Afford Anything

#692: Anonymous (02:01) is excited about early retirement and family time but worried about his brother-in-law, who just returned from a vacation in Mexico with a bold plan: sell everything, move there, and buy an Airbnb to live in one unit and rent out the others. He wants to support him without watching him get in over his head. How can he navigate this tricky mix of family loyalty and financial risk? Maryanne (33:41) is retired and living on Social Security. Her IRA has doubled in value in the past year and a half, leaving her unsure whether to sell and live off interest or reinvest in ETFs. How do you manage sudden growth in retirement savings responsibly without taking unnecessary risks? Brandon (48:18) has rolled over two old 401(k)s into IRAs but just learned that 401(k)s are generally better protected from lawsuits than IRAs. Now he’s hesitant to roll over his latest 401(k) from his recent job. Is it ever worth keeping a 401(k) separate, or should all retirement accounts eventually be consolidated? *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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#691: Your IQ used to be your biggest career asset. Then AI scored in the 99th percentile on the LSAT, the SAT, and the MCAT — and suddenly the cognitive skills that once set you apart became something anyone can access for free. Executive coach Liz Tran joins us to talk about what actually drives career success and earning power now. Her answer: AQ, or agility quotient — your capacity to handle change, learn new skills fast, and keep moving when your industry shifts beneath you. The personal finance implications are real. The average half-life of a technical skill is five years. In tech, it's closer to two. That means the expertise you spent years building — and the salary that came with it — can become obsolete faster than a mortgage term. Tran argues the people who protect their earning power long-term aren't necessarily the most credentialed. They're the ones who can unlearn old ways and adapt quickly. We walk through her four AQ archetypes — the neurosurgeon, the astronaut, the firefighter, and the novelist — each with a different default approach to change. Knowing your type helps you understand where you might freeze up during a career pivot, a market downturn, or a high-stakes financial decision. Tran points out that analysis paralysis, something many real estate investors and career changers know well, often comes down to archetype — and there are practical fixes. We also cover her ABCD framework — anchors, bets, classroom, and discomfort — which maps out how to stay functional and decisive during volatile periods. And we get into the six thinking hats theory, specifically how pairing black-hat (downside) thinking with green-hat (future-focused) thinking can sharpen any major financial or career decision. 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. (00:00) Intro to AQ — agility quotient defined (03:19) IQ vs. EQ vs. AQ — how the three differ (04:09) Origins of IQ — born from industrialization (04:41) Birth of EQ — rise of the knowledge worker (05:01) Why AQ matters now — the tech revolution (06:19) AI and IQ — cognitive skills are now commoditized (07:51) Technical vs. durable skills — and why both matter (10:48) Half-life of skills — technical skills expire fast (13:41) Measuring durable skills — how to spot your gaps (15:59) The four AQ archetypes — neurosurgeon, astronaut, firefighter, novelist (25:08) Improving your weak spots — run toward discomfort (30:59) The ABCD framework — four pillars of high AQ (43:56) Anchors — people, places, routines that ground you (54:25) Six thinking hats — six ways to approach any problem (01:04:28) AQ is changeable — it's never too late to grow Learn more about your ad choices. Visit podcastchoices.com/adchoices

