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#664: Have any of these thoughts ever crossed your mind? If I had more willpower, I’d achieve my financial goals. I’m doomed to fail with money. Budgets suck. They only show me what I did wrong and make me feel horrible. If so, you’re not alone. It’s not that you lack willpower. It’s not that you’re doomed to fail with money. It’s not that you’re a horrible person for blowing your budget. It’s that you’re human. And humans make emotional decisions all the time. Decisions that often defy logic. But making emotional decisions doesn’t have to be a financial death sentence. Money management is a skill, which means we can improve. When we understand the “why” behind our decisions, coupled with the marketing tactics that retailers use, we can guard ourselves against cognitive biases and sales strategies. That’s what today’s guest is here to discuss. Jeff Kreisler, co-author of Dollars and Sense and Editor-in-Chief of PeopleScience.com, joins us to talk about common money mistakes people make and h

#663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism? In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model. Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes. We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI

#662: Most teams hire for skills. The best teams hire for wiring. What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé? This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive. We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches. After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper. We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win. Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy,

#661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin? Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage. And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about te

#660: Caring for an aging parent can morph into a second full-time job, and even the most financially savvy adults get blindsided. Bank accounts freeze, home sales stall, and family savings disappear faster than anyone expects. In this episode, we dig into what really happens when you take over a parent’s financial life, from the first power of attorney to the final tax return. We explore the emotional and logistical realities of dementia care, Medicaid, trusts, probate, and why a single smartphone setting can determine whether you can access the information you need. Veteran financial journalist and certified financial planner Beth Pinsker joins us to share the hard lessons she learned while managing her parents’ money, housing, and estate. She opens up about the “you don’t know what you don’t know” moments that hit even experts. We look at why almost every caregiver reaches a breaking point, the two documents that can save a year of stress and tens of thousands of dollars, how a forgotten zero-

#659: Imagine that you’re at the absolute peak of your career. You’re the CEO of a prominent advertising company at the age of 36, but you feel like you’re driving in the wrong lane. It’s wrong.Then you make a hard career pivot and it works out beautifully.My guests today know exactly what that’s like. We’re joined by James Patterson, the author who has sold more than 425 million copies of his books. He has co-authored books with President Clinton, Dolly Parton, and now his latest co-author is Dr. Patrick Leddin, who also joins us to talk about disruption. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Defining disruption versus gradual change (5:20) Positive disruption mindset and overcoming fear (8:12) Process for uncovering personal passions (10:25) Patterson disrupts publishing with six books per year (13:45) Research reveals 16

#658: An unusual First Friday episode because we don't have a jobs report. However, we do know that in October, U.S. companies announced more job cuts in a single month than they have over any single month of the last 20 years. In other words, October was peak job cut month. By contrast, private payrolls, as reported by ADP, rose by 42,000 in October, so we have a little bit of conflicting data. Some pessimistic, some optimistic. We're going to take a deeper look at that in today's episode. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Conflicting Job Market Data (03:40) Youth Unemployment and AI’s Impact (10:16) Fed Rate Cuts and Housing Market (20:23) New Job Postings Lowest in 4 Years (20:54) Consumer Sentiment (22:04) Social Security Payments Increase in 2026 (23:33) Rising Car Costs and Repossessions (24:46) Good New

#657: This week, Paula and Joe dig into a listener’s question about ETFs that track the stock trades of U.S. politicians — including the Democratic “NANC” fund and its Republican counterpart “KRUZ.” They explore whether this strategy is smart investing or just expensive entertainment. Then, they shift gears to home ownership headaches. Another listener asks how to control ballooning maintenance costs, and Paula shares her best advice for finding trustworthy contractors, budgeting for repairs, and knowing when DIY doesn’t actually save money. Finally, an anonymous caller wonders if starting a small business just for tax breaks makes sense. Paula and Joe explain the IRS rules — and why energy and purpose matter more than deductions. From “fun money” investing to financial planning that actually works, this episode is all about balancing curiosity, caution, and common sense. Key Takeaways Congressional-trade ETFs aren’t a shortcut to wealth. They’re speculative, lag behind real trades, and carry hi

#656: What would you do if someone in authority told you to do something that felt wrong? Most of us like to think we'd speak up, push back, stand our ground. But research tells a very different story. In fact, when Yale researchers conducted a famous experiment in the 1960s, they found that 65% of people would administer what they believed to be deadly electric shocks to another human being... simply because someone in a lab coat told them to. Today's guest has spent over 15 years studying why humans comply with authority - even when every fiber of our being is screaming that we shouldn't. And when it comes to our money, this tendency to comply with authority figures - from financial advisors to real estate agents to car salespeople - can cost us dearly. Dr. Sunita Sah began her career as a physician in the UK's National Health Service. During one particularly exhausting period as a junior doctor, she agreed to meet with a financial advisor who had contacted her at work. That meeting sparked questions tha

