Afford Anything | Get Smarter With Money

#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney. At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Steve Jobs to hire him to build the Apple Store. Years later, he took over JCPenney and watched it fail for a reason that had nothing to do with his vision. Ron Johnson created the Apple Store and worked directly for Steve Jobs for 12 years, after bringing designer products to Target. He later served as CEO of JCPenney and is the author of Shop Different. In this episode, we discuss: How to weigh a lower-paying job that teaches you more How to set goals big enough that people work harder How to persuade a team whose top priority is not getting fired How to change a strong-willed boss’s mind Why a bold plan fails without trust, and how to build trust first What a rush of early customers can hide about a new business How to get out of your head when you’re overthinking a decision Whether you’re weighing a career risk,…

#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a portfolio designed so he never goes through that again. Jared Dillian was a trader at Lehman Brothers from 2001 until its collapse, and ran its exchange-traded fund desk. He's the author of The Awesome Portfolio and taught finance at the university level for 13 years. In this episode, we discuss: Why to sell your company stock as soon as you're allowed to How living below your means gave him the freedom to start a business when Lehman fell How to gauge your real risk tolerance with a simple Las Vegas test How a portfolio split five ways (stocks, bonds, cash, gold, real estate) held up in 2008 Why a 20% cash cushion can be an advantage instead of a drag What long-term bond yields reveal about the economy that stocks don't What it would actually take to close the Social Security funding gap If most of your money sits…

#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berger says if you're worried about all that, it's a sign you're thinking clearly. Rob Berger is a former securities lawyer, founder of the personal finance site Dough Roller, and host of a nearly 300,000-subscriber YouTube channel on investing and retirement planning. He started writing about money in 2007, just months before the Great Recession. In this episode, we discuss: How to tell whether today's high stock prices should change your plan When to trim a stock that's grown too big, and when to let it ride Why a booming economy can still leave so many people feeling squeezed What a looming Social Security shortfall could mean for your retirement How to cover your basic bills with guaranteed income, whatever markets do How to ease into retirement instead of going from 40 hours to zero Why daily spending habits…

#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund into an emergency. A 42-year-old UK listener asks how to split money between an emergency fund, a career break, and retirement. Then we map out a 30-something couple's sabbatical and ask whether you can objectively grade a politician on the economy. In this episode, we discuss: How to tell a true emergency from an expense you know is coming How to rank competing savings goals when you can't fund them all How to protect retirement without putting your life on hold How to cover a sabbatical when your cash runs short Why low-income years are a prime window for Roth conversions How to test whether you can stomach an all-stock portfolio How to judge a politician's economic record without the spin If you're juggling short-term plans and long-term goals and feel pulled in every direction, this episode will help you…

#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixing them up. Kenny Burgos is CEO of the New York Apartment Association, which represents owners of rent-stabilized buildings, and a former New York State Assemblymember from the Bronx. In this episode, we discuss: How New York's rent rules work, and why they've lasted since 1969 Why the typical New Yorker pays about $1,600 while listings ask $5,500 Why some buildings now sell for $50,000 an apartment, and why that isn't a deal How a rent freeze pushes costs onto market-rate renters and delayed repairs Why a targeted rent freeze for seniors and disabled residents works better What Vienna's housing model accounts for that New York's doesn't What aspiring landlords should weigh before buying rent-regulated property Whether you own rentals, hope to, or just want to understand the rent-control debate, this episode…

#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — it's a hire she hasn't made yet. This week, Joe joins Paula to help a caller decide whether to sell a rental property from abroad, then dig into new data on why women's labor force participation dropped in July while their share of new jobs surged in August. In this episode, we discuss: How to tell if you're making the right call for the wrong reason Why a new roof or a set of windows can be a form of forced investing The one hire that can solve the same problem as selling your rental A simple way to estimate a rental property's real return What to weigh before selling a working investment on gut feel alone Why women's labor force participation fell in July even as their job gains led the year Why the trades are becoming a stronger bet than a four-year degree for some new grads This one's for anyone facing a big…

#751: The belief that’s quietly sabotaging your progress might not even be true. Free worksheet to question it: https://affordanything.com/turn-it-around Two people can grow up with the exact same test scores — and as adults, one of them ends up earning double the other. Psychologist Marisa Franco says the deciding factor isn't intelligence, and it isn't luck. It's whether you actually believe good things are allowed to happen to you. Dr. Marisa Franco is a psychologist and professor at the University of Maryland, and the New York Times bestselling author of Platonic. She's back to talk about her new book, Worth: The New Science of Self-Esteem and Secure Attachment. In this episode, we discuss: How self-worth — not intelligence or family income — predicts how much you'll earn as an adult Why some people quietly sabotage their own portfolio right before they hit financial independence The difference between "good" and "bad" high self-esteem, and why one of them wrecks relationships Why getting more love or…

