The Weekly Wealth Podcast

David Chudyk

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

  1. Ep 269: The Necessary Evil

    3 days ago

    Ep 269: The Necessary Evil

    About This EpisodeHere's something that almost never gets talked about in personal finance: most people are both overpaying for insurance and dangerously underinsured — at the same time. In this episode, David Chudyk, CFP® breaks down exactly how that happens, which gaps most commonly cost people everything, and the four-step annual insurance audit every wealth-builder should be doing. What You'll LearnWhy insurance gets ignored — and why the industry is designed to let it happenThe four most common places people overpay (including one hiding in plain sight for business owners)The single most underutilized piece of asset protection available — and why it costs less than most people thinkThe three insurance gaps that can end a business, not just hurt itA four-step annual insurance audit you can actually doWhy your financial advisor and your insurance agent are probably never talking to each other — and what that gap costs you Episode Timestamps0:00 — Cold Open: The two insurance problems most people have simultaneously2:00 — Why insurance gets ignored: the set-it-and-forget-it trap6:00 — Where people overpay: collision on old vehicles, duplicate coverage, whole life misuse12:00 — Where people are underinsured: umbrella policies, life insurance drift, disability18:00 — The business owner's trifecta: key person, cyber liability, E&O23:00 — The annual insurance audit: four steps to close the gaps28:00 — Close and how to connect with David Key TakeawaysMost people are carrying policies designed for who they were — not who they are now. Income, assets, and risk profile all change. Insurance usually doesn't keep up.A $1 million umbrella liability policy costs roughly $150–$300/year. It's the most underused, underpriced form of asset protection available to individuals with meaningful net worth.About 20% of Americans with $5M+ in assets carry no umbrella policy — leaving their full net worth exposed in a lawsuit.Business owners face three specific coverage gaps that can end a company: no key person insurance, no cyber liability coverage, and no errors & omissions (E&O) policy.Your ability to earn income is your most valuable financial asset — and most people have almost no protection for it through private disability coverage.The biggest structural problem: your financial advisor and your insurance agent are almost never talking to each other. That gap is where wealth gets destroyed. The Annual Insurance Audit: 4 StepsStep 1: Pull every policy you have — home, auto, life, disability, umbrella, all business lines.Step 2: Match coverage to current reality — net worth, home value, business size, family situation.Step 3: Check for the five gaps — umbrella, disability, life insurance adequacy, business trifecta (key person / cyber / E&O), and outdated or duplicate coverage.Step 4: Make sure your advisor sees the full picture — someone needs to look at insurance and wealth planning together. Connect With DavidFree 20-Minute Vision Call: weeklywealthpodcast.com/visionBusiness Owner Exit Score: weeklywealthpodcast.com/prescoreAll Episodes & Resources: weeklywealthpodcast.com

    20 min
  2. EP 267:  What if you have already won?

    12 Jun

    EP 267: What if you have already won?