#655: What would you do if, at the age of 23, you found yourself with $70,000 a year leftover after expenses? Would you pour everything into retirement and coast to financial independence, or stockpile a down payment before life gets pricier with kids, a mortgage, and maintenance costs? This week, we dive into that real-life dilemma and explore how to strike the perfect balance between freedom now and security later. Along the way, we question whether a 0.40% fee for automated tax-loss harvesting is really worth it, and debate if the rise of mega-corporations means small-cap value investing is dead. Listener Questions in This Episode “Julio” asks: How should we split savings between Coast FI and a future down payment, and where should that down payment sit? (01:48) Lindsay asks: Is 0.40 percent worth it for Fidelity’s tax loss harvesting and how do we unwind back to self managed index funds? (32:31) Greg asks: If a handful of giants dominate, should we ignore history and tilt to only the to

#654: Fights about money are common, but they're rarely about math. They're about power, shame, vulnerability, and trust. And no amount of data or fancy spreadsheets is going to fix it. What you need is a better system for fairness, more open communication, and a shared ambition. In this candid conversation with Heather and Doug Bonaparte, we explore how two partners rebuilt confidence, handled their six-figure student loans, and designed a rhythm for money talks that actually works. Together they share how early money stories, law school debt, and the Great Recession shaped their dynamic, plus the tools they used to find fairness at home and in their finances Key Takeaways Why 50/50 isn't always fair and how to do it better The small ritual that turned dreaded money talks into something they actually look forward to How borrowing a strategy from the office made household decisions way less stressful The surprising fix for resentment that had nothing to do with chores or budgeting Why ta

#653: What happens when we actually check our predictions? In this episode we play clips from our 2023 conversation with Scott Trench from BiggerPockets and ask the uncomfortable question: were we right? Two years ago we made some big calls about the housing market. Mortgage rates had doubled. Prices hadn’t crashed. Inventory was vanishing. Everyone had a theory about what would happen next. Now we look back with data and receipts to see which forecasts held up and which ones fell flat. Scott joined us in 2023 to talk about the lock-in effect, the shortage of sellers, and why homebuilders might be stronger than expected. At the time it sounded contrarian. Two years later the evidence is in. Homeowners with low mortgage rates are still staying put. Builders have taken market share by offering creative incentives. Multifamily supply has exploded in some cities, while small residential properties have held their value better than many expected. We revisit our old clips and grade them one by one. What di

#652: What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke? That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path to freedom. In this conversation, Rose shares how she broke out of that cycle and built a seven-figure business that gives her time, independence, and peace of mind. We explore how she reframed her relationship with money, learned to scale her income, and built a life that aligns with her values. Key Takeaways When a “side hustle” becomes just a second job How your uniqueness is your greatest asset The slow season that led to a million-dollar leap Resources and Links Rose Han on YouTube Add a Zero by Rose Han Chapters Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are

#651: Many who reach CoastFI find themselves in a strange in-between: financially independent enough to stop saving, but not ready to fully retire. When you’re living off a taxable brokerage for decades, does the “never hold bonds in taxable” rule still apply? This episode explores how traditional asset location advice meets real-life spending. We unpack how to balance growth, taxes, and stability when your taxable account becomes your paycheck. Then we shift to two more listener dilemmas: helping a parent retire through shared home ownership, and using covered-call strategies to earn income from a stock-heavy portfolio. Listener Questions in This Episode Brandon (1:28): “I’m CoastFI and will withdraw from my taxable account for the next 20 years. Should I hold bonds in taxable, or keep it all in stocks?” Brandon’s retirement accounts can grow untouched, but his taxable brokerage will fund two decades of living expenses. The classic rule says avoid bonds in taxable, yet Paula explains why that advic

#650: Sarah Williamson is the kind of person who shapes the decisions that move trillions of dollars. She earned her MBA with distinction from Harvard Business School and holds both the CFA and CAIA designations, two of the most demanding credentials in finance. In this episode, she helps us understand how investing really works, who the major players are, how capital flows through the system, and why the incentives driving investors, activists, and asset managers often collide. Sarah spent more than twenty years at Wellington Management, where she rose to Partner and Director of Alternative Investments, after working at Goldman Sachs, McKinsey & Company, and the U.S. Department of State. Today she leads FCLTGlobal, an organization dedicated to helping companies and investors focus on long-term value creation. She is also the author of The CEO’s Guide to the Investment Galaxy. She explains why index funds now dominate corporate ownership, how Reddit and retail traders changed the market’s dynamics, and wha

