The Weekly Wealth Podcast

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.

Round 1: The Scoreboard

• Dow Jones: why the most famous number in finance is a headline, not a benchmark
• S&P 500: why “I own the index” is a bigger bet on a few companies than you think
• Nasdaq: the exchange vs. the Composite vs. the Nasdaq-100
• Futures: a mood ring, not a crystal ball
• Private equity: lockups, capital calls, and “two and twenty”

Round 2: Rates & Washington

• Yield: the bond price seesaw
• Fed funds rate: why the Fed doesn’t set your mortgage rate
• Deficit vs. national debt: why a smaller deficit still grows the debt

Round 3: Investing & Taxes

• Fiduciary: the one question to ask every advisor
• Marginal 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 of
• Replacement cost vs. actual cash value: same storm, same roof, very different check
• Own-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 funded
• EBITDA & multiples: how buyers decide what your business is worth
• Sequence 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

• A 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.

Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision

Business owners, take the Sellability Score: weeklywealthpodcast.com/sellabilityscore

Follow the show, leave a rating, and send this episode to the friend who uses “EBITDA” in casual conversation.

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

• Domicile vs. statutory residency, and why buying a condo in Florida doesn’t automatically end your old state’s claim
• The 183-day test and how even part of a day in your former state can count as a full day
• The “convenience of the employer” rule in New York, Pennsylvania, and other states that can tax remote work done somewhere else
• How one remote employee can create tax and registration obligations for the employer in a new state
• What state auditors actually pull: phone records, toll transponder logs, credit card swipes, utility usage, and building key card data
• Why changing your payroll address without truly moving isn’t a planning strategy, and the civil fraud penalties that follow
• The five domicile factors and the checklist for a clean break: property, licenses, voter registration, banking, doctors, clubs, and even where the family dog lives
• A preview of the next episode: the 10-year rule for inherited retirement accounts

Where 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.

• Previous Tax Alpha Protocol episodes: [link to Parts 1–3]
• Next up: Inherited IRAs and the 10-year distribution rule

• LinkedIn: Cliff Morgan, Net Worth Accelerant
• Book 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: [email protected]

This 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 [email protected].

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.

“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.

• Why income is not a strategy. The U-shaped curve showing financial stress climbs back up above $300K
• The three outcomes of the formula: building, treading water, or borrowing from future you
• What “appropriate” really means. It’s measured against your income, your goals, and your values
• Why over-saving can be just as inappropriate as overspending
• The warning signs David listens for when clients answer his question
• How a 5% price increase can be a 33% raise for a business owner
• The business owner trap: the great year sets the lifestyle, and the bad year pays for it
• Why simple isn’t easy, and how an advisor acts as a behavior coach
• The Freedom Point version of the formula, and why every dollar of lifestyle has to be funded twice

• 00:00 – The one question David asks every new client
• 02:45 – The formula doesn’t care what you make
• 05:30 – Tyson, Cage, and the NFL: when big income isn’t enough
• 08:45 – Unpacking the word “appropriate”
• 14:30 – Expenses are only half the equation: the income lever
• 20:30 – Simple isn’t easy: the advisor as behavior coach
• 25:30 – The Freedom Point version, plus your one move this week

• 36.6% 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)

• “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.”

Pull 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?

• Book a 20-minute Vision Call with David: weeklywealthpodcast.com/vision
• Business owners, get your free Sellability Score: weeklywealthpodcast.com/sellabilityscore. See how a buyer would view your business today.

• Goldman Sachs Asset Management, Retirement Survey & Insights Report 2026, as reported by Fortune
• Carlson, Kim, Lusardi & Camerer, “Bankruptcy Rates among NFL Players with Short-Lived Income Spikes” (NBER Working Paper 21085)
• Bill Bachrach, values-based financial planning
• Dan Sullivan & Dr. Benjamin Hardy, Who Not How

Want more on this topic? Check out David’s episode on the Freedom Point for a deeper look at when work becomes optional.