    You've spent years building your business. But what if you've already crossed the finish line — and nobody told you? Most business owners spend their entire careers trying to reach financial freedom. But there's a specific, calculable threshold — called The Freedom Point — where the net proceeds from selling your business would fund the rest of your life without financial worry. And the uncomfortable truth is: a lot of owners have already crossed it. They're still grinding, still taking on risk, still saying "five more years" — without realizing they've technically already won. In this episode, CFP® David Chudyk breaks down The Freedom Point framework, walks through the exact math to calculate yours, and explains why so many smart, successful business owners stay past it without a plan — and what that costs them. What You'll Learn in This EpisodeWhat The Freedom Point is — and the precise formula to calculate itWhy your business growing could actually be increasing your financial risk (not reducing it)The "4 D's" that can destroy business value overnight — and why none of them care about your timelineHow to figure out if you've already crossed your Freedom Point using a 7-step frameworkWhat your options are once you've crossed it (hint: selling isn't the only one)The three psychological traps that keep smart owners grinding past the point of financial freedomWhy "one more year" syndrome might be the most expensive story you're telling yourself Episode Timestamps[0:00] — Cold Open: What if you've already won?[2:00] — What is The Freedom Point?[6:00] — Meet Tim: The business owner with 80% concentration risk[11:00] — The 4 D's: Death, Disability, Divorce, Departure[15:00] — How to calculate your own Freedom Point (7-step framework)[20:00] — What to do when you've crossed the line: 4 options[24:00] — Why smart owners stay too long: Identity, One More Year Syndrome, Fear of Irrelevance[28:00] — The free tool to calculate your Freedom Point today The Freedom Point FormulaThe Freedom Point is reached when: (Value of Outside Investments) + (Net Proceeds from Business Sale) > (Desired Annual Income × 33) Here's how to run it yourself: Step 1: Estimate the annual income that would make you feel completely financially freeStep 2: Multiply by 33 (based on a conservative 3% withdrawal rate)Step 3: Calculate your wealth outside your business — investments, rental properties, brokerage accounts (not your primary residence)Step 4: Get a realistic business valuation estimateStep 5: Subtract the frictional cost of selling — taxes, broker commissions (~10–12%), legal fees (~2%)Step 6: Add back any long-term business debt you'd need to pay off at closingStep 7: If Steps 3 + 5 exceed Step 2, you've reached The Freedom Point Example: If you want $150,000/year of income, you need $4.95M in total investable assets. If your business would net $4M after selling costs and you have $1M outside the business — you've crossed it. The 4 D's Every Business Owner Needs to KnowThese four events can destroy business value overnight — and none of them are in your control: Divorce — Especially devastating when both spouses work in the business or when business value becomes contested in settlementDeparture — A key partner, co-founder, or critical employee leaves, triggering buy-sell agreements and operational disruptionDisability — You become unable to work; most disability policies protect income, not business valueDeath — Your beneficiaries inherit a business they don't know how to run, often resulting in forced sales at the worst possible time Why Smart Owners Stay Past The Freedom PointThe math alone doesn't explain why successful business owners keep grinding after they've technically won. David breaks down three psychological forces: Identity: When the business is who you are, the idea of stepping back feels like erasing yourself — not a financial decision at allOne More Year Syndrome: The goal line keeps moving. $2M becomes $3M becomes $5M. Every milestone