The Weekly Wealth Podcast

David Chudyk

Exploring the Mindsets, Tactics, and Strategies to help you to build and maintain wealth.

  1. 1d ago

    You think you know, but do you REALLY know?

    You’ve nodded along when someone said “futures are up” or “don’t worry, it’s a write-off.” So has almost everyone. In this episode, David Chudyk, CFP®, breaks down 18 financial terms that even successful business owners, executives, and physicians get wrong, plus one bonus term that changes how you measure success. From the Dow Jones vs. the S&P 500, to bond yields, the national debt vs. the deficit, what a fiduciary really is, marginal vs. effective tax rates, the 2026 charitable deduction rules, umbrella insurance, own-occupation disability, buy-sell agreements, EBITDA, and sequence of returns risk. Each term gets a plain-English definition and the “gotcha” most people miss. In This EpisodeRound 1: The Scoreboard Dow Jones: why the most famous number in finance is a headline, not a benchmarkS&P 500: why “I own the index” is a bigger bet on a few companies than you thinkNasdaq: the exchange vs. the Composite vs. the Nasdaq-100Futures: a mood ring, not a crystal ballPrivate equity: lockups, capital calls, and “two and twenty” Round 2: Rates & Washington Yield: the bond price seesawFed funds rate: why the Fed doesn’t set your mortgage rateDeficit vs. national debt: why a smaller deficit still grows the debt Round 3: Investing & Taxes Fiduciary: the one question to ask every advisorMarginal vs. effective tax rate: why a raise never shrinks your paycheck (and where the real cliffs are)Write-off: why “it’s a write-off” means the IRS chips in, not that it’s free Round 4: Risk Management Umbrella liability: cheap protection most wealthy families don’t carry enough ofReplacement cost vs. actual cash value: same storm, same roof, very different checkOwn-occupation disability: the definition that decides whether a claim gets paid Round 5: Business Owners & Retirees Key person & buy-sell funding: the agreement most owners signed but never fundedEBITDA & multiples: how buyers decide what your business is worthSequence of returns risk: why your first few years of retirement matter more than your average return Bonus: Wealth, and why it’s measured in time, not dollars Key TakeawaysA write-off is a discount, not a refund. A $1,000 gift in the 32% bracket still costs you about $680.Rising yields mean falling prices on the bonds you already own.“Fiduciary” isn’t automatic. Ask every advisor to put it in writing.A buy-sell agreement with no funding isn’t a plan.Wealth isn’t what you earn or own. It’s how long you could live your life if the paychecks stopped. Resources MentionedBook a free 20-minute Vision Call: weeklywealthpodcast.com/vision Business owners, take the Sellability Score: weeklywealthpodcast.com/sellabilityscore Enjoyed This Episode?Follow the show, leave a rating, and send this episode to the friend who uses “EBITDA” in casual conversation.

    You think you know, but do you REALLY know?
  2. 5d ago

    The Tax Alpha Protocol # 4 .... Domicile vs Statutory Residency.

