Afford Anything

#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 how to avoid them. Jeff attended Princeton University and practiced as a lawyer before he became an author and a speaker. He co-authored Dollars and Sense with Dr. Dan Ariely, a bestselling book that explores behavioral economics and asks why we make faulty financial decisions. In this interview, Jeff names five common money mistakes and offers four solutions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 a role so it knows how to “think.” We also explore how to stress-test optimism bias, how to analyze companies like a forensic accountant or a short seller, and how to build prompts that match your own investing personality. Whether you’re an index-fund loyalist with a little “fun money” or a hands-on analyst, this conversation will expand the way you evaluate businesses and make decisions. Key Takeaways How a single prompt can transform AI from a loose generalist into a sharp, reliable research assistant.
 The surprising way optimism bias shows up in AI tools, and how to flip it to your advantage.
 Why limiting your data sources can make your analysis dramatically stronger.
 The role-play trick that helps you see a company the way a short seller, value investor, or even Warren Buffett might.
 A simple reframing that turns AI from a stock picker into something far more powerful for decision-making.
 The moment in the demo that revealed a blind spot even seasoned investors often miss. Resources and Links Get Brian’s free business-analysis prompt at longtermmindset.co/ai Check out Brian’s YouTube channel: Long-Term Mindset @BrianFeroldiYT Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (03:02) Pros and cons of using AI for stock research
 (4:55) Why Brian invests heavily in individual stocks 
(12:52) Guardrails for reducing AI hallucinations
 (17:22) How to write step-by-step prompts 
(24:02) Using roles to shape AI’s output
 (35:57) Running Brian’s prompt on Kava
 (46:22) Understanding pricing power and recession behavior
 (01:00:02) Evaluating management teams
 (01:06:02) Using AI to reflect your investing personality Share this episode with a friend, colleagues, and your family around the Thanksgiving table: https://affordanything.com/episode663 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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, and make long-term decisions. Key Takeaways Response speed can signal mental wiring, not politeness, which makes it a powerful hiring clue. The real interview starts long before the formal meeting, which means every informal interaction counts. Agility shows up when plans change, so micro-tests can reveal how someone handles shifting conditions. Many high performers are driven either by purpose or measurable progress, and knowing which matters. Understanding our own lane helps us hire better, delegate better, and build systems that reduce friction. Resources and Links Simon Sinek, Start With Why https://www.youtube.com/watch?v=u4ZoJKF_VuA Vanderbloemen Group https://vanderbloemengroup.com/ Be the Unicorn by William Vanderbloemen https://www.amazon.com/Be-Unicorn-Data-Driven-Separate-Leaders/dp/1400247101 Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) What thousands of executive searches revealed (10:35) The nine markers of high performers (22:01) Fast thinkers, slow thinkers, and finding your lane (25:35) Why response time predicts performance (25:48) Testing agility in real-world scenarios (47:16) Why purpose matters more to younger workers (55:13) Why curiosity is a career superpower Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode662 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 tech valuations. Listener Questions in This Episode Veronica asks (02:06): How do I dig out of debt, repair my credit, and stabilize my rental after nearly going into foreclosure. Daniel asks (28:17): What should I do with my surplus side hustle cash when I already max tax-advantaged accounts and have a 3.5 percent rental mortgage. Scarlet asks (49:20): If AI stocks are in a bubble like the dot-com era, is there any relatively safe way to profit from a crash, such as put options. Key Takeaways Why tackling the right problem first can change the entire trajectory of a debt recovery plan. How downsizing one major expense can unlock breathing room you didn’t realize you had. The surprising factor that often matters more than interest rates when choosing between investing and debt payoff. Why flexible money becomes essential when planning for early retirement. What most people misunderstand about betting against a bubble, especially in fast-moving tech sectors. The simple portfolio shift that can help calm bubble anxiety without trying to time the market. Resources and Links GreenPath Financial Wellness – nonprofit credit counseling and debt management support for people overwhelmed by payments and afraid of bad actors in the debt relief world. Our course: Your Next Raise – a deep dive on how to negotiate a higher salary at work, with a special comp offered in this episode. Paul Merriman Four-Fund Portfolio – the simple, diversified investing framework Daniel uses inside his retirement accounts. The Big Short movie Michael Lewis and the film adaptation. 