Step by Step Series | How to Open, Invest and Use an HSA Like the Wealthy Do | Episode 18 episode artwork

EPISODE · Jun 3, 2026 · 23 MIN

Step by Step Series | How to Open, Invest and Use an HSA Like the Wealthy Do | Episode 18

from What The Wealthy Do · host What The Wealthy Do

You have probably heard that you should open an HSA. But has anyone actually walked you through what to do after you open it? That is what today is about.This is Episode 18 of What the Wealthy Do and the first episode of the Logistics Series, breaking down the exact mechanics of how these wealth building strategies actually work in real life.The health savings account is the only account with a triple tax advantage: tax deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses. Most people open one, get the debit card, and spend it on copays. That is the wrong move.Stephanie Dorsey walks through every step: how to check eligibility, employer HSA versus opening your own, how to invest the contributions, and how the wealthy use the HSA as a stealth retirement account worth hundreds of thousands of dollars by paying medical expenses out of pocket, saving every receipt, and reimbursing themselves tax-free decades later.A real example: maxing out your HSA at 40 for 25 years at 7% annual growth gives you $290,000 tax free at 65 from $107,500 in contributions.The HSA Quick Start Checklist is in the show notes below.Join the next Sovereign Collective cohort: joinsovereign.coHSA QUICK START CHECKLISTWeek 1:- Check if you have an HDHP (ask HR or check benefits portal)- If yes, check if your employer offers an HSA- If yes, enroll during next open enrollment- If no, open one with FidelityWeek 2:- Max out contributions ($4,300 individual / $8,550 family)- Set payroll deduction or automatic monthly bank transferWeek 3:- Log into your HSA provider- Move funds to investments (keep $1,000 to $2,000 in cash)- Invest in low-cost index fundsWeek 4:- Set up a system to track medical expenses- Pay all medical expenses out of pocket- Save every receiptEvery Year:- Max out contributions- Rebalance investments- Keep saving receipts- Watch it grow tax-freeThis podcast provides financial education and not financial advice.

You have probably heard that you should open an HSA. But has anyone actually walked you through what to do after you open it? That is what today is about.This is Episode 18 of What the Wealthy Do and the first episode of the Logistics Series, breaking down the exact mechanics of how these wealth building strategies actually work in real life.The health savings account is the only account with a triple tax advantage: tax deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses. Most people open one, get the debit card, and spend it on copays. That is the wrong move.Stephanie Dorsey walks through every step: how to check eligibility, employer HSA versus opening your own, how to invest the contributions, and how the wealthy use the HSA as a stealth retirement account worth hundreds of thousands of dollars by paying medical expenses out of pocket, saving every receipt, and reimbursing themselves tax-free decades later.A real example: maxing out your HSA at 40 for 25 years at 7% annual growth gives you $290,000 tax free at 65 from $107,500 in contributions.The HSA Quick Start Checklist is in the show notes below.Join the next Sovereign Collective cohort: joinsovereign.coHSA QUICK START CHECKLISTWeek 1:- Check if you have an HDHP (ask HR or check benefits portal)- If yes, check if your employer offers an HSA- If yes, enroll during next open enrollment- If no, open one with FidelityWeek 2:- Max out contributions ($4,300 individual / $8,550 family)- Set payroll deduction or automatic monthly bank transferWeek 3:- Log into your HSA provider- Move funds to investments (keep $1,000 to $2,000 in cash)- Invest in low-cost index fundsWeek 4:- Set up a system to track medical expenses- Pay all medical expenses out of pocket- Save every receiptEvery Year:- Max out contributions- Rebalance investments- Keep saving receipts- Watch it grow tax-freeThis podcast provides financial education and not financial advice.

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Step by Step Series | How to Open, Invest and Use an HSA Like the Wealthy Do | Episode 18

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This episode was published on June 3, 2026.

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You have probably heard that you should open an HSA. But has anyone actually walked you through what to do after you open it? That is what today is about.This is Episode 18 of What the Wealthy Do and the first episode of the Logistics Series,...

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