    Tax Alpha Protocol · Part 4 You packed the truck, changed your address in Workday, and started working from a state with lower taxes. Your old state may still consider you a resident, and it has the cell tower records to argue the point. In Part 4 of the Tax Alpha Protocol series, CFP® David Chudyk and Cliff Morgan unpack state domicile: the rules that decide which state gets to tax your income, why remote workers keep getting caught in multi-state audits, and what a clean, defensible move actually requires. 183days: the common statutory residency threshold 365days you may need to document in an audit 5factors courts weigh to decide your domicile In This EpisodeDomicile vs. statutory residency, and why buying a condo in Florida doesn’t automatically end your old state’s claimThe 183-day test and how even part of a day in your former state can count as a full dayThe “convenience of the employer” rule in New York, Pennsylvania, and other states that can tax remote work done somewhere elseHow one remote employee can create tax and registration obligations for the employer in a new stateWhat state auditors actually pull: phone records, toll transponder logs, credit card swipes, utility usage, and building key card dataWhy changing your payroll address without truly moving isn’t a planning strategy, and the civil fraud penalties that followThe five domicile factors and the checklist for a clean break: property, licenses, voter registration, banking, doctors, clubs, and even where the family dog livesA preview of the next episode: the 10-year rule for inherited retirement accounts Key TakeawaysWhere you work isn’t the same as where you’re taxed. Your employer approving a move is not the same as your old state agreeing you’ve left. The burden of proof is on you. In a residency audit, you may have to document where you were every day of the year. Gaps tend to get counted against you. Keeping the old house can keep the old tax bill. A home you can still use in your former state can work against a non-residency claim, even if you only visit. A real move is a complete move. Licenses, voter registration, banks, doctors, advisors, memberships, and the things you care most about should all point to the new state. Resources MentionedPrevious Tax Alpha Protocol episodes: [link to Parts 1–3]Next up: Inherited IRAs and the 10-year distribution rule Connect with Cliff MorganLinkedIn: Cliff Morgan, Net Worth AccelerantBook a 15-minute complimentary call: nwabriefing.com Thinking about a move, or not sure which state you really belong to on paper? Let’s talk before the auditor does. Book a Strategy Call Or email David: david@parallelfinancial.com This Episode’s SponsorThis episode is brought to you by The National Insurance Agency (NIA). Get a complimentary risk management review of your home, auto, umbrella, and business coverage. Email Ashleigh at ashleigh@jointheNIA.com. The information presented on this podcast is for general educational purposes only and does not constitute financial, investment, legal, or tax advice. Parallel Financial is registered with the U.S. Securities and Exchange Commission (SEC) as a registered investment advisor. Registration does not imply a certain level of skill or training, nor does it constitute an endorsement by the SEC. All investing involves risk, including the potential loss of principal. Please consult a qualified financial professional before making any financial decisions.

  3. Oct 23

    Why 1 in 3 People Making $500K Live Paycheck to Paycheck

    “Do you spend an appropriate amount of money on your lifestyle?” It’s one of the first questions David Chudyk asks every new client. It sounds easy. It isn’t. And the most important word in it is appropriate. Underneath that question is the most important formula in personal finance: income minus expenses must be greater than zero. A fourth grader can do the math. Yet Goldman Sachs’ 2026 retirement survey found that more than a third of households earning over $500,000 a year say they live paycheck to paycheck. That’s a higher share than households earning $50,000 to $100,000. In this episode, David breaks down why this formula applies at every income level. He covers what “appropriate” spending really means (and why spending too little can be a problem too), and how business owners, executives, and salespeople can pull the income lever, not just the expense lever. He also explains why the simplest rule in finance is so hard to follow, and why a good advisor is part behavior coach. Along the way: Mike Tyson’s $23 million bankruptcy, Nicolas Cage’s stolen dinosaur skull, and what the real data says about NFL players going broke. What You’ll LearnWhy income is not a strategy. The U-shaped curve showing financial stress climbs back up above $300KThe three outcomes of the formula: building, treading water, or borrowing from future youWhat “appropriate” really means. It’s measured against your income, your goals, and your valuesWhy over-saving can be just as inappropriate as overspendingThe warning signs David listens for when clients answer his questionHow a 5% price increase can be a 33% raise for a business ownerThe business owner trap: the great year sets the lifestyle, and the bad year pays for itWhy simple isn’t easy, and how an advisor acts as a behavior coachThe Freedom Point version of the formula, and why every dollar of lifestyle has to be funded twice Episode Chapters00:00 – The one question David asks every new client02:45 – The formula doesn’t care what you make05:30 – Tyson, Cage, and the NFL: when big income isn’t enough08:45 – Unpacking the word “appropriate”14:30 – Expenses are only half the equation: the income lever20:30 – Simple isn’t easy: the advisor as behavior coach25:30 – The Freedom Point version, plus your one move this week Key Numbers From This Episode36.6% of households earning over $500K say they live paycheck to paycheck, compared with 22.2% at $100K–$200K (Goldman Sachs, 2026)46% of $500K+ households pay only the credit card minimum or less, nearly the same as households under $50K (47%)1 in 6 NFL players filed for bankruptcy within 12 years of retiring (NBER, 2015), with little difference based on career length or earnings$250,000 is roughly what it takes to support each $10,000 of annual spending in retirement, using the 4% rule of thumb (a starting point, not a guarantee) Quotable Moments“If your income minus your expenses is less than zero, you’re borrowing from future you. And future you did not sign off on this.”“A $15,000 vacation can be completely appropriate for one family and reckless for another. Same trip. Different formula.”“For business owners, the great year sets the lifestyle. The bad year pays for it.”“Nobody hires me to do subtraction. The math isn’t the hard part. Behavior is the hard part.”“Every dollar of lifestyle has to be funded twice: once by your paycheck, and again by your portfolio.” Your One Move This WeekPull the last 12 months of your bank and credit card statements. Before you total them, write down your guess. Then compare, and sit down with your spouse or partner to answer the question honestly: Do we spend an appropriate amount of money on our lifestyle? Take the Next StepBook a 20-minute Vision Call with David: weeklywealthpodcast.com/visionBusiness owners, get your free Sellability Score: weeklywealthpodcast.com/sellabilityscore. See how a buyer would view your business today. Resources MentionedGoldman Sachs Asset Management, Retirement Survey & Insights Report 2026, as reported by FortuneCarlson, Kim, Lusardi & Camerer, “Bankruptcy Rates among NFL Players with Short-Lived Income Spikes” (NBER Working Paper 21085)Bill Bachrach, values-based financial planningDan Sullivan & Dr. Benjamin Hardy, Who Not How Related EpisodesWant more on this topic? Check out David’s episode on the Freedom Point for a deeper look at when work becomes optional. About the HostDavid Chudyk, CFP®, CLTC, and Certified Value Builder Advisor, works with business owners, executives, and physicians on wealth management, risk management, and exit planning. He helps clients reach their Freedom Point, the moment when work becomes optional. New episodes of the Weekly Wealth Podcast drop every week. Enjoyed this episode? Follow the show and leave a rating or review. It’s how other business owners and families find us.