reveals the next one. The exit that was "five years away" has been five years away for fifteen years.Fear of Irrelevance: The quiet one. Not afraid of selling — afraid of what comes after. Who are you without the title, the team, and the 8am calendar? "The biggest threat to your financial freedom isn't market risk. It's the story you're telling yourself about who you are without the business." Your Options Once You've Crossed The Freedom PointSell a Minority Stake — Take chips off the table while keeping control; often done with private equity in a minority recapitalizationSell a Majority Stake — Significant liquidity event now, keep some equity, continue running the business under new ownershipEarn-Out Exit — Full sale with a 1–3 year transition; ideal if you're ready to step back in the next three to five yearsStay and Build Around the Risk — Keep building, but do it intentionally: key person insurance, a funded buy-sell, disability coverage, and a real succession plan Calculate Your Freedom Point — Free ToolDon't guess where you stand. Take the free Personal Readiness to Exit assessment — it walks you through the exact Freedom Point calculation in about 10 minutes and shows you a real number. → Take the Free Assessment at weeklywealthpodcast.com/prescore Rather talk it through with someone? Book a free 20-minute strategy call: → Book a Vision Call at weeklywealthpodcast.com/vision Quotable Moments"What if you've already won — and you're still playing like you haven't?""Before The Freedom Point, risk is how you build. After it, risk is how you lose what you've already built.""Tim diversifies his 401(k) like a pro. But 80% of his net worth is a single, illiquid, non-publicly-traded asset. That's not diversification. That's concentration in a tuxedo.""One more year syndrome feels responsible. But what it often is — if we're honest — is a way of avoiding a decision you're not emotionally ready to make.""The Freedom Point isn't a feeling. It's a formula. And once you run the math, you can't unsee what it shows you." Who This Episode Is ForThis episode is essential listening if you are: A business owner with a company worth $1M or more wondering if you're "there yet" financiallyAn entrepreneur approaching your 50s who hasn't run a real exit planning calculationA high earner whose business represents more than 50% of your total net worthAnyone who has said "I'll sell when the business hits $X" — and then moved the goalpostA spouse or partner of a business owner trying to understand the financial risk your household is carrying Resources & Related EpisodesPersonal Readiness to Exit (Prescore) — Free AssessmentVision Call — Free 20-Minute Strategy SessionSellability Score — Free Business Valuation AssessmentRelated: Ep. 264 — Is Your CPA Only Looking in the Rearview Mirror? (tax planning before a sale matters enormously)Related: Ep. 265 — This Is Exactly Who You've Been Looking For (David's background and advisory approach) About David Chudyk, CFP®David Chudyk is a CERTIFIED FINANCIAL PLANNER™ professional, CLTC, and Certified ValueBuilder Advisor with nearly two decades of experience working with business owners and high-net-worth individuals. He is the founder and host of the Weekly Wealth Podcast and a fiduciary advisor with Parallel Financial, LLC. David specializes in helping business owners align their personal financial plans with their business exit strategies — so they can make the biggest financial decision of their lives with clarity and confidence. weeklywealthpodcast.com The Weekly Wealth Podcast is produced by Parallel Financial, LLC, a registered investment advisor. All content is for educational and informational purposes only and should not be construed as personalized financial, tax, or legal advice. All examples, including "Tim," are hypothetical illustrations only. Consult a qualified financial advisor before making any financial decisions. Investment advisory services offered through Parallel Financial, LLC.

