Health Savings Account
- The Chairman

- 2 days ago
- 3 min read

1. They Treat the HSA Like a Stealth Retirement Account
Most Americans use HSAs to pay for yearly medical expenses.
Rich individuals don’t.
They pay out-of-pocket for medical bills and let their HSA money grow untouched for decades, because:
• Contributions are tax-deductible
• Growth is tax-free
• Withdrawals for medical expenses are tax-free
This is the only account in America with triple tax advantages.
No 401(k).
No IRA.
Not even a Roth IRA comes close in flexibility.
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2. They Invest the HSA (Most People Don’t)
Most people let HSA cash sit idle.
Wealthy individuals invest the entire balance in:
• S&P 500 index funds
• Total stock market funds
• High-yield ETFs
• Sometimes conservative bond ETFs later in life
With decades of compounding, an HSA can grow to $250,000–$500,000 tax-free, assuming consistent contributions.
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3. They Save Their Medical Receipts — But Don’t Get Reimbursed Yet
This is a sophisticated strategy:
They keep all medical receipts in a folder (or digital archive)…
…but they wait YEARS to reimburse themselves.
Why?
Because you can reimburse yourself at any point in the future for a qualified medical expense, as long as:
You had the HSA at the time
You kept the receipt
That means someone could:
• Rack up $20,000 in receipts
• Let their HSA grow for 20 years
• Then reimburse the $20,000 tax-free — effectively making a tax-free withdrawal for any purpose.
This is a legal HSA “loophole” the wealthy maximize.
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4. They Use the HSA to Pay Medicare Premiums in Retirement
After age 65, HSA funds can be used tax-free for:
• Medicare Part B
• Medicare Part D
• Medicare Advantage premiums
• Long-term care insurance premiums (limits apply)
This acts like a private tax-free medical pension.
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5. After Age 65, the HSA Becomes a Traditional IRA (With Bonus Perks)
Once you turn 65:
• You can withdraw HSA funds for any non-medical reason without penalty
• You only pay income tax (just like a traditional IRA)
But unlike an IRA:
• You still get tax-free withdrawals for medical expenses
• And tax-free withdrawals for Medicare premiums
• And tax-free withdrawals for long-term care costs
So the wealthy keep it invested and use it as a medical Roth IRA hybrid.
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6. They Max Out The Family Contribution Every Year
2024 numbers (for example):
• Single: up to $4,150
• Family: up to $8,300
• Age 55+ catch-up: +$1,000
Wealthy families nearly always make:
The maximum contribution
Automatic yearly investments
Minimal withdrawals
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7. They Combine It With a High-Deductible Health Plan (HDHP) Strategically
The wealthy select HDHPs because:
• Premiums are lower
• They can fully fund the HSA
• They can self-insure for small medical costs
• It shifts more money into tax-advantaged investment accounts
Most wealthy people rarely use low-deductible insurance because they prefer tax efficiency to out-of-pocket comfort.
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In Summary — Why the Wealthy Love HSAs
Advantage Why It Matters
Triple tax benefit The strongest tax shelter in the U.S.
Investable Grows like a retirement account
Tax-free spending on medical costs Major expense category for older Americans
Flexible after 65 Works like IRA + medical Roth
Delayed reimbursements Turns old medical receipts into tax-free cash later
No required distributions Unlike 401(k)s and IRAs
For high-income earners, HSAs are free money, reduced taxable income, and a powerful wealth-building tool.
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