The Pete the Planner® Show

Most people don’t know how to tell if their financial advisor is great—or just great at sounding confident. In this episode, Pete and Dame unpack the real red flags to watch for when you’re getting financial advice… without turning it into a witch hunt. They’ll break down the difference between a bad actor and a bad fit, decode advisor-speak (“We’ll rebalance with a tactical overlay!”), and show you how to spot when someone’s more interested in selling than solving. Plus, they’ll explain what good advice actually feels like—clear, consistent, and curious about your life. This isn’t an “advisors are evil” episode. It’s a smarter take on how to protect yourself and still believe in the power of good guidance.

💥 This week, Pete and Damian face off against their newest (and possibly most intimidating) competitor: Artificial Intelligence. Can two seasoned money nerds outthink an algorithm? In each round, Pete or Dame tackles a real financial dilemma — from whether to raid an emergency fund to pay off debt, to deciding between a Roth or traditional 401(k). Then, they read the AI’s answer and debate which response wins on accuracy, empathy, and practicality. It’s human experience versus machine logic — and the results might surprise you. Who gives the better advice: the pros with decades of experience or the robot with instant access to infinite data? Tune in for laughs, sharp insights, and a fresh look at the future of financial guidance. 🎧 Featuring rounds like “The Credit Card Conundrum,” “The Roth Riddle,” and “The College Crunch.” 👾 Man. Machine. Money. Only one can win.

Ever notice how the smartest people you know sometimes make the worst financial decisions? In this episode, Pete Dame unpack why intelligence doesn’t always translate to good money habits. From overconfidence and analysis paralysis to emotional blind spots and ego-driven decisions, we explore the psychology behind financial self-sabotage. We’ll share real-life examples of “smart” money mistakes — from chasing complex investments to ignoring basic budgeting — and discuss why simplicity often wins. Plus, we’ll reveal the subtle ways our brains trick us into believing we’re the exception to every financial rule. 💡 Being smart with money isn’t about IQ — it’s about self-awareness.

This week on The Pete the Planner Show, we’re tackling one of the toughest money dilemmas families face today: when helping your adult children turns into hurting yourself. A listener writes in about her 31-year-old daughter who still lives at home, contributes nothing financially, and has become the center of a tug-of-war between supportive love and enabling behavior. Pete, Kristen, and Damian unpack the concept of financial enmeshment—those blurred parent/child roles where support becomes indefinite, boundaries vanish, and retirement plans quietly suffer. Why is this happening more than ever? Sky-high housing costs, student debt, and the return of loan payments all play a role, but so do fear, guilt, and a desire to shield kids from failure. We’ll explore the emotional conflict between partners who disagree on rules, the hidden cost of Parent PLUS loans, and why “support without structure is just deferred conflict.” Then, we’ll lay out practical tools for parents: aligning as a couple, having honest conversations with adult kids, and creating a phased transition plan that respects both love and limits. If you’ve ever wondered where generosity ends and enabling begins, this is an episode you won’t want to miss.

Young adults are increasingly turning to risky bets — sports gambling, meme stocks, crypto, even leveraged ETFs — not just for the thrill, but because traditional wealth-building feels out of reach. In this episode, Pete, Damian, and Kristen dig into the rise of “financial nihilism,” a mindset fueled by housing costs, student loans, job market uncertainty, and fading confidence in the American Dream. We’ll unpack the CNBC stories of 20-somethings chasing fast money on Discord and betting platforms, explore whether these strategies are truly new or just speculation repackaged, and debate whether they’re desperation or savvy risk-taking. Finally, we’ll look at healthier alternatives: ways to channel risk appetite without blowing up your future. Because when people stop believing in long-term financial security, they don’t stop trying — they just look for shortcuts.

Claire and Ethan, a newly married couple in their early 30s, are sitting on $450,000 in cash after selling property and combining finances — and instead of feeling secure, they’re feeling anxious. With a baby on the way, strong incomes, no debt, and a net worth north of $2 million, their dilemma is how to balance competing goals: buying a home, investing for the future, keeping travel flexibility, and raising their child. In this episode, Pete and Dame break down the psychology of “too much cash,” explain how to bucket money by time horizon, and show why timing often matters more than returns. They’ll also walk through the conversations every couple should have when life goals collide with financial uncertainty. If you’ve ever wondered how to turn money stress into money direction — whether you’ve got $4,500 or $450,000 — this episode is for you.