#750: Free worksheet: question the belief that might be keeping you stuck — before reality forces the update for you: http://affordanything.com/turn-it-around Alec Litowitz spent three decades building one of the world's largest hedge funds, and he says the highest-IQ people in the room are often the last to notice the world has changed. His answer isn't more intelligence — it's the willingness to be wrong, quickly, and update before everyone else catches up. Alec co-founded Citadel alongside Ken Griffin and later founded Magnetar Capital, one of the largest alternative asset managers in the world. His new book, The Adaptability Quotient, is out September 15. In this episode, we discuss: How adaptability quotient (AQ) differs from IQ and EQ — and why it matters more now What a doomed Antarctic expedition reveals about real adaptability Why AI makes knowledge abundant and judgment scarce How to stop needing to be right so you can update faster The real reason Blockbuster lost to Netflix (it wasn't a bad…

#749: Michael Hingson was on the 78th floor of the North Tower of the World Trade Center when the first plane hit on Sept. 11. He felt the impact, but couldn’t see it. Michael has been blind since shortly after birth. Alongside his guide dog, Roselle, they descended 1,463 steps – escaping just before the South Tower, 100 yards away, collapsed. They then helped a woman who was temporarily blinded by the dust. Michael's story answers the question – What do you do when something terrifying is happening, you don't have enough information, you cannot control the outcome, and everyone around you is beginning to panic? Michael's answer is surprisingly practical. 1. Prepare before you need the preparation. 2. Know what you know, know what you don't know. 3. Stop mentally rehearsing outcomes you cannot control 4. Keep acting on the part that remains within your control. He had deliberately learned the World Trade Center's exits, emergency procedures, physical layout, and systems long before Sept 11 because he…

#748: The real question behind quitting a job you love or paying off debt anyway? Your money mindset. Take our free quiz to find yours: https://affordanything.com/fiire A listener with $686,000 saved and a job she loves wants to take her family on a year-long trip — but Paula says her real question isn't about money at all. Later: a dad chooses to stop maxing his IRA to pay off a mortgage, even though the math says otherwise. Joe joins from the road to help answer three listener questions: a family weighing a year off against a job she loves, a dad debating whether to stop maxing his IRA to pay off a house, and a longtime listener with a smarter way to save for college. In this episode, we discuss: How to decide whether a job you love is worth walking away from for a family gap year The three factors that actually predict whether you'll love your next job Why "retiring early" might be the wrong goal — and what to aim for instead How to know if you're financially ready for a career break, and what to prep…

#747: We have good news on multiple fronts to share about the job market, the stock market, the commodities market, and volatile news around the bond market. And we begin it with some great news coming out of Nepal. Welcome to the First Friday episode for September 2026. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Rescued workers in Nepal (04:53) Strong August jobs report (10:14) Conflicting employment data (12:27) Strong jobs, weaker stocks (17:43) Why bonds matter more (23:17) Inflation drives Treasury yields (29:45) Hidden risks in bonds (36:50) Treasury buyback controversy (43:32) Liquidity versus warning signs 🔗 RESOURCES MENTIONED 👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire Learn more about your ad choices. Visit podcastchoices.com/adchoices

#746: We begin today’s episode with a discussion of the disastrous flash flooding in Nepal, a personal topic for Paula given her family there. There’s both a human story, one of the resilience of the Nepalese people and the strong community bonds there, and an economic story, where poor infrastructure and a lack of economic development have hindered disaster response and exacerbated the tragedies of recent events. Listeners can donate to help the victims here: The Prime Minister Relief Fund: https://pmdrf.nchl.com.np/ Caritas Nepal: https://www.caritasnepal.org/donate-now/ Learn more about the ongoing rescue efforts at https://help.ekantipur.com/ A caller wants to put part of her mom's $80,000 home-sale proceeds into an annuity — and it left her financial-planner co-host doing a double take. Turns out it might be the first caller in the show's history the product was actually built for. This week's Q&A tackles two retirement questions from listeners: when it makes sense to ease off maxing out a 401k in favor…