David 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.

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 wealth
• How an irrevocable non-grantor trust differs from a revocable living trust, and what accidentally turns it back into a grantor trust
• Why trust timing matters: transfer equity after a deal is effectively done and the IRS can tax the proceeds to you anyway
• The four hurdles that knock most founders out of Section 1202
• Why buyers want an asset purchase and sellers want a stock sale
• How 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 income
• Previously depreciated equipment triggers Section 1245 recapture, taxed as ordinary income in what's likely your highest-bracket year
• Depreciated real property can create gain taxed at higher rates than long-term capital gain
• Some 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 [email protected].

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 the founder of Net Worth Accelerant. Schedule time with Cliff directly at nwabriefing.com.

The Tax Alpha Protocol Series

• Part 1: The One Big Beautiful Bill Act, estate exemptions, and step-up in basis
• Part 2: Deconstructing active income offsets and real estate tax traps
• Part 3: Complex exit liquidity and private contract trust structures (this episode)
• Part 4: The state income tax nexus trap and remote work liabilities
• Part 5: The generational tax bomb and wealthy psychology
• Part 6: Alternative liquidity and the family office triad

Sponsor

This episode is brought to you by a partnership with The National Insurance Agency (NIA). If something went wrong tomorrow, would your insurance actually cover it? Get a complimentary Risk Management Review of your home, auto, umbrella, and business coverage. Email Ashleigh at [email protected].

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. Hypothetical examples are for illustration only. Please consult a qualified financial, tax, or legal professional before making any financial decisions.

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 call
• Cliff: www.networthaccelerant.com for a complimentary 15-minute consult, or find him on LinkedIn

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.

• Mostly 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.

"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)

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.

A 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.

• Website: jaxcrider.com
• Podcast: Financial Mastery Simplified

• Who Not How by Dan Sullivan & Dr. Benjamin Hardy

Where 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

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. 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

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.

• The 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.

Signed 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 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 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.

This 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®

• How 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.

Not 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.

Sometimes 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

David 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.

Not 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.

• Part 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 traps
• Part 3: Complex exit liquidity and private contract trust structures
• Part 4: The state income tax nexus trap and remote work liabilities
• Part 5: The generational tax bomb and wealthy psychology
• Part 6: Alternative liquidity and the family office triad

Cliff 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 LinkedIn: Cliff Morgan, Net Worth Accelerant
• Book a 15-minute call: NWA Briefing

• Who Not How by Dan Sullivan and Dr. Benjamin Hardy
• IRC Section 1014 (step-up in basis) and Section 1015 (carryover basis on gifts)
• Free Vision Call with David

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 adviser. Registration does not imply a certain level of skill or training, nor does it constitute an endorsement by the SEC. Guest opinions are their own. All investing involves risk, including the potential loss of principal. Please consult a qualified financial professional before making any financial decisions.

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 a Chief Storytelling Officer actually is, and why the role has exploded in the past year
• Why storytelling is the foundation of trust — and why every business, even the "boring" ones, has a story worth telling
• Why competing on price alone is a race to the bottom, and what to do instead
• Why a clear story will alienate some potential customers, and why that's exactly the point
• The growth story behind a youth soccer program that scaled from one coach and eight kids to three schools and 96 families in three years
• How to spot the self-limiting story you've been telling yourself since childhood
• Why social media algorithms may be writing a story for you, and how to take back the pen
• Donald Miller's four characters of every story — hero, villain, victim, and guide