    Why 1 in 3 People Making $500K Live Paycheck to Paycheck
  4. Oct 16

    Ep 285: The Tax Alpha Protocol # 3...Your Exit tax bill is written before your LOI

    Most founders assume the tax bill on their exit gets settled at the closing table. By then, most of it is already locked in. The entity you chose years ago, when (or whether) equity moved into a trust, and how you respond when the buyer asks for a tax election all decide how much of that check you actually keep. In Part 3 of our six-part Tax Alpha Protocol series, wealth strategist Cliff Morgan, founder of Net Worth Accelerant, explains how irrevocable non-grantor trusts can hold equity ahead of a liquidity event. Then David Chudyk, CFP®, takes the other side of the table: who really qualifies for the Section 1202 small business stock exclusion, why buyers push for a Section 338(h)(10) election, and how to make sure a gross-up actually makes you whole. 100%Federal gain Section 1202 can exclude, if you qualify $15M1202 cap for stock issued after July 4, 2025 5 yrsHolding period for the full exclusion $75MGross asset limit for newly issued QSBS What You'll Learn Why your operating company is the wrong place to manage post-exit wealthHow an irrevocable non-grantor trust differs from a revocable living trust, and what accidentally turns it back into a grantor trustWhy trust timing matters: transfer equity after a deal is effectively done and the IRS can tax the proceeds to you anywayThe four hurdles that knock most founders out of Section 1202Why buyers want an asset purchase and sellers want a stock saleHow a 338(h)(10) election can turn capital gain into ordinary income, and how to price the gross-up correctly Your Operating Company Isn't a Wealth Structure LLCs and corporations are built to run a business: sell, grow, and manage liability. Once a liquidity event is on the horizon, the priority shifts to preserving capital, diversifying risk, and governing family wealth. Cliff explains why parking large post-sale proceeds inside the original operating entity usually creates friction instead of solving it. Irrevocable Non-Grantor Trusts, Explained In an irrevocable non-grantor trust, the founder transfers ownership of selected equity to an independent trustee who manages it for named beneficiaries. The trust is its own taxpayer, with its own EIN, its own books, and its own annual Form 1041 return, which keeps those assets separate from the founder's personal estate. Not the same as a revocable living trust: a revocable trust mainly keeps assets out of probate. It isn't a separate taxpayer and doesn't wall assets off during a sale.Control is the trap: keep too much administrative control, retain the power to revoke, or borrow from the trust without adequate interest and collateral, and the IRS treats it as a grantor trust. Everything flows right back onto your personal 1040.Modern governance tools: an independent trust protector can review performance and replace trustees, and directed trust provisions let a specialized investment manager run the portfolio while a corporate trustee handles reporting and compliance. Worth knowing: non-grantor trusts reach the top federal income tax bracket at a far lower income level than individuals do, and funding one is generally a taxable gift that uses lifetime exemption. Design and distribution policy matter. Timing Is the Whole Game Under the assignment of income doctrine, transferring equity to a trust after a sale is effectively locked in, such as after a signed purchase agreement, can lead the IRS to tax the proceeds to the founder anyway. When planning starts early, the trust can be the genuine owner of record and sell as the legal seller at closing. Section 1202: The Best Deal in the Tax Code, If You Qualify Qualified small business stock can let you exclude up to 100% of your federal capital gain on a sale. Not defer it. Exclude it. The cap is the greater of 10 times your basis or a flat dollar amount: $10 million for older stock, and $15 million (indexed for inflation going forward) for stock issued after July 4, 2025. The catch? Most founders David talks to don't qualify. Hurdle 1: It has to be a C corporation. Most closely held businesses are LLCs, partnerships, or S corps. You can convert, but value built before the conversion doesn't get the exclusion, and the holding clock starts on the conversion date.Hurdle 2: The holding period. Stock issued after July 4, 2025 gets 50% excluded at three years, 75% at four, and 100% at five. Older stock is five years or nothing. Buyers don't time offers around your clock.Hurdle 3: The size test. Gross assets can't exceed $50 million ($75 million for newly issued stock) before and immediately after issuance. A big outside capital raise can push you over the line.Hurdle 4: The type of business. Many service businesses are excluded outright, including health care, law, accounting, consulting, financial services, and hotels and restaurants. If you run a medical practice or professional firm, 1202 likely isn't your tool. Asset Sale vs. Stock Sale: You and the Buyer Want Opposite Things Once you agree on a price, the deal structure decides how much you keep. Buyers prefer an asset purchase because they get a stepped-up basis: fresh depreciation on equipment and 15-year amortization of goodwill and customer lists, deductions that shelter their future profits. Sellers prefer a stock sale: clean capital gain on the full price and no depreciation recapture. The 338(h)(10) Election and the Gross-Up For S corporations and subsidiaries of another corporation, buyers often propose a Section 338(h)(10) election as a compromise. Legally it's a stock sale, so contracts, licenses, and permits stay put. For tax purposes, it's treated as if the company sold its assets and liquidated. Great for the buyer. Potentially expensive for you. Receivables and inventory can produce ordinary incomePreviously depreciated equipment triggers Section 1245 recapture, taxed as ordinary income in what's likely your highest-bracket yearDepreciated real property can create gain taxed at higher rates than long-term capital gainSome states treat a deemed asset sale differently than the IRS, adding state tax David's rule: don't agree to a 338(h)(10) election without a gross-up in the purchase agreement. Your accountant calculates what you'd net after tax in a straight stock sale, then what you'd net under the election, and the buyer pays the difference. The piece people miss: the gross-up is more purchase price, so it's taxable too. In a purely hypothetical example, if the election costs you an extra $500,000 in tax and the buyer writes a $500,000 check, you'll owe tax on that check and still come up short. The math has to solve for the full amount. If the buyer wants the step-up, the buyer pays for it. The Bottom Line C corp in a qualifying industry that can hold five years? Section 1202 may wipe out your federal gain. Plan for it early, not at the letter of intent.S corp owner facing a 338(h)(10) request? Negotiate the gross-up. Don't give away the step-up for free.Considering a trust or deferral structure? Go in with your eyes open, get independent tax counsel and a written opinion, and understand how the IRS has treated similar arrangements before you commit. Coming Up in Part 4 Protecting the sale is a big win, but for most owners and executives the bigger ongoing number is income. Next time, David and Cliff dig into multi-state tax exposure: nexus audits, remote executives, and how to stay compliant when your income touches more than one state. Planning an Exit in the Next Few Years? The best time to talk structure is before a buyer shows up. Book a free Vision Call with David and walk through your situation at the 30,000-foot level. Schedule your Vision Call Prefer email? Reach David at david@parallelfinancial.com. Own a business? Find out how sellable it really is, and what drives its value to a buyer, with the free Sellability Score. About Cliff Morgan Cliff Morgan is a wealth strategist and