#649: Many first-time buyers feel like they’re watching the train pull out of the station. If you’ve saved for years but can’t afford a home nearby, should you stretch to buy further (maybe hours) away or invest that cash instead? In this episode, we dig into the psychology, math, and lifestyle tradeoffs behind the “buy now or wait” dilemma. Plus, we unpack total return, explain when umbrella insurance is worth it, and share what every teen should learn about money. _______________________________________________ Listener Questions in This Episode Anonymous (aka “Lydia”) (3:26): ”I saved six figures for a down payment, but houses are still out of reach. Do I buy far away, rent forever, or invest the cash instead?” Lydia, an Australian listener, spent eight years saving for a home, only to find that every option feels like a compromise. Sky-high prices close to work, or long commutes for affordability. It’s a dilemma many face: does owning mean freedom, or does it just tie you down? We explore how to

#648: The U.S. government is shutting down. Bitcoin just hit a record high. Inflation whispers are back. And Wall Street is buzzing with speculation. What does this all mean for your money, your portfolio, and your long-term financial freedom? On this First Friday episode, we unpack the economic headlines you can’t ignore — and help you separate signal from noise. In this episode, we cover: Government Shutdown: What happens when Washington goes dark, and how it could ripple into the markets, interest rates, and your daily life Bitcoin at Record Highs: Why crypto is rallying, what history tells us about speculative manias, and whether this time might be different Jobs Report and Inflation Watch: The latest labor market data, its implications for the Fed, and how it could shape borrowing costs Investor Behavior in Uncertainty: Why volatility can make us overreact, and how to stay grounded in your long-term strategy Key Takeaways Government shutdowns create noise, but historically their long

#647: What if you and your partner want to take a few months – or even a year – off work?  How do you handle health insurance once you leave your jobs?  And how do you make sure the time off isn’t wasted, but becomes a launchpad for what’s next? In this week’s Q&A, we dive into those questions.  We also cover three more listener questions: what to do with a leftover $125,000 in a 529 account, how one listener landed a fully remote job with a 30 percent raise, and whether you can amend your taxes after a FEMA-declared disaster. Listener Questions: Danielle (04:35): “We want a mini-retirement. What should we do about health insurance – and how can we make the most of the time off?” Danielle and her husband want a break, but don’t want to go uninsured, and they also don't want to squander their mini-retirement. We look at what happens when you leave a job, where to find coverage, and how to design a mini-retirement that sparks discovery instead of regret. Lee (32:17): “We have $125,000 left in a 529 acc

#646: What if you didn’t have to choose between grinding full-time until retirement or quitting work altogether? By 40, Andy Hill and his wife had built a $500,000 portfolio and paid off their home. Instead of racing toward early retirement, they chose a third way: scaling back to part-time work, becoming equal partners in parenting, and reclaiming their time. In this episode, recorded live at FinCon, Andy shares his 10-step framework for building a “Coast FIRE” lifestyle — where your investments can coast toward retirement while you focus on living today. __________________________ The Middle Path Beyond FIRE Most of us think of retirement as a cliff: one day you’re working, the next day you’re not. Andy challenges that binary. He and his wife structured their careers to work 20–25 hours per week each, creating a rhythm that gave them more time with their children, each other, and their health. He breaks down the mindset shifts and tactical steps — from eliminating debt and protecting your family wit

#645: Mike (02:50): After 15 years of intentional living, Mike is 80 percent of the way to financial independence. Now he’s trying to help friends take control of their own financial future. But what happens when one spouse is eager to learn and invest, while the other isn’t interested? Michael (27:07): For two years, Michael has tracked his net worth monthly. So far, growth has been driven almost entirely by how much he saved. But when will investment returns begin to take over and shift that steady line into an exponential curve? Alvaro (34:00): After 15 years of investing in U.S. and European real estate, Alvaro has a big decision to make. Should he leverage a commercial loan to build an ADU for short-term rental income, or take on more personal debt to expand their family home? Jonathan (58:50): After hearing Paula and Joe discuss the efficient frontier — and then listening to Big ERN, Paul Merriman, and JL Collins — Jonathan can’t help but wonder: has Joe’s perspective evolved? Is the simple path st