The Weekly Wealth Podcast

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.

73% of business owners who say they're ready to sell are missing at least one of the two numbers required to know if a sale will actually work. In this episode, David breaks down a new data study of 10,548 business owner assessments and lays out the Readiness 360 — the three questions every owner has to answer honestly before they sit across from a buyer. Are you personally ready to let go? Is your business actually ready to be sold? And does the math even work?

• The two numbers every owner needs before they can know if a sale will work — and why 73% of owners are missing at least one
• Why even owners who did the homework still get bad news: 1 in 5 discover their business is worth less than they need
• The “pushed vs. pulled” problem — why burnout and stress are driving more exits than actual planning
• Why 25% of owners can't name a single thing they're excited about after the sale, and what that means for a deal
• The eight drivers that determine whether your business survives buyer diligence — separate from how much cash it generates

• 0:00 — Cold open: You've decided to sell. Here's why you're not ready.
• 0:45 — Intro: framing the Readiness 360
• 2:30 — Segment 1: Are you financially ready? The two numbers
• 9:30 — Mid-episode: the Sellability Score
• 10:00 — Segment 2: Are you personally ready? Pushed vs. pulled
• 16:30 — Segment 3: Is your business ready to be sold?
• 21:30 — Wrap-up: putting the 360 together
• 24:00 — Where to start: Sellability Score and PREScore

“Wanting to sell is not the same as being ready to sell.”

Only 27% of business owners have both a minimum number and a recent valuation — the two things required to know whether a sale will fund the life they want afterward. And even among owners who have both, roughly 1 in 5 find out the business is worth less than they need. Readiness isn't a feeling. It's a diagnosis, and the earlier you run it, the more options you have.

Start with the free Sellability Score — a 15-minute assessment that shows you where your business stands on the eight drivers that determine what it's worth:

weeklywealthpodcast.com/sellabilityscore

Want to go deeper on personal readiness? The PREScore assessment measures whether you — not just the business — are ready for what comes next:

weeklywealthpodcast.com/prescore

Success is boring. That's not a knock — it's the whole point. The best tennis players in the world don't win with highlight-reel shots; they win by making almost every easy shot and missing almost nothing. Wealth-building works the same way. This week, David Chudyk, CFP®, breaks down BASICS — a six-letter framework covering the unglamorous, "advanced" fundamentals that actually move the needle for people who are already building real wealth.

B — Budget. Not a lecture about canceling subscriptions. The real question isn't "can I afford this," it's "is this appropriate for my current situation." For some listeners — especially those with a solid nest egg — an appropriate spending plan means spending more, not less.

A — Allocation. Where should your money actually live — checking, real estate, retirement accounts, an emergency fund, speculative positions? "Should I buy the hot new IPO?" is really an allocation question in disguise, and there's no universal right answer without knowing the full picture.

S — Systems. We don't rise to the level of our goals, we fall to the level of our systems. This segment covers the financial habits — recurring money check-ins, subscription audits, auto-pay, systematic investing — that quietly determine whether goals actually happen.

I — Insurance. Insurance isn't exciting, and David doesn't pretend otherwise — but its job is simple: it protects your money, nothing more, nothing less. Includes a breakdown of life insurance, liability coverage, and why finding a great local independent insurance agent is real advice, not a throwaway line.

C — Caring. Tying back to David's core philosophy — how we handle our money should positively impact our lives and the lives of those around us — this segment covers generosity beyond the tax-deductible check, and a candid look at whether your spending actually reflects what you say you value.

S — Support. Borrowing from Dr. Benjamin Hardy's Who Not How, David makes the case that the right question isn't "how do I figure this out myself," it's "who already knows how to do this." Financial advisors, CPAs, attorneys, fractional CFOs, and mastermind groups all make the list.

Stick around after the outro for a bonus deep-dive on allocation: why the goal of investing isn't always the highest possible return, how David solves for the required rate of return needed to hit a goal, and why a 79-year-old getting a lucky 40% return doesn't mean their money was allocated correctly.