  5. Oct 8

    Ep 284: The Tax Alpha Protocol with Cliff Morgan (part duex)

    You’re not eliminating tax, you’re moving it.” CFP® David Chudyk and Cliff Morgan of Net Worth Accelerant cover two topics this week. First, how families in states with their own lower estate tax thresholds can plan around them. Second, the real estate strategies high earners hear about most, and what has to be true before those strategies hold up. In this episode: Decoupled state estate taxes. Twelve jurisdictions, including New York, Massachusetts, Oregon and D.C., tax estates well below the federal exemption. Cliff walks through state-only QTIP elections, formula-clause trusts, lifetime gifting and look-back rules, and domicile changes.The hidden trade-off. Several of these techniques give up the second basis step-up at death. Survivorship life insurance in an ILIT is a common way to give heirs liquidity for the capital gains that follow.The passive “wall.” Long-term rental losses generally can’t offset W-2 wages, no matter how many hours you put in.The short-term rental exception. If the average guest stay is 7 days or less, the property is treated as a business rather than a rental. That only helps if you can prove material participation with a contemporaneous log. Hiring a manager who logs more hours than you is a common way to fail.Real Estate Professional Status. It requires 750+ hours and more than half of your total working time. For most surgeons and executives, that math doesn’t work.Depreciation recapture. Cost segregation and bonus depreciation shift tax to a later date rather than erasing it. Converting a short-term rental to a long-term rental is a reclassification event worth planning around.1031 exchanges, done right. You need a qualified intermediary, a 45-day identification window and a 180-day closing deadline. And don’t let the tax tail wag the dog by buying a property you’d never otherwise own. Next week: Complex exit liquidity, private contract trust structures, and the limits of QSBS (§1202) for LLC owners. Connect: David: weeklywealthpodcast.com/vision for a 10–15 minute vision callCliff: www.networthaccelerant.com for a complimentary 15-minute consult, or find him on LinkedIn

  6. Oct 2

    Ep 283: Bathroom Floor Moments: Why Smart People Make Emotional Money Decisions with Jax Crider

