The Bracket - Retirement Tax Strategy for High Net Worth Households

Roth conversions have one deadline that doesn’t move. December 31. Miss it, and this year’s low tax brackets are gone for good. Since 2018, you can’t undo a conversion either.

In this episode, Ryan Knoll, CFP®, walks through how Nav Wealth Partners handles the year-end conversion true-up. He uses the Calloways, a composite household whose spring income estimate missed by $21,000. You’ll learn.

• Why we convert in two steps. A conservative amount early, the rest in December
• How a surprise final paycheck (or expense) shrinks your conversion room
• The 3.8% net investment income tax line sneakily costs retiress thousands of dollars
• Why the IRMAA lookback means Medicare planning starts at 63, not 65
• Custodian cut-offs, safe-harbor estimates, and paying the tax from outside the IRA
• A five-step December checklist

Doing conversions this year? Book a year-end review before December 10: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

"My advisor has me converting $100,000 a year to Roth."

Ryan Knoll, CFP®, hears this all the time, and his first question is always the same: why $100,000? A Roth conversion is a decision you make once a year with that year's numbers in front of you. Some years the right amount is much larger. Some years it's zero.

In this episode, Ryan explains why fixed-dollar amounts, "fill the 24% bracket" targets, and "convert everything before RMDs" rules all break down. He replaces them with one test. Convert a dollar when taxing it today costs less, all-in, than taxing that same dollar later. Then he follows the Calloways, a composite household with $2.9 million, through four years of conversions: $45,000, then $130,000, then $230,000, then zero.

In this episode:

• Why the argument that tax rates were about to rise went away in 2025, and what the case for converting rests on now
• Portfolio composition: how the size of your IRA, your brokerage account, and your charitable plans set how much you should convert
• Today's rate vs. tomorrow's: the hidden costs that make a "12% conversion" cost 15% or more, and the three future taxpayers to plan for (you, your surviving spouse, your heirs)
• IRMAA now vs. later: the two-year lookback, the cliff math that makes crossing a line by a little the worst outcome, and when paying one year of IRMAA on purpose makes sense
• Why a down market can be the best year to convert, and why you shouldn't go all in mid-year
• The five-question conversion review Nav Wealth Partners runs with clients every fall
• Who should rarely convert at all

Work with us: If you're within ten years of retirement with $2–5 million invested and want to see what your own conversion review looks like, contact Nav Wealth Partners through this link https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast.

"I've got about three million. Am I okay?"

Ryan Knoll, CFP®, gets asked some version of this every week and his honest answer is that nobody can tell you, because the question can't be answered. A balance is a snapshot. It tells you what you've saved, not what that money has to do.

In this episode, Ryan replaces "is my number big enough?" with the question that actually has an answer: what after-tax income do I need, where does each dollar come from, and in what order? Then he runs the whole process on the Calloways, a composite household with $2.9 million, a pension, five years of deferred comp, and two Social Security checks that don't start until seventy.

What's covered:

• "The Number" fails because it treats a pre-tax dollar the same as a Roth dollar, ignores every income source that isn't the portfolio, assumes one flat spending level forever, and answers the wrong emotional question in both directions
• Building an income target that's actually yours using the three-layer method: real baseline spending (not what you think you spend), what's new in retirement (pre-65 healthcare, Medicare, IRMAA, long-term care reserve), and inflation
• The income inventory. every source, three questions: when does it start, does it inflate, how is it taxed. Social Security, pensions with no COLA, nonqualified deferred comp and the 409A election you made years ago, and the three tax buckets inside the portfolio
• Why deferred comp is the blind spot a five-year payout you can't change fills your brackets whether you want it to or not, and can close your Roth conversion window until it ends
• The honest pushback — where rules of thumb still belong, and why the income framing handles sequence-of-returns risk better than a withdrawal rate ever could

Your homework this week: Don't check your balance. Pull twelve months of real spending, add what's new, inflate it, and lay every income source on a timeline. You'll see your retirement as a shape instead of a dot.

Nav Wealth Partners is a fee-only fiduciary firm in Sewickley, PA, working with households with $2–5 million in investable assets who are within about ten years of retirement. The income target, the inventory, and the sequencing plan described in this episode are where every client relationship starts.

→ Learn more or request a conversation: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

The Bracket is produced by Nav Wealth Partners, a registered investment adviser. This episode is for educational purposes only and is not individualized investment, tax, or legal advice. Mike and Susan Calloway are a fictional composite household; any resemblance to actual clients is coincidental. Tax figures reflect 2026 law as of the recording date and are subject to change. Consult your own advisor, tax professional, and plan documents before acting on anything discussed.

