Afford Anything

#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

#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever. Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiations and net worth. __________ You've mastered the art of asking for what you want — or have you? Jeff Wetzler, Ed.D., a former education executive, joins us to reveal why most of us fail to extract crucial information from the people around us. Think about it: when was the last time someone told you what they really thought about your work? Or shared that game-changing idea they'd been sitting on? Wetzler discovered four categories of information people routinely withhold — and the cost runs deeper than you might expect. We explore why people stay silent about their struggles, unpopular opinions, observations about us, and innovative ideas. The reasons range from fear to simple exhaustion, but one stands out: they don't think we want to know. Here's a startling example from Harvard Business School research: investigators planted smudges on their faces and surveyed people. Less than three percent told them about the mark that they could wipe off in one second. But when asked later, 100 percent had noticed it. If people won't share something that simple, what else are they keeping from us? Wetzler shares his Ask Approach — five steps that unlock hidden information in any negotiation or relationship. We walk through real scenarios, from salary negotiations to buying cars, showing how curiosity beats strategy every time. One mechanic story drives this home. Facing a $2,000 air conditioning repair, Wetzler asked one question: "Do you have any other creative ideas?" The mechanic paused, then offered a $75 solution that worked perfectly. That five-second question saved $1,925. We discuss practical listening techniques, including the "doorknob moment" — why therapists know the most important information comes at minute 49 of a 50-minute session. Wetzler explains why our minds process 900 words per minute while our mouths manage only 125, creating a massive information gap. The conversation includes AI's surprising role in sharpening these skills, helping us frame conversations into content, emotion, and action. Wetzler demonstrates how technology can enhance rather than replace our uniquely human ability to connect and learn from each other. 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) What's at stake in asking better questions (02:33) Four categories of information people withhold (06:33) The smudge experiment reveals our silence (09:13) Why people don't tell us what they think (12:53) The Ask Approach begins with curiosity (14:48) Making it safe for truth-telling (18:53) CEOs share how to get honest feedback (22:13) Posing quality questions vs crummy questions (30:58) Listening across three channels (34:28) The doorknob moment phenomenon (37:43) How to listen better in negotiations (42:13) Reflect and reconnect strategies (44:53) Applying the Ask Approach to car buying (51:33) Working through a complete negotiation (01:02:13) Using AI to sharpen your asking skills (01:06:13) Why this approach is learnable Learn more about your ad choices. Visit podcastchoices.com/adchoices

#671: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter F stands for Financial Psychology. And we're diving deep with a conversation that changed how thousands of our listeners think about money. This episode originally aired in November 2022, but the insights feel more relevant than ever. Dr. Daniel Crosby reveals why your brain is your portfolio's worst enemy — and what you can do about it. ______ Money is the number one stressor in American lives. Every single year. Without exception. That's what Dr. Daniel Crosby discovered when he looked at decades of research from the American Psychological Association. In this rerun episode from our Greatest Hits Vault, Crosby joins us to reveal why your brain sabotages your investment decisions. He's both a clinical psychologist and behavioral finance expert. His findings will change how you think about money. Your body hijacks your financial judgment in strange ways. For example: People who need to pee become more risk-averse investors. It's called inhibitory spillover. When you're controlling your bladder, you also restrict your financial decisions. Here's another one: judges give harsher sentences when they're hungry. Thousands of court decisions prove it. The best predictor of whether you get jail time? When the judge last ate. We explore four behavioral risks that destroy wealth: ego, conservatism, attention, and emotion. Crosby shares data that stock pickers rarely hear: 74 percent of individual stocks have a lifetime expected return of zero. Three out of four companies eventually go bankrupt. Yet people keep betting on single stocks, dreaming they'll find the next Apple. Value investors suffer from depression and social isolation. Why? Because contrarian investing fights our deepest evolutionary wiring. Humans survived through cooperation. It's literally our only advantage over other animals. Bears have claws. Turtles have shells. We have teamwork. Crosby shares the Ash experiment, which shows how peer pressure warps reality. When nine people give the wrong answer about line lengths, three-quarters of participants follow along. New brain scans reveal something darker: social pressure physically changes how people see the lines. Their perception actually shifts. We discuss solutions through Crosby's "three E's": education, environment, and encouragement. Reading about biases won't fix them. You need systems and people. One powerful study: people who saw their children's photo for five seconds before banking saved twice as much money. The conversation reveals that money problems don't disappear with wealth. They just change form. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort. We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple. We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact. We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.” If you want to earn more points (or waste less time chasing them), this conversation will help you reset your credit card strategy for 2026 with a clearer definition of what “worth it” even means. Key Takeaways “Credits” are not value unless we were already going to buy the thing, and we’d happily pay close to face value for that discount The points game is still powerful, but mostly through welcome offers, not micro-optimizing bonus categories Flexibility is the hidden lever in award travel, the best deals often show up when we loosen the date, airport, or destination constraints Cash back is having a moment, especially if we want simplicity and fewer mental tabs open. Before canceling a fee card, we can often negotiate, downgrade, or product change and keep the credit history we’ve built Sometimes the best move is to stop “maximizing,” take the trip, and protect our time for higher-impact work (or actual rest) Resources and Links Chris Hutchins, All the Hacks (https://www.chrishutchins.com) Our deep dive on credit reports and scores, Episode 221 YouTube video mentioned on why airline loyalty programs can be worth more than the airlines themselves FlyFlat.com Seats.Aero Point.me Rome Travel AwardTool.com PointsYeah.com Daydream Explorer Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (01:22) The 2025 reset for premium credit cards (06:18) How the points game actually works in 2025 (10:29) Rethinking economy flights versus business class (16:37) Managing credit cards during major life transitions (23:57) Simplicity versus optimization in the points ecosystem (36:45) Luxury perks, rising fees, and who premium cards serve (43:34) Buying points directly instead of playing the game (58:44) Using AI and systems to build better money habits Learn more about your ad choices. Visit podcastchoices.com/adchoices

