Afford Anything

#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. 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) Nick's mistake of obsessing over investments while partying away returns (05:31) The Save-Invest Continuum explained (08:11) When savings matter more than investment returns (12:31) Focusing on both saving and investing in midlife (13:11) Crossover point: when investment returns exceed spending (14:11) The 2X Rule for guilt-free spending (15:31) Save 50 percent of future raises (20:41) Five ways to increase income (26:31) Selling time versus selling skills (28:11) Teaching and creating products for income (30:11) Climbing the corporate ladder (31:11) Converting human capital to financial capital (32:31) Income-producing versus speculative assets (36:11) Individual stocks and cryptocurrency allocation (43:51) Farmland investing basics (45:31) Royalty investing example (49:31) Art and non-income producing assets (51:11) Inflation and debt strategies 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. 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) Finance as America's top stressor (02:33) Psychology moving from brokenness to wellness (04:33) Money touches every part of life (07:33) Income plateaus and happiness (10:13) How hunger affects financial decisions (13:38) We're wired wrong for investing (17:28) Laziness and cognitive shortcuts (23:43) Cooperation as human survival trait (26:43) Four behavioral risks (32:13) Ego and overconfidence (37:48) Conservatism and familiarity bias (46:38) Three E's of behavior change (50:23) Attention risk and probability (54:48) Emotion derails decisions (58:28) When fear helps versus hurts 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? Share this episode with a friend, colleagues, and your family at the holiday part: https://affordanything.com/episode669 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 Share this episode with a friend, colleagues, and the "automatitions" in your life: https://affordanything.com/episode668 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 Share this episode with a friend, colleagues, and your family: https://affordanything.com/episode666 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 Have a question for Paula and Joe? Call it in at https://affordanything.com/voicemail 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. For more information, visit the show notes at https://affordanything.com/episode664 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism? In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model. Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes. We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI a role so it knows how to “think.” We also explore how to stress-test optimism bias, how to analyze companies like a forensic accountant or a short seller, and how to build prompts that match your own investing personality. Whether you’re an index-fund loyalist with a little “fun money” or a hands-on analyst, this conversation will expand the way you evaluate businesses and make decisions. Key Takeaways How a single prompt can transform AI from a loose generalist into a sharp, reliable research assistant.
 The surprising way optimism bias shows up in AI tools, and how to flip it to your advantage.
 Why limiting your data sources can make your analysis dramatically stronger.
 The role-play trick that helps you see a company the way a short seller, value investor, or even Warren Buffett might.
 A simple reframing that turns AI from a stock picker into something far more powerful for decision-making.
 The moment in the demo that revealed a blind spot even seasoned investors often miss. Resources and Links Get Brian’s free business-analysis prompt at longtermmindset.co/ai Check out Brian’s YouTube channel: Long-Term Mindset @BrianFeroldiYT Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (03:02) Pros and cons of using AI for stock research
 (4:55) Why Brian invests heavily in individual stocks 
(12:52) Guardrails for reducing AI hallucinations
 (17:22) How to write step-by-step prompts 
(24:02) Using roles to shape AI’s output
 (35:57) Running Brian’s prompt on Kava
 (46:22) Understanding pricing power and recession behavior
 (01:00:02) Evaluating management teams
 (01:06:02) Using AI to reflect your investing personality Share this episode with a friend, colleagues, and your family around the Thanksgiving table: https://affordanything.com/episode663 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#662: Most teams hire for skills. The best teams hire for wiring. What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé? This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive. We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches. After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper. We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win. Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy, and make long-term decisions. Key Takeaways Response speed can signal mental wiring, not politeness, which makes it a powerful hiring clue. The real interview starts long before the formal meeting, which means every informal interaction counts. Agility shows up when plans change, so micro-tests can reveal how someone handles shifting conditions. Many high performers are driven either by purpose or measurable progress, and knowing which matters. Understanding our own lane helps us hire better, delegate better, and build systems that reduce friction. Resources and Links Simon Sinek, Start With Why https://www.youtube.com/watch?v=u4ZoJKF_VuA Vanderbloemen Group https://vanderbloemengroup.com/ Be the Unicorn by William Vanderbloemen https://www.amazon.com/Be-Unicorn-Data-Driven-Separate-Leaders/dp/1400247101 Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (00:00) What thousands of executive searches revealed (10:35) The nine markers of high performers (22:01) Fast thinkers, slow thinkers, and finding your lane (25:35) Why response time predicts performance (25:48) Testing agility in real-world scenarios (47:16) Why purpose matters more to younger workers (55:13) Why curiosity is a career superpower Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode662 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin? Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage. And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about tech valuations. Listener Questions in This Episode Veronica asks (02:06): How do I dig out of debt, repair my credit, and stabilize my rental after nearly going into foreclosure. Daniel asks (28:17): What should I do with my surplus side hustle cash when I already max tax-advantaged accounts and have a 3.5 percent rental mortgage. Scarlet asks (49:20): If AI stocks are in a bubble like the dot-com era, is there any relatively safe way to profit from a crash, such as put options. Key Takeaways Why tackling the right problem first can change the entire trajectory of a debt recovery plan. How downsizing one major expense can unlock breathing room you didn’t realize you had. The surprising factor that often matters more than interest rates when choosing between investing and debt payoff. Why flexible money becomes essential when planning for early retirement. What most people misunderstand about betting against a bubble, especially in fast-moving tech sectors. The simple portfolio shift that can help calm bubble anxiety without trying to time the market. Resources and Links GreenPath Financial Wellness – nonprofit credit counseling and debt management support for people overwhelmed by payments and afraid of bad actors in the debt relief world. Our course: Your Next Raise – a deep dive on how to negotiate a higher salary at work, with a special comp offered in this episode. Paul Merriman Four-Fund Portfolio – the simple, diversified investing framework Daniel uses inside his retirement accounts. The Big Short movie Michael Lewis and the film adaptation. 1929 book by Andrew Ross Sorkin – a historical look at bubbles and crashes. Chapters Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads. (0:00) Veronica’s debt crisis and rental challenges (16:46) Cutting car costs and rebuilding cash flow (22:28) Debt relief programs and avoiding bad actors (28:17) Daniel’s surplus cash and retirement strategy (37:52) Brokerage vs mortgage payoff discussion (49:20) Can you profit from an AI bubble burst (1:00:40) Why shorting and puts rarely pay off (1:08:18) Safer ways to position your portfolio Got a question: Call it in: https://affordanything.com/voicemail Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode661 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

#659: Imagine that you’re at the absolute peak of your career. You’re the CEO of a prominent advertising company at the age of 36, but you feel like you’re driving in the wrong lane. It’s wrong.Then you make a hard career pivot and it works out beautifully.My guests today know exactly what that’s like. We’re joined by James Patterson, the author who has sold more than 425 million copies of his books. He has co-authored books with President Clinton, Dolly Parton, and now his latest co-author is Dr. Patrick Leddin, who also joins us to talk about disruption. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Defining disruption versus gradual change (5:20) Positive disruption mindset and overcoming fear (8:12) Process for uncovering personal passions (10:25) Patterson disrupts publishing with six books per year (13:45) Research reveals 16 disruptive behaviors (16:30) Academia embracing different voices and perspectives (21:00) Mountain climber story shows gradual disruption (24:14) Framework for navigating career transitions (28:19) Limiting beliefs and psychological barriers (30:55) Being open to change versus stability (35:00) Taking ownership of disruptive choices (41:00) Mission versus purpose distinction (46:37) Advice for embracing positive disruption Share this episode with a friend, colleagues, and James Patterson book fans: https://affordanything.com/episode659 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#658: An unusual First Friday episode because we don't have a jobs report. However, we do know that in October, U.S. companies announced more job cuts in a single month than they have over any single month of the last 20 years. In other words, October was peak job cut month. By contrast, private payrolls, as reported by ADP, rose by 42,000 in October, so we have a little bit of conflicting data. Some pessimistic, some optimistic. We're going to take a deeper look at that in today's episode. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Conflicting Job Market Data (03:40) Youth Unemployment and AI’s Impact (10:16) Fed Rate Cuts and Housing Market (20:23) New Job Postings Lowest in 4 Years (20:54) Consumer Sentiment (22:04) Social Security Payments Increase in 2026 (23:33) Rising Car Costs and Repossessions (24:46) Good News for Prescription Drug Prices (31:50) Government Shutdown Impacts Learn more about your ad choices. Visit podcastchoices.com/adchoices