Five Rules for a Concentrated Stock Position

If you've spent fifteen or twenty years at one company, there's a good chance a third or more of your net worth is sitting in a single ticker and your paycheck, your bonus, and your next four years of vesting are riding on the same one.

Selling it all tomorrow is lazy advice and usually creates a tax bill you didn't need. This episode lays out a better way: five rules for unwinding a concentrated position built through equity compensation, in the order you'd actually execute them.

We cover:

• Why you can't build a selling plan until you've read your company's blackout calendar and hedging policy and how a 10b5-1 plan lets you sell through the closed windows
• The one instruction that should be attached to every future RSU, ESPP purchase, and ISO exercise before it arrives
• How collars and protective puts put a floor under a position you're stuck holding and the constructive-sale trap that turns a hedge into a tax bill
• Using the 2026 capital gains brackets, direct indexing, and charitable gifting to sell low-basis shares at a fraction of the tax cost
• Why "buy a diversified fund" can quietly rebuild the same risk you just sold, and what real diversification looks like when your salary is already the overweight

We walk the whole framework through the Calloways a 54-year-old senior director with 42% of a $3.6M household in her employer's stock and a retirement date four years out.

The Calloways are a fictional composite household. This episode is educational and not individualized advice. Figures cited are 2026 federal thresholds; consult a qualified professional before acting on anything discussed. Options involve risk and are not suitable for all investors.

Have a single stock north of 10% of your net worth? Request a concentrated stock review at www.navwealthpartners.com.

You spent thirty years being told to max out the 401(k). Defer, defer, defer. Nobody told you that the account determining your lifetime tax bill is the boring one. The one with no deduction, no match, no special name, the one your statement just calls "individual."

The taxable brokerage account isn't the most tax-efficient account you own. It's the one that makes every other account work. In this episode, Ryan Knoll makes the case for the brokerage account as the control account and puts 2026 numbers on exactly what that control is worth.

What's inside:

• MAGI is the number that runs your retirement — not your bracket. Why $120,000 out of an IRA generates $120,000 of income and $120,000 out of a brokerage account generates $48,000, and every cliff, phase-out, and surcharge that difference touches
• The 0% capital gains bracket. $98,900 of taxable income for a married couple in 2026, how to reset your cost basis for free, and why there's no wash sale rule on gains
• One bracket, two claims. The conflict nobody discusses: the 0% capital gains ceiling and the top of the 12% bracket occupy the same real estate, so every dollar of Roth conversion pushes a dollar of gain out of 0% and into 15%. Which one wins, and the survivor-filing-single problem that usually decides it
• Direct indexing, honestly. What the harvest actually generates, why the yield decays hard after year five, the wash sale trap that permanently destroys a loss when your IRA buys the same security, and why it's a deferral machine that needs a planned exit
• The $119,400 question. What happens when you pay Roth conversion tax from the brokerage account instead of withholding it from the IRA, and why your conversion capacity is limited by your taxable balance, not your IRA balance
• The ACA cliff is back. The enhanced premium tax credits expired January 1, 2026, and the 400%-of-poverty cutoff returned with them. A 63-year-old couple, the same $120,000 of spending, and a $22,800 swing in a single year decided by nothing but which account the money came from
• IRMAA and the Double Assessment. The $218,000 line, the two-year lookback, and a $15,200 difference on an $80,000 roof
• Why you want to die owning this account. Step-up in basis versus the ten-year rule, and what your kids actually inherit
• The honest case against. Annual tax drag, asset location most people have inverted, creditor protection, and the one account that beats all of these

The one-sentence thesis: the brokerage account is not the best account for building wealth but it's the account that gives you options, and the households who arrive at retirement without one find that every good idea their advisor brings them is unaffordable.

If you retire at 63 with $3.4 million and buy the target-date fund with your retirement year on the label, you'll end up holding roughly $1.7 million in bonds. If you spend $10,000 a month, that's eleven years of spending parked in an asset class that has historically done little more than keep pace with inflation.

Nobody chose eleven years. It fell out of a percentage rule that has nothing to do with what you actually spend.

In this episode, Ryan Knoll makes the case that most households between $2M and $5M aren't too aggressive in retirement. They're dangerously conservative, and the culprit is the rule itself. Percentage-of-portfolio allocations scale with your account balance, not your life. That makes them accidentally correct at exactly one portfolio size and wrong everywhere else.

Then the part almost nobody covers: it's not just how much you hold in bonds, it's which account you hold them in and that decision is worth more over thirty years than getting the percentage right.