#690: Blanca (01:28): Blanca, an immigrant mother raising a 14-year-old, wants her son to think critically about college—not just as an experience, but as a financial decision. With the rising cost of higher education, she’s wondering how families can assess whether an undergraduate or graduate program is likely to pay off over time. Brandon (30:05): Brandon in his forties, recently left full-time work to pursue per diem work and a side project. Planning to draw down his taxable brokerage account for supplemental income over the next 20 years, he’s wondering whether to continue reinvesting dividends or take them as cash for flexibility. Anon (40:15): Anon has been following Paula’s advice on financial advisors. They’ve heard her recommend fiduciaries and caution against the assets-under-management (AUM) model. They’re eager to understand the reasoning and want guidance on finding trustworthy advisors. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#689: Most people think forgetting a name means their brain is failing. Dr. Majid Fotuhi, a neurologist who taught at Johns Hopkins and Harvard, sees thousands of patients convinced they have Alzheimer's – only to discover they're dealing with poor sleep or stress. Dr. Fotuhi joins us to break down the difference between cognitive decline, dementia and Alzheimer's disease. He explains why chronic stress physically shrinks your hippocampus — the thumb-sized memory center in your brain — and how twelve weeks of lifestyle changes reversed cognitive decline in 84 percent of his patients. We talk about the five hidden taxes draining your brain: sedentary lifestyle, poor sleep, junk food, chronic stress and mental laziness. Scrolling social media after work counts as mental laziness, even if your day job involves intense focus. Dr. Fotuhi offers a different framework: five pillars that compound over time. Exercise ranks first because it multiplies mitochondria in your brain cells, reduces inflammation and generates new neurons in your hippocampus. Walking 10,000 steps daily cuts Alzheimer's risk by 50 percent. Sleep comes second. Your brain rinses itself during deep sleep, flushing out amyloid — the core protein in Alzheimer's disease. One night of poor sleep increases amyloid in your brain. We cover nutrition (skip the junk food debate), mindset (heart rate variability breathing reduces Alzheimer's footprints) and brain training. Dr. Fotuhi memorizes 70 names in a single lecture and explains his technique for remembering credit card numbers using mental imagery. The conversation covers London taxi drivers who grew their hippocampus by memorizing 10,000 streets, why stress management beats supplements, and how Swedish students learning Arabic increased their brain volume in three months. 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) Defining cognitive decline, dementia and Alzheimer's disease (05:19) Why cognitive issues don't always mean Alzheimer's (07:24) Thinking of your brain as an asset to manage (07:51) The five hidden taxes draining your brain (10:45) How poor sleep prevents brain rinsing and causes inflammation (14:20) Oral health and brain health connection (16:40) Brain plasticity and the Broca lobe (27:02) The five pillars of brain health (35:23) Cardiovascular fitness versus strength training for brain health (38:51) Sleep as the second pillar of brain health (48:05) When exercise beats sleep (51:33) Different types of intelligence beyond IQ tests (1:03:53) Reversing brain damage from decades of bad habits (1:10:25) Nutrition and avoiding junk food (1:25:09) Mindset and stress management as pillar four (1:33:35) Breathing exercises for stress reduction (1:39:24) Brain training as the fifth pillar (1:51:52) Memory techniques for names and numbers (2:02:46) Nootropics and supplements for brain health Learn more about your ad choices. Visit podcastchoices.com/adchoices

#688: Anonymous: "Anonymous Sheryl" is 38, mortgage-free and exhausted after 15 years of teaching. She’s torn between pushing a few more years toward FIRE or switching to relief teaching now for better work-life balance. How do you trade speed to FIRE for sustainability without blowing up the plan? Anonymous : "Anonymous Ray" hired a bank portfolio manager but isn’t sure how to judge the results after just a few years. With mixed performance, dividend-heavy funds and higher fees, when is it fair to evaluate a manager — and would a simple index ETF outperform? Nathan: Nathan’s 14-year-old just earned his first W-2 income, and Nathan wants to jump-start his son’s investing journey with a Roth IRA. But with household income above the Roth limits, is there a legal way to make this work without sacrificing the child tax credit? Learn more about your ad choices. Visit podcastchoices.com/adchoices

#687: Your tax refund might be $300 to $1,000 bigger this year, and that's just the beginning of what's changing with your money. The Tax Foundation estimates most Americans will see significantly larger refunds thanks to seven major tax cuts. The child tax credit increased by $200. The standard deduction jumped by $750 for individuals or $1,500 for couples. The state and local tax deduction cap now sits at $40,000. Seniors get an extra $6,000 deduction, and deductions for auto loan interest, tips, and overtime work all increased. Retirement accounts saw major changes too. Catch-up contributions for high earners now must go into Roth accounts, which pushed thousands of employers to add Roth options to their 401k plans between 2024 and 2026. Kevin Warsh, the new Fed chair nominee, thinks the Federal Reserve has been doing it all wrong. The former Fed governor and Wall Street banker believes the Fed focuses too much on backward-looking data and reacts too slowly. He wants strategic, forward-thinking policy instead of chasing lagging indicators. President Trump clarified he never asked Warsh to lower interest rates and wanted to "keep it pure." The labor market shows serious cracks. Job openings dropped by nearly one million year over year to 6.5 million. Unemployment claims jumped to 231,000 last week. January layoffs hit 108,435 people — up 118 percent from last year and the worst January since 2009 during the Great Recession. Big Tech continues its massive AI spending spree. Microsoft, Amazon, Google, Meta, and Oracle will collectively spend over $500 billion on AI infrastructure this year. Google's spending alone doubled from 2025, reaching up to $185 billion focused on data centers and Gemini development. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#686: Rachel: Rachel is new to investing and has noticed the stock market being dominated by AI companies. She wants to make sure her portfolio is balanced without overexposing herself.Should she rethink her index fund strategy to protect against a potential AI bubble? Sarah: Sarah just turned 65, owns her home outright, and has been relying on credit cards since losing her job last year. She’s weighing whether to claim Social Security now, pay off debt, remodel her home, or convert her traditional IRA to a Roth.How should she prioritize these major financial moves while balancing income, debt, and retirement accounts? Anonymous “Julie”: This listener is on COBRA after her spouse took a federal buyout and is exploring starting a small business with her two young kids to teach them entrepreneurship.Will employer-provided health insurance fade away, and how can she test business ideas before fully committing? Resources Mentioned: Books: So Good They Can't Ignore You by Cal Newport The E-Myth by Michael Gerber Traction by Gino Wickman The Lean Startup by Eric Ries Learn more about your ad choices. Visit podcastchoices.com/adchoices