Americans are feeling strangely upbeat about retirement — maybe too upbeat. A new survey shows confidence is soaring, with fewer people saying it will take a “miracle” to retire comfortably. But optimism fueled by a hot stock market can be a dangerous thing if it leads to complacency. In this episode, Pete and the team break down the new retirement mood, the hidden worries still keeping people up at night, and the math behind what it actually takes to stop working for good. From the half-million-dollar savings gap to the real meaning of the 4% rule, this conversation cuts through the delusion and gets to what matters: how to build a plan that works even when the market doesn’t.

Are all financial red flags truly dealbreakers? Not necessarily. This week, Pete and the team dig into the money habits that look risky on paper—but can actually be fine if managed with discipline. From Buy Now, Pay Later to car leases to living paycheck-to-paycheck, we explore the nuance between a red flag in isolation and a pattern that leads to real trouble. You’ll learn how to spot the difference, set guardrails, and balance risks with financial strengths. Because sometimes the red flag is just a reminder, not a reason to panic.

When love and real estate collide, things can get messy. A new listener writes in after moving into their partner’s home—a home that’s been theirs for nearly a decade, kids and all. The couple is serious, even planning to elope, but the money side of the relationship? Totally unplanned. How do you contribute fairly when you don’t technically own the house? How do you protect yourself without seeming selfish? And what conversations should couples really have before moving in together? Pete and Kristen unpack the unwritten rules of cohabitation, from cohab agreements to avoiding the “floating system” trap. Whether you’re dating, shacking up, or already living in a blended household, this episode explores the fine line between romance and responsibility—because building a future together requires more than just sharing groceries.

This week’s listener email comes from a 40-something who admits they’ve fallen behind on retirement savings—and they’re wondering if it’s too late to catch up. Pete and the team tackle the emotional weight of realizing you’re behind, the math of what’s still possible, and the practical moves to make right now. From cutting expenses and boosting savings, to making the most of peak earning years and catch-up contributions, we’ll show how to turn midlife money panic into a realistic plan for retirement.

Downsizing sounds like a simple way to save money—sell the big house, pocket the cash, live leaner. But real life isn’t that tidy. In this week’s episode, Pete, Damian, and Kristen unpack the hidden math, emotional pull, and lifestyle trade-offs behind the “should we move?” question. From rising taxes and leaky roofs to property tax freezes and priceless neighborhood ties, we dig into when staying put might secretly be the better deal—and when it’s time to pack the boxes. Plus, we explore creative options for making your home (or your housing budget) work harder without automatically going smaller. Whether you’re a retiree with an empty nest or just wondering if your house fits your future, this conversation will help you decide what’s truly right for your wallet and your well-being.

When one listener gets a job offer in the Midwest with a 40% pay bump, it sparks more than just career contemplation—it opens the door to a bold family experiment: combining households with the in-laws. In this episode, Pete, Kristen, and Damian tackle the emotional and financial complexities of multigenerational living. From structuring ownership and avoiding sibling drama to protecting retirement assets and managing expectations, we walk through the pros, cons, and creative setups that can make this kind of arrangement work. Spoiler: Loving your in-laws might be easier than figuring out who pays the property taxes.

After 40 years of saving diligently, listener Jeff is retiring next month—and like many new retirees, he’s asking the question the industry rarely answers: How do I actually spend my 401(k)? In this episode, Pete and Damian walk through the critical decisions that come after the last paycheck: how much to withdraw, which accounts to pull from first, and how to invest your portfolio for a retirement that could last 30+ years. From the 4% rule to bucket strategies and tax-efficient withdrawal planning, we’re breaking down the complex into the practical. Whether retirement is right around the corner or still a decade away, this episode will help you think differently about what it means to turn savings into sustainable income.

This week on The Pete the Planner Show, we tackle a question from a listener couple in their 30s who’ve nailed the basics—no debt (besides the mortgage), a healthy emergency fund, steady retirement savings, and even monthly money check-ins that end in high fives, not fights. So… do they really need a financial planner? We dive into when DIY is good enough—and when a second set of (professional) eyes might help you uncover what you don’t know you don’t know. Whether you love spreadsheets or break into a cold sweat at the word “fiduciary,” this episode will help you figure out if it’s time to level up your planning—or if you’re already crushing it on your own. You’ll learn: The tipping point between DIY and delegation What a financial planner can (and can’t) do for you How to avoid blind spots even when you're doing everything "right" It's a practical, honest conversation for anyone who's ever wondered: Do I need help, or am I just fine?