    Knowing the math doesn't make you immune. Just ask Jax Crider. About four years ago, with a down market shrinking her income and a daughter born eight weeks early who spent 47 days in the NICU, Jax and her husband did the financially responsible thing: they listed their big house. Then somebody left the half-bath water running. For three and a half days. Nearly half a million dollars of damage later, the family was in a financial tailspin. David and Jax, a 24-year mortgage and financial services veteran and host of the Financial Mastery Simplified podcast, dig into what happens after the bathroom floor moment: how to separate what was your fault from what was just life, why brilliant people still make emotional money decisions, and why the bank's maximum approval isn't the same as what you can actually afford. In This EpisodeMostly life, partly you. Jax's honest self-audit puts her setback at roughly 75% life and 25% choices she'd make differently, and why high achievers are often too hard on themselves.Credit is fixable. How 24 years in mortgage reminded Jax that credit is malleable and the situation was temporary.The math is simple; the emotions aren't. How childhood money programming quietly drives adult decisions.Two ways smart people freeze. Avoiding decisions to keep from feeling stupid, or researching forever. Either way, not making a choice is still a choice.Qualifying is not affording. Why a good mortgage professional should challenge you whether you're stretching too far or letting fear hold you back.David's Four Healths. Physical, relationship, spiritual, and financial, and why money alone isn't a win.Swipe vs. cash. How a card-first generation experiences spending differently.Who, not how. Why the right expert in your corner beats Googling your way through big financial decisions. Featured Quote"When you can stop thinking about every single thing that happens as something that's happening to you, and you start thinking about how it's happening for you, everything will change." (Advice from Jax's coach, shared on the show) What Is Wealth?Jax's answer: freedom. The ability to do what she wants, when she wants, without asking permission, to spend in line with her values, and to say yes when someone asks her to give. Bonus ContentA mortgage is one of the biggest financial decisions you'll make, so don't make it in a silo. Your financial advisor, mortgage professional, CPA, and attorney should all be working together, and typically your financial advisor is the quarterback of that team. Connect with Jax CriderWebsite: jaxcrider.comPodcast: Financial Mastery Simplified Resources MentionedWho Not How by Dan Sullivan & Dr. Benjamin Hardy Book Your Free Wealth Vision CallWhere is your money actually taking you? Grab a free, no-pressure Wealth Vision Call. Bring your biggest financial question and walk away with clarity, confidence, and direction. weeklywealthpodcast.com/vision DisclaimerThe information presented on this podcast is for general educational purposes only and does not constitute financial, investment, legal, or tax advice. Parallel Financial is registered with the U.S. Securities and Exchange Commission (SEC) as a registered investment advisor. Registration does not imply a certain level of skill or training, nor does it constitute an endorsement by the SEC. All investing involves risk, including the potential loss of principal. Guest views are their own. Mortgage services discussed are offered by the guest and are not affiliated with Parallel Financial. Please consult a qualified financial professional before making any financial decision