#685: You're not an investor. You're a saver. That's the first of 10 principles Cullen Roche shares in this conversation about building what he calls "the perfect portfolio." Roche, the founder and chief investment officer of Discipline Funds, argues that when you buy stocks on the secondary market, you're not actually funding companies or making investments in the traditional economic sense. You're just swapping your cash for someone else's stock position – reallocating your savings. This reframe matters because it changes your entire approach. Instead of trying to beat the market, you focus on the boring, prudent work of allocating your savings across different time horizons. We walk through all ten of Roche's principles. He explains why you are your portfolio's worst enemy – not just because fear makes you panic-sell during crashes, but because FOMO during bull markets leads you to chase performance at exactly the wrong time. He breaks down why diversification is the only free lunch in investing, why costs matter more than you think, and why real returns are the only ones that count after you strip out inflation, taxes, and fees. Roche introduces some concrete strategies most people have never heard of. The 351 exchange lets you swap concentrated stock positions into diversified ETFs without triggering immediate capital gains taxes. The "defined duration" approach matches specific pools of money to specific future expenses—like pairing a six-month treasury bill with next year's bathroom remodel. He also tackles the hardest allocation question: what to do with money earmarked for three to ten years from now. That awkward middle timeframe sits between "keep it in cash" and "put it in stocks," and Roche explains why traditional approaches like sixty-forty portfolios don't always work. The conversation covers everything from why long-term bonds make terrible matches for long-term goals to why thinking in time horizons beats thinking in investment styles. 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. (00:00) Principle 1: you're a saver, not an investor (04:48) Real wealth comes from direct business ownership (06:43) Principle 2: you are your portfolio's worst enemy (09:58) FOMO during bull markets vs fear during crashes (12:43) Principle 3: beating the market is hard (15:18) The 5 percent "fun money" allocation debate (16:18) What to do when your position explodes (17:18) The 351 exchange tax strategy explained (20:28) Should you rebalance concentrated stock positions (22:18) Principle 4: diversification is the only free lunch (31:03) Gold and stock market both high simultaneously (35:43) When diversification becomes diworsification (40:03) Principle 5: the cost matters hypothesis (44:23) HSAs, 401ks and unavoidable fee structures (47:03) Why ETFs beat mutual funds on taxes (51:03) Principle 6: real, real returns matter most (1:00:58) Principle 7: risk is uncertainty of lifetime consumption (1:06:18) Longevity risk and unpredictable healthcare costs (1:13:03) Principle 8: asset allocation as temporal conundrum (1:24:43) The 3-10 year allocation problem explained (1:28:03) Principle 9: past performance doesn't predict future (1:31:18) Principle 10: set realistic expectations, stay the course Resources: Cullin's website and newsletter: https://disciplinefunds.com Grab the FREE handbook: https://affordanything.com/financialgoals Learn more about your ad choices. Visit podcastchoices.com/adchoices