1929 book by Andrew Ross Sorkin – a historical look at bubbles and crashes. Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (0:00) Veronica’s debt crisis and rental challenges (16:46) Cutting car costs and rebuilding cash flow (22:28) Debt relief programs and avoiding bad actors (28:17) Daniel’s surplus cash and retirement strategy (37:52) Brokerage vs mortgage payoff discussion (49:20) Can you profit from an AI bubble burst (1:00:40) Why shorting and puts rarely pay off (1:08:18) Safer ways to position your portfolio Got a question: Call it in: https://affordanything.com/voicemail Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode661 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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-balance home equity line nearly torpedoed a real estate deal, and why phone access now belongs at the center of estate planning. We also confront the brutal math of long-term dementia care, the real differences between Medicare and Medicaid, how to evaluate facilities beyond brochures, and what happens when a parent dies without updated paperwork. Through it all, we focus on how clear conversations about wishes and values can reduce guilt and burnout for the people left steering the ship. Key Takeaways Financial caregiving comes for almost everyone eventually, and even experts hit roadblocks, so the goal is not perfection but reducing avoidable chaos. Power of attorney and healthcare proxy documents are foundational, often more urgent than a will, and they need to be current, state-appropriate, and shared with the people who may need to use them. A locked smartphone without a legacy contact can become a financial brick, cutting caregivers off from essential clues about accounts, subscriptions, and bills. Long-term dementia care can run five to six figures per year, outlasting even solid nest eggs, so families need to confront the realities of Medicaid and state-specific safety nets before the money runs out. How assets are titled, from bank accounts to real estate, determines whether heirs inherit smoothly through a trust or spend years and thousands of dollars navigating probate. The most important “plan” is knowing a loved one’s wishes for quality of life and end-of-life care, so financial and medical decisions feel like honoring them instead of guessing in the dark. Key moments (0:00) Why financial caregiving blindsides even the experts (05:18) The hidden home equity line that almost killed a real estate deal (10:54) Two documents every adult in your life should have (14:29) The critical phone setting that protects access to accounts and memories (21:23) What Prince’s estate taught us about wills and inertia (31:39) Planning for a decade of dementia care without going broke (35:16) How Medicaid really works and why “running out of money” is a process (38:46) The menu of care options from in-home help to CCRCs and nursing homes (44:31) The “smell test” for evaluating facilities in the real world (51:06) What to do in the first weeks after a parent dies (54:38) Trusts, titles, probate, and how one frozen account cost $5,000 to unlock (01:01:04) Knowing their wishes so money decisions feel like honoring, not guessing Resources and Links Beth Pinsker’s website: bethpinsker.com Beth’s retirement and financial planning columns at MarketWatch Beth’s book, My Mother's Money, on financial caregiving and planning for aging parents and loved ones Share this episode with a friend, colleagues, and anyone who is thinking about caregiving: https://affordanything.com/episode660 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 disruptive behaviors (16:30) Academia embracing different voices and perspectives (21:00) Mountain climber story shows gradual disruption (24:14) Framework for navigating career transitions (28:19) Limiting beliefs and psychological barriers (30:55) Being open to change versus stability (35:00) Taking ownership of disruptive choices (41:00) Mission versus purpose distinction (46:37) Advice for embracing positive disruption Share this episode with a friend, colleagues, and James Patterson book fans: https://affordanything.com/episode659 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 News for Prescription Drug Prices (31:50) Government Shutdown Impacts Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 high costs Home maintenance is predictable — plan for it. Create a repair timeline and build relationships with investor-friendly contractors DIY isn’t