#745: A friend once asked Sahil Bloom how often he saw his parents. About once a year, Sahil said. How old are they? Mid-60s. His friend did the math out loud. If they live to 80, you'll see them 15 more times. Sahil was 30, living in California and making great money at a venture fund. Within 45 days of that conversation, he quit his job, sold his house and moved across the country to be near family. He's now managing partner of SRB Ventures, an early-stage fund backing more than 60 startups, and he writes The Curiosity Chronicle, a newsletter read by millions. His book, "The 5 Types of Wealth," is a New York Times bestseller. His framework starts with a scoring problem. Financial wealth gets measured every day. Time, social, mental and physical wealth run in the background, unmeasured, until something forces you to look. You'll get exercises for each. Build an energy calendar that tracks which activities charge you up and which drain you. Map your relationships by how healthy and how frequent they are. Ask…

#744: With about $200 and a crypto exchange, historian Joseph Moore turned himself into a legitimate billionaire — a stunt that says more about how money actually works than most financial advice does. It's also a preview of the 300-year argument he makes in this episode: that almost everything we're told about money is newer, and far less permanent, than we think.Joseph Moore, PhD, is a historian and the national bestselling author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn't). His own self-experiments with historical money strategies helped him become financially independent in his mid-40s. In this episode, we discuss: How "never save your money" used to be completely reasonable financial advice Why bonds quietly beat stocks for nearly all of the 1800s How to spot when today's "obvious" financial rules are about to expire Why real estate booms always show up right alongside inflation spikes Why young people's unemployment is outpacing everyone else's — and…

#743: Everyone talks about a loneliness epidemic — but Luke Burgis argues the opposite problem is just as real: we now have so much easy, frictionless community that we never have to develop a solid sense of who we actually are. Luke Burgis is a professor of business at The Catholic University of America and the founder of the Cluny Institute, and the bestselling author of Wanting: The Power of Mimetic Desire in Everyday Life. He returns to the show to talk about his new book, The One and the Ninety-Nine. In this episode, we discuss: Why having too much easy community can be just as damaging as having none at all How to tell whether your beliefs are actually yours — or something you inherited without ever examining it Why cutting people off has quietly become the default response to conflict How to stop shrinking yourself just to keep other people comfortable The zero-tolerance rule Luke enforces at his own company to kill passive-aggressiveness before it starts How Luke actually decides who to trust, hire,…

#742: A listener hit her $1.4 million early-retirement goal three years ahead of schedule — and now she's stuck deciding whether paying off a low-interest mortgage is smart, or just fear in disguise. Later, a former financial planner explains why he still won't recommend one of the most talked-about "safer" investing strategies in the FIRE community. This week's Q&A tackles three listener questions: hiring your first accountant amid a complicated tax situation, whether to pay off a mortgage or retire early once you've already hit your number, and why one half of the show won't touch a popular alternative investing strategy. In this episode, we discuss: How to tell the difference between a CPA, an EA, and a tax attorney — and which one you actually need Why software can't keep up once your tax situation gets complicated How to interview and choose an accountant with confidence How to know if "one more year" at work is a smart plan or a sign of fear Why loving your job can change the entire math on early…

#740: Jack Raines turned $6,000 into $400,000 trading blank-check stocks during the 2020–2021 bubble — and he says it was some of the least fun money he's ever made. Jack Raines is a writer and investor at Slow Ventures, and the author of the new book Young Money: A Field Guide to Wealth and Purpose in Your Twenties. In this episode, we discuss: Why "golden handcuffs" are almost always a choice, not a trap How to tell if you're staying in a job for the right reasons, or just fear Why the same decision can be exactly right at 24 and wrong at 34 What actually helps when comparison and "falling behind" turn into apathy How he turned $6,000 into $400,000 trading a stock bubble, then gave much of it back Why hitting your number rarely feels like the finish line people expect Two questions worth asking before you spend years on something that isn't working This one's for anyone who feels behind, stuck, or unsure if their current path is a smart trade-off or just fear in disguise — Jack's way of thinking about…

#740: Paula and Joe rarely butt heads — but a caller's side hustle, which pulled in $5,500 in a single day, sparked their most heated disagreement in months. This week's mailbag: a couple weighing an early retirement built on $1.2 million, a wedding-dress side hustle deciding whether to go all in, and a listener whose small stock investment turned into a $25,000 tax puzzle. In this episode, we discuss: How to build a bucket strategy so you can retire early and still stay aggressive with your portfolio The real markers that tell you it's time to go back to work — not just a number How one listener turned a marketplace side hustle into a $5,500 day When to leave a stable paycheck for a growing side business, and when to wait Why a popular plan to gift a winning stock to your kids usually backfires Whether it's worth paying taxes now to raise your stock's cost basis Where a single winning stock belongs — taxable, Roth, or a solo 401(k) Whether you're weighing an early exit from a stable career, deciding if your…