#684: Most people search for the perfect portfolio — the one allocation that works in every market, at every age, for every goal. This interview starts by explaining why that portfolio does not exist. We talk with Cullen Roche, founder and chief investment officer of Discipline Funds, about why copying someone else’s portfolio can backfire, and why portfolio design works better when it starts with your own constraints instead of rules of thumb. We walk through real portfolio models. The conversation begins with the classic 60-40 portfolio. You hear where it came from, how it held up during the Great Depression, and why it became so widely adopted. We also talk about its trade-offs — why it feels boring in strong markets and comforting in crashes, and how that emotional balance plays a role in investor behavior. Next, we shift to a Buffett-style portfolio. You hear why the takeaway is less about stock picking and more about structure. The discussion covers why Buffett keeps a small allocation to cash-like assets, how that “dry powder” functions during downturns, and why psychological stability matters as much as returns. The episode then turns to cash management. We talk about high-yield savings accounts, money market funds and Treasury bills. You hear how many cash products are built on T-bills, how banks capture part of the yield, and when managing cash directly may make sense. The concept of “T-bill and chill” comes up — along with when the extra effort may or may not be worth it. Finally, the conversation zooms out to time horizons. We discuss why income from a job functions like a bond allocation, how that changes risk capacity when you are younger, and why the early years of retirement carry the most danger. The episode closes by explaining sequence-of-returns risk and why portfolios need to work not just on paper, but in moments of fear. Resource: Cullin's website and newsletter: https://disciplinefunds.com 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. (00:00) Intro (02:00) No perfect portfolio (03:34) 60-40 portfolio starts (06:38) 60-40 keeps calm (08:00) Buffett portfolio basics (12:11) Stocks vs cash fear (13:34) T-Bill and Chill (18:22) TreasuryDirect is clunky (23:42) Income as bond proxy (25:33) Bond tent buffer (29:12) Sequence risk explained (31:42) Early retirement mindset (32:36) COVID panic calls (42:49) Three-fund portfolio basics (58:41) Get-rich-quick trap (1:18:21) Risk parity and All-Weather Learn more about your ad choices. Visit podcastchoices.com/adchoices

#683: Candy now — or a toy later? You slide play money across the table and let your kid choose. That moment kicks off this episode, where Dr. Stephen Day joins us to talk about building a “mini economy” at home. Dr. Day is the director of the Center for Economic Education at Virginia Commonwealth University. He also holds a PhD in social studies and economics curriculum and instruction. His work looks at how kids form money habits long before they deal with real paychecks, budgets, or credit cards. We break down how a mini economy actually works. Kids have job titles tied to age-appropriate chores. They earn play money. They spend it at a small household store set up on the kitchen table. The store might sell candy, small toys, or privileges like extra screen time. Parents set the prices. Kids decide whether to spend right away or save for something bigger. You hear how this plays out inside Day’s own house. A three-year-old takes on the role of “zookeeper,” feeding the cat and picking up stuffed animals. A seven-year-old creates a weekly plan that alternates spending and saving, using patterns she learns at school. A five-year-old chooses to donate part of his earnings instead of spending anything. The system stays the same. The choices vary by kid. The conversation moves through childhood stage by stage. Early years center on routine, structure, and basic trade-offs. Elementary school becomes the key period for practice, when habits and norms take shape. Middle and high school bring longer planning timelines, more independence, and deeper conversations about work, contribution, and goals. We also dig into questions parents ask all the time. Should kids get paid for chores, or should chores come with living in the house? Day explains how families can separate family work, paid jobs, and service work so kids understand why they are doing each task. Clear categories help avoid confusion about motivation and responsibility. Busy schedules come up, too. Sports practices, travel, school events, and late workdays often knock chore systems off track. Day explains how vague expectations create conflict and why job titles and defined duties bring structure even during chaotic weeks. Throughout the episode, the focus stays on practice, not lectures. Kids do not learn money by hearing explanations. They learn by earning, choosing, saving, spending, and living with trade-offs — all inside a system small enough to fit on a kitchen table. Resource: EconEdLink, a CEE program https://econedlink.org 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. (00:00) Intro (02:00) Teaching kids money (03:59) Mini economy basics (06:20) Money skills by stages (10:41) Starting at age three (12:02) Cat job example (16:08) Goods versus privileges (17:27) Bugging versus choices (18:11) Paying for chores (20:22) Family job service (24:56) Busy weeks and chores (33:21) Low-consumption kid example (39:17) Shared jobs and teamwork (43:34) Exchange rate to dollars (1:00:28) Investing, 529, compound interest Learn more about your ad choices. Visit podcastchoices.com/adchoices