In this episode:

Why percentage rules are the wrong shape. Two couples, same age, same spending, same 40% bond allocation. One ends up with three years of spending in bonds, the other with thirteen. Why "100 minus your age" answers a question you never asked.

Sizing the bond sleeve to years, not percentages. The Nav Wealth framework: three to five years of gross, pre-tax withdrawals. Why using your spending number instead of your withdrawal number quietly builds a four-year sleeve when you thought you built five.

What over-allocation actually costs. A composite $3.4M household, three different allocation methods, and the compounding gap between them across a 25-year retirement.

The Lost Decade objection, handled honestly. 2000–2009 was a large-cap growth event, not a diversified portfolio event. Why the answer to concentration risk is diversification, not de-risking and why those get substituted for each other constantly.

The refill rule. Four states, written down in advance, no judgment calls. When you rebalance into the sleeve, when you stop, and the point at which you cut discretionary spending instead of selling equities at the bottom.

Where the bonds live. Why the entire sleeve belongs in the IRA, why you should never hold a bond in a Roth, and how bond interest in a taxable account quietly consumes the Roth conversion corridor and the 0% capital gains window during the most valuable tax years of your life.

When this framework is wrong. The four situations where a three-year sleeve breaks, including the behavioral one nobody wants to admit.

Work with us: If you want to see how this applies to your own numbers, our team does exactly this work tax strategy for the distribution years. Schedule a conversation: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

Do it yourself: Download the Retirement Income Architecture Blueprint and work through your own situation: https://nav-wealth-resources.netlify.app/income-blueprint.html

Watch on YouTube: https://www.youtube.com/@NavWealthPartners

The Last Five Years: What You Control Before the Doors Close

Two households, both 61, both with $2.8 million. One will pay hundreds of thousands more in lifetime tax than the other and the difference was decided before either of them stopped working.

The five years before retirement are the last window where you control both variables that set your lifetime tax bill. Your income and where your money sits. After you retire, the stack is built and the elections are made.

In this episode:

• Why your spending number has to come first and why the corridor math is meaningless without it
• The deferred comp election that can erase your conversion window before it opens
• Why cash outside your 401(k) is what actually buys conversion capacity
• Retiring at 63½ instead of 62 and how COBRA creates the most tax-efficient window of your life
• The two-year lookback: the tax return you file at 63 sets your Medicare premium at 65
• Why Roth conversions and 0% capital gains harvesting compete for the same bracket space and how to choose
• The widow's penalty, and the strongest argument for converting that almost nobody makes

Plus the form that gets your IRMAA surcharge reduced after you stop working most people never file it.

Educational content only. Not individualized tax, legal, or investment advice. Nav Wealth Partners is a fee-only fiduciary RIA.

The Pension Asterisk: How a Pension Rewrites Everything We've Told You

If you're retiring with a pension whether it's corporate, government, military, or union, most retirement tax advice wasn't built for you. Including ours.

In the tier-list episode, we said a pension changes everything and that it deserved its own episode. This is that episode.

A pension is one of the best assets you can bring into retirement: guaranteed income you can't outlive. But it quietly rewrites the three frameworks we've built on this show the retirement tax stack, the Roth conversion corridor, and the Social Security timing decision and running the standard no-pension playbook on a pension household is one of the most expensive mistakes we see.

This episode is the revision, built specifically for households with $2–5M in investable assets spread across brokerage, traditional IRA, and Roth accounts.

In this episode:

• The raised floor. Why a pension means you never experience "phase one" of the retirement tax stack and how a household that "doesn't need the portfolio" can silently build the biggest RMD problem of all.
• The compressed corridor. How a pension pre-fills your cheapest Roth conversion space, why the first conversion dollar starts brackets higher than your neighbor's and the counterintuitive reason conversions often still make sense anyway.
• The Pseudo-Roth, re-priced. The strategy we ranked A-tier for the general audience takes the hardest hit from a pension. What survives, what gets substituted, and what that means for a large brokerage account with embedded gains.
• Social Security, revised. Why the "tax torpedo" stops mattering for pension households, why delaying to 70 quietly becomes a tax strategy not just a longevity bet and why pension households are uniquely positioned to afford the delay.
• The survivor system. How your pension survivor election, Social Security timing, and conversion plan interact as one decision with three levers and why the widow's penalty is where pension planning is won or lost.
• The revised playbook. The order of operations for a pension household: floor first, corridor second, Social Security inside that map, and the whole plan run to the second death — not the first.