#739: The U.S. just lost 23,000 jobs — and unemployment fell anyway. The numbers were strange enough that Paula broke a years-long, all-stocks habit and bought her first bond, ever. In this month's First Friday economic roundup, Paula breaks down the jobs report, the bond market, mortgage rates, gold, and a new kind of account for kids. Topics include: How to make sense of a jobs report that seems to contradict itself What actually happens when you buy a 30-year Treasury bond Why bond yields hitting a two-decade high matters for your money Why mortgage rates are climbing again, and what that means for housing Why home prices are surging in some states while crashing in others Why gold is quietly staging a comeback What the new government-seeded kids' accounts actually do Whether you're deciding where your next dollar should go, watching mortgage rates before a purchase, or wondering if your kid needs a new account this year, this episode gives you the full economic picture in one sitting. ⏱️ TIMESTAMPS Note:…

#738: Hackers broke into a real estate closing company's servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table. Dr. Eric Cole was a former CIA hacker, Cybersecurity Commissioner under President Obama, and longtime security advisor to Bill Gates. We're resharing this conversation, originally released in June 2025, in honor of his sudden passing this year and the practical security knowledge he left behind. In this episode, we discuss: -How to spot a phishing scam before you click the link -Why turning on two-factor authentication blocks almost every account takeover -The simple bank alert setting that can stop a fraudulent transfer -Why cybersecurity experts sometimes recommend paying a ransomware demand -How AI-cloned voices are powering a new wave of grandparent scams -What your phone's app permissions reveal about who's tracking you -Why "it won't happen to me" is exactly what scammers…

#737: Beth Kobliner has covered personal finance for people in their 20s and 30s for over three decades — and she says this is the hardest she's ever seen it. One in four young people now believe that betting on gambling sites and prediction markets counts as investing. Beth Kobliner is a personal finance journalist and New York Times bestselling author of Get a Financial Life, who served on President Obama's Advisory Council on Financial Capability for Young Americans. In this episode, we discuss: Why unemployment for college grads is now worse than the general population Why the average first-time homebuyer is now 40 instead of 28 How tap-to-pay and neobank apps quietly drive up spending without you noticing Why so many young people believe gambling sites count as investing — and what the real odds say Whether AI is making it harder or easier for young workers to break in Why index funds still beat both active management and a lucky bet, long-term Whether college is still worth the cost in today's job…

#736: A bride wants to spend $60,000 on her wedding — money that could grow to $800,000 in 40 years if she invested it instead. This week, three very different listener questions all boil down to the same fight: what the math says versus what actually makes you happy. 👉 Figure out your own money mindset — free FiiRE Playbook: https://affordanything.com/fiire This week, Paula and Joe tackle three listener questions: a professor trying to retire in 12 years while his daughter starts college, a bride wondering if $60,000 is too much to spend on love, and a couple in Luxembourg deciding whether a 1.2% fee is worth paying to keep themselves from touching their own money. In this episode, we discuss: How to know if you can retire in 12 years while your kid starts college A little-known tax-advantaged account almost nobody realizes their child can use Why a 7% return assumption isn't a "set it and forget it" number Whether a $60,000 wedding is a smart use of money — or a mistake How to decide if a big purchase is…

#735: Cody Berman failed at more than 30 side hustles — from a disc golf manufacturing company to sweaty bike deliveries in the Australian heat — before three of them got him to financial independence at 25. Cody is the bestselling author of Retire by 30, who reached financial independence at 25 by stacking income from real estate, digital products, and the stock market. In this episode, we discuss: How a nest-egg approach to financial independence differs from a cash-flow one A simple framework for sorting any side hustle into one of four types Why calculating real rental cash flow means more than rent minus mortgage Why the gap between what you earn and spend matters more than your returns How a failed side hustle can still hand you a skill that pays off later Why rebuilding an old idea from scratch can prove your skills weren't luck How to know when a side hustle needs more time versus when to quit Whether you're juggling five side hustles or just starting your first one, this episode will help you figure…