#682: Grab the FREE handbook: affordanything.com/financialgoals For 76 years, the British cycling team lost — every season, without exception. Then they changed how they approached improvement, focusing on tiny gains instead of dramatic overhauls. In today's episode, we unpack how they became champions – and apply those same tactics to our financial life. This episode originally aired in January 2025. It was our most popular episode of the year on Spotify. You hear how the British cycling team used “aggregation of marginal gains” — tiny improvements like adjusting bike seats, improving sleep with custom mattresses, even repainting floors so dust was easier to spot. Those details seemed trivial on their own. Over time, they added up to Olympic gold medals and Tour de France wins. We apply the same logic to money. The episode lays out a full roadmap for the year, broken down by quarter. Early weeks focus on foundations. You start by writing a short financial motivation statement, calculating your net worth, choosing one metric to track, and creating a spending decision catchphrase that forces trade-offs into the open. Later weeks shift into action. You raise your savings rate by one percent at a time. You declutter physical items that cost money to store. You add a waiting period before purchases. You trim subscriptions, set up credit monitoring, commit to meal planning, and try a one-week spending fast to reset habits. As the year progresses, the tweaks move into optimization. You plan for irregular expenses, build buffers for price shocks, automate goals, check tire pressure to save on fuel, and calculate the real cost of transportation. You review investment fees, workplace benefits, insurance deductibles, and estate planning basics. Toward the end of the year, the focus turns to fine-tuning and reflection. You map out major expenses for the next five years, create rules for handling market volatility, repeat your most effective tweak, and close the year by reviewing progress and setting intentions for 2026. The episode frames the year as a steady climb. One week. One small move. No overhaul required. Just consistent attention, applied over time. Download the guide: https://affordanything.com/financialgoals Learn more about your ad choices. Visit podcastchoices.com/adchoices

#681: Barry Ritholtz's mom sold real estate. Those dinner table conversations about mortgages helped him spot the 2008 crash before most of Wall Street did. Now he runs Ritholtz Wealth Management and joins us to explain why we're often our own worst investment enemy. He breaks investing mistakes into three categories: bad ideas, bad numbers, and bad behavior. Here's what stood out. Research shows just 2 percent of stocks create all the market's value. The other 98 percent? Pretty much worthless. Barry says 90 percent of everything is garbage — from science fiction to investment advice. Even experts have blind spots. Michael Jordan dominated basketball but couldn't make it in minor league baseball. The lesson? Being brilliant at one thing doesn't make you brilliant at everything. Those financial memes everyone shares? They're misleading. Take Kevin's Home Alone groceries — $20 in 1990, $75 today. Sounds terrible until you realize wages went up the same amount. We actually spend less of our income on food now. Or that scary stat about the dollar losing 96 percent of its value over 100 years. Barry asks: who buries cash for a century? His math: $1,000 buried in 1925 buys almost nothing today. Same $1,000 invested in stocks? It's worth $32 million. Markets don't die of old age. Alan Greenspan warned about "irrational exuberance" in 1996. The Nasdaq kept climbing another 431 percent over four years. Recessions need triggers. They don't show up on schedule like buses. Fear wrecks more portfolios than anything else. Barry quotes neurologist William Bernstein: "Control your amygdala or die poor." Our fight-or-flight response helped us escape predators. It doesn't help us navigate market crashes. Make your investment plan before crisis hits. As Barry says, reading emergency instructions while the engine falls off at 25,000 feet is too late. He's seen every crash since 1987. Markets drop 30 to 40 percent about once a decade. Accept it. Plan for it. Barry advocates for Roth conversions and something called the "Mega Roth." Pay taxes now, withdraw tax-free later. We know today's tax rates. Future rates are anyone's guess. His bottom line: humans are terrible at predicting the future. Build portfolios that can survive anything, because anything will happen. 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. (00:00) Intro (02:00) How fear of mistakes can make investors too conservative (06:00) Bad ideas vs good ideas in investing (09:00) Process over outcome in decision making (15:00) Thinking probabilistically about market outcomes (20:00) Why recessions and bull markets don't follow calendars (26:00) AI's real capabilities vs hype (33:00) Different market commentator archetypes (41:00) Expertise doesn't transfer between domains (50:00) Misleading financial statistics everywhere (56:00) Managing emotions when markets crash (1:00:00) Creating an investment plan before crisis (1:05:00) Tax strategies and Roth conversions Learn more about your ad choices. Visit podcastchoices.com/adchoices