    21 min
  3. EP: 266 Your Financial Advice is Probably Wrong

    5 Jun

    EP: 266 Your Financial Advice is Probably Wrong

    Someone in your life is giving you financial advice right now. They're confident. They say it like it's gospel. And they might be completely wrong. Not because they're bad people — but because they're handing you a prescription without doing the diagnosis. And in financial planning, that's how people end up behind where they should be. In this episode, CFP® David Chudyk dismantles four of the most repeated pieces of financial advice in America — the kind you've heard so many times you stopped questioning them. The kind that sounds responsible, feels virtuous, and breaks down the moment someone runs the actual numbers on your situation. This isn't a contrarian rant for its own sake. It's a masterclass in why the difference between generic advice and a real financial partner might be the most important financial decision you ever make. What You'll Learn in This Episode Why "pay off all your debt before you invest" can be the most expensive advice you ever followThe brutal math behind waiting for the market to "calm down" — and what it actually costs youThe truth about homeownership as an investment (spoiler: the numbers aren't what you think)Why "always max your 401(k) first" is right for some people and dead wrong for others — especially business ownersThe three-bucket framework that separates strict financial rules from flexible ranges from personal preferences — and why mixing them up is where real financial damage happens The Four Myths — Broken Down Myth #1: "Pay Off All Your Debt Before You Invest" This one sounds disciplined. It feels responsible. And it can cost you a fortune. If your employer offers a 100% 401(k) match and you're skipping it to pay down a 4.9% car loan, you just turned down a guaranteed 100% return to avoid a 4.9% interest rate. The math doesn't care how debt makes you feel. There's a real difference between high-interest consumer debt (pay it down aggressively) and low-interest, tax-advantaged debt (the calculus is very different). A real financial partner helps you know which is which. Myth #2: "I'll Start Investing When Things Calm Down" Here's the uncomfortable truth: things don't calm down. They never have. The dot-com crash, 9/11, 2008, a global pandemic, 40-year inflation highs — there has always been a reason to wait. Meanwhile, missing just the ten best trading days in a decade can cut your returns in half. And the best days almost always come right after the worst ones. Waiting for calm isn't strategy. It's fear wearing a suit. Myth #3: "Your Home Is Your Best Investment" Homeownership builds equity, provides stability, and for many people is an excellent financial decision. But "best investment"? The national average home appreciation rate over the last century is roughly 1% above inflation annually. The stock market has returned about 7% above inflation over the same period. And most people forget to subtract property taxes, insurance, maintenance (1–2% of home value per year), mortgage interest, closing costs, and commissions. Your house is a valuable asset. It is not a substitute for a portfolio. Myth #4: "Always Max Your 401(k) First" Employer match? Take every dollar of it — that's a strict rule, full stop. Beyond the match, though, this gets complicated fast. Traditional vs. Roth decisions depend on your current and expected future tax bracket. Business owners may have access to SEP-IRAs, Solo 401(k)s, or defined benefit plans that dwarf standard contribution limits. And locking every available dollar into a retirement account while running a business that needs capital can leave you technically wealthy and practically cash-poor. "Max it first" is often right. It's not always right. The Framework That Changes Everything Here's what David explains that most financial conversations never get to: not every financial question has the same type of answer. Strict rules: Get your employer match. Pay down high-interest consumer debt aggressively. Maintain liquidity before locking money away. These aren't preferences — they're math.Ranges of acceptable action: How to sequence your accounts. Roth vs. traditional. How much house makes sense. The best answer within the range depends entirely on your specific situation.Personal preferences: Your emotional relationship with debt. How much market volatility you can handle without making a bad decision. How important liquidity feels to you. These are legitimate inputs to a real financial plan — not weaknesses, data. Treating preferences like rules, or ignoring real rules because they're uncomfortable — that's where the damage happens. A real financial partner helps you sort the buckets and make decisions that actually fit your life. Quotable Moments from This Episode "They're handing you a prescription without doing the diagnosis. And in financial planning, that's how people end up broke." "Missing just the ten best trading days in a decade can cut your returns in half — and the best days almost always come right after the worst days." "Your house is a valuable asset. It is not a substitute for a portfolio." "There are strict rules, there are ranges of acceptable actions, and there are personal preferences. Mixing them up — that's where the damage happens." "How we handle our money should positively impact our lives and the lives around us. Not just optimize for a spreadsheet." Who This Episode Is For This episode is essential listening if you are: A business owner who has been running on financial autopilotA high earner who suspects they might be leaving money on the tableSomeone who has been following "common sense" financial rules without ever stress-testing themAnyone who has said "I'll start investing when things settle down" — in any year, everA homeowner who considers their house their primary retirement strategy Work With David Free Vision Call — If you're a business owner or high earner who wants a real conversation about whether your financial plan actually fits your life, David offers a complimentary 20-minute strategy call. No pitch. No pressure. Just clarity. weeklywealthpodcast.com/vision Free Sellability Score — If you own a business and haven't seriously evaluated what it's worth or what it would take to sell it someday, this free 15-minute assessment will show you exactly where you stand — and what's costing you value right now. weeklywealthpodcast.com/sellabilityscore About David Chudyk David Chudyk is a CFP® (Certified Financial Planner), CLTC, and Certified ValueBuilder Advisor with nearly two decades of experience helping business owners and high earners build real, lasting wealth. He is the founder of Parallel Financial, LLC, a fiduciary registered investment advisor, and host of the Weekly Wealth Podcast. David is based in Seneca, SC and works with clients across the Upstate South Carolina region and beyond. His approach is simple: financial planning shouldn't just optimize a spreadsheet. It should positively impact your life — and the lives of the people around you. The Weekly Wealth Podcast is available on Apple Podcasts, Spotify, and wherever you listen to podcasts. If this episode made you question financial advice you've been taking for granted — good. Share it with someone who needs to hear it.