This week’s episode begins with a heartfelt listener question that cuts to the core of a topic we all tend to avoid—death, and the financial planning that surrounds it. Pete, Kristen, and Damian explore whether prepaying for funeral arrangements is a sound financial decision—or an expensive emotional shortcut. With compassion and clarity, the team breaks down the pros (like locking in today’s prices and reducing stress on loved ones), cons (think: lack of flexibility and risk of mismanaged funds), and alternatives (including payable-on-death accounts and funeral trusts). We also explore Medicaid planning implications and what to watch for if you're in a state like Indiana with specific caps. Then in Segment 2, it’s Estate Planning 101—without the intimidating legalese. What documents matter most? Why is this an act of love, not just a legal to-do list? The trio walks through wills, powers of attorney, healthcare directives, and the often-overlooked step of updating beneficiaries. Finally, we wrap with the emotional labor of planning ahead. Why is it so hard to talk about money and mortality with family? How do you start the conversation without freaking everyone out? We offer gentle scripts, relatable stories, and encouragement to be the planner your future self—and your family—will thank. You’ll laugh, you’ll cry, and—if we do our job—you’ll make at least one meaningful step toward peace of mind.

Congress just dropped the “One Big Beautiful Bill” (yes, that’s really what they’re calling it), and it could reshape everything from your paycheck to your student loans. In this fast-moving episode, Pete, Kristen, and Damian unpack what OBBB actually is—and more importantly, how it affects you. Segment 1 sets the stage: from expiring 2017 tax cuts to new SALT caps, we simplify the headlines and help you emotionally prepare for what’s coming at tax time. Segment 2 dives into the biggest student loan shake-up in a generation: new repayment plans, forgiveness tweaks, and tighter borrowing limits that could change how families approach college altogether. And in Segment 3, we highlight the under-the-radar changes: boosted child tax credits, deductions for tipped workers, Social Security tax relief, and new Medicaid work rules you need to know. Whether you’re a student, a parent, a retiree, or just trying to keep up—this episode is your guide to navigating the chaos with clarity (and a few laughs along the way). Call to Action: What’s the one part of your financial life you hope this bill improves—or doesn’t mess up? Let us know!

When the market is a rollercoaster and headlines won’t stop screaming, even the savviest investors can start second-guessing everything. In this episode, Pete, Damian, and Kristen unpack what confidence in investing actually means—and how to build it, rebuild it, and protect it when doubt creeps in. Segment 1 kicks off by normalizing the fear that even seasoned investors feel, especially in today’s world of economic whiplash and geopolitical uncertainty. Then in Segment 2, the team breaks down the four pillars of a trustworthy portfolio—clarity of purpose, evidence-based design, behavior as the engine, and regular (not obsessive) reviews. Finally, Segment 3 offers practical tools to reset your mindset when confidence takes a hit. Whether you’re a hands-on investor or someone who treats their 401(k) like a haunted house, this episode will help you shift your focus from predicting the market to trusting your plan. Because calm isn’t magic—it’s a skill.

Summer break is here—which means your kids are home, your fridge is empty, and your wallet is… nervous. In this episode, Pete, Kristen, and Dame explore whether the old rules of teaching kids about money still hold up, or if today’s world demands something new. From toddler toy budgets to teen summer job paychecks, we break down how to raise money-smart kids without turning into a lecture machine (or losing your mind). You’ll learn how to: Use summer moments as money teaching tools Talk to kids at different ages without getting eye-rolls Help teens manage their own money—without a meltdown Equip them for real life, not just allowance life Plus, the team shares their favorite (and most hilarious) wins and fails from teaching their own kids about money.

In this episode, we tackle a sneaky problem: confusing financial motion with actual progress. Just because you’re constantly doing money-related tasks—paying bills, checking balances, moving money around—doesn’t mean you’re getting ahead. Pete opens with a gym analogy that hits a little too close to home, then brings in Kristen and Dame to break down why so many people feel stuck despite their efforts. We explore what real progress looks like—both on paper and emotionally. From Power Percentage and savings rate to the peace of mind that comes with financial confidence, we’re separating the signal from the noise. And with the year halfway over, we wrap with a "mid-year compass check" to help you course-correct before it’s too late. If January’s goals are now a blurry memory, this is your wake-up call. Don’t wait for December to figure out whether you made progress—let’s find out now.

The markets are soaring, the economy is expanding, and everyone's wondering—are we in a bubble? In today’s CalmCast, Pete breaks down the difference between market momentum and market mania, explores what real economic growth looks like, and helps you focus your energy on what matters most: your personal financial vision. Whether you’re tempted to chase hot stocks or just trying to make sense of the noise, this episode will help you zoom out, calm down, and plan forward.