always cheaper. Factor in time, tools, and opportunity cost Never open a business just for taxes. If it doesn’t make a profit or bring joy, it’s an energy drain, not a strategy Separate fun money from freedom money. Keep speculation playful, and build wealth with focus and purpose Chapters 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) Should You Follow Congress’s Trades? (06:00) The Lag Problem and Investor Bias (10:30) The “Fun Money” Rule (11:20) The Hidden Cost of Home Repairs (15:00) Finding Investor-Friendly Contractors (18:00) Planning Ahead for Repairs (22:00) DIY vs. Opportunity Cost (26:00) Starting a Small Business for Tax Breaks (29:00) The IRS “3-of-5 Rule” (32:00) Purpose Over Deductions (34:00) Final Thoughts https://affordanything.com/voicemail Share this episode with a friend, colleagues, and all the Nancys in your life: https://affordanything.com/episode657 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 that would shape the rest of her career: Why did she feel pressured to trust this advisor, even after learning he had a conflict of interest? Today, she's a tenured professor at Cornell University, where her groundbreaking research on compliance and influence has been featured in The New York Times and Scientific American. She's advised government agencies, served on the National Commission on Forensic Science, and helps leaders understand the psychology behind why we say "yes" when we really want to say "no." Whether you're meeting with a financial advisor, negotiating the price of a home, or discussing rates with a contractor, understanding the psychology of compliance could save you thousands of dollars - and help you make better financial decisions. Today's conversation isn't just about psychology - it's about protecting your wealth by learning when and how to say "no." Resources Mentioned in the Episode: - Website: sunitasah.com - Newsletter: Defiant By Design | Dr. Sunita Sah | Substack - Connect with Dr. Sunita Sah - Follow Dr. Sah on Instagram About Dr. Sunita Sah Dr. Sunita Sah is a tenured professor at Cornell University specializing in organizational psychology. Her research focuses on how and why people comply with authority, even against their better judgment. A former physician in the UK's National Health Service, Dr. Sah brings a unique perspective to understanding human behavior and decision-making. Her work has been featured in leading publications including The New York Times and Scientific American, and she has served as a Commissioner on the National Commission on Forensic Science. Share this episode with a friend, colleagues, and your cohorts: https://affordanything.com/episode656 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 top companies instead of broad markets and small cap value? (50:51) Key Takeaways The right savings balance may depend less on math and more on clarity about what “home” really means to you Building a down payment might be the fastest way to reach Coast FI, but not for the reason you’d expect Parking cash safely is trickier than it sounds, especially when the market tempts you with higher returns That 0.40 percent fee could be either a silent drag or a smart trade-off, depending on one often-overlooked detail The rise of mega-caps might look unstoppable, yet history has a way of surprising even the biggest players True diversification isn’t about predicting winners, it’s about protecting future you from overconfidence today Chapters 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) Are we headed for a dystopian future (01:48) A 23-year-old with a $125k income and a big savings gap 08:52) House price, down payment size, and the numbers that drive the split (10:47) The savings snowball case, match protection, and timeline trade-offs (25:14) Where to park the down payment, why cash beats stocks for readiness (32:31) Is 0.40 percent worth it for tax-loss harvesting (36:24) Fees versus claimed tax savings, turnover, and exit options (50:51) Should dystopia change our portfolio (54:36) Small-cap value beyond tech, acquisitions, and global opportunity (1:11:02) Optimism, innovation, and why investing still assumes progress P.S. Got a question? Leave it at https://affordanything.com/voicemail For more information, visit the show notes at https://affordanything.com/episode655 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 tackling six-figure student loans together became a turning point in their relationship The mindset shift that helped them see debt not as a burden but as a shared opportunity Resources and Links Money Together, the book DoMoneyTogether.com, learn more about the book and project The Joint Account, weekly newsletter on joint finances at ReadTheJointAccount.com Fair Play by Eve Rodsky, a framework for dividing household responsibilities Share this episode with a friend, colleagues, and anyone who is