#680: Mia: Mia and her husband are planning early retirement and want to draw down their taxable brokerage accounts for the next decade. She’s considering a securities-backed line of credit to defer taxes during market downturns. Can a securities-backed line of credit smooth taxes in early retirement, or are there hidden risks? Jean: Jean, a freelance creator, wants to take a self-made sabbatical in three years and fund it without stress. She’s unsure whether to keep her savings in a high-yield account, a brokerage account, or split between the two. How should she balance growth and safety when saving for a short-term sabbatical? Jared: Jared has been reading about pensions and 401(k)s and sees pros and cons on both sides. He wants to know whether pensions really offer an advantage or if the nostalgia is misleading. Are pensions truly better than 401(k)s, or is the preference mostly sentimental? Resources Mentioned: affordanything.com/community affordanything.com/newsletter affordanything.com/financial-goals affordanything.com/your-next-raise quince.com/paula Learn more about your ad choices. Visit podcastchoices.com/adchoices

#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night. Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger than any economic disruption. In this conversation, Kass explains why everyone wants everyone else's job automated (faster legal services, cheaper healthcare) but nobody wants their own work to disappear. He shares why some jobs will vanish while others explode in demand, and which professions might actually benefit from AI disruption. You'll discover why the real threat isn't job loss — it's that we've become addicted to our devices and forgotten how to live without constant work. Kass reveals how financial illiteracy keeps people trapped in debt cycles that AI could help break. He explains why housing, healthcare, and education costs stay high while everything else gets cheaper, and what might finally change that dynamic. The conversation explores what happens when AI makes basic needs affordable for everyone. Kass predicts some people will pursue passion projects, others will double down on work, and many will struggle to answer a simple question: What do you actually want to do with your day? We discuss practical realities like how a 53-year-old attorney might reinvent herself, why accountants face bigger challenges than lawyers, and which human skills will become more valuable as machines get smarter. Kass shares his theory about competing on kindness rather than intelligence when AI can outthink us all. This isn't another doom-and-gloom AI prediction. Kass makes a compelling case that automation could free us to rediscover community, creativity, and purpose … if we can get past our addiction to both work and screens long enough to imagine what that life looks like. 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) Introduction (2:00) Zack's AI background at OpenAI (3:15) Will knowledge workers have jobs (4:52) Job automation is complex (7:53) Longshoremen strike over automation (9:06) Everyone wants others' jobs automated (10:14) Identity crisis bigger than economics (13:36) Lawyers might enjoy job loss (21:42) Societal thresholds stop automation (28:52) Bespoke services always find demand (41:34) AI won't replace human therapists (47:11) Dehumanization threatens physical connections (54:55) Financial illiteracy costs billions (1:03:21) Predatory lending traps explained (1:11:51) Housing healthcare education stay expensive (1:26:31) Screen time hides free time Resource: AffordAnything.com/financialgoals Learn more about your ad choices. Visit podcastchoices.com/adchoices

#678: Anonymous (02:36) - "Victoria" (Anonymous) is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for retirement, and wondering how much traditional money to leave untouched. Should Alex prioritize tax efficiency, or focus on growth and flexibility? Anonymous (37:18): Anonymous "Gwyneth" and her husband moved to the U.S. to start a sanctuary for senior dogs and cats. With $100,000 in debt soon paid off, two properties in hand, and a dream to buy land for their sanctuary, they’re torn: sell, refinance, or keep their rental property? What’s the best way to fund a long-term dream while building wealth? Soyman (48:17): Soyman is 25, saving aggressively, and planning to take all of 2027 off to go backpacking. They see a rare tax opportunity to convert nearly $30,000 to a Roth at a negative tax rate—but is the strategy worth the small cash buffer and other risks? Learn more about your ad choices. Visit podcastchoices.com/adchoices

#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now. The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages. The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are stuck around 6.2%. And 80% of homeowners are unlikely to sell because they locked in rates below 6%. The Big Picture: The stock market is outperforming the economy. How It Affects You: I call it "millionaire malaise." Your 401k looks great. Your home equity is through the roof (no pun intended). If you bought before 2022, your assets look good on paper. Yet you're stressed out at the grocery store. Everything costs more – insurance, groceries, everything except gas. Jobs are stagnant. People are stuck. We're experiencing the difference between wealth and income. This is 2026: Wealthy on paper. Broke at the checkout line. Whether you're new to money management or a long-timer looking for clarity, this episode cuts through the noise to tell you what actually matters for your finances this year. Download the free resource: AffordAnything.com/financialgoals Learn more about your ad choices. Visit podcastchoices.com/adchoices

