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Recent episodes
Map Your Taxes
Jun 25, 2026
Unknown duration
Multi-Generational Dividend Legacy Plans
Jun 18, 2026
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Dividend Barbell Strategy
Jun 11, 2026
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Should You Change Your Dividend Portfolio
Jun 4, 2026
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K-1 Stocks Explained: Are The Higher Dividends Worth The Tax Headache?
May 28, 2026
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/25/26 | ![]() Map Your Taxes | You spent decades saving, investing, and building your retirement nest egg. But what if a large portion of that money isn't actually yours?In this episode of Planning Made Simple, Paul, Kyle, and the team uncover one of the biggest retirement planning blind spots: taxes. From Required Minimum Distributions (RMDs) to the hidden tax snowball that can grow throughout retirement, they explain why many retirees unknowingly face larger tax bills than expected and what can be done years before retirement to prepare.If you've accumulated money in IRAs, 401(k)s, or other tax-deferred accounts, this conversation could change the way you think about retirement income forever.www.planningmadesimple.com | — | ||||||
| 6/18/26 | ![]() Multi-Generational Dividend Legacy Plans | Most people think inheritance is about leaving money behind. But what if the real goal is leaving behind an income stream that lasts for generations?In this episode, the Planning Made Simple team explores how dividend investing can create a multi-generational legacy that continues producing income long after you're gone. They discuss the critical difference between passing down assets and passing down financial wisdom, why so many families lose wealth within a few generations, and how teaching your children about dividend income may be more valuable than the money itself.www.planningmadesimple.com | — | ||||||
| 6/11/26 | ![]() Dividend Barbell Strategy | Is the “Barbell Strategy” a brilliant investing framework… or just another flashy trend?In this episode, the team breaks down the growing popularity of barbell portfolios — putting most of your money into dividend investments while using a smaller percentage for speculative growth plays like crypto or aggressive investments.Most importantly, this episode challenges investors to stop starting with solutions before understanding the actual problem they’re trying to solve.www.planningmadesimple.com | — | ||||||
| 6/4/26 | ![]() Should You Change Your Dividend Portfolio | Should you change your dividend portfolio when the market gets scary, a stock drops, or YouTube says it’s time to buy something new?In this episode, we break down the difference between smart portfolio management and emotional overactivity. From dividend cuts and free cash flow concerns to rebalancing, concentration risk, and fear-based selling, this conversation helps investors understand when patience matters — and when a real change may be. necessary.www.plannningmadesimple.com | — | ||||||
| 5/28/26 | ![]() K-1 Stocks Explained: Are The Higher Dividends Worth The Tax Headache? | K-1 investments can confuse even experienced investors — especially during tax season. In this episode, the team breaks down what K-1s actually are, why they often pay significantly higher yields than traditional dividend stocks, and whether the extra tax complexity is truly worth it. They also explain the difference between owning shares of a corporation versus being treated like a partner in a business structure such as an MLP or LLC.You’ll learn:What a K-1 actually meansWhy K-1 investments often produce higher incomeThe tax pros and cons investors need to understandHow K-1s work inside IRAs and brokerage accountsWhy some investors avoid them entirelyThe long-term strategy behind using K-1 positions in dividend portfoliosIf you’ve ever received a mysterious tax form in March and wondered what to do next — this episode is for you.www.planninmadesimple.com | — | ||||||
| 5/21/26 | ![]() SCHD Isn’t as “Diversified” as You Think | Is SCHD really the ultimate dividend ETF… or are investors overlooking some major tradeoffs?In this episode, we break down the truth about diversification, dividend yield, portfolio turnover, and what actually happens behind the scenes inside SCHD. We also discuss the emotional side of investing, why many investors misunderstand diversification, and whether owning individual dividend stocks may offer more control and long-term income stability.If you’re building a retirement income portfolio or trying to live off dividends, this conversation will challenge a lot of conventional investing wisdom.www.planningmadesimple.com | — | ||||||
| 5/14/26 | ![]() Starting at Fifty With Nothing and Still Being Able to Retire | In this episode, we break down the reality of starting late—and why it's NOT too late to retire. Whether you've gone through a setback, started saving late, or feel behind, this conversation will give you clarity, direction, and hope.We cover the emotional side of investing, how to calculate what you actually need for retirement, and why most people are in the exact same position (even if they don’t admit it). Plus, we dive into practical strategies to start building income immediately—even if you're starting small. It’s not about where you start. It’s about what you do next!www.planningmadesimple.com | — | ||||||
| 5/7/26 | ![]() 5% Income Plan vs 4% Rule | Most investors ask the wrong question: “How much can I withdraw?” But what if the better question is, “How much income can my portfolio generate?” In this episode, we break down the popular 4% rule, why it dominates the industry, and the hidden risks behind relying on withdrawals. We also compare income generation vs. selling assets—and how each approach impacts your long-term financial security. If you want clarity, confidence, and a strategy built to last, this conversation is a must-watch.www.planningmadesimple.com | — | ||||||