• Free E-Book: The Rainmaker's Dilemma — for business owners stuck as the primary revenue driver in their own company
• Book Referenced: Who Not How by Dr. Benjamin Hardy
• Related Episode: "The Richest Corpse in the Graveyard" (referenced in the Budget segment)

Leave David a voicemail at weeklywealthpodcast.com and tell him which of the six basics you need to work on. Or skip straight to a conversation: Book your free Vision Call.

Guest: Peyton Hoppes, ProVest Wealth Advisors (Spartanburg, SC)

David sits down with longtime friend and fellow financial advisor Peyton Hoppes to talk shop. Peyton recently joined ProVest Wealth Advisors in Spartanburg, SC, where he and colleague Gabe are stepping in to take over the client relationships of a retiring advisor. The two dig into what they're seeing with clients day-to-day: how busy families in their "formation years" actually manage cash flow, the real difference between Roth and pre-tax retirement accounts (and when each makes sense), and — for anyone who's ever dreamed of owning a beach house — a breakdown of the smartest (and riskiest) ways to actually pay for one.

• Purposeful money management beats default money management. Peyton runs a system of segregated accounts (savings, taxes, vacation/project fund) so every dollar has a job — and vacations get booked only once the savings cover them.
• Family formation years (roughly age 28–47) are the most expensive of your financial life. Most people's spending peaks here, then tapers as kids move out.
• Wealth isn't a number — it's time. Peyton's definition: wealth is the amount of time you can spend not working, not a dollar figure on a screen.
• Roth vs. pre-tax isn't a "which is better" question — it's a "which serves this purpose" question. Younger earners in lower tax brackets often benefit more from brokerage/Roth flexibility than maxing out pre-tax accounts; higher earners in higher brackets benefit more from pre-tax now with planned Roth conversions later.
• The three-bucket strategy: pre-tax, Roth (post-tax), and brokerage (post-tax, flexible) — where you focus your dollars should shift as your income and life stage change.
• Funding a dream property (like a beach house) has real tax tradeoffs. David and Peyton walk through three scenarios: cashing out a brokerage account (and eating the capital gains tax), a HELOC against your primary residence, and a securities-backed line of credit — each with very different risk profiles.
• Late-in-life cash flow planning is about spending well, not just accumulating. For those in their late 60s+ with fixed income covering expenses, the conversation shifts to strategic giving and enjoying wealth now rather than only growing net worth.

Peyton recently joined ProVest Wealth Advisors in Spartanburg, SC, focusing on families with busy lives and high financial complexity — business owners, medical professionals, and families with special-needs children. He and David worked together for several years before Peyton's move.

Connect with Peyton:

• Email: [email protected]
• LinkedIn: Peyton Hoppes
• Website: provestwealth.com

Book a complimentary 20-minute Wealth Optimization Call with David — a CFP® who works with successful individuals and business owners. 👉 Book Your Call → weeklywealthpodcast.com/vision

📧 Questions? Email [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.

If you ran out of money, when would it happen? For a growing number of retirees — paid-off home, pension, Social Security, a seven-figure portfolio sitting quietly in the background — the honest answer is probably never. And yet study after study shows this exact group is still the most hesitant to spend a dollar of it.

In this episode, David uses a composite family — paid-off home, $3 million invested, pension and Social Security covering nearly all of their monthly expenses — to unpack why disciplined savers keep saving long after saving has stopped being the point, what the research actually says about it, and what to do instead: fund a business start for someone who needs it, launch a scholarship, or hand your grandkid the keys to a car while you're around to watch her drive it away.

Research from the Employee Benefit Research Institute found that roughly one-third of retirees still have 100% or more of their original retirement assets remaining by their mid-80s. Married couples 65 and older withdraw, on average, just 2.1% of their portfolio per year — well below the roughly 5% that current research considers a safe withdrawal rate. David calls this FORO — Fear Of Running Out — the retirement version of FOMO, except what you're missing is your own life.

The people this happens to aren't reckless with money — they're the most disciplined savers in the room. As advisor Zach Teutsch puts it, "Overspending is risky. But underspending is risky too."