    24 min
  4. 29 May

    Ep 269: Retirement planning is Life planning

    Retirement planning is not about retirement. That's the provocation David opens with — and he means it. This episode isn't another checklist. It's a ground-up rethink of what the 5-to-10-year sprint before retirement actually demands: emotionally, philosophically, and financially. Starting with a question no financial podcast has the nerve to ask — is retirement even a biblical concept? — David works through everything from the psychology of stopping work to the hard mechanics of income portfolios, tax strategy, and the risks that blow up otherwise solid plans. If you've been coasting toward retirement on autopilot, this episode is the alarm clock. In This Episode0:00 — Cold Open Why the conventional framing of retirement is wrong, and what this episode is actually going to cover. ~3:00 — Is Retirement Even a Biblical Concept? The word never appears in Scripture. The one exception in Numbers 8, what the parables actually teach about accumulation, and why the biblical model looks more like a pivot than a finish line. ~9:00 — The Behavioral Trap: What Will You Actually Do? The identity crisis nobody warns you about, retirement depression, underspending vs. overspending, and five questions worth sitting with before you make any financial decisions. ~15:00 — The Purpose Problem: Should You Even Fully Retire? The happiest retirees David has seen, the financial benefits of partial work, and why "retire to something" beats "retire from something" every time. ~20:00 — Business Owner or Employee: The Decisions Are Different W-2 employees: catch-up contributions, pension options, the healthcare gap before Medicare, Social Security timing. Business owners: exit planning, retirement plan vehicles, tax-efficient value extraction, and the concentration risk problem. ~26:00 — Accumulation vs. Distribution Portfolios Why the portfolio that built your wealth can destroy your retirement. Sequence of returns risk explained plainly — same average return, completely different outcomes. ~29:00 — The Bucket Strategy Three buckets, three time horizons, one framework that eliminates panic selling. How Bucket One is your shock absorber and why Bucket Three can still be aggressive. ~32:00 — Roth vs. Pre-Tax: The Great Debate It's almost always "and," not "or." Tax diversification, the Roth conversion window, and why business owners have unique opportunities here. ~35:00 — The Risks Nobody Wants to Talk About Longevity risk (you live longer than your money does) and long-term care (70% of retirees will need it). What hybrid products exist now and why waiting to have this conversation is itself a costly decision. ~38:00 — Spend on Experiences While You Can + Legacy Planning The go-go, slow-go, no-go framework. Why retirees wait too long. Legacy basics: beneficiary designations, powers of attorney, donor-advised funds, and the "talk while you can" imperative. Key Takeaways🔑 Retirement isn't in the Bible — and that matters. The concept is newer than sliced bread. The biblical model is transition, not cessation — shift how you contribute, not whether you do. 🔑 Your identity is a retirement risk. High achievers and business owners are most vulnerable. "What will I actually do?" is a harder question than "do I have enough money?" 🔑 Sequence of returns can break a perfect plan. Two retirees with identical savings and identical average returns can have completely different outcomes depending on when the market drops. 🔑 Business owners: exit planning = retirement planning. If your business is your biggest asset, these aren't two separate conversations. A business not ready to sell will either sell for less — or not sell at all. 🔑 Tax diversification beats the "Roth vs. pre-tax" debate. The real goal is options in retirement. The 5–10 year window is your best opportunity for strategic Roth conversions before RMDs arrive. 🔑 Spend on experiences in the go-go years. Health isn't guaranteed. Build experiences into the plan intentionally. A financial plan that doesn't include living is just a savings plan with extra steps. Who This Episode Is ForBusiness owners 5–10 years from exiting or stepping backCorporate employees who haven't looked closely at their 401(k) allocation in yearsAnyone who has defined themselves by their work and hasn't thought through what comes nextCouples who haven't had an honest conversation about what their retirement actually looks likeAnyone sitting on a large pre-tax balance wondering if Roth conversions make sensePeople who have delayed the long-term care conversation because it feels too far away Referenced ConceptsNumbers 8:23–26 — The Levite transition model: step back from heavy labor at 50, continue in a support and advisory role.Luke 12 / Matthew 25 — The Rich Fool and the Parable of the Talents. Neither endorses accumulation for its own sake.Sequence of Returns Risk — Why the timing of market losses matters enormously in distribution, not just the average return over time.The Bucket Strategy — Short-term (1–3 yrs, cash/stable), medium-term (3–10 yrs, moderate growth), long-term (10+ yrs, growth-oriented).Go-Go / Slow-Go / No-Go — The three phases of retirement spending and why the go-go years are the time to invest in experiences.Roth Conversion Window — The years between retirement and RMDs/Social Security can offer a unique opportunity to convert pre-tax assets at lower effective tax rates. Work With David📅 Book a Vision Call — A free 20-minute conversation about where you are and what you actually need. No pitch. Just honest planning. 👉 weeklywealthpodcast.com/vision 📊 Take the Sellability Score (business owners) — A 20-minute assessment that shows where your business stands from a buyer's perspective — even if you're 10 years out. 👉 weeklywealthpodcast.com/sellabilityscore About David T. Chudyk, CFP® David is a fiduciary financial advisor and Certified Financial Planner® based in Seneca, SC, operating under Parallel Financial, LLC. He works with business owners, high earners, and wealth-builders who want their financial decisions to positively impact their lives — and the lives around them. This podcast is for informational and educational purposes only and does not constitute personalized investment, tax, or legal advice. Advisory services offered through Parallel Financial, LLC, a Registered Investment Advisor.

    33 min
  5. Ep 268: The Best Hire You'll Ever Make Lives Under Your Roof.

    22 May

    Ep 268: The Best Hire You'll Ever Make Lives Under Your Roof.