part of a couple: https://affordanything.com/episode654 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 did we get right about the housing market’s resilience and where did we miss? You’ll hear how rate volatility created bursts of demand, how regional migration reshaped supply, and why small investors can still find opportunities even when the headlines say otherwise. This episode isn’t about victory laps. It’s about accountability. If you’ve ever wondered whether experts truly revisit their own calls, you’ll love this one. Key Takeaways The lock-in effect remains one of the most powerful forces in today’s housing market Builders have been surprisingly resilient thanks to incentives and creative financing Multifamily oversupply is pressuring rents in some regions while small residential properties remain steady Market outcomes are more local than ever; national averages hide major differences Real estate predictions matter only if we’re willing to go back and test them Resources and Links Our course Your First Rental Property open for enrollment through October 30 at affordanything.com/enroll Chapters 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. (0:00) Why we’re replaying our 2023 predictions (4:24) The strange housing market of 2023 (5:04) The lock-in effect and vanishing inventory (6:03) Builders finding ways to keep selling homes (12:12) How rate dips created bidding wars (14:03) The construction pipeline and what happened next (37:24) 2025 check-in on prices and incentives (55:06) Regional winners and losers (58:27) Small residential versus large multifamily (1:06:08) Final reflections and what we learned Share this episode with a friend, colleagues, and anyone in the real estate space: https://affordanything.com/episode653 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 approximate and may be several minutes off due to changing ad lengths. (0:00) Rose Han’s story begins: doing everything right yet still ending up broke (5:45) The Cancun moment that sparked Rose’s financial awakening (9:12) Discovering the three types of income and why some buy freedom while others don’t (13:45) How Rose Han built her “Add a Zero” framework for lasting wealth (21:30) From employee mindset to entrepreneur mindset (25:15) The three levels of leverage and how to scale your income (28:55) Why not every side hustle creates freedom (31:45) Overcoming the fear of selling (39:16) How to build a business while working full-time (47:10) Rose’s real estate lessons and the myth of passive income (53:55) Knowing when to walk away from an investment (1:10:15) What financial freedom really means and how to find your own version Share this episode with a friend, colleagues, and anyone who is interested in entrepreneurship and investing: https://affordanything.com/episode652 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 advice isn’t universal. When your taxable account funds your life, it needs to act as a complete portfolio. We discuss how to balance risk, prioritize liquidity, and plan your glidepath into CoastFI life. Andrew (22:07): “My spouse and I co-own a home with my mother-in-law. How can we help her retire without creating family tension?” We explore fair, flexible ways to support an aging parent while keeping relationships healthy. Paula explains how to design a win-win deal and why seller financing can help balance cash flow and peace of mind. Chandan (49:16): “Can covered-call ETFs help me generate income from my stock portfolio and RSUs?” We explain how covered calls work, what “covered” really means, and the tradeoff between steady income and limited upside. For those with concentrated stock positions, Paula shares when covered calls make sense—and when simpler plans win. Key Takeaways The “no bonds in taxable” rule isn’t universal. When you’re drawing solely from taxable accounts for many years, that account needs to function as its own mini-portfolio, including bonds or cash for stability. Asset location follows purpose, not dogma. Tax efficiency matters, but liquidity and risk management take priority when the account funds your life. Think in terms of buckets. Your retirement accounts can stay growth-oriented while your taxable account carries the ballast for spending. Plan ahead for rebalancing. When taxable balances decline, know how and when to refill your bond/cash sleeve from other sources to keep your glidepath intact. The transition to CoastFI is a mental shift. You’re no longer optimizing for maximum returns, you’re designing for peace of mind and steady withdrawals. Chapters Note: Timestamps are approximate and may differ across listening platforms due to dynamically inserted ads. (01:28) Brandon’s CoastFI question: bonds in taxable when withdrawals start now (03:56) Why “no bonds in taxable” is a rule of thumb, not a law (12:42) How to treat taxable as a stand-alone