David — who holds the CLTC designation alongside his CFP® — also draws a hard line between vague, unfocused fear and one actual, named risk worth planning for: an extended long-term care event. Solve that risk on purpose, and the rest of the portfolio is free to be used.

David's core mission for the show: how we handle our money should positively impact our lives and the lives of those around us. A growing balance doesn't do that on its own — it only matters once it moves.

• Fund a business start. More than a quarter of people who've helped fund someone's business gave to a close family member. David's practical note: decide up front whether it's a gift, a loan, or an equity stake, and put it in writing.
• Start a scholarship. A scholarship is legacy you get to watch unfold now — not legacy that waits for a will to activate.
• Buy the car, watch them drive it. Cash left invested usually outperforms a depreciating asset financially — but if the goal is connection rather than optimization, watching your grandchild's reaction beats a line item in probate. Give with a warm heart, not a cold hand — it doesn't need a tax deduction to be worth doing.

• 0:00 — Cold open: one grandfather, two very different versions of the same gift
• 2:15 — The data: why one-third of retirees barely touch their savings
• 6:30 — Why disciplined savers are the most likely to underspend
• 10:30 — The one legitimate fear worth naming: long-term care
• 13:30 — The mission statement, and why a growing balance isn't the goal
• 14:15 — Funding a family member's business start
• 17:00 — Starting a scholarship while you're alive to see it work
• 19:30 — The car in the driveway, and the tax-deduction question, answered directly
• 23:30 — Permission to spend: why the gap only closes with a real plan
• 27:00 — Wrap-up and next steps

If your expenses are mostly covered and your portfolio is quietly growing untouched, you don't need a guess — you need an actual answer. Book a free 20-minute Vision Call with David: weeklywealthpodcast.com/vision

• Ep. 267: What If You Have Already Won? — the Freedom Point episode this one builds directly on.
• Ep. 261: Six Retirement Philosophies — a broader look at the mindsets that shape how people actually spend, or don't, in retirement.

Replay Episode — This one's a "blast from the past." David originally recorded this conversation in the last quarter of 2022, right in the middle of heavy recession fear and a rough year in the markets. He's bringing it back now because 2026 has had its own share of ups and downs, and the mindset underneath this conversation hasn't gone stale.

Joining David is Mike DiJoseph of Vanguard's Investment Advisory Research Center, whose team studies why investors make the decisions they make — and how a good advisor changes the outcome.

• Why financial news functions more like entertainment than information
• Vanguard's "Advisor's Alpha" research: the roughly 3% net-return value a good advisor adds over time
• A real 2020 case study: bailing out at the bottom turned $1M into $800K, while staying the course turned it into $1.2M
• Why the political party in power has a surprisingly weak relationship with market returns
• The behavioral finance reason your brain forgets years of gains the moment there's one bad year
• Reframing downturns: lock in the loss on the portfolio, or lock in the loss on the goal

Mike DiJoseph works within Vanguard's financial advisor services division, on the Investment Advisory Research Center team. He and David connected through the Financial Planning Association.

Approximate timestamps — this is a replay, so times are estimated from the conversation flow.

• 00:00 — Why David is replaying this episode now
• 03:30 — Meet Mike DiJoseph and Vanguard's research team
• 06:00 — Is a recession actually bad for the stock market?
• 10:30 — The Tesla thought experiment
• 13:00 — How one word turns a headline from bullish to bearish
• 16:00 — Staying the course doesn't mean standing still
• 19:00 — Does the party in power actually move the markets?
• 24:00 — The recency bias problem
• 27:00 — The 2020 case study: $800K vs. $1.2M
• 33:00 — What a good advisor is actually worth
• 37:00 — Insurance and estate-planning blind spots
• 41:00 — Personal definitions of wealth

"You can either lock in the loss on the portfolio, or you lock in the loss on the goal."

"There is never going to be an all-clear signal. And to the extent that there is one, it's probably too late."

"When your values are clear, your decisions are easy."

Not sure if your portfolio — or your plan — is actually built for moments like this? Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision

Connect with David directly: [email protected]

If this episode helped reframe how you're thinking about the market right now, share it with someone who needs to hear it — and follow the show so you don't miss what's next.