  7. Sep 25

    Ep 282: Welcome to the Tax Alpha Protocol with Cliff Morgan

    For fifteen years, the estate planning playbook said the same thing: get assets out of your estate before you die. That advice made sense when the exemption was $5 million. It makes a lot less sense now that it's $15 million per person and $30 million per married couple, and permanent. In the first episode of our six-part Tax Alpha Protocol series, David Chudyk, CFP®, is joined by wealth strategist Cliff Morgan, founder of Net Worth Accelerant. They break down what the One Big Beautiful Bill Act actually locked in, the SALT deduction trap hiding between $500K and $600K of income, and why gifting appreciated assets during your lifetime can quietly hand your heirs a seven- or eight-figure capital gains bill. In This EpisodeThe federal estate exemption is $15M per person ($30M per couple) for 2026 and permanent. For most families, capital gains is now the bigger threat.Gifting appreciated assets during life passes along your low basis. Assets inherited at death get a step-up in basis.If your MAGI sits between roughly $500K and $600K, the SALT phase-out can push your marginal rate into the mid-to-high 40s.The expanded SALT cap expires January 1, 2030. Plan around it now, not in 2029.Residents of states with their own estate tax, and business owners with valuable companies, may need a custom strategy.Donate appreciated securities directly; never sell first and donate the cash. What the One Big Beautiful Bill Act Locked InSigned on July 4, 2025, the One Big Beautiful Bill Act (OBBBA) removed the cliff that had high-net-worth families scrambling. Instead of the estate exemption falling to roughly $7 million per person when the Tax Cuts and Jobs Act sunset, it rose to $15 million per person for 2026 and will be indexed for inflation going forward. Income tax brackets are permanent: 10%, 12%, 22%, 24%, 32%, 35%, and a top rate of 37% (instead of reverting to 39.6%).Bracket creep protection: bracket thresholds keep adjusting for inflation every year, so a cost-of-living raise doesn't automatically push you into a higher bracket.Charitable cash gifts: the 60%-of-AGI limit is now permanent. But starting in 2026, itemizers only get a deduction for contributions above 0.5% of AGI, and corporations only above 1% of taxable income (still capped at 10%). The Asterisk: State Estate TaxesThe federal number isn't the only number. Roughly a dozen states plus Washington, D.C. levy their own estate tax with far lower exemptions, as low as $1 million in Oregon. If you live in one of them, you need a custom strategy. And business owners get there faster than they think. David raised the point on air: a company doing a few million in revenue with healthy EBITDA can be worth $7–9 million on paper, even if you don't have anywhere near that in cash. Add a couple of well-funded 401(k)s and a house, and a "huge" state exemption stops looking so huge. The SALT "Squeeze Zone"The state and local tax (SALT) deduction cap jumped from $10,000 to $40,000 for 2025 ($40,400 for 2026), rising 1% a year through 2029. That's real money for people who itemize. But there are two catches. Catch #1: the income test. Once your modified adjusted gross income passes roughly $500,000, you lose 30 cents of that extra deduction for every dollar you earn above the threshold, until you're back down to the $10,000 floor at around $600,000. Inside that band, your effective marginal rate spikes. Catch #2: the expiration date. On January 1, 2030, the expansion disappears and the cap drops back to $10,000 for everyone. Cliff's example: a specialist earning around $500,000 agrees to pick up one extra ER shift. Because every extra dollar also shrinks their SALT deduction, the federal tax on that shift lands in the mid-to-high 40% range. Nearly half the shift, gone. The fix is planning ahead: maximizing pre-tax retirement contributions and timing deductions to keep MAGI below the phase-out while the window is open. Carryover Basis vs. Step-Up in BasisThis is the heart of the episode. Two sections of the tax code have worked the same way for decades. What changed is the context around them. Section 1015 (lifetime gifts): if you give an asset while you're alive, the recipient inherits your original cost basis, along with every dollar of unrealized gain. Section 1014 (inheritance): if that same