#734: Depending on which source you ask, the U.S. is short somewhere between 1.2 million and 10 million homes — and the reason for that wild range says as much about who's counting as it does about the shortage itself. 👉 Free cheat sheet: which investments belong in which account: https://affordanything.com/assetlocation This week, Paula and Joe tackle three listener questions: whether the housing shortage is real or a wealth-concentration problem, whether a 26-year-old should pay off his mortgage or keep investing toward financial independence, and how to simplify a portfolio spread across 13 funds. We discuss: Whether the housing shortage is real — or just wealthy people buying vacation homes Why entry-level starter homes are in shorter supply than luxury homes - A simple way to add housing supply in your area while increasing your own rental income How to simplify a $1.5 million portfolio spread across 13 funds without losing tax efficiency Which investments belong in a Roth account vs. a 401(k) vs. a…

#733: Venture fund managers can collect years of fees before a single dollar comes back to investors — and the bar to hand over your money is lower than you'd think. David Bell spent 20 years as a chaired professor at Wharton before co-founding the venture firm Idea Farm Ventures, where he's backed early-stage brands like Bonobos, Warby Parker, and Jet.com. In this episode, we discuss: How venture funds actually make money, and why nearly every one runs on the same fee formula Why fund managers get paid before they've invested anything Why the bar to invest in risky private deals is lower than you'd think What to ask before trusting any fund manager with your money The one red flag that should make you think twice about an eager fund manager How some investors make an all-or-nothing bet on a single breakout company Why taking outside money can quietly change what a founder is optimizing for Whether you're weighing becoming a fund investor yourself or you're a founder deciding whether outside money is worth…

#732: Where you live is already deciding what you'll buy today, before you've even made up your mind. And it turns out the customers your local stores ignore completely are often a brand's most valuable ones. David Bell spent twenty years as a Wharton marketing professor before becoming one of the earliest investors in Warby Parker, Bonobos, and Diapers.com. He's now co-founder of the consumer venture studio Idea Farm Ventures. In this episode, we discuss: Why the same person makes different purchases depending on where they live How four college students' "nutty idea" became Warby Parker Why the customers your local store ignores can become your best customers Why a failed meal-kit startup accidentally proved a rule about demand How a founder turned a boring hand sanitizer into a ten-dollar status symbol Why AI can now replicate a $100,000 market research study for almost nothing This episode is for anyone building — or dreaming of building — their own brand, product, or side hustle, and who wants to…

#731: What if the best way to test a new hire wasn't a resume, but a two-hour breakfast? One CEO built his entire hiring process around it — and it worked. Lorraine Marchand spent three decades in leadership roles at companies like IBM, Bristol-Myers Squibb, and LabCorp, and interviewed more than 120 CEOs for her book on what actually makes teams innovate. Now she teaches at Wharton and Columbia Business School, and in this episode she joins Paula to share what really works. In this episode, we discuss: How one CEO used a casual team breakfast to test whether a new hire was the right fit before they came on board A simple three-question test to figure out if a bad job culture is fixable, or if it's time to start looking elsewhere Why a weekly 30-minute habit of talking about what's not working can make a team stronger How to network your way into opportunities early in your career, even if you're worried AI will replace you first What new research on memory loss and heavy AI use means for how you should be…

#730: What does it actually mean to have "enough" — and how do you know when it's time to stop optimizing and start living? AVOIDING THE REAL ESTATE MISTAKES IN THIS FREE GUIDE COULD SAVE YOU $10,000 OR MORE 👉https://affordanything.com/mistakes In today's episode: Jax, a longtime listener, has hit a mindset shift — prioritizing sabbaticals and shared experiences over pure accumulation. He wants to know if his financial strategy still matches his values, how to deploy his home sale proceeds, when to assemble a financial team, and whether he and his wife have truly reached Coast FI. Megan and her wife are realtors in Baltimore who also flip houses. They're weighing whether to keep flipping, build a rental portfolio, or lean harder into retirement accounts and index funds — and want a framework for balancing it all as they plan for more travel and time with family. And Reema lives with her husband in the home she grew up in — which her mother still owns. As they plan renovations and think ahead to her mother's…