    The IRS actually built a legal way for business owners to pay their kids, cut their tax bill, and start building generational wealth — all at the same time. Most business owners have no idea it exists. And the ones who do usually aren't doing it right. In this episode, David breaks down the Hire Your Kids strategy from top to bottom — including the part most people skip — and adds two more powerful moves to set your kids up for financial success long before they need it. What You'll Learn in This EpisodeHow to legally hire your minor children in your business and deduct their wagesWhy sole proprietors and single-member LLCs get an extra tax break most people don't know aboutWhat counts as legitimate work (and what the IRS will reject)Why teaching your kids to manage money matters just as much as saving itHow a Roth IRA opened at age 15 can grow to over $2.4 million tax-free by retirementThe authorized user strategy for building your kid's credit before they ever need it — and the real risk you have to know aboutHow David's family bought a college house that paid for itself (and then some) The Numbers That MatterRoth IRA compounding example (8% average annual return): Contribute $5,000/year from age 15 to 30 → $164,000 at age 30Never add another dollar → $2.4 million tax-free at age 65Total out of pocket: $80,000 2026 Roth IRA limits: Under 50: $7,500/yearAge 50+: $8,600/yearSingle filers: full contribution below $153K MAGI, phases out by $168KMarried filing jointly: full contribution below $242K, phases out by $252K Strategy #1 — Hire Your KidsIf you own a legitimate business, you can hire your minor children to do real work and pay them a reasonable wage. Here's why that's a big deal: Their wages are a deductible business expense. If you're in the 32–37% federal bracket, that's real money shifted out of your tax bill.Sole props and single-member LLCs get an extra break. Wages paid to children under 18 are exempt from Social Security and Medicare taxes — that's another 15.3% in savings.Your kids pay taxes at their own rate. With the 2026 standard deduction, most minors owe zero federal income tax on the first chunk of their earnings. What counts as legitimate work? Social media content, filing, office cleaning, errands, video editing, client file organization. The work has to match the child's age, be documented with timesheets, and pay a reasonable market wage. Run payroll like any other employee. The rule of thumb: You can't pay a seven-year-old $40,000 to "organize your desk." You can pay a fourteen-year-old $10–12/hour to manage your social media scheduling. The Part Most People Skip — Teach Them to Actually Manage MoneyDon't just funnel every dollar straight into a Roth IRA and call it done. When your kids get paid, let them manage some of that money. Give them real decisions. Let them feel what it's like when $200 disappears faster than expected. Let them experience the satisfaction of saving up and buying something themselves. David's philosophy: "How we handle our money should positively impact our lives and the lives around us." That doesn't start at 25. It starts when they're young, when the stakes are low and the lessons are cheap. The Roth IRA AngleOnce your child has earned income, they're eligible for a custodial Roth IRA. You can contribute up to their earned income (max $7,500 for 2026) — and you can gift them the money to fund it. The IRS only cares that the earned income exists. Sit with this number: $5,000 per year from age 15 to 30, at a very average 8% return, becomes $164,000 by age 30. Let it sit untouched until 65 and it becomes over $2.4 million. Tax-free. That's not a typo. Strategy #2 — Build Their Credit Before They Need ItAdd your child as an authorized user on one of your credit cards. When you do, your account history — payment history, utilization rate, account age — starts showing up on their credit report. By the time they're 18 and applying for an apartment or a car loan, they're not starting from zero. The honest risk: If your child has the physical card, they can max it out. And there's very little you can do about it legally — you added them, the bank doesn't care about family dynamics. The practical solution: Add them to the account for the credit-building benefit, but keep the card in your wallet. The credit history still builds. That's the whole point. When they're ready, have the real conversation about credit before the card becomes a spending tool. Strategy #3 — The College House PlayWhen David's first child went to college, instead of paying for a dorm, the family bought a house. Three bedrooms — their kid took one, they rented out the other two. The rental income covered the entire cost of the house: mortgage, taxes, insurance, everything. Free housing. Plus the house appreciated in value. Compare that to four years of dorm payments: money gone, no equity, no asset, nothing to show for it. Is this for everyone? No — you need capital for a down payment, a market where the numbers work, and a kid who can manage roommates. But if you're a business owner with assets and your kid is heading to a college town with reasonable real estate, this is worth running the numbers on seriously. Resources Mentioned📊 Free Sellability Score Assessment — Find out how valuable and sellable your business is right now: weeklywealthpodcast.com/sellabilityscore📅 Book a Free Vision Call — A real conversation about your business, your family, and your financial future. No pitch, no pressure: weeklywealthpodcast.com/vision Connect With DavidIf this episode was useful, the best thing you can do is subscribe wherever you're listening — it takes about four seconds and makes sure you never miss an episode. The Weekly Wealth Podcast is published weekly for business owners, high earners, and anyone serious about building wealth the right way. Find us on Apple Podcasts, Spotify, or wherever you listen. This content is for educational purposes only and is not intended as tax or legal advice. Please consult a qualified professional regarding your specific situation.