asset passes at death, the basis resets to fair market value on the date of death. The built-up gain isn't deferred. It's gone. David's illustration: $10,000 invested in Microsoft roughly 40 years ago would be worth about $62 million today (past performance is not indicative of future results). Gift those shares to your kids while you're alive and they're holding a $10,000 basis. If they sell, the federal capital gains tax alone runs well north of $10 million. Leave the shares to them at death, and that gain is wiped clean. When the estate tax kicked in at $2 or $5 million, paying that basis cost to dodge a 40% estate tax often made sense. At $15 to $30 million, the math has flipped for the overwhelming majority of families. "Don't let 2017-era tax anxiety drive a 2026 decision. The law changed, the threats changed, and the playbook has to change with it." David Chudyk, CFP® Three Filters Before You Gift an AssetHow much growth has already happened? A low-basis asset that has already done most of its appreciating usually favors holding until death. Gifting it just turns a future tax-free event into a taxable one.How much room is left to run? Early-stage assets, like pre-IPO equity or a young, fast-growing business, can be better lifetime-gift candidates, but only if moving that future growth out of your estate actually changes your outcome.Are you charitably inclined? Gifting appreciated securities directly to a charity or donor-advised fund can be the cleanest move on the board: no capital gain, a fair-market-value deduction, and no basis problem. Just don't sell first and donate the cash, which gives up the benefit. The "Wrong" Financial Decision Can Be the Right Life DecisionNot every choice should be optimized for taxes. Paying a grandchild's tuition or helping with a first car while you're here to see it can be worth a tax bill. As David puts it: don't make every decision based on taxes, and don't make decisions without considering taxes. Your health, life expectancy, and goals all belong in the conversation. Doing Some of Both: Securities-Backed Lines of CreditSometimes it doesn't have to be either/or. A securities-backed line of credit lets you borrow against a portfolio instead of selling it, so you can help family now without realizing the gain, while the shares can still receive a step-up at death. The loan is repaid from the estate, and Cliff noted that life insurance can be used to replace that amount for heirs if you're insurable. It's a tool, not a free lunch: you pay interest, market drops can trigger collateral calls, and a large gift to a family member still counts as a gift for reporting purposes. This is exactly the kind of move to model with an advisor before you pull the trigger. "If you really know how the game is played and you can play the game, it's truly to your advantage." Cliff Morgan Who Not HowDavid closes with one of his favorite ideas from Dr. Benjamin Hardy and Dan Sullivan's Who Not How: when you face a complex problem, ask "who can help me solve this?" instead of "how do I figure this out myself?" A surgeon, a business owner, or any high earner creates the most value doing what they're trained for, not reading the tax code at midnight. Your Vision Deserves 10 MinutesNot sure whether to gift now, hold for the step-up, or do some of both? Book a free Vision Call with David and talk through your situation at the 30,000-foot level. Schedule your Vision Call Own a business? Find out what it's really worth to a buyer, and how that value affects your estate, with the free Sellability Score. The Tax Alpha Protocol SeriesPart 1: The One Big Beautiful Bill Act, estate exemptions, and step-up in basis (this episode)Part 2: Deconstructing active income offsets and real estate tax trapsPart 3: Complex exit liquidity and private contract trust structuresPart 4: The state income tax nexus trap and remote work liabilitiesPart 5: The generational tax bomb and wealthy psychologyPart 6: Alternative liquidity and the family office triad About Cliff MorganCliff Morgan is a wealth strategist and the founder of Net Worth Accelerant. After years helping Fortune 500 companies cut costs and build new revenue streams, he moved into finance and commercial real estate and has spent more than five years working with a family office, learning the strategies and mindset of generational wealth. Find Cliff on...