• 00:00 — Cold open and introduction to Rain Bennett
• 02:00 — What is a Chief Storytelling Officer?
• 04:30 — Why storytelling is the foundation of every business relationship
• 09:00 — Price vs. value, and the Walmart/Target example
• 12:00 — Two types of car mechanics: chains vs. relationship-driven shops
• 15:00 — Why a story lets you charge a premium: the veteran-owned coffee example
• 17:30 — Devil's advocate: does a clear story alienate customers?
• 20:00 — Case study: The People's Game and its three-year growth story
• 26:00 — Mid-roll: the 10-Minute Wealth Vision Call
• 26:30 — The story you tell yourself, and where it comes from
• 31:00 — Social media, algorithms, and the story being fed to you
• 34:00 — Donald Miller's four characters: hero, villain, victim, guide
• 36:00 — Where to find Rain, and his book offer for listeners
• 37:30 — Rain's definition of wealth, and closing thoughts

Rain 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.

• Rain Bennett's website
• Get a signed copy of The Chief Storytelling Officer for $10
• Book a free 10-Minute Wealth Vision Call

Every business owner has that one person. Not a partner, not family — just an employee who makes the whole place run. And every business owner has, at some point, faced the moment when that person gets a call from a recruiter.

The instinct is to counter with a bigger number. The problem? A raise is just a number, and someone can always beat a number. What actually keeps a key employee in place is a reason to stay that a bigger paycheck somewhere else can't undo.

In this episode, David Chudyk, CFP®, CLTC breaks down one of the most underused retention tools available to business owners: the executive bonus plan. He walks through why it beats the alternatives, what it actually costs once taxes are factored in, and — most importantly — the difference between a version that barely works and a version that actually has teeth.

A 401(k) or profit-sharing plan sounds like the obvious retention tool, but it's built for retaining everyone, not one or two irreplaceable people. Qualified plans have to pass IRS nondiscrimination testing, which means you generally can't do something generous for your top performer without doing something for the whole team. That makes qualified plans expensive, slow to build meaningful value, and — frankly — impersonal.

Small business owners with one or two key people are often stuck choosing between "give everyone the perk" or "give no one the perk." An executive bonus plan is the middle option nobody talks about.

Sometimes called a Section 162 bonus plan, the mechanics are simple: the company pays a bonus to a key employee, and that employee uses it to purchase a permanent life insurance policy on their own life. The employee owns the policy outright. Cash value builds inside it over time, and a death benefit protects their family.

There's no IRS approval process, no plan document filing, and no nondiscrimination testing required. It can be set up for one employee and no one else — because legally, it's just a bonus. What the employee chooses to do with it is what makes it an executive bonus plan.

• Deferred compensation: the promised money still technically belongs to the company, leaving the employee as an unsecured creditor if the business runs into trouble.
• Qualified plans: broad-based by law, slow to build value for any one person.
• A straight cash bonus: gets spent, builds nothing, and gives the employee no reason to think twice about the next recruiter call.
• An executive bonus plan: deductible to the company, fully selective, and builds real value over time.

Here's the detail that trips up a lot of owners: a bonus is taxable income to the employee. Hand someone $10,000 and they may only net around $7,000 after taxes — which means the policy doesn't get funded the way you intended.

The fix is a "double bonus," or gross-up: bonusing enough extra to cover the employee's tax liability so the full intended amount actually lands in the policy. As a rough rule of thumb, funding $10,000 into the policy often means bonusing closer to $13,000–$14,000, depending on the employee's tax bracket. It's a five-minute conversation with the right advisor — and one worth having before the first check goes out, not after.

There's a simpler version of this plan that a lot of owners stumble into first: pay the bonus, and simply suggest the employee use it to buy a policy. No plan document, no contract, nothing tying the bonus to the insurance at all. This is sometimes called a "naked" bonus plan.

It's appealing because it's free to set up and takes one conversation. But it has a serious flaw: there's nothing stopping the employee from spending the bonus on something else entirely, or from buying the policy and then cashing it out the same day they resign. The tax treatment is identical to a formal plan — but the retention benefit is close to zero. As David puts it on the show: trust isn't a plan.