#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets? I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people. Here’s my breakdown: Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000 Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62,000 Vanguard Roth IRA: VTSAX $228,000, ISCV $6,000 Pre-tax 401(k): Active stock fund $218,000 (0.01% expense ratio), Equity dividend fund $55,000 (0.01% expense ratio) Russell 1000: $270,000 (0% expense ratio) HSA: $9,000 in the Russell 1000 and Russell 2000 ESPP: $90,000 Savings account: $12,000 I view my brokerage accounts as savings, where I can sell assets if I need cash, as well as sell my company shares. My questions: How far am I from the efficient frontier? How efficient is my asset allocation? I’ve mostly been a “VTSAX and chill” type. If I rebalance, what’s the best way to do it without incurring taxes? Next year, I’ll make more than $150,000, even after contributing $24,500 to my pre-tax 401(k) in 2026. Can I still do a backdoor Roth, given that I already have an IRA balance? I was told it could be complicated. Am I out of luck investing in a Roth next year? Also, should I roll over my 401(k) into my existing Rollover IRA to gain more investment options, even though the 401(k) fees are very low? I’ve reached over $1 million in assets, but I’m not confident my first million was invested efficiently. I want to correct it before reaching my next million. Emma: Can We Split a Dependent’s Tax Status Midyear to Maximize Health Insurance Subsidies? We’re a family of four with two adults and two children, ages 15 and 21. Our 21-year-old is a full-time university student and is expected to graduate in May 2026. The hope is that she’ll secure a full-time job after graduation. Our health care broker told us that we could claim her as a dependent for half of the year and then have her claim herself for the second half. According to the broker, this would allow her to stay on our health insurance and help us qualify for a larger premium subsidy. Is it actually possible to split a dependent’s tax status this way within a single year, or is this a misunderstanding? Anonymous: Is It Wise to Hold Some Investments Outside the U.S. for Geopolitical Diversification? I’ve always believed that “this time isn’t different,” but lately I’m feeling uneasy. I’m increasingly concerned about what seems like a slow erosion of institutional trust in the U.S., especially regarding agencies and structures that support our financial system. From leadership changes at key government institutions to growing political influence over economic policy, I’m starting to wonder if it’s prudent to hold a small portion of assets physically and legally outside the U.S. I’m not talking about exotic offshore schemes. I mean legitimate ways to invest in broad index funds or ETFs through a brokerage account based abroad—as a form of geopolitical diversification and personal contingency planning. I’d love to hear your perspective. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth. ____ In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then? Build a startup. Raise capital. Scale fast. Get rich. That was the dominant story. But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture. Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business. He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure. From there, we move into one of the most misunderstood ideas in entrepreneurship: the difference between service businesses and product businesses. Rand breaks down the trade-offs. Services generate income faster. Product businesses rely on outside capital. And founders often earn far less than people expect. That leads to a deeper conversation about incentives. Once venture capital enters the picture, priorities shift. Profits matter less. Growth matters more — and it affects both the business and your personal finances. High revenue does not automatically translate into personal wealth. We also talk about the side of entrepreneurship that rarely makes the highlight reels: Loneliness. Anxiety. Depression. And the relief that comes from realizing that even the most successful founders often feel lost while they’re building. This conversation feels less like startup advice and more like a long-term framework for thinking clearly about risk, money, and meaning. If you’ve ever questioned whether entrepreneurship automatically leads to financial freedom, this episode offers a grounded and very honest answer. 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. (00:00) Facing creditors and repayment negotiations (08:50) How a services business really works (11:40) From consulting to software (15:00) Services vs. product businesses (12:20) Why high revenue doesn’t mean personal wealth (25:05) Venture capital incentives (27:50) Founder salaries and financial reality (30:40) Startup mythology vs. lived experience (33:20) Loneliness and mental health (36:15) Founder strengths and weaknesses (39:50) Feedback and self-awareness (42:30) Designing a business that fits your life Learn more about your ad choices. Visit podcastchoices.com/adchoices

