why the average healthy founder is overpaying $5,000 to $10,000 a year on insurance
The Charge Master scam: how hospitals anchor a fake $80K price to negotiate with insurance
Why insurance companies are incentivized to RAISE healthcare prices, not lower them
The denial rate gap: 33% at United Healthcare vs. less than 1% at CrowdHealth
What a health share plan actually is (and the two waiting-period rules that make it work)
How a family of five can pay $343/month for healthcare instead of $1,800

Chapters:
00:00 What the fuck are we even paying for
01:00 Welcome to Full Stack Founders
02:20 The health insurance war zone for the self-employed
04:34 Michael’s ACA marketplace nightmare
07:00 How Big Pharma, Big Insurance, and Big Hospital actually work together
09:49 The healthcare system isn’t broken. It’s working perfectly.
11:18 Why the healthy are subsidizing the sick
13:00 Why insurance companies want prices to go up
15:17 The $80K hernia surgery that costs $8K in cash
16:33 The Charge Master scam: how hospital pricing actually works
17:32 What a health share plan actually is
20:08 $343 a month for a family of five
21:00 The waiting period and the pre-existing condition rule
27:48 PBMs: how Big Insurance hides 40% of profits
29:14 The 100x Ozempic markup
31:44 Why insurance should be like car insurance
33:36 33% denial rate vs. less than 1%
36:07 Inside CrowdHealth’s transparency model
40:01 The personal responsibility clause
44:28 What a health share covers (pregnancy, midwives, travel)
49:09 How to pick the right plan as a founder
51:08 ShareWise vs. Virtuous Benefits
54:50 Where to find the marketplace
55:30 Ted’s recap and gems

Where does this fit in the Stack? This episode focuses on OUTPUT. To learn how to integrate this into your daily leadership practice, take our free training “See The Game” inside the Full Stack community: https://www.skool.com/the-mission-after-2227/about?ref=12e63552edce482b85cc08369565c495

Connect with Michael Caz: ShareWise (the health share marketplace): https://www.sharewize.com/about
Virtuous Benefits:

Follow Ted:
Website: https://www.themodernmanpodcast.com/
X: https://x.com/TheModernMan8
YouTube: https://www.youtube.com/channel/UCnyA3-wtyv7xVqUbPyB0eOg
Instagram: https://www.instagram.com/themodernmanpodcast/
Facebook: https://www.facebook.com/TheModernManShow

Follow Mike:
Website: https://bledsoe.life/
YouTube: https://www.youtube.com/@MikeBledsoe
Instagram: https://www.instagram.com/mike_bledsoe/

#fullstackpodcast #fullstackfounders #healthshare #sharewise #healthinsurance #operatorfounder #selfemployed #healthinsuranceforentrepreneurs #mikebledsoe #tedphaeton #michaelcaz #crowdhealth #healthcarecosts #leadership

Show notes

Mike Bledsoe paid $80,000 for a hernia surgery. His friend got the same surgery for $8,000 in cash. That's the entire game.
Michael Caz, founder of ShareWise and producer at Virtuous Benefits, walks Mike and Ted through what most operator-founders don't know about US health insurance, and the alternative that costs a family of five $343 a month.
The conversation goes deep on why insurance companies want prices to go up, what a "Charge Master price" actually is, why United Healthcare's denial rate is 33% and CrowdHealth's is less than 1%, how Pharmacy Benefit Managers hide 40% of Big Insurance's profits, and the 100x markup on drugs like Ozempic.
If you're a self-employed founder, a business owner running 6 to 7 figures, or a W-2 employee staying at a job you hate just for the benefits, this one's for you.
Key insights from this episode:
Why the average healthy founder is overpaying $5,000 to $10,000 a year on insurance
The Charge Master scam: how hospitals anchor a fake $80K price to negotiate with insurance
Why insurance companies are incentivized to RAISE healthcare prices, not lower them
The denial rate gap: 33% at United Healthcare vs. less than 1% at CrowdHealth
What a health share plan actually is (and the two waiting-period rules that make it work)
How a family of five can pay $343/month for healthcare instead of $1,800

Chapters:
00:00 What the fuck are we even paying for
01:00 Welcome to Full Stack Founders
02:20 The health insurance war zone for the self-employed
04:34 Michael's ACA marketplace nightmare
07:00 How Big Pharma, Big Insurance, and Big Hospital actually work together
09:49 The healthcare system isn't broken. It's working perfectly.
11:18 Why the healthy are subsidizing the sick
13:00 Why insurance companies want prices to go up
15:17 The $80K hernia surgery that costs $8K in cash
16:33 The Charge Master scam: how hospital pricing actually works
17:32 What a health share plan actually is
20:08 $343 a month for a family of five
21:00 The waiting period and the pre-existing condition rule
27:48 PBMs: how Big Insurance hides 40% of profits
29:14 The 100x Ozempic markup
31:44 Why insurance should be like car insurance
33:36 33% denial rate vs. less than 1%
36:07 Inside CrowdHealth's transparency model
40:01 The personal responsibility clause
44:28 What a health share covers (pregnancy, midwives, travel)
49:09 How to pick the right plan as a founder
51:08 ShareWise vs. Virtuous Benefits
54:50 Where to find the marketplace
55:30 Ted's recap and gems

Where does this fit in the Stack? This episode focuses on OUTPUT. To learn how to integrate this into your daily leadership practice, take our free training "See The Game" inside the Full Stack community: https://www.skool.com/the-mission-after-2227/about?ref=12e63552edce482b85cc08369565c495

Connect with Michael Caz: ShareWise (the health share marketplace): https://www.sharewize.com/about
Virtuous Benefits:

Follow Ted:
Website: https://www.themodernmanpodcast.com/
X: https://x.com/TheModernMan8
YouTube: https://www.youtube.com/channel/UCnyA3-wtyv7xVqUbPyB0eOg
Instagram: https://www.instagram.com/themodernmanpodcast/
Facebook: https://www.facebook.com/TheModernManShow

Follow Mike:
Website: https://bledsoe.life/
YouTube: https://www.youtube.com/@MikeBledsoe
Instagram: https://www.instagram.com/mike_bledsoe/

#fullstackpodcast #fullstackfounders #healthshare #sharewise #healthinsurance #operatorfounder #selfemployed #healthinsuranceforentrepreneurs #mikebledsoe #tedphaeton #michaelcaz #crowdhealth #healthcarecosts #leadership

The writing

Read what comes next.

Once a week. New essays on ownership, the AI shift, and the long game.

From the show

Want the room, not just the audio?

Full Stack Founders is also a community on Skool. Operator-founders thinking out loud with each other — not just with us.

Join the community

$49 / month