A REBA solves the naked bonus plan's biggest weakness. The company still pays the bonus and the employee still owns the policy — but the company places a restrictive endorsement on it that limits the employee's access to the cash value for a set number of years. If the employee leaves before that restriction lifts, the retention teeth stay in place.

Because the employee still technically owns the policy throughout, the arrangement avoids the rules and testing that come with qualified plans — while giving the business an actual reason for a key employee to stay, not just a handshake.

This isn't a broad-based benefits strategy. It's built for the one or two people a business genuinely can't afford to lose — especially when there's no appetite for a qualified plan, or when an owner wants something more targeted for the people who matter most. Structuring it correctly means getting the comp strategy, the tax treatment, and the insurance design all right at the same time, which is exactly the kind of decision worth bringing in the right people for rather than tackling alone.

What is an executive bonus plan?

It's an arrangement where a company bonuses a key employee, who then uses that money to buy a life insurance policy they own personally. It's deductible to the company, fully selective, and requires no IRS approval or plan filings.

What's a "double bonus" or gross-up?

Because a bonus is taxable income to the employee, a gross-up bonuses extra money to cover that tax liability — so the full intended amount actually reaches the policy instead of being reduced by taxes first.

What is a naked bonus plan?

It's an informal version of an executive bonus plan where the company simply pays a bonus and suggests the employee buy life insurance with it, without any contract or restriction. It carries no real retention protection, since the employee can spend the money elsewhere or cash out the policy immediately upon leaving.

What is a Restrictive Endorsement Bonus Arrangement (REBA)?

A REBA is the formal version of an executive bonus plan. The company places a restriction on the policy's cash value for a set number of years, so a key employee who leaves early forfeits access to those funds — giving the plan actual retention power.

Is this the same as a buy-sell agreement?

No. A buy-sell agreement funds the transfer of a business owner's stake if they die or exit. An executive bonus plan is about retaining a key employee, not transferring ownership.

If your business depends heavily on one or two people, that's not just a staffing question — it's a valuation risk. Get a free Sellability Score assessment at weeklywealthpodcast.com/sellabilityscore.

Want to talk through whether an executive bonus plan makes sense for your business? Book a free 20-minute Vision Call at weeklywealthpodcast.com/vision.

Every September, the insurance industry runs Life Insurance Awareness Month — and most of the advice sounds the same: buy term, protect your family, don't wait. That advice is correct. It's also, at best, half the story.

Life insurance has two entirely different jobs depending on where you are in life. For a young parent with a mortgage and a new baby, it's the thing standing between "we'll be okay" and financial free-fall. For a business owner who's spent decades building something real, it's a liquidity and legacy tool that has almost nothing to do with dying too soon and everything to do with protecting what's already been built. Most people only ever hear about the first version. This episode covers both — plus a living-benefit feature almost nobody explains correctly, and the reason you should be skeptical the moment someone tells you they've "properly structured" your policy.

By the numbers:

• Roughly 100 million American adults are uninsured or believe they need more life insurance coverage (LIMRA & Life Happens, 2025–2026 Insurance Barometer Study).
• Healthy young adults overestimate the true cost of term coverage by 10–12 times.
• Estate taxes are typically due within 9 months of death — often with little cash on hand to pay them.
• The average life insurance coverage gap is approximately $200,000 per U.S. household.

For young families, term life insurance isn't complicated and it isn't expensive — it's one of the most misunderstood products in personal finance, largely because people wildly overestimate what it costs. David breaks down why term, not whole life, is the right starting point for most families, how to calculate a real coverage number instead of relying on a lazy "10x income" rule, and the three mistakes that quietly leave families underinsured: relying on employer coverage alone, never revisiting the policy after major life changes, and cutting coverage because of sticker shock instead of shopping it properly.

"A healthy 35-year-old can often get $1,000,000 of 20-year term coverage for the cost of a streaming subscription or two per month."