Ready to see what your pension means for your plan? Schedule a conversation with the team at Nav Wealth Partners → https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

Follow The Bracket on YouTube for the visual breakdowns → https://www.youtube.com/@NavWealthPartners

This episode is for educational purposes only and is not individualized tax, legal, or investment advice. Tax figures referenced are as of the current tax year and are subject to change. Consult a qualified professional regarding your specific situation.

Ep. 6 — The Index You Actually Own: Direct Indexing & The Tax Machine Under the Hood

The market's up 12% — so you assume there's nothing to harvest. Meanwhile, 150+ stocks inside that "up" index are down double digits, and your ETF won't let you touch a single one of them. Direct indexing breaks the box open: same index, same return, but you own the stocks and the losers become fuel.

In this episode, Ryan Knoll walks through the full machine. What direct indexing actually is, what it can realistically do, and where it absolutely does not belong.

What's inside:

• How the harvest actually works — why losses live at the stock level, what a long-only direct index realistically generates (~30% of principal in cumulative losses over the early years), and why the biggest harvest happens in years 1–3
• The Roth conversion connection — how harvested losses clear the runway around your conversion so lifestyle-funding gains stop crowding out your bracket headroom, IRMAA cushion, and ACA subsidy room
• The big one-time event — stockpiling losses for years ahead of a business sale or concentrated stock unwind, and how tax-aware long/short (130/30) strategies harvest in any market, not just down years
• A real case walkthrough — a two-stage business sale with ~$4M in gains now and $2–3M coming in five years, and the loss-harvesting + donor-advised fund architecture built to defuse both bills
• The evolution — from a millionaires-only SMA product to a ~$100K-minimum strategy, thanks to zero-commission trading and fractional shares, and what "custom indexing" and long/short overlays added at the frontier
• Who this fits — and who's getting sold — the five-part framework: taxable account size, gains on the horizon, sequencing before the event, wash sale coordination, and the exit plan nobody talks about

The one-sentence thesis: this is a deferral machine, not a tax eraser — and the exit (the planned event, the low-income drawdown, or the step-up at death) is where it either pays off or turns into a slow-motion tax bomb with fees attached.

📊 Is direct indexing worth it for YOUR numbers? Grab the free Income Architecture Blueprint — answer a few questions, get your bracket map: https://nav-wealth-resources.netlify.app/gate-income.html

📅 Want this analysis built for your actual situation? Schedule a conversation with the Nav Wealth Partners team: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

▶️ Watch The Bracket on YouTube: https://www.youtube.com/@NavWealthPartners

You Make Too Much for a Roth? No You Don't. The High Earner's Roth Playbook

There's a retirement account the IRS never touches again once the money is inside: no tax on growth, no tax on withdrawals, no forced distributions in your lifetime, and heirs who can inherit it tax-free. High earners are told they make too much to open one. That's not true there's a door. A few of them.

In this episode, Ryan Knoll does the complete teardown of the Roth IRA: who can actually use one, the backdoor and mega backdoor, the rule that trips up almost everyone, and why this is one of the most powerful estate-planning tools in the code.

What's covered:

• The core bet: Pay tax now or pay tax later and why the "lazy math" assumption that your rate drops in retirement is frequently backwards once you factor in RMDs, IRMAA, an uncertain rate environment, and the widow's penalty.
• Who can actually contribute: The earned-income gate, the 2026 MAGI phase-outs, and the 6%-per-year excess-contribution penalty plus how to fix an over contribution before it costs you.
• The backdoor Roth: The two-step workaround, and the pro-rata rule that blows people up why an old pre-tax IRA balance can turn a "tax-free" backdoor into a surprise tax bill, and how to clear the slate before you convert.
• The mega backdoor: How the right 401(k) plan lets you move ten times the standard amount into Roth treatment, and the two questions to ask your plan administrator.
• The five-year rule which is actually two rules: One for earnings, one for conversions, each with its own clock, and why both largely dissolve once you're past 59½ with a seasoned account.
• Conversions and the strategy layer: Filling low brackets in the conversion corridor without tripping the next bracket, Social Security taxation, or an IRMAA threshold by a single dollar.
• The estate case: No lifetime RMDs, tax-free inheritance for your kids, and how paying the conversion tax now is a form of tax-free wealth transfer that shrinks a taxable estate.

The Roth isn't just a retirement account. For a family thinking in generations, it's one of the cleanest wealth-transfer vehicles that exists.

Book a time to map this onto your situation with a Nav Wealth advisor: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast

Follow Nav Wealth on YouTube: https://www.youtube.com/@NavWealthPartners

This episode is educational and not individualized tax, legal, or investment advice.