    23 min
  6. 15 May

    Ep 267: The Psychology of Social Security

    The Psychology of Social SecurityThe conventional wisdom says almost always delay Social Security until 70. New research says that advice is wrong for more people than you'd think — and the reason it's wrong isn't purely math. It's psychology. In this episode, David covers the 90-year history of Social Security, how it fits into a real retirement income plan, the four most overlooked risks of delay, and what the 2025 Trustees Report actually says about the program's solvency — including the number most people get completely wrong. What We CoverA brief history — From the Great Depression to the 1983 near-collapse, and Ida May Fuller's legendary $24.75 investmentThe retirement income pyramid — Where Social Security belongs in your plan, and what it was never designed to doFour hidden risks of delay — Mortality, sequence of returns, regret, and health span — risks that almost never show up in the standard researchThe solvency picture — 2025 Trustees Report data, depletion dates, and what "81 cents on the dollar" actually means (hint: it's not zero)Your personal discount rate — The framework for finding the right claiming age for your specific situation The Four Risks of Delay Nobody Talks About1. Mortality Risk A terminally ill 72-year-old takes no comfort in knowing their mortality-adjusted benefits went up. The standard research averages across everyone who lives and everyone who dies. That works for actuarial tables. It doesn't work for advising one individual human being about their own life. 2. Sequence of Returns Risk If you retire at 62 and delay Social Security until 70, you're spending down your portfolio for eight years before the checks start. Run that scenario through the 2008 financial crisis: same spending, same portfolio — but $578,000 left at claim-at-62 vs. $171,000 at claim-at-70. Same spending. Vastly different cushion. 3. Regret Risk Risk = Hazard + Outrage. Two scenarios with the same expected value can feel completely different. If a client's psychological wellbeing matters to us — and it should — we can't ignore the emotional weight of the decision. 4. Health Span + Spending Optionality A dollar at 62 is worth more than a dollar at 95. At 62 you can take the trip, help your kids with a down payment, do the things that require energy and mobility. Social Security won't advance you five months of benefits to take your daughter on the trip she'll talk about forever. A healthy portfolio can. Key Numbers From This EpisodeAge 89 — How long you need to live for delaying from 67 to 70 to break even, assuming a 4% real return (Smith & Smith, Journal of Financial Planning, 2024)81 cents on the dollar — Benefits payable at trust fund depletion. Not zero.2033 — Projected OASI trust fund depletion date (2025 Trustees Report)36% — Americans confident in Social Security's future (AARP, 2025)$800,000 — Households at or below this investable asset level are often better served by claiming at 62, per Tharp (2025) A Brief Timeline1935 — Social Security Act signed by FDR. Over half of elderly Americans lacked sufficient income. Average state pension payout: 65 cents a day.1940 — First check mailed to Ida May Fuller, Vermont. Lifetime SS taxes paid: $24.75. Benefits collected before her death in 1975: $22,000+.1956 — Disability benefits added for the first time.1975 — Automatic COLAs begin. Before this, Congress had to raise benefits manually.1983 — Greenspan Commission reforms. The trust fund was months from insolvency. Bipartisan fix: higher payroll tax, FRA raised to 67, benefits made partially taxable.2025 — 2025 Trustees Report projects OASI depletion in 2033 — one year earlier than 2024's estimate. Timestamps0:00 — Cold open: the question that frames the whole episode1:45 — A brief history: 1935 to Ida May Fuller to the 1983 near-collapse4:45 — How Social Security fits your retirement plan8:45 — The conventional wisdom and why it oversimplifies11:30 — Risk #1: Mortality13:30 — Risk #2: Sequence of returns — $578k vs. $171k16:15 — Risk #3: Regret risk18:15 — Risk #4: Health span and spending optionality20:45 — The framework: your personal discount rate23:45 — The solvency question: 2025 Trustees Report data25:45 — What to do with all of this: four questions worth answering Sources2025 Social Security Trustees Report — Social Security Administration, June 18, 2025Analysis of the 2025 Trustees Report — Committee for a Responsible Federal Budget, June 18, 20252025 Trustees Report Explained — Bipartisan Policy Center, November 2025What the 2025 Trustees Report Shows — Center on Budget and Policy Priorities, July 2025"Revisiting the Social Security Claiming Puzzle" — Derek Tharp, PhD, CFP®, University of Southern Maine (working paper, 2025)"When Should You Claim Social Security?" — Smith & Smith, Journal of Financial Planning, 2024Historical Background and Development of Social Security — SSA.govSocial Security History Timeline — AARP, 2025 Work With DavidThe right Social Security claiming decision depends on your health history, your portfolio, your values, and your exit plan. David works with business owners and high earners who want a plan built around their actual life — not a software default. 🔢 Run your Sellability Score (free, 12 minutes): weeklywealthpodcast.com/sellabilityscore 📅 Book a Vision Call: weeklywealthpodcast.com/vision

    25 min
  7. Ep 266:  Paying Homage to Small Business owners during National Small Business Week

    8 May

    Ep 266: Paying Homage to Small Business owners during National Small Business Week