#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K brokerage account and plan withdrawals to make the transition financially smooth. David (21:50) - David has a high school senior and is deciding how to pay for college. Should he tap the $60K 529 plan now or the $200K 457(b) from his wife’s former employer to maximize tax efficiency and preserve future growth? Graham (37:52) - Graham loved the episode on holding bonds in a taxable account, but he’s curious about a tax-efficient twist. Can an asset swap strategy let you rebalance and pull cash without triggering capital gains? Learn more about your ad choices. Visit podcastchoices.com/adchoices

#668: We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his last big launch as he heads into retirement. Together, we wrestle with a problem our listeners know well: what happens when you’ve built the habit of saving, investing, optimizing … and then feel weirdly unable to spend. We talk about mini-retirements, the psychology of “spend and enjoy,” and why waiting to touch retirement money can be its own kind of risk. Key Takeaways Think about retirement as a series of deliberate mini-retirements, not one finish line you might reach with less energy than you expected. If you’re a dedicated saver, build a plan for the “spend and enjoy” phase so you do not accidentally optimize away the years you wanted freedom for. Run the numbers on “small” spending habits, not to guilt yourself, but to see which choices actually buy future optionality. Treat withdrawals, benefits, and deadlines as part of the strategy, not a paperwork problem you’ll deal with later. If your finances feel out of reach, anchor yourself with a simple projection and one automated action, momentum beats motivation. Resources and Links David Bach’s website: http://davidbach.com/ David Bach’s books The Automatic Millionaire (updated edition) The Latte Factor Smart Women Finish Rich Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (0:00) Introducing David Bach (4:50) Radical sabbaticals, Florence and rethinking retirement (9:10) Health scares, widowhood stats and enjoying life earlier (11:00) Updating The Automatic Millionaire for 24 million millionaires (15:30) Social Security strategy, RMD parties and claiming earlier (31:30) The latte factor, avocado toast and $10 dollar decisions (33:00) How $10 a day turns into $678,000 (34:20) Oprah behind the scenes, bricks of cash and an audience gasp (47:10) Tiffany Aliche, $75,000 dollars of debt and other success stories (54:25) A $53,000 income couple who retired as multimillionaires (1:25:40) Careers in advising, hiring trends and women advisors (1:28:37) Social Security taxes, new ideas and an eight year tax window (1:41:27) Remembering the “why,” values based choices and using money well Learn more about your ad choices. Visit podcastchoices.com/adchoices

#667: Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk. In this episode we sit down with Karsten Jeske, PhD, CFA from Early Retirement Now, a former Federal Reserve economist known for forensic financial modeling. Together we walk through when a 50-year mortgage might make sense, when it clearly does not, and why the math is rarely as simple as “higher payment versus lower payment.” We also dig into how ultra-long mortgages could push home prices even higher, and what this means for today’s buyers and tomorrow’s retirees. If you’ve wondered whether extended loan terms offer real affordability or just disguise the cost, this conversation gives you a clearer lens. Key Takeaways Why stretching to a 50-year mortgage can look affordable on paper yet leave you with far slower equity growth in the years that matter most. The few cases where a longer mortgage term can support a deliberate strategy, such as freeing cash flow to invest, and why this only works for certain borrowers. How inflation, appreciation, and opportunity cost change the “true” math behind 30-year versus 50-year loans. Why ultra-long mortgages may raise home prices more than they help buyers and what this means for generational wealth. How late-life mortgage decisions, downsizing, and step-up in basis reshape your legacy far more than the length of the loan itself. Resources and Links Early Retirement Now blog, Karsten’s research and mortgage modeling. Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) 50-year mortgage debate begins (02:52) Karsten says it expands options for sophisticated investors (05:42) Paula focuses on owner-occupants who can't afford houses (11:03) Equity difference: $80K vs $20K after 10 years (18:26) Lower payments could fund other investments (25:17) Lenders package mortgages for institutional investors (29:18) US doesn't issue 100-year bonds despite stability (34:00) Small term premiums create huge returns (43:31) Paying more interest isn't automatically bad (48:08) First-time buyers now average age 40 (56:08) Geographic arbitrage enables mortgage payoff (01:00:20) 50-year mortgages could inflate home prices (01:04:51) Supply constraints drive housing affordability crisis (01:07:29) Fed might pause rate cuts in December Learn more about your ad choices. Visit podcastchoices.com/adchoices