#674: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market. We tackle the five biggest challenges of investing far from home – from fear of the unknown to managing contractors remotely – and reveal four compelling benefits that make it worth the effort, especially when you're competing in markets where million-dollar properties are the norm. ________ Remember when inflation was high and rates were rising? What were people saying about real estate back then? And with the benefit of hindsight, how much of what we thought at the time proved to be correct? If you feel unsettled, join the club. At this present moment – December 2025 – interest rates are falling, but not enough. Inflation is mostly under control, but not enough. The noise makes everything feel new. When you only see the present moment, everything looks obvious. When you remember the past, patterns start to show. That's why we’re rewinding the clock back to May 2022 – when interest rates were rising and inflation was near its peak. So what was on our mind three years ago? We start with the basics. Why the Federal Reserve raises rates. What higher borrowing costs do to spending. Why falling stock prices often reflect fear – not proof that housing prices must fall next. We explain the difference between recession and deflation, and why the two are often confused. We walk through what made the housing market in 2022 different from 2008. Inventory was tight. Builders had not overbuilt. Many homeowners held fixed-rate mortgages and record levels of equity. Those conditions mattered then. They still matter now. That equity becomes the next focus. We talk about cash-out refinances, HELOCs, and reverse mortgages – and what happens when homeowners borrow against rising values. You hear how higher rates can slow borrowing, why that matters for inflation, and what risks appear if some borrowers struggle to repay. From there, we outline four ways investors might encounter properties if foreclosures rise: bank-owned homes, short sales, “subject to” deals, and wraparound mortgages. The episode then shifts to long-distance real estate investing. You hear the real challenges. Fear of the unknown. Managing people you cannot see. Contractors who disappear. Agents who stop returning calls. You also hear what makes distance workable: education, relationships, local investor networks. We walk through how investors think when conditions feel unstable — and why looking backward sharpens how you see what comes next. 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) Trade-offs and priorities (07:41) Fed hikes rates (09:16) Inflation drivers explained (11:26) Recession vs housing (13:21) Home equity surge (15:21) Borrowing against equity (17:11) Foreclosures and options (18:26) Subject-to and wraps (21:11) Shift to distance investing (25:31) Education and networks (31:36) Choosing markets (36:11) Accountability challenges Learn more about your ad choices. Visit podcastchoices.com/adchoices

#673: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we've shared for building wealth at any age. Nick Maggiulli joins us to reveal why most young investors obsess over the wrong metrics — and shares his Save-Invest Continuum that shows exactly when your savings beat your investment returns, and when that changes. _____ When Nick Maggiulli was in his twenties, he spent countless hours obsessing over his investment portfolio – tweaking his asset allocation, running net worth projections, and building complex spreadsheets. Meanwhile, he was blowing $100 every weekend partying in San Francisco. It took him years to realize the absurdity. His annual investment returns on his tiny $1,000 portfolio might earn him $100 – the same amount he'd spend in a single night out. Maggiulli joins us to explain why young investors focus on the wrong things and shares his framework for knowing when to prioritize saving versus investing. He introduces the Save-Invest Continuum, which compares your expected annual savings against your expected investment returns. When you're starting out, your ability to save dwarfs any investment gains. A $6,000 annual savings capacity beats a $100 investment return every time. We discuss the math behind saving 50 percent of future raises, not for guilt or deprivation, but to maintain lifestyle balance while building wealth. This rule applies only to real raises above inflation. If you get a 3 percent raise during 3 percent inflation, you haven't actually gotten ahead. The conversation turns to unconventional income-producing assets. Beyond stocks and bonds, Maggiulli explores farmland investing, which offers returns uncorrelated with traditional markets. He shares the story of someone who bought the royalty rights to Jay-Z and Alicia Keys' "Empire State of Mind" for $190,000. The song earned $32,733 in royalties the previous year — an 11 percent return if that income stays constant. We examine why 85 to 90 percent of your portfolio should generate income through dividends, rent, interest, or business profits. Maggiulli keeps his speculative investments — cryptocurrency, art, and individual stocks — under 10 percent of his net worth. He admits his two individual stock picks are down 60 to 70 percent, proving his own point about avoiding stock picking. The episode reveals that time remains your most important asset. Warren Buffett would likely trade his entire fortune — and go into debt — to be 35 again. This perspective shapes every financial decision, from choosing income strategies to deciding between assets that merely appreciate versus those that pay you while you sleep. Learn more about your ad choices. Visit podcastchoices.com/adchoices