#729: The U.S. added 57,000 jobs in June. Economists expected 115,000. Meanwhile, inflation hit a three-year high. The Personal Consumption Expenditures index - the Fed's favorite inflation gauge - jumped 4.1 percent year-over-year. That combination creates a problem. Weak jobs usually push the Fed to cut rates. Hot inflation pushes them to hike. In this First Friday episode, we break down which way the Fed might lean at its September meeting, and why traders see an 80 percent chance rates stay frozen for now. We also dig into Kevin Warsh's debut as Fed Chairman. His first official statement ran only 132 words, one of the shortest in Fed history. He cut forward guidance – the practice of making guesses about what the Fed will do next. He removed the names of dissenting voters. His statement mentioned price stability but skipped maximum employment, and we explain why that omission matters. Central banks around the world moved in the opposite direction. The European Central Bank raised rates for the first time…

#728: What do you do when you suddenly have $850,000 and no idea what to do with it? GET TOTAL CLARITY ON WHERE EVERY DOLLAR BELONGS 👉 https://affordanything.com/cornerstone On today’s Q&A, one caller recently inherited $850,000 from his mother. He's already wealthy, earns over $500K a year, and has a solid net worth — but he's anxious, lost, and doesn't want to make a decision he can't undo. Paula and Joe walk him through exactly what they'd do. Then, a federal law enforcement officer responds to Jane from episode 722. He pushes back on our diagnosis of her stress — and makes a compelling case that it's not the mandatory retirement age that's the problem. It's the minimum. He shares how he's survived the final stretch of a career he no longer loves, and what he'd tell Jane about the years she still has ahead. Finally, a caller who is pregnant, recently promoted, and about to have a very hard conversation with her employer. She wants to go part-time after maternity leave — but HR is bureaucratic and the…

#727: Not sure what your next money move should be? Start with the free FiiRE Playbook 👉 https://affordanything.com/fiire Dr. Julia Garcia is a psychologist, behavioral researcher, and author of The Five Habits of Hope — and she's spent years studying why smart, hardworking people stay stuck. What if the biggest thing standing between you and your financial goals isn't your income, your debt, or the housing market — but your own brain? I sat down with Dr. Garcia to unpack the neuroscience of hope, why apathy is more dangerous than despair, and the five habits that can rewire your brain — and your relationship with money — for good. (00:00) Hope is not a feeling — it's a cognitive process (05:00) The real reason you can't save money (it's not imposter syndrome) (08:11) Hopelessness vs. despair — and why the difference matters (13:05) The biggest danger isn't despair — it's apathy (21:10) How avoiding feelings leads to avoiding financial decisions (23:45) The "maybe" technique that interrupts negative thought…

#726: Hey, we're mixing it up today with a super deep dive. We normally go fairly deep on this show, but today we're going even deeper and turning one caller's question into a case study. Download the Four Cornerstone Worksheet to follow along: ⁠www.affordanything.com/cornerstone⁠ An anonymous caller is reevaluating their finances after a series of health challenges, caregiving responsibilities, and major life changes. With most of their wealth tied up in retirement accounts, they’re wondering how to balance tax advantages against the need for greater flexibility and access to their money. We spend most of the episode answering this question in deep detail. At the end of the episode, we talk to another caller whose HOA hit her with a massive unexpected bill. She bought into an HOA, turned her former home into a rental, and years later was hit with a surprise $15,000 special assessment—with only months to pay and no payment plan available. Now she's wondering why the risks of HOA ownership, especially the…

#725: Most people assume their financial advisor is legally required to put their interests first. That's not always true. Andrea Baumann Lustig, a wealth advisor with 30 years of experience, joins us to walk through the blind spots she sees most often in legacy planning -- the deeply held beliefs that quietly undermine people's financial futures. We start with something most people never think to ask: how is your advisor actually registered? There are three categories. Registered representatives (stockbrokers) are held to a "best interest" standard - but they don't have to disclose when they earn a higher commission for recommending a specific investment. Fiduciaries are held to a stricter standard - they must put your interests ahead of their own. And 45 percent of advisors are dually registered, meaning they can switch between those two standards depending on which account they're discussing with you. Most clients have no idea this is happening. From there, we dig into what Lustig calls the "quarterback"…

#724: Linda Hill, a Harvard Business School professor, and Jason Wild, an innovation consultant who has led projects in 40 countries, join us to break down how organizations innovate. Linda and Jason have spent decades studying companies that consistently produce breakthroughs - from Pixar to Delta Airlines to Cleveland Clinic - and they've identified three leadership roles that matter most: the Architect, the Bridger, and the Catalyst. The Architect builds a culture where people feel safe enough to take risks. The Bridger - which Linda calls the "revenge of middle management" - spans the gaps between departments, partners, and outside organizations where innovation often stalls and dies. The Catalyst builds coalitions across broader ecosystems to get things done. We get into what separates co-creation from consensus - and why consensus almost never produces anything great. Linda explains what she calls "creative abrasion": the practice of rubbing ideas against each other through debate and discourse, rather…

#723: This episode originally aired in July 2025. Here's the thing about personal finance advice: what works when you have $10,000 won't work when you have $1 million. Yet most financial guidance treats everyone the same, whether you're scraping together a $1,000 emergency fund or deciding whether to upgrade to business class. Nick Maggiulli, author of "The Wealth Ladder," joins us to break down how money strategies must evolve as your net worth grows. He's mapped out 6 distinct wealth levels, each requiring different approaches to spending, saving and investing. The levels start simple. Level 1 covers anyone with less than $10,000 in net worth — that's 20 percent of American households. Here, bad luck gets amplified. A flat tire that costs $200 could spiral into job loss and debt if you can't afford the repair. Level 2 spans $10,000 to $100,000 in net worth. Maggiulli calls this "grocery freedom" — you can splurge on the nicer eggs without checking your bank balance. Level 3, from $100,000 to $1 million,…

#722: Free lesson: affordanything.com/mistakes Ask us a question: affordanything.com/voicemail What happens when your financial plan is technically working — but emotionally, it still doesn’t feel secure? Caitlin and her husband have their core expenses covered, but her side hustle brings in an extra $600 a month. With young kids, daycare costs, and long-term retirement goals all competing for attention, she’s wondering where that extra money should go right now. Anonymous is in a strong financial position for retirement, with a pension, solid investments, and high savings rates—but is still constantly checking accounts, rerunning projections, and struggling to feel at peace with money. Charlotte is calling back several years after asking whether short-term rentals could fund her early retirement. After buying, renovating, and eventually selling two Airbnb properties—just before a devastating hurricane hit the area—she’s reflecting on what she learned about risk, hype, and investing with emotion. Resources…

#721: The US economy showed robust job growth in May, adding 172,000 new jobs, exceeding expectations. This suggests a broadening of economic recovery beyond essential services. Treasury yields have climbed significantly, reflecting investor concerns about inflation. Inflation remains a significant concern, driven largely by surging energy costs. And there's good news emerging in prescription drug prices. We're going to discuss all of this and more in the June 2026 First Friday 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. (0:00) May jobs surge (04:31) Fed rate hike outlook (06:08) Bond yields and stocks (11:57) Home prices keep falling (16:15) Austin housing correction (17:18) Inflation and energy costs (21:21) Gas prices hit budgets (23:05) Consumer sentiment weakens (28:11) JPMorgan market outlook (29:14) Mag Seven loses dominance…

#720: At what point does making the “right” financial decision start to feel emotionally harder than the math itself? Rebecca: is wondering whether the Rule of 72 means she can ease up on retirement contributions—or whether continuing to max out her Roth 401(k) is still the smarter move despite multiple mortgages, car loans, and college savings goals. Kate: feels trapped between the math and psychology of homeownership. A low-interest rental property could be sold to dramatically reduce a much larger 7 percent mortgage, but she’s struggling with whether giving up that “golden” loan would be a long-term mistake. Emily: is now just a few years away from early retirement, but after watching his net worth grow rapidly during the bull market, he’s finding that the closer he gets to financial independence, the harder it becomes to emotionally trust that he finally has enough. Resources mentioned: Financial Planning Tools: go.boldin.com/affordanything Leave Paula a message for the show: affordanything.com/voicemail…

#719: Most of us spend 93 percent of our time indoors, and it's making us sicker, more tired, and less productive than we realize. Dr. John La Puma is a physician and researcher who studies what happens to the human body when it's indoors too much. He joins us to explain the science behind what he calls the indoor epidemic: the chronic diseases, burnout, insomnia, and cognitive decline that stem from a life lived almost entirely inside. Dr. La Puma walks through the specific biological mechanisms at play. Indoor living disrupts your circadian rhythm and bombards your brain with more screen time than it can process — what he calls "digital obesity." Too many pixels, he says, burn out your brain the same way too much sugar burns out your metabolism. Burnout isn't a character flaw. It's a biology problem. The good news: the minimum effective dose of outdoor time is just two hours a week in a green or blue space. And it doesn't have to be a national park. The park down the street counts. We get into the…

