Pete the Planner on Humor, Habits and the Psychology of Money On this episode of Off the Record, host Nate Feltman sits down with Peter Dunn, better known as Pete the Planner, one of America’s most trusted voices on personal finance. Dunn shares how a sixth-grade stock market contest launched his career, how he blends comedy and financial coaching to help people build better habits, and why the psychology of money matters more than math. He opens up about building Your Money Line, a fast-growing financial technology company using AI to deliver personalized advice to more than 800,000 people, and how leading a startup taught him hard-earned lessons about leadership, responsibility and giving back. A former columnist for USA Today and author of 10 books, Dunn discusses his national media presence, his roots in Indianapolis, and why financial wellness is critical in today’s workplace.

Let’s be honest: most New Year’s resolutions don’t make it to Valentine’s Day. So instead of pretending this year will be different, we’re drafting financial resolutions that actually survive real life. In this episode, we run The Financial Resolution Draft—fantasy-football style—selecting the smartest, most realistic financial moves for three life stages: your 20s, your 40s with kids, and your 60s nearing retirement. No vague goals. No financial TikTok nonsense. No personality changes required. Just one system per life stage that reduces stress, works with the money you already make, and doesn’t fall apart the first time something goes wrong. Because if your resolution needs motivation, it’s already dead.

In this week’s episode, Pete breaks down the ten biggest financial mistakes Americans are making right now — from investing too little and too late, to overspending on housing, to making car decisions that haunt their budgets for years. With the economy shifting under everyone’s feet, these missteps are more common (and more costly) than ever. Pete walks through why these mistakes happen, what they really cost you over time, and the simple, practical changes that can keep your financial life from drifting off-course. If you’ve ever wondered whether your biggest threat is debt, bad timing, or Future You procrastinating… this is the episode to reset your path. Bite-sized, honest, and packed with clarity — this is your roadmap to avoiding the pitfalls that hold most households back.

This week on The Pete the Planner Show, we tackle a classic early-retirement temptation: what happens when you want out of the workforce before 59½, but almost all your money is locked inside qualified retirement accounts? A listener from Dayton writes in with solid savings, a paid-off home, and a serious case of “I can’t do this job anymore.” The problem? He wants $80,000 a year in retirement income, but he’s only 54 — and bridging those five and a half years before penalty-free withdrawals is tougher than people think. We break down his real numbers, explore strategies like 72(t) distributions and Roth conversion ladders, and explain why early retirement is often less about “Can I quit?” and more about “Can I cash-flow the gap years without blowing up my future?” If you’ve ever dreamed of early retirement (or Googled ‘how bad is the 10% penalty really?’), this episode is for you.

Pete and Kristen read a listener email who seems to indicate they greatly regret their recent home purchase

This week on The Pete the Planner Show, Pete, Damian, and Kristen dive into one of the most universal workplace mysteries: why everyone treats HR like a certified financial planner… even though HR can barely tell you which parking pass to choose without checking a binder. Open enrollment, confusing benefits forms, retirement questions—employees fire all of it straight at HR hoping for guidance, clarity, or honestly just someone to make the decision for them. And while HR can walk you to the forms, they definitely cannot walk you through your medical history, risk tolerance, or whether your spouse is accident-prone. In this episode, we break down: Why HR gets stuck with financial questions in the first place The top “Please do not ask HR this” questions (yes, including the 401(k) ones) What HR is actually allowed to help you with How to get real answers without putting your HR team in legal jeopardy If you’ve ever stared at a PPO vs. HDHP page like it was ancient hieroglyphics—or asked HR which investments you should pick—this one’s for you. And for HR professionals everywhere: you’re welcome.

As the calendar barrels toward its final pages, Pete sits down for a solo episode to talk about the strange, sloppy, wonderful chaos of the year’s final weeks. From an economy that can’t decide what mood it’s in, to holiday spending that threatens to turn December joy into January regret, Pete breaks down what Americans are really wrestling with right now — and how to keep your financial head on straight while everything else gets weird. In classic Pete fashion, he mixes practical advice with self-deprecating humor, heartfelt reminders, and a gentle nudge toward sanity. If you're feeling behind on your goals, confused by the markets, or tempted to buy your nephew a $400 gaming headset “because it’s the holidays,” this is your permission to slow down, reset, and approach the end of the year with clarity instead of chaos. A funny, grounding, down-to-earth episode for anyone trying to finish the year strong — or at least finish it without crying into their January bank statement.

On this week’s episode of The Pete the Planner Show, Pete tackles what might be the most misguided “solution” to housing affordability ever pitched: the 50-year mortgage. On the surface, it sounds like a clever way to make homes more affordable — smaller payments, easier approval, and a chance for more people to buy. But dig a little deeper, and it’s clear this “innovation” is really a long-term financial trap. Pete breaks down the math, explores who really benefits, and explains why stretching your loan to half a century could make you the bank’s favorite customer — and your future self’s worst enemy.

This week, Pete is joined by veteran podcaster and political enthusiast Chris Spangle to wrestle with the myth and the muscle of willpower. Why do we think it’s the key to every success story—money, fitness, food, or habits—when in reality, it often lets us down? Pete and Chris explore how environment, emotion, and even exhaustion can overpower our best intentions. From political discipline to personal finance, from calorie tracking to credit card restraint, they break down what really drives behavior—and why relying on sheer willpower alone is like trying to bench press your way out of bad decision-making. Funny, honest, and occasionally self-incriminating, this episode will make you rethink how you “control yourself” and maybe show a little more grace when you can’t.

Forget the convertible and the questionable haircut — the real midlife crisis happens when you open your retirement account and realize the math isn’t mathing. In this solo episode, Pete explores the emotional and financial crossroads that hit in your 40s and 50s — when time feels shorter, careers plateau, and money goals start bumping into real life. He unpacks why financial growth slows down, how priorities shift, and what to do when your sense of progress feels stuck on pause. From redefining success to right-sizing your lifestyle, this episode is part therapy session, part pep talk, and entirely relatable. Key takeaway: Your midlife crisis isn’t a breakdown — it’s a recalibration.

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.