Dear Reader,

Before we go into today’s newsletter on health insurance…

This Sunday, October 25 at 7:00 P.M. ET…

​I’m hosting a FREE live event where I’ll reveal what could be the biggest threat to your financial health in decades.

It’s called the Great Repression – and it’s what happens when the government locks you into the system, then forces YOU to pay for its reckless spending.

And once the midterms are over, I believe this threat could move into its next dangerous phase.

That’s why I’m holding this free event on Sunday, where I’ll show you:

• Why a 71-page paper released by the IMF PROVES Washington is set to revive an 80 year old playbook to legally rob millions of American retirement and savings accounts to pay its $40 trillion debt (and how this goes far beyond simply "inflating the debt" away)
  ​
• Why buying traditional inflation hedges like gold, hard assets, real-estate, and even Bitcoin may prove useless as Washington rolls out a plan to lock you into the U.S. dollar system (and why once this plan is in place there may no longer be a way out. In fact, it's already happening in the UK, France, China and Japan)
  ​
• What I’m doing personally to get ready (including details on creating a "Financial Escape Hatch". One that has not only helped protect people's wealth from financial repression in the past but also allowed them to build a small fortune in the process)

​Click here to register for the event (note that the login link will ONLY be sent to those who register)​

Now, back to the newsletter.

I can’t tell you how many times I’ve heard some version of this.

Someone wants to retire early…

Or leave their job for a side business that’s rapidly gaining traction.

But when I recommend that they go ahead, they hit me with the same refrain:

“But what would I do about health insurance?”

And look, I understand why.

According to the Kaiser Family Foundation, about 166 million Americans under 65 get their health insurance through employer-sponsored plans.

So that means leaving your job often means giving up your health insurance as well.

And considering how insane healthcare costs can get here…

It’s rational that it is a huge barrier for those trying to exit traditional employment.

But When I Quit My Job as a Stockbroker in 2019, That Barely Crossed my Mind

My business wasn’t already profitable when I left.

In fact, it took about a year and a half before I was finally making enough money to pay my bills.

During that early period, my family and I simply went without health insurance.

Naturally, I expected my family’s healthcare costs to shoot up.

Instead, the opposite happened – our healthcare costs DECREASED.

Previously, when we had insurance and took one of our kids to the doctor, we’d hand over the insurance card, pay a $20 or $50 copay, and the insurer handled whatever happened behind the scenes.

Without insurance, when we went back to the same doctors for the same sort of routine care and told them we were paying cash…

The entire cash-pay visit was, in many cases, less than the copay I had been paying before.

And my experience isn’t as rare as it may sound.

Researchers looked at cash prices for 70 common, shoppable services across 2,379 U.S. hospitals.

In 47% of cases, the cash price was lower than or equal to the median price commercial insurers had negotiated.

For evaluation and management services – which include the kinds of visits most similar to routine office care – that number rose to 55%.

But even in other categories, cash rates are lower than insured prices very close to half the time.

As for why this is the case, one review had a pretty simple answer – accepting cash can be faster and cheaper for providers than dealing with insurance billing, claims and collections.

Now, I’m NOT recommending you go out and ditch your health insurance.

Even if cash-pay rates are lower, if you have a serious medical condition – you could easily be looking at 6-figures (or even 7-figures) in medical bills.

That’s why I eventually bought health insurance again once my business gained enough traction.

However, if – for whatever reason – you find yourself in such unfortunate circumstances without health insurance, there’s one thing you need to remember…

That Giant Medical Bill May Not Be the Final Bill

Here’s something else too few people don’t realize.

Medical bills can often be negotiated.

A 2024 JAMA Health Forum study looked at people who received medical bills they either disputed or couldn’t afford.

Among those who contacted the billing office about an unaffordable bill, 75.8% received some form of financial relief.

And among the people who specifically tried to negotiate the price, 61.8% got the price reduced.

So when a massive medical bill lands in your mailbox, don’t automatically assume the first number printed on it is carved in stone.

Call and ask about financial assistance.

Ask whether they’ll reduce the balance for cash.

Ask what kind of payment arrangement they can offer (even if the payment plan lasts decades, you may find that the costs are about equivalent to your monthly health insurance bill).

There’s also some protection if a true emergency strikes.

Under federal EMTALA rules, most hospital emergency departments MUST screen and stabilize an emergency medical condition regardless of whether you have insurance or can pay.

But I want to be very clear here.

Going uninsured is NEVER risk-free.

Emergency stabilization is different from guaranteeing months or years of follow-up treatment, and a giant uninsured medical bill can still wreck you financially.

Which is why I eventually started looking for something between traditional insurance and simply taking all of that risk myself.

The Crowdfunding Option I Use Today

That’s how I found CrowdHealth.

CrowdHealth is not an insurance company.

It’s a healthcare crowdfunding platform where members generally interact with the medical system as cash-pay patients.

You pay a monthly membership fee and help fund other members’ eligible healthcare expenses.

When you have a larger eligible health event yourself, you submit it through CrowdHealth and other members help fund your bill.

For instance, on its standard $500 Member Commitment option, you generally handle the first $500 of an eligible health event before asking the crowd to fund the rest.

CrowdHealth also helps you shop for providers and negotiate prices.

That price-shopping piece has been genuinely helpful for me.

I once developed an eye floater and wanted an exam.

I messaged CrowdHealth, explained what I needed, and they helped identify providers.

Once I told the office I was paying cash, the exam cost me around $50.

There was none of the back-and-forth I’d gotten used to with insurance.

And because CrowdHealth may ultimately help fund larger eligible bills, they have an incentive to help members find reasonably priced care in the first place.

Now, CrowdHealth does actually publish its historical monthly costs.

As of its current data, the reported average monthly total is around $145 for a single member under 55, about $225 for someone 55 to 64, and roughly $485 for a family of four.

Those numbers include the advocacy fee plus the average monthly crowdfunding ask, but they don’t include whatever routine medical care you pay for yourself or payment-processing fees.

And even when bigger bills are submitted, the vast majority of them still get funded.

In September 2026, CrowdHealth reported that 100% of eligible bills were funded, while 4.01% of submitted bills were deemed ineligible.

CrowdHealth is not insurance, so it does not contractually guarantee that every medical bill will be funded.

Certain conditions that were diagnosed, documented or symptomatic within five years before joining aren’t eligible for crowdfunding during the first two years, with limited funding beginning in year three.

So I would never tell you this is simply “health insurance, except cheaper.”

It’s a different model with different trade-offs.

But I believe it is one that could work better for a lot of people.

For someone who already has major chronic healthcare needs, traditional insurance may be far more appropriate.

But for somebody in a situation closer to mine – generally healthy, comfortable paying routine care in cash, but unwilling to shoulder every catastrophic expense alone – I find the model very attractive.

But the main point I want to get across is this:

Don’t Let Health Insurance Become Golden Handcuffs

Again, I’m not writing this to tell you to cancel your insurance tomorrow.

I’m writing it because I’ve watched too many people treat employer-sponsored health insurance like handcuffs.

I understand that fear. And like I said, it’s completely rational.

However, cash pricing has become much more transparent.

Large medical bills can often be negotiated.

And alternative models like CrowdHealth now exist for people willing to step outside the traditional insurance system (plus, the more people use these models, the more competitive health insurance companies will have to be).

If health insurance is the one thing stopping you from retiring, leaving a job you hate, or giving your own business a real shot…