In Stack Play #2, we introduced the concept of the three tax buckets — pre-tax, taxable, and tax-free — and made the case that most high earners arrive at retirement having never meaningfully filled the tax-free bucket.
There’s a fourth bucket almost nobody fills.
It’s not as well-known as the Roth. It has no income limit blocking access. It carries a tax advantage that technically exceeds the Roth for one specific and highly predictable category of expenses. And right now, the overwhelming majority of people who have access to it are using it as a healthcare checking account — spending every dollar in and watching every dollar out, year after year, building nothing.
The Health Savings Account is not a healthcare spending tool. In the hands of a high earner with a deliberate strategy, it is permanent capital with a triple tax wrapper — the only account in the US tax code that is never taxed going in, never taxed growing, and never taxed coming out.
This is Stack Play #4.
This play is designed for:
High earners enrolled in a High Deductible Health Plan (HDHP) — either through an employer or self-purchased — who currently contribute to an HSA but treat it like a spending account
Healthy professionals with manageable annual medical costs who can afford to pay medical expenses out of pocket rather than drawing from the HSA
Stack builders who have already implemented or are pursuing Stack Plays #1–#3 and are looking for the next permanent capital layer to fill
Anyone who has been told to “use their HSA for medical expenses” without being told they don’t have to — and that not using it may be the smarter long-term move
The HSA has one hard eligibility requirement: you must be enrolled in a qualified High Deductible Health Plan. In 2026, that means a plan with at least a $1,700 deductible for individual coverage or $3,400 for family coverage, with out-of-pocket maximums not exceeding $8,500 (individual) or $17,000 (family).
If you are on an HDHP and not maximizing this play, you have an actionable gap in your wealth stack.
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.