#657: This week, Paula and Joe dig into a listener’s question about ETFs that track the stock trades of U.S. politicians — including the Democratic “NANC” fund and its Republican counterpart “KRUZ.” They explore whether this strategy is smart investing or just expensive entertainment. Then, they shift gears to home ownership headaches. Another listener asks how to control ballooning maintenance costs, and Paula shares her best advice for finding trustworthy contractors, budgeting for repairs, and knowing when DIY doesn’t actually save money. Finally, an anonymous caller wonders if starting a small business just for tax breaks makes sense. Paula and Joe explain the IRS rules — and why energy and purpose matter more than deductions. From “fun money” investing to financial planning that actually works, this episode is all about balancing curiosity, caution, and common sense. Key Takeaways Congressional-trade ETFs aren’t a shortcut to wealth. They’re speculative, lag behind real trades, and carry high costs Home maintenance is predictable — plan for it. Create a repair timeline and build relationships with investor-friendly contractors DIY isn’t always cheaper. Factor in time, tools, and opportunity cost Never open a business just for taxes. If it doesn’t make a profit or bring joy, it’s an energy drain, not a strategy Separate fun money from freedom money. Keep speculation playful, and build wealth with focus and purpose Chapters Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Should You Follow Congress’s Trades? (06:00) The Lag Problem and Investor Bias (10:30) The “Fun Money” Rule (11:20) The Hidden Cost of Home Repairs (15:00) Finding Investor-Friendly Contractors (18:00) Planning Ahead for Repairs (22:00) DIY vs. Opportunity Cost (26:00) Starting a Small Business for Tax Breaks (29:00) The IRS “3-of-5 Rule” (32:00) Purpose Over Deductions (34:00) Final Thoughts https://affordanything.com/voicemail Share this episode with a friend, colleagues, and all the Nancys in your life: https://affordanything.com/episode657 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#656: What would you do if someone in authority told you to do something that felt wrong? Most of us like to think we'd speak up, push back, stand our ground. But research tells a very different story. In fact, when Yale researchers conducted a famous experiment in the 1960s, they found that 65% of people would administer what they believed to be deadly electric shocks to another human being... simply because someone in a lab coat told them to. Today's guest has spent over 15 years studying why humans comply with authority - even when every fiber of our being is screaming that we shouldn't. And when it comes to our money, this tendency to comply with authority figures - from financial advisors to real estate agents to car salespeople - can cost us dearly. Dr. Sunita Sah began her career as a physician in the UK's National Health Service. During one particularly exhausting period as a junior doctor, she agreed to meet with a financial advisor who had contacted her at work. That meeting sparked questions that would shape the rest of her career: Why did she feel pressured to trust this advisor, even after learning he had a conflict of interest? Today, she's a tenured professor at Cornell University, where her groundbreaking research on compliance and influence has been featured in The New York Times and Scientific American. She's advised government agencies, served on the National Commission on Forensic Science, and helps leaders understand the psychology behind why we say "yes" when we really want to say "no." Whether you're meeting with a financial advisor, negotiating the price of a home, or discussing rates with a contractor, understanding the psychology of compliance could save you thousands of dollars - and help you make better financial decisions. Today's conversation isn't just about psychology - it's about protecting your wealth by learning when and how to say "no." Resources Mentioned in the Episode: - Website: sunitasah.com - Newsletter: Defiant By Design | Dr. Sunita Sah | Substack - Connect with Dr. Sunita Sah - Follow Dr. Sah on Instagram About Dr. Sunita Sah Dr. Sunita Sah is a tenured professor at Cornell University specializing in organizational psychology. Her research focuses on how and why people comply with authority, even against their better judgment. A former physician in the UK's National Health Service, Dr. Sah brings a unique perspective to understanding human behavior and decision-making. Her work has been featured in leading publications including The New York Times and Scientific American, and she has served as a Commissioner on the National Commission on Forensic Science. Share this episode with a friend, colleagues, and your cohorts: https://affordanything.com/episode656 Learn more about your ad choices. Visit podcastchoices.com/adchoices