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All pillars
Pillar 09 · Tax Advantage

The best guaranteed return
is unused shelter space.

Live contribution tracking against current limits, employer-match capture, bracket visualization, and HSA receipt records that hold up.

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The number

401k · IRA · HSA · 529

shelters tracked against current-year contribution limits

Illustrative outcome target for this pillar. Not a guarantee — your results will vary based on your situation.
What's inside

Everything you need for tax advantage.

Straight answer on timing: everything below ships with the app on September 1, 2026, except the items marked Coming soon — those land in a later release, and we'd rather tell you now than surprise you inside the app.

Live contribution tracker

At launch

401(k), IRA, Roth, HSA and 529 contributions year-to-date against this year's limits — derived from your linked accounts or edited by hand.

Employer match capture

At launch

The single most expensive thing to leave on the table. We calculate your match formula and flag any dollars you're walking away from.

Bracket visualizer

At launch

Marginal vs. effective rate, and what one more pre-tax dollar actually saves you — modeled, not hand-waved.

Backdoor & mega-backdoor walkthroughs

At launch

Step-by-step checklists for the Roth strategies high earners use, with the pro-rata traps called out before you trigger one.

HSA receipt vault

At launch

Store qualified medical receipts indefinitely so you can reimburse yourself years later — the HSA's most under-used feature.

Stacking order

At launch

Match → HSA → high-interest debt → Roth → 529 → taxable, personalized to your income and bracket.

How it works

Three steps. No fluff.

Step 01

Tell us your income and plan details

Filing status, employer match formula, coverage type for HSA eligibility.

Step 02

Sync or enter contributions

We derive year-to-date amounts from custodian transactions, or you enter them.

Step 03

Fill shelters in the right order

Progress bars per shelter, a finish-these-next queue, and windfall alerts.

Common questions

Specifics, not slogans.

Is this tax advice or tax preparation?
Neither. Boss Finances is not a CPA firm, does not prepare or file returns, and does not give personalized tax advice. The Tax Advantage pillar tracks contributions against published limits, shows how brackets work on your numbers, and explains widely-used strategies in plain English. For your specific return or an unusual situation, work with a CPA or enrolled agent.
What if my contributions don't sync automatically?
You can always enter and edit them manually. Automatic tracking works by reading transfers to custodian accounts you've linked, which covers most payroll and brokerage contributions — but some plans don't surface cleanly. Manual entries are treated identically everywhere: progress bars, limit warnings, and the stacking order all update the same way.

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Pillar 01 · Budget

Explore budget

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Estate Planning & Legacy

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Budget & Cash Flow

Stop leaving free money. Fill the shelters.

Tax Advantage is pillar nine of nine — the quiet compounding at the top of the Boss Path.

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