portfolio (18:31) Balancing tax efficiency with cash-flow reality (25:26) Helping a parent retire through shared property ownership (01:05:40) Options: Buying or selling with Options (01:07:07) Covered calls explained simply, income with a ceiling Resources & Links Asset Location Cheat Sheet (free): affordanything.com/assetlocation Guide to Double-I FIRE (free): affordanything.com/fiire Share this episode with a friend, colleagues, your the person you buy garbage bags from: https://affordanything.com/episode651 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 what it means when activists push companies to “bring earnings forward.” She also introduces a framework for understanding the “five solar systems” of investing, a map that connects everyone from day traders to trillion-dollar sovereign wealth funds. Whether you are a passive investor or simply curious about what drives the market, this episode gives you the clarity to see how capital really moves and why it matters. Key Takeaways Reddit and the meme-stock movement permanently changed how individual investors move markets Index funds now dominate ownership, creating both stability and new corporate challenges Activists often prioritize short-term profit over long-term innovation Sovereign wealth funds act like national endowments, investing with century-long horizons Understanding who owns what (and why) makes you a more informed, confident investor Resources and Links The CEO’s Guide to the Investment Galaxy by Sarah Williamson FCLTGlobal, a nonprofit that helps companies and investors focus on long-term value creation Chapters 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) Meet Sarah Williamson: CEO, CFA, Harvard MBA, global finance leader (5:41) The five “solar systems” that organize the investing world (7:55) Reddit and the rise of the retail investor (16:25) Tesla, brand loyalty, and shareholder activism (22:57) How sovereign wealth funds invest for generations (28:57) Inside asset managers and their incentives (41:56) Activist investors and the tension between short and long term If you want to understand the real power dynamics behind modern investing, from Reddit traders to trillion-dollar endowments, don’t miss this episode. Share this episode with a friend, colleagues, and your cousin who is obsessed with latest meme stocks: https://affordanything.com/episode650 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 separate fear from opportunity, why “starter-home-turned-rental” plans often backfire, and how to measure the real cost of lost time when you move hours from work. Ultimately, it’s about aligning your money with your life, not the headlines. Anonymous (aka “Aristotle”) (29:38): “My ETF is up 10% and yields 3%. Is my net return 13%?” It’s a common question for anyone tracking their investments. We unpack the difference between total return and your personal rate of return, and why those two numbers rarely match. You’ll learn what actually drives performance, and how to read your brokerage dashboard like a pro. Joel (39:44): “Umbrella insurance; do we need it and how much?” If you own a home, drive a car, or rent out a property, you’re exposed to more liability than you might realize. We break down how umbrella insurance works, when it’s essential, and how much coverage makes sense. It’s one of the cheapest ways to protect your wealth. Julia (56:13): “I’m building a high-school personal finance course. Should I cover insurance or credit?” When teaching teenagers about money, where do you start? We explore why understanding decision-making (opportunity cost, compounding, and spotting bad financial advice) matters more than memorizing credit scores or insurance terms. Key Takeaways Don’t buy from FOMO; let lifestyle goals—not market panic—drive your choices. Total return includes price changes and income, but your broker’s “personal rate of return” shows the truest number. Umbrella insurance offers millions in protection for relatively little cost; bundle it with home and auto. Teach teens the “why” behind money choices before the “what.” Understanding tradeoffs beats memorizing rules. Chapters 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. (4:14) Anonymous Lydia’s question: should I buy now or invest my down payment? (8:23) The emotional trap of FOMO and rising prices (11:45) Why “live there now, rent it later” rarely works (22:14) The hidden cost of long commutes and lifestyle tradeoffs (29:38) Anonymous Aristotle’s question: how do I calculate my true investment return? (39:44) Joel’s question: Is umbrella insurance worth it and how much should I buy? (56:13) Julia’s question: what high schoolers should learn first about money Share this episode with a friend, colleagues, or with the person at your school that teaches personal finance classes: https://affordanything.com/episode649 