| 4/30/26 | ![]() Do You Really Need 1 Million Dollars to Retire? | Is $1 million really the magic number for retirement—or just a myth? In this episode, we break down where that number came from and why it may not apply to your life. We explore what actually determines financial independence, including income needs, lifestyle, and dividend strategies. If you’ve ever wondered whether you’re “on track” or behind, this conversation will give you clarity and confidence. Retirement isn’t about hitting a number—it’s about building reliable income. | — | ||||||
| 4/23/26 | ![]() The Power of Rebalancing✨ | rebalancingportfolio management+1 | — | — | — | portfoliomarket volatility+2 | — | 20m 16s | |
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| 4/16/26 | ![]() The Hidden Reason Investing Feels So Stressful!✨ | investingfinancial stress+1 | Jeff Holmsworth | Planning Made SimpleVigr8 | — | systemsemotional decision-making+4 | — | 25m 56s | |
| 4/9/26 | ![]() Why Retirement Gets Harder at 3 Million✨ | retirementtax strategy+2 | — | Medicare | — | RMDsinherited IRAs+2 | — | 19m 33s | |
| 4/2/26 | ![]() Can You Really Live Off Of Dividend Income (The Honest Answer)?✨ | dividend incomeretirement planning+1 | — | Dividend Starter KitSocial Security | — | dividendsincome streams+1 | — | 16m 33s | |
| 3/26/26 | ![]() Do You Really Need to Have International Dividend Stocks?✨ | international dividend stocksglobal diversification+3 | — | — | — | dividend investorsportfolio+1 | — | 15m 21s | |
| 3/19/26 | ![]() Will the Iran War Crush the Stock Market?✨ | stock marketgeopolitical events+3 | — | — | — | Iran Warmarket reactions+1 | — | 16m 54s | |
| 3/12/26 | ![]() Why We Hold Losers in a Dividend Portfolio✨ | dividend investingemotional investing+2 | — | — | — | dividend cutssector downturns+2 | — | 23m 23s | |
| 3/5/26 | ![]() Social Security Decisions Without the Stress✨ | Social Securityretirement planning+2 | — | Social Security | — | retirement confidenceclaiming benefits+1 | — | 22m 58s | |
| 2/26/26 | ![]() Retirement Tax Blindspot✨ | retirement planningtax liability+2 | — | IRAs401(k)s+1 | — | retirement tax blindspotprincipal tax concern+2 | — | 25m 27s | |
| 2/19/26 | ![]() Listener Q&A: Your Top Dividend Questions Answered!✨ | dividend investinginvestment myths+1 | — | — | — | dividend stockshigh yield+1 | — | 17m 43s | |
| 2/12/26 | ![]() What Your Favorite Teams Can Teach You. | What do football dynasties and dividend portfolios have in common? More than you think.In this episode, we use real-world sports analogies—from the Panthers and Bills to powerhouse programs and underdog teams—to explain how successful investing mirrors successful team-building. You’ll learn why flashy stars don’t always win championships, how consistency beats hype, and why dividend investing is more about structure than speculation.www.planningmadesimple.com | — | ||||||
| 2/5/26 | ![]() Is Social Security Really Going Away? | There’s a lot of fear online right now about Social Security “running out,” but how much of it is actually true? In this episode, we cut through the noise and explain what’s really happening behind the scenes with Social Security funding, government obligations, and what retirees can realistically expect in the coming decades.We discuss why Social Security isn’t going away, how the government has handled it historically, what the projected shortfalls actually mean, and why future changes are more likely to be gradual adjustments—not sudden cuts. If you’re worried about retirement, taxes, or whether Social Security will still exist for you, this conversation brings clarity without the panic.www.planningmadesimple.com | — | ||||||
| 1/29/26 | ![]() The Myth of the Perfect Retirement Number | Most people believe there’s a magic number that guarantees a perfect retirement — but that idea may be doing more harm than good.In this episode, we break down why the “perfect retirement number” is a myth, how fear and market noise distort retirement planning, and why income, not net worth, is the real foundation of financial freedom. We explore how lifestyle, inflation, health, and emotional decision-making all impact retirement far more than a single dollar figure ever could.If you’ve ever asked:“How much do I really need to retire?”“Will I outlive my money?”“What happens if markets drop or inflation rises?”“How do I retire with confidence instead of fear?”This episode will change how you think about retirement forever.www.planningmadesimple.com | — | ||||||
| 1/22/26 | ![]() The Case Against Stock Buybacks | Dividend investing can be one of the most powerful strategies for long-term income—but only if you avoid the traps. In this episode, we unpack why high dividend yields often signal danger, how dividend cuts create a triple-whammy for investors, and the emotional mistakes that cause people to abandon dividend investing altogether.www.planningmadesimple.com | — | ||||||
| 1/15/26 | ![]() Avoiding Dividend Traps | Chasing high dividend yields can feel exciting — until the income disappears. In this episode, we break down dividend traps, why dividend cuts are so painful, and how investors get lured into unsustainable yields. We walk through the most common red flags, including high payout ratios, weak cash flow, and poor balance sheets, and explain how to stress-test dividends before you invest. If you want to build long-term, reliable income and avoid emotional investing mistakes, this is a must-watch for dividend investors at any stage.www.planningmadesimple.com | — | ||||||
| 1/8/26 | ![]() Warren Buffett's Dividend Strategy | Warren Buffett is frequently misunderstood as either a pure growth investor or a market timer—but his real strategy is far more patient and disciplined.In this episode, we break down Warren Buffett’s dividend strategy, explaining why he prioritizes strong balance sheets, predictable cash flow, and long-term dividend growth over flashy returns and short-term gains. We explore how Buffett stays calm during market downturns, why dividends can provide emotional and financial stability, and what everyday investors can realistically copy from his approach.Whether you’re building income for retirement or trying to avoid emotional investing mistakes, this conversation highlights why time, quality businesses, and sustainable dividends remain Buffett’s greatest edge.👉 Want our FREE Dividend Starter Kit? Comment “Dividend Starter Kit” below and we’ll send it to you.www.planningmadesimple.com | — | ||||||
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