Here's the part of the episode that surprises almost everyone: modern life insurance can pay out while you're still alive. Drawing on his CLTC (Certified in Long-Term Care) designation, David explains how a long-term care or chronic illness rider lets you access a portion of your death benefit if you survive a stroke, a serious diagnosis, or another disabling health event — the kind of moment traditional life insurance does nothing for, because nobody died. This isn't a retiree-only conversation; it's relevant the moment you have a family depending on your income.

"Don't just ask 'how much life insurance do I have?' Ask 'what happens if I get sick and don't die?'"

Not sure what's actually in your policy? If you don't know whether your coverage includes living benefits — or whether it still fits your life — that's a five-minute conversation, not a five-month project. Book your free Vision Call.

For business owners, life insurance stops being a safety net and starts being a strategic tool. This segment covers two scenarios every co-owned business needs to plan for: a properly funded buy-sell agreement that lets a surviving owner keep control of the business instead of unexpectedly co-owning it with a deceased partner's estate, and key-person insurance that funds the runway to recover if someone critical to revenue is suddenly gone.

"If my partner died tomorrow, what happens? In most cases, their ownership stake doesn't just evaporate."

You can be genuinely wealthy and still face a liquidity crisis the moment you die. When a large share of net worth is tied up in a business, real estate, or concentrated stock, an estate tax bill can come due with almost no cash available to pay it — forcing a rushed sale of assets at a discount. David explains how life insurance, often held inside an irrevocable trust, creates exactly the liquidity needed to pay that bill without touching the underlying assets — and how it can be used to equalize an inheritance when one child takes over the business and the others don't.

Curious how ready your business actually is for a transition? Get your free Sellability Score.

Permanent insurance — including indexed universal life (IUL) — has a legitimate use as a tax-advantaged savings and growth vehicle, for the right person, in the right situation. But David draws a hard line around a specific phrase circulating on social media: "properly structured IUL." If someone leads with that phrase, treat it as a warning label, not a credential. This segment covers what illustrated vs. guaranteed rates actually mean, why "no market losses" isn't the whole picture, and the one question to ask before you ever sign an IUL application.

"When someone leads with the phrase 'properly structured,' that's usually the tell, not the reassurance."

How much life insurance do I actually need?

A useful starting framework is DIME — Debt, Income, Mortgage, Education — which totals what it would take to eliminate debt, replace income for a meaningful runway, pay off the house, and fund your kids' education. It's a strong starting point, but a real needs analysis that reflects your specific family and goals will always beat a formula.

What's the difference between term and permanent life insurance?

Term life covers you for a defined window at a much lower cost. Permanent insurance (whole life or IUL) lasts your entire life and builds cash value, but costs significantly more and serves a different purpose: savings, estate liquidity, or wealth transfer rather than pure income replacement.

What is a long-term care or chronic illness rider?

It's a feature that lets you access a portion of your death benefit while you're still alive if you experience a qualifying health event — a stroke, a serious diagnosis, or a need for long-term care. It addresses a risk traditional life insurance ignores entirely: surviving, but with a serious financial disruption.

What is a buy-sell agreement and why does my business need one?

A buy-sell agreement is a contract, funded by life insurance, that determines what happens to a business owner's stake if they die. Without one, that ownership stake typically passes to the deceased owner's spouse or estate — leaving the surviving owner unexpectedly co-owning the business with someone who may not want to run it, and may need cash instead.

Is "properly structured IUL" a real thing, or a red flag?

IUL can be a legitimate planning tool, but the phrase itself — used as a blanket reassurance on social media — is usually a sign to slow down. The real question isn't whether it's "structured properly," it's whether you've seen the guaranteed rate, not just the illustrated one, and whether the person recommending it is held to a fiduciary standard.

Wherever you landed in this episode — that's exactly what a Vision Call is for. Whether you need your first policy or a real review of what you already have, it's a free 20-minute conversation, not a sales pitch. Book your free Vision Call.