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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-term market impact is minimal Bitcoin’s surge reflects both speculation and broader demand for decentralized assets — but extreme volatility remains The labor market remains resilient, keeping inflation risks on the radar and Fed policy in focus Emotional investing is costly: staying calm during uncertainty is one of the best ways to protect your wealth. This month’s headlines feel dramatic — shutdowns, soaring crypto, inflation fears. But the timeless principles of money management still apply: diversify, stay disciplined, and don’t let headlines dictate your portfolio. Key moments: (00:00) Jobs Reporting from ADP (08:28) Interest Rates and Mortgages (18:07) Social Security Age (25:36) Consumer Spending and Inflation (31:56) Bitcoin and Gold reach new highs (34:31) Quarterly Reporting for Publicly Traded Companies may go to twice-a-year Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode648 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 account. No one needs it for school. What should we do?”A six-figure leftover balance sounds great, but it comes with tricky rules. Can you roll it into a Roth IRA? Use it for other programs? Withdraw without a tax hit? We explore the surprising flexibility inside a 529. Pedro (44:06): “I followed your job search advice – and just landed a new role!”Pedro once struggled with dead-end applications. Now he’s celebrating a fully remote job, a big raise, and better alignment. How did he do it? By targeting the intersection of his skills and industry, instead of casting a wide net. Melanie (53:35): “I spent $45,000 after a FEMA-declared disaster. Later, Congress passed retroactive tax relief. Can I benefit?”Disaster tax relief is confusing, especially when laws apply after the fact. Melanie asks if she can amend her return to capture new benefits. We talk timelines, amended return rules, and why professional help matters. 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. Key Highlights How to get health insurance during a mini-retirement. Why treating time off as a “science experiment” can reshape your career. Smart options for a leftover 529 account (including new Roth IRA rollovers). A real listener’s success story: from stalled applications to a remote job with a 30% raise. What to know about amended returns for FEMA-declared disasters. Resources Pedro's original question on Episode 605 Healthcare.gov — ACA marketplace for insurance enrollment The Power of Fun by Catherine Price Digital Minimalism by Cal Newport Freedom app — tool for blocking distractions Share this episode with a friend, colleagues, your cousin who is obsessed with latest meme stocks: https://affordanything.com/episode647 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 with insurance to stockpiling FU money and designing a three-day workweek. Along the way, he explains how Coast FIRE frees you from mandatory retirement contributions and opens doors to a flexible, meaningful life. __________________________ Key Takeaways: Balance beats extremes. Neither full-time grind nor full-time stay-at-home felt right; designing a flexible, part-time work life created the equilibrium their family needed. Cash buffers change behavior. A 3–6 month emergency fund reduces stress and scarcity thinking, making it easier to parent calmly and make better money decisions. Choose time over trappings. Fancy upgrades aren’t worth trading away presence; prioritizing family time beats lifestyle escalation. Resources mentioned: Andy Hill's book on Amazon: Own Your Time Marriage, Kids, and Money Podcast (4:01) Why the shift (5:35) What their life looks like now (9:08) Why extremes didn’t work for Andy and Nicole (14:45) Step 1 Dream and define your ideal life (18:21) Step 2 Commit to living without high-interest debt (20:38) Step 3 Protect your family (insurance, estate plan, emergency fund) (27:04) Step 4 Invest to reach Coast FIRE (30:29) Step 5 Pay off your home (or optimize if renting (36:21) Step 6 Stockpile FU money (47:53) Step 7 Design a three-day workweek (57:02) Step 8 Plan your intentional four-day weekend (1:02:39) Step 9 Simplify to avoid lifestyle creep (1:08:56) Step 10 Teach your kids the path to time freedom Share this episode with a friend, colleagues, or with your neighbor with the tricked-out basement : https://affordanything.com/episode646 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 still enough, or is there merit in a more complex approach? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it ⁠here⁠. Resources Mentioned: JL Collins Part 1 and Part 2 Karsten Jeske (Big Ern) Episode 643 Paul Merriman Episode 550 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. Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode645 Learn more about your ad choices. Visit podcastchoices.com/adchoices