Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories.
Every Tuesday, we pick three headlines worth paying attention to and break down the category underneath. Every other Friday, we go deeper with a Deep Dive Report, calling where the category goes next. Become a Founding Member to get every Deep Dive Report, mini-book, audiobook, and access to the Pirate Eddie and Christopher bots.
Piratey disclaimer: This is NOT financial advice. None of us have Series 63, Series 6 7, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS. Think of this like professional wrestling. It’s entertainment.Don’t be so smart you’re stupid and suplex your safety net savings.
And, while we are writing to parents, this also applies to anyone with a niece, nephew or anyone with a young person in their life they want to invest in.
Dear Friend, Subscriber, and Category Pirate,
“If we ever get married, don’t forget…DNR.”
Do Not Resuscitate.
This was something Pirate Eddie’s wife said to him on one of their early dates. His wife was working at the University of Chicago Hospitals as an ICU and Oncology nurse. She saw the dark side of families dealing with the worst decision ever.
Do we keep our loved one on life support or not?
She saw patients who would never recover being kept alive. Patients who barely resembled the wonderful human they used to be, being kept alive for conversations they can’t have. Conversations that should have happened years prior. All of this end of life pain and suffering cost families hundreds of thousands of dollars they did not have. Pirate Eddie’s wife was watching family after family go through this and wanted it to be clear what her personal wishes were, if she was ever in that situation.
It was a dark way to start dating.
But they have been married for 25 years and counting. And she did say, “Do make sure there is no chance I can recover.”
This was the first time Pirate Eddie realized how healthcare costs and retirement were inextricably linked.
Most retirement savings marketing showcases sandy beaches and shuffleboard. But the data says that 12% to 29% of all retirement dollars goes towards healthcare costs.
Health Savings Accounts (HSA) have total assets that add up to just 0.35% of all retirement savings assets.
This makes no sense given that HSAs are by far the superior tax deferred vehicle.
Twice as many tax benefits as a 401K, Roth IRA or 529 college savings account. You can save and use it immediately, not decades later. And saving enough to cover your healthcare costs for life is way more achievable for the average person compared to actually saving enough for retirement or college.
What are HSAs?
That is something Pirate Eddie couldn’t embarrassingly answer until just a few years ago.
HSAs are a way to save pre-tax money into an account that you can use exclusively for healthcare costs. You can invest it in the HSA and it grows tax deferred. You can use it anytime to pay for out of pocket healthcare expenses.
Pirate Eddie just bought an 8 Sleep at Pirate Cole’s recommendation.
Pirate Eddie was trying to improve his sleep. And Pirate Cole loved how 8 Sleep would lower the temperature of his bed right before sleep and adjust it through the night. 8 Sleep has a list price of $3,000. Pirate Eddie used his HSA to pay for it. So instead of paying for it with $3,000 of after tax dollars, he paid for it with $3,000 of pre-tax dollars.
He basically bought the 8 Sleep for nearly half off.
Say you make $83,000 per year, the average US household income. In 2026, you can set aside $4,400 in pre-tax dollars for an individual or $8,750 for a family. At that income the federal tax rate is 22%. You would owe $968 in federal tax on $4,400 of income. But if you put $4,400 into a HSA, you can use that $968 to spend on out of pocket healthcare expenses instead of giving the US government $968.
That’s not all the tax savings.
Shaq got his first million dollar paycheck after signing with the Orlando Magic. He looked closer at the taxes withheld from his check and said, “Yep, I did this. Yo, who the hell is FICA? I don’t know nobody named FICA and I didn’t give FICA no money.” Shaq was pissed.
FICA is the Federal Insurance Contribution Act, which funds social security and medicare. It is a straight 7.65% off your paycheck, and your employer pays another 7.65%
If you have a HSA with your employer, not only does your HSA contribution dodge FICA, your employer does too!
Secret #1: HSAs Have Twice As Many Tax Breaks
Pirate Eddie was embarrassed he didn’t use his HSA until his 40’s.
Because it is so far superior to every other tax deferred account like 401K, IRAs, Roth IRAs and 529s. It has double the tax breaks of every other tax deferred account. You get a triple crown of tax breaks immediately when you put money in (Federal, State and FICA). If you invest it, it grows tax deferred like all the other accounts. And you don’t pay federal, state or capital gains when you use the money on the way out.
Here’s an example using a $1,000 of pre-tax income as an example so you can compare across different tax-deferred vehicles.