  8. Sep 18

    EP 281: Storytelling in your business with Rain Bennett

    Guest: Rain Bennett, Emmy-nominated filmmaker, keynote speaker, and author of The Chief Storytelling Officer This week's episode takes a detour from taxes and markets to talk about the invisible force behind every sale, every client relationship, and every business decision: storytelling. David sits down with Rain Bennett — two-time Emmy-nominated filmmaker and host of The Storytelling Lab podcast — to break down why "chief storytelling officer" has become one of the fastest-growing titles in corporate America, and what that has to do with a lawn care business, an HVAC company, or a financial advisory practice. The conversation moves from brand strategy into something more personal: the stories we unknowingly tell ourselves about what we're capable of, where those stories come from, and how to start rewriting them. What You'll LearnWhat a Chief Storytelling Officer actually is, and why the role has exploded in the past yearWhy storytelling is the foundation of trust — and why every business, even the "boring" ones, has a story worth tellingWhy competing on price alone is a race to the bottom, and what to do insteadWhy a clear story will alienate some potential customers, and why that's exactly the pointThe growth story behind a youth soccer program that scaled from one coach and eight kids to three schools and 96 families in three yearsHow to spot the self-limiting story you've been telling yourself since childhoodWhy social media algorithms may be writing a story for you, and how to take back the penDonald Miller's four characters of every story — hero, villain, victim, and guide Episode Timestamps (approximate)00:00 — Cold open and introduction to Rain Bennett02:00 — What is a Chief Storytelling Officer?04:30 — Why storytelling is the foundation of every business relationship09:00 — Price vs. value, and the Walmart/Target example12:00 — Two types of car mechanics: chains vs. relationship-driven shops15:00 — Why a story lets you charge a premium: the veteran-owned coffee example17:30 — Devil's advocate: does a clear story alienate customers?20:00 — Case study: The People's Game and its three-year growth story26:00 — Mid-roll: the 10-Minute Wealth Vision Call26:30 — The story you tell yourself, and where it comes from31:00 — Social media, algorithms, and the story being fed to you34:00 — Donald Miller's four characters: hero, villain, victim, guide36:00 — Where to find Rain, and his book offer for listeners37:30 — Rain's definition of wealth, and closing thoughts About Our GuestRain Bennett is a two-time Emmy-nominated filmmaker, author, and keynote speaker who helps businesses and individuals harness the power of storytelling to build trust, connection, and growth. He hosts The Storytelling Lab podcast, featuring conversations with the world's top storytellers, and is the author of The Chief Storytelling Officer. Connect with Rain: rainbennett.com Rain is offering Weekly Wealth listeners a personally signed copy of his book for $10 (retail ~$19) at rainbennett.com/guest. Resources MentionedRain Bennett's websiteGet a signed copy of The Chief Storytelling Officer for $10Book a free 10-Minute Wealth Vision Call

    EP 281: Storytelling in your business with Rain Bennett
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