#666: In this First Friday economic update, we explore the paradox defining our current economy: record-breaking retail numbers alongside plummeting consumer confidence. In this First Friday economic update, we explore the paradox defining our current economy: we're spending more than ever, while feeling worse about money than we have in years. The Bureau of Labor Statistics hasn't released jobs data for two consecutive months. The Federal Reserve must make a critical interest rate decision flying blind. Meanwhile, private sector data reveals troubling trends. Small businesses are hemorrhaging jobs while discount chains like Dollar General see their stock prices soar 44%. Americans are spending differently this holiday season. They're shopping earlier, using AI to find deals, and turning to buy-now-pay-later options. Households are spending less than last year, yet total spending increases because more people are participating. This K-shaped recovery benefits luxury retailers and bargain stores while crushing the middle market. We also cover essential year-end financial moves. From maximizing retirement contributions to tax-loss harvesting strategies, we help you navigate your personal finances amid economic uncertainty. The disconnect between what the numbers say – and how people feel – reveals deeper truths about an economy that's technically growing while leaving many behind. 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) Spotify Wrapped and podcast listener data (2:05) Jobs report missing, BLS delays (5:01) ADP shows 32,000 job losses (8:00) Youth unemployment over 10% (10:32) Fed meeting without data (12:24) Mortgage rates might drop below 6% (20:06) Holiday spending hits $1 trillion (23:43) Consumers spend less individually (26:36) Discount stores outperform market (28:29) Shopping starts in October now (30:22) AI helps holiday shopping (36:09) Giving Tuesday up 11% (38:28) Year-end money moves (45:00) Charity and gift tax limits Learn more about your ad choices. Visit podcastchoices.com/adchoices

#665: If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting. In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about protection, exposure, and the parts of your portfolio that may already be shielded. Along the way, we unpack how shifting household risks, driver ages, and asset location change the insurance strategy year by year. From there, we take questions about Roth choices, future tax brackets, and whether it’s worth giving up investment flexibility to build a stronger tax triangle. These conversations get to the heart of how we balance risk, taxes, and long-term planning in the FI journey. Listener Questions in This Episode Andy asks: How can I protect my $2 million net worth without paying nearly $950 a month for increased auto, home, and umbrella coverage, especially with a teenage driver in the mix? (01:47) Mike asks: Given our high current tax bracket and expected lower tax rate in retirement, does contributing to a Roth still make sense for us? (25:50) Cindy asks: Should I move my rollover IRA into my new 401(k) so I can start doing backdoor Roth contributions, even if the investment choices are more limited? (39:47) Key Takeaways Sometimes the question isn’t “umbrella or nothing,” it’s “what risk am I truly trying to insure, and for how long,” especially when a teenage driver temporarily changes the household risk profile. You already may have more asset protection than you think. Retirement accounts and primary residences often carry their own layers of protection, which influences how much liability insurance you actually need. The Roth decision hinges less on math in isolation and more on your likely future earnings, work style, and appetite for locking in today’s tax rates. Building a balanced tax triangle gives you flexibility later, especially when future tax rates are unknowable and retirement timing is uncertain. Backdoor Roths can be powerful, but only when the tradeoff between investment choice and long-term tax flexibility makes sense for your goals and timeline. Related Episode: Episode 649: Umbrella insurance deep dive Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) Offense versus defense and setting up today’s questions (01:47) Andy asks about protecting a $2 million net worth (12:00) What’s already protected and how coverage layers work (17:00) Managing short-term risk when a teenager starts driving (29:50) Mike asks whether high earners should prioritize Roth contributions (35:07) How career trajectory and future tax rates shape Roth logic ( 45:54) Building a balanced tax triangle (47:47) Cindy asks about using a backdoor Roth to shift her tax triangle ( 52:10) Tradeoffs of moving an IRA into a 401k (54:06) How long Roth dollars need to grow to matter Share this episode with a friend, colleagues, your tax advisor: https://affordanything.com/episode665 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices