The Bracket - Retirement Tax Strategy for High Net Worth Households

About The Bracket - Retirement Tax Strategy for High Net Worth Households

You spent thirty years building real wealth. Now the hardest financial decisions of your life are the ones nobody prepared you for and most of them come down to taxes. The Bracket is a show for people with $2 million or more who are approaching or living in retirement and have figured out something their neighbors haven't: at this level, the threat to your money isn't the market. It's the tax code. Required minimum distributions that detonate in your seventies. Roth conversion windows that open and slam shut. The IRMAA surcharges, the widow's penalty, the capital gains decisions, the order you draw down accounts these are the levers that quietly decide whether you keep your wealth or hand a needless slice of it to the IRS over the next thirty years. Most retirement advice is written for people with a few hundred thousand dollars. This isn't that show. The Bracket is built for the household with a $2M, $5M, or $10M-plus balance sheet, where the planning is more complex, the stakes are higher, and the cost of getting it wrong is measured in hundreds of thousands of dollars. Every episode maps the specific tax decisions of the distribution years, the phase where you stop accumulating and start drawing down and shows you where the lines are, where the cliffs are, and where the opportunities hide that your CPA, who's looking backward at last year's return, will never flag. This is not a show about beating the market or picking funds. It's about the part of your financial life you actually control: when income hits, in what form, and in what order. Done right, that's worth more to a high-net-worth retiree than another point of return and unlike the market, it's a decision you get to make. The Bracket is produced by Nav Wealth Partners, a fee-only fiduciary registered investment advisory firm specializing in tax-optimized planning for the distribution phase of retirement. Nav works with high-net-worth retirees and pre-retirees who want their drawdown years engineered with the same rigor that built their wealth in the first place. The firm's focus is narrow on purpose: the years between the end of a paycheck and the end of a plan, where coordinated tax strategy compounds into real, spendable dollars. The show is hosted by Ryan Knoll, founder and CEO of Nav Wealth Partners. Ryan built Nav around a conviction that the retirement industry has the problem backwards that for households who've already accumulated enough, the next great lever isn't a better portfolio, it's a smarter tax strategy across the decades ahead. On The Bracket, he breaks down the frameworks his firm uses with its own clients, including "the stack" and the conversion corridor, in plain language, with real numbers, no jargon left undefined, and no sales pitch. The goal is simple: make you the most informed person in the room about your own retirement tax picture, whether you ever become a Nav client or not. If you've worked hard enough to have a tax problem worth solving, this show is for you. New episodes weekly. Subscribe wherever you listen. [Disclosure: The Bracket is produced by Nav Wealth Partners, a registered investment adviser. Content is educational and for general information only; it is not personalized investment, tax, or legal advice. Listening does not create an advisory relationship.]

Publisher

Ryan Knoll

Category

business

Language

en

Explicit

No

First episode

2 Jul 2026

Latest episode

28 Oct 2026

Latest episodes

16 episodes in the feed.

1. 

   28 Oct 2026

   Episode 16 - Company Stock in Your 401(k)? Read This Before You Roll It Over

   If your 401(k) holds your employer’s stock, the standard rollover to an IRA could be one of the most expensive forms you ever sign. A tax rule called net unrealized appreciation, or NUA, can let you pay capital gains rates on that stock’s growth instead of ordinary income rates. You generally get one clean shot at it. In this episode, Ryan Knoll, CFP®, walks through Tom Calloway’s 401(k): $310,000 of company stock with a $60,000 cost basis. You’ll learn: How NUA works, and what it saves in the Calloways’ illustration The three rules you have to meet: a triggering event, a lump-sum distribution and shares moved in kind The early withdrawal that can close the door for good When NUA isn’t worth it Taking out only your lowest-basis shares Timing NUA with Roth conversions and Medicare’s income lookback Unwinding a concentrated stock position once it’s out Holding company stock in a 401(k)? Book a company-stock review before any money moves:

2. 

   21 Oct 2026

   Episode 15 - Your Kids’ Tax Bomb. The 10-Year Inherited IRA Rule

   If your children inherit your IRA, they generally have ten years to empty it, and every dollar is taxed at their rate, often during their peak earning years. Under the IRS’s final 2024 rules, many heirs also owe a distribution every year along the way, and missed distributions are now penalized. In this episode, Ryan Knoll, CFP®, follows the Calloways’ IRA to their two kids. For one child, their parents’ Roth conversions barely matter. For the other, the conversions are worth six figures. You’ll learn: What the SECURE Act changed and who still gets the “stretch” The annual distribution rule heirs keep missing Why your Roth conversion decision depends on which child inherits which account Leaving IRA dollars to charity and other dollars to your kids The step-up in basis, and how it pulls against conversions State tax implications on retirement accounts The one-page letter every heir should get Haven’t reviewed your beneficiary forms lately? Book a legacy review: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast)

3. 

   14 Oct 2026

   Episode 14 -December 31 Is a Wall: The Year-End Roth Conversion True-Up

   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 (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast)

4. 

   30 Sept 2026

   Episode 13 - Stop Converting to Roth Every Year

   "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 (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast).

5. 

   16 Sept 2026

   Episode 12 - "Is $3 Million Enough?" Is the Wrong Question

   "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 (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.

6. 

   9 Sept 2026

   Episode 11 - Too Much of One Stock: 5 Rules for Getting Out Without a Tax Bomb

   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 (http://www.navwealthpartners.com).

7. 

   2 Sept 2026

   Episode 10 - The Control Account: Why Your Brokerage Account Runs Your Retirement

   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.

8. 

   26 Aug 2026

   Episode 9 - If You Are Following These Retirement Rules...Stop

   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 (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 (https://nav-wealth-resources.netlify.app/income-blueprint.html) Watch on YouTube: https://www.youtube.com/@NavWealthPartners (https://www.youtube.com/@NavWealthPartners)

9. 

   12 Aug 2026

   Episode 8 - The 5 Things to Do In the 5 Years Before You Retire

   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.

10. 

    5 Aug 2026

    Episode 7 - The Pension Asterisk: How a Pension Rewrites Everything We've Told You

    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 (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) Follow The Bracket on YouTube for the visual breakdowns → https://www.youtube.com/@NavWealthPartners (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.

11. 

    29 Jul 2026

    Episode 6 - The Index You Actually Own: Direct Indexing and The Tax Machine Under the Hood

    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 (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 (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) ▶️ Watch The Bracket on YouTube: https://www.youtube.com/@NavWealthPartners (https://www.youtube.com/@NavWealthPartners)

12. 

    22 Jul 2026

    Episode 5 - The Complete Roth IRA Teardown: Backdoors, the Five-Year Rule, and the Tax-Free Estate

    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 (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) Follow Nav Wealth on YouTube: https://www.youtube.com/@NavWealthPartners (https://www.youtube.com/@NavWealthPartners) This episode is educational and not individualized tax, legal, or investment advice.

13. 

    15 Jul 2026

    Episode 4 - The 3-Year Head Start: How Business Owners Sell for $10M and Keep the IRS Out of It

    $9 Million in Gains, Almost Zero Tax: The Business Owner's Exit Playbook Sell a business for $10 million with a $1 million basis, and there's $9 million of capital gain sitting on the table — and a federal tax bill north of $2 million before your state takes its cut. Most owners treat that number like weather: unavoidable. It isn't. It's what happens when you do no planning. In this episode, Ryan Knoll maps the full arc of a business sale — the moves you make before the sale to shrink that $9 million gain, and the moves you make after, when most of your wealth is sitting in a taxable brokerage account, to build a retirement where you realize gains year after year and pay the IRS close to nothing. The pre-sale playbook: QSBS (Section 1202) — the nuclear option: How the July 2025 OBBBA overhaul added a tiered holding schedule (50% at 3 years, 75% at 4, 100% at 5), raised the exclusion cap to $15M, and lifted the company-size ceiling — and why this is a seven-figure conversation almost nobody has early enough. Plus the "stacking" move that multiplies the exclusion across trusts. Charitable Remainder Trusts: Turning a single-year taxable event into a smooth lifetime income stream, with the pre-tax amount compounding inside a tax-exempt trust. Deferral structures: Installment sales and ESOPs (Section 1042) — spreading the gain over years or rolling it into a tax-advantaged buyer, and the credit risk you take on when you become the bank. The loss machine: Why standing up a direct-indexing portfolio years before the sale banks a war chest of carryforward losses to deploy against the sale-year gain. The post-sale playbook: Why a big taxable brokerage pile is the best raw material for a tax-free retirement — because you control your income. The zero-percent capital gains bracket, and the "sell and rebuy" move that walks your basis up tax-free (no wash-sale rule on gains). How direct indexing does double duty post-sale: extending your tax-free harvest past the bracket ceiling and unwinding concentrated stock positions. The traps that wreck all of it: NIIT, state tax, ACA subsidies, Roth conversions competing for bracket space, and the estate-tax threshold a growing portfolio can quietly cross. The through-line: the owner who calls after the letter of intent gets a haircut. The owner who calls three years out builds a tax-free retirement. Near a sale? The clock is the most valuable thing you own. Book a time to map your exit with a Nav Wealth advisor: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) Follow The Bracket on YouTube: https://www.youtube.com/@NavWealthPartners (https://www.youtube.com/@NavWealthPartners) This episode is educational and not individualized tax, legal, or investment advice.

14. 