    This week is National Small Business Week — and before we get into strategy, David takes a moment to do something he thinks doesn't happen nearly enough: genuinely honor the people who build and run small businesses in America. Because it's hard. Really hard. And the numbers tell a story that most press releases never will. Then, in true Weekly Wealth fashion, he makes the turn: Small Business Week celebrates the business. But nobody's talking about the owner's financial future. This episode fixes that. 🎙️ In This EpisodeDavid walks through five financial conversations that almost nobody is having with small business owners right now — and at least one of them is probably going to hit close to home. #1 — Your CPA Is Only Looking in the Rearview Mirror There's a big difference between tax preparation and tax planning. Your CPA records history. A real financial strategy looks forward. For most business owners, nobody is having the proactive tax conversation — and it's costing them tens of thousands of dollars a year they don't have to pay. #2 — Your Business and Personal Finances Are One Big Knot Mixed accounts. Inconsistent owner pay. No clean separation between what the business earns and what you personally spend. This isn't just messy — it makes it impossible to know your real number. And if you don't know your number, you can't plan. There's even a name for the trap many business owners fall into: busy broke — fully booked, running ragged, and still wondering where the money went at the end of the month. #3 — Your Business IS Your Retirement Plan "I'll sell the business someday" is not a retirement strategy. Most businesses don't sell for what the owner thinks they're worth. Some don't sell at all. Your business is a single, illiquid asset — and that concentration risk needs to be managed, not hoped away. #4 — You're Underinsured in Ways You Don't Even Know General liability and property coverage are just the beginning. What about disability insurance for you, the owner? Key person life insurance? A properly funded buy-sell agreement? Business insurance isn't set-it-and-forget-it. If you haven't had a real review in the last two to three years, there are likely gaps you don't know about. #5 — You Have No Exit Strategy Not having an exit plan doesn't mean you'll stay forever — it means you'll leave on someone else's terms. The business owners who get the best outcomes are the ones who started planning five or ten years out, not the ones who woke up ready to be done and scrambled. What does your exit look like? 📊 Small Business by the Numbers34 million small businesses in the U.S. — 99.9% of all businesses in the country61 million Americans are employed by small businesses — nearly half the private workforceSmall businesses have created more than 12 million net new jobs over the last 25 years1 in 5 small businesses won't survive their first year. About half are gone by year five. Nearly two-thirds by year ten.82% of small business failures are tied to cash flow problemsThe median small business owner pays themselves about $57,600/year — half make less than thatThe bottom 10% of small business owners make $36,000 or less per year1 in 3 small business owners cut their own salary in the last year to keep the business running 🔗 Resources Mentioned📋 Sellability Score (Free Assessment) Find out what your business is actually worth to a buyer — and what you can do to change that number. Scores your business across 8 key value drivers. Free. Takes about 15 minutes. 👉 weeklywealthpodcast.com/sellabilityscore 📅 Book a Vision Call with David A real conversation about your financial picture — where you are, where you want to be, and what the gap looks like. No pressure. No pitch. Just clarity. 👉 weeklywealthpodcast.com/vision 🎧 Related Episode Episode 264 — "Is Your CPA Only Looking in the Rearview Mirror?" — David's deep dive on the difference between tax prep and tax planning, and what proactive strategy actually looks like. 💬 Quotable Moments"Small Business Week celebrates the business. Nobody's celebrating the owner's financial future." "That's not a business decision. That's a sacrifice. That's someone who loves what they built so much, and cares so much about the people around them, that they'll personally absorb the hit before they'll let anyone else feel it. I think that is genuinely heroic." "You can be busy broke. Slammed, exhausted, fully booked — and still not making real money because your pricing doesn't reflect your true costs, your time, or your value." "Your business is an asset. But it's a single, illiquid asset. That's a risk that needs to be managed, not hoped away." "Planning your exit is the most optimistic thing you can do. It means you believe the business has value worth capturing." "Nobody's asking whether you're building wealth — or just building a job with a really complicated org chart." 👤 About David ChudykDavid Chudyk, CFP®, CLTC is the founder of CFSIG and a fiduciary financial advisor with Parallel Financial. He works with business owners, high earners, and families who are serious about building — and protecting — real wealth. He is also a Certified ValueBuilder Advisor, helping business owners understand what their company is truly worth and how to maximize it. 📍 Based in Seneca, SC | Serving clients throughout the Southeast and beyond 🌐 weeklywealthpodcast.com The Weekly Wealth Podcast is produced by Parallel Financial LLC, a registered investment adviser. This podcast is for informational and educational purposes only and should not be construed as personalized financial, tax, or legal advice. Past performance is not indicative of future results. Please consult with a qualified professional before making any financial decisions.

    21 min

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