    8 Jul 2026

    Episode 3 - The Retirement Tax Stack

    The Three Phases of Retirement Income: How to Beat the RMD Tax Bomb For the disciplined saver, the largest expense in retirement often isn't healthcare or travel — it's taxes. Decades of deferring into your 401(k) and traditional IRA built an enormous pile of money the IRS has a claim on. The only question is how big that claim gets. In this episode, Ryan Knoll breaks down the retirement income tax stack and the three distinct phases every retiree moves through — each offering a very different amount of control over your tax bill. You'll learn: Phase One — The Golden Window: The handful of years between retirement and Social Security/RMDs, when you have near-total control over your taxable income. Why celebrating a near-zero tax bill here is often a catastrophic mistake, and how Roth conversions and capital gains harvesting let you fill low-rate bracket space before it disappears forever. Phase Two — Social Security Turns On: How the "tax torpedo" can spike your effective rate as withdrawals drag previously tax-free Social Security into taxability, plus the tighter dance of managing conversions, IRMAA surcharges, and provisional income. Phase Three — The RMD Cliff: Why the retiree who kept income low and let the traditional IRA grow untouched arrives here with the biggest possible problem — six-figure forced withdrawals, inflated Social Security taxation, IRMAA surcharges, and the widow's penalty — and almost no levers left to pull. The core philosophy in one sentence: use the flexibility of Phases One and Two to shrink the problem in Phase Three. Same money, same lifestyle, wildly different lifetime tax outcome — the only variable is whether someone was paying attention during the years that mattered. Want to map out what your three phases actually look like with your numbers? Book a time with a Nav Wealth advisor — link in the show notes. Want to map out what your three phases actually look like with your numbers? Book a time with a Nav Wealth advisor: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) Follow Nav Wealth Partners on YouTube for more retirement tax strategy: https://www.youtube.com/@NavWealthPartners (https://www.youtube.com/@NavWealthPartners) This episode is educational and not individualized tax, legal, or investment advice.

15. 

    2 Jul 2026

    Episode 2 - The Roth Conversion Corridor

    The Roth Conversion Corridor: How to Slash Your Retirement Tax Bill Before RMDs Force Your Hand If you have a seven-figure IRA or 401(k), you may be sitting on a tax bomb you don't even know about. In this episode we break down the Roth Conversion Corridor, the strategy high-net-worth retirees use to voluntarily convert traditional IRA and 401(k) dollars to a Roth at today's lower tax rates, before Required Minimum Distributions (RMDs) force you into a higher bracket for life. You'll learn how to estimate your future tax bracket at RMD age, how bracket targeting (also called bracket filling) works, and why your capital gains, dividends, and interest income quietly eat up your conversion window every year. We cover the 2026 tax brackets, the standard deduction, taxable income calculation, and the new RMD start ages under SECURE 2.0, age 73 if you were born before 1960, and age 75 if you were born in 1960 or later. This is the exact framework we use with clients at Nav Wealth Partners to build tax-efficient retirement income plans and defuse the RMD tax bomb before it detonates. ⏰ Ready to see your own Roth conversion corridor modeled with your actual numbers? Book a free retirement tax planning call here 👉 https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) In this episode: Why RMDs at 73/75 can lock you into a higher tax bracket for the rest of your life How to estimate your expected tax bracket at RMD age Bracket targeting: filling the 12% or 22% bracket on purpose How to calculate taxable income (and why the standard deduction creates free conversion room) How capital gains, dividends, and interest income use up your conversion space The 0% long-term capital gains bracket and the conversion trade-off Avoiding the over-conversion cliff 📩 Want the retirement tax planning resources we mention? Grab them and book your call: https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) Disclaimer: This video is for educational purposes only and is not individualized tax, legal, or investment advice. 2026 figures are current as of publication and subject to change. Consult a qualified fiduciary advisor before implementing any strategy. Nav Wealth Partners is a fee-only, fiduciary Registered Investment Adviser.

16. 

    2 Jul 2026

    Episode 1 - The Bracket Intro

    You spent thirty years building real wealth. Now you're facing the financial decisions nobody prepared you for and most of them come down to one thing: taxes. In this first episode of The Bracket, Ryan Knoll, founder of Nav Wealth Partners, lays out what this show is, who it's built for, and why the biggest threat to a multi-million-dollar retirement isn't the market. It's the tax code. If you've got at least $2 million and you're approaching or already in retirement, the standard retirement advice you keep hearing was written for someone else, someone with a fraction of what you've built. Your problem is different. A huge share of your money has never been taxed, and the IRS hasn't forgotten. Ryan walks through one example that shows the shape of it: how decades of "smart" tax deferral can quietly build a tax bomb in your seventies and the narrow window you have to defuse it before it goes off. This episode covers: Why the market is no longer your real financial risk — and what is The tax trap hiding inside the accounts you were told to max out The planning window most retirees don't know they have (and waste) What's ahead: Roth conversions and the over-conversion cliff, withdrawal sequencing, IRMAA surcharges, and the income-spike year that can wreck a decade of planning No products. No pitch. Just the frameworks Nav uses with its own clients in plain language, with real numbers so you become the most informed person in the room about your own retirement tax picture. If you've worked hard enough to have a tax problem worth solving, you're in the right place. Want to talk through your own situation? Meet with us here https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast (https://calendly.com/ryan-navwealthpartners/nav-introductory-call-podcast) New here? Follow The Bracket and leave a rating it's the single biggest thing that helps another retiree find the show. — Disclosure: The Bracket is produced by Nav Wealth Partners, a registered investment adviser. Content is educational and for general information only and is not personalized investment, tax, or legal advice. Listening or contacting us does not create an advisory relationship. Consult a qualified professional before acting on anything discussed.

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Contact The Bracket - Retirement Tax Strategy for High Net Worth Households

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