#718: What happens when the financial strategy that once felt obvious suddenly becomes a lot more complicated? Les is approaching financial independence but has realized there’s one thing missing from the traditional FIRE equation: how do you continue meaningful charitable giving after you stop earning a paycheck? Jaime has built a sizable retirement portfolio, but now he’s wondering whether the complexity inside his 401(k) actually matters—or if he’s overthinking the mechanics of retirement accounts and Roth conversions. Tina has owned a successful rental property near the University of Central Florida for more than a decade, but changing market conditions and growing competition from corporate landlords are making them wonder whether it’s finally time to sell. We’re diving into all of that today, so let’s get started. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#717: Clare Flynn Levy was a hedge fund manager in London in the summer of 2007, watching her trading screens turn red — every single day. Merger arbitrage spreads were widening. Investors were pulling out. She didn't yet realize she was watching the early tremors of a global financial crisis. Clare joins us to talk about what that experience taught her about investor behavior, emotional bias, and the hidden forces that drive financial decisions. She now runs a firm that helps professional fund managers analyze their own decision-making patterns. Her core argument: most investors aren't making rational choices. They're rationalizing them. We get into two specific biases that cloud judgment — sunk cost fallacy and the endowment effect — and how they show up whether you're picking individual stocks or rebalancing a 529 plan. Clare shares a personal example. After the 2024 election, she moved her kids' college funds from equities into bonds, recorded her reasoning in her calendar, and came back nine months…

#716: When does a financial decision stop being purely about maximizing returns—and start becoming about building the life you actually want? Karen recently inherited sizable trusts for their children and is now navigating the complicated intersection of investing, taxes, legacy planning, and future financial aid eligibility. Matt has spent years building a solid index fund portfolio, but as retirement gets closer, he’s wrestling with a familiar investor problem: how do you know when optimizing becomes overthinking? Kate is trying to decide whether $35,000 should go into the stock market—or into building a backyard gym that could generate income while dramatically improving her family’s day-to-day quality of life. We’ve got a lot to unpack today, so let’s get into it. Book by Michael J. McFall - Grind: A No-BS Approach to Take Your Business from Concept to Cash Flow Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode716 Learn more about your ad choices. Visit…

#715: She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s. Here's what changed. Haley Sacks - known online as Mrs. Dow Jones - joins us to talk about the five-step financial framework she calls IBIZA. Despite every advantage, she spent her twenties anxious, financially dependent, and charging dinners to her parents' credit card. One birthday trip to a Toronto restaurant crystallized the problem: she couldn't afford the life she wanted, so she borrowed someone else's money to fake it - and spent the rest of the night avoiding her phone while her mom texted about the charge. We talk about how money beliefs form by age seven, even when parents never say a word about finances. Haley's father had watched wealthy clients' children lose ambition and kept money out of the family conversation entirely. The lesson Haley absorbed anyway: money comes from outside yourself. The IBIZA framework walks through five steps - identify your earliest money memory, interrupt the patterns it created, zhuzh…

#714: When you’re making big financial decisions, what matters more: optimizing for the best long-term outcome, or choosing the path that gives you the most flexibility and peace of mind right now? Melissa retired early and now lives off rental income, but she’s considering selling one property to pay off another. The catch? Her monthly income would stay about the same—so the real question is whether giving up future appreciation is worth the simplicity and stability today. Von is trying to better understand how real estate returns actually work—specifically, whether cap rates tell the full story for multifamily properties, or whether there’s more going on beneath the surface. Layla is planning to retire at 50 and has built a strong portfolio—but she’s wondering if she’s leaned too heavily into Roth accounts. Should she keep maximizing a mega backdoor Roth at a high tax rate, or shift toward a taxable brokerage to better bridge the early retirement years? We’ll get into all of that—the tradeoffs, the…

The US economy added 115,000 jobs in April -- and the numbers look solid on the surface. But dig a little deeper and you'll find a tech sector in freefall, a housing market frozen in place, and consumer sentiment that hit a 74-year low. This bonus episode breaks down the May jobs report, which came out a week late because the Bureau of Labor Statistics pushed its release from the first Friday to the second Friday of the month. The job gains were concentrated in healthcare, transportation, warehousing, and retail. Healthcare alone added 37,000 jobs, driven largely by nursing facilities and home health care services for an aging population. Retail gains clustered in discount stores and warehouse clubs - not department stores or electronics retailers - which tells you consumers are spending more carefully. Tech got hit hard. The information sector lost another 13,000 jobs in April and is now down 342,000 jobs - about 11 percent - from its November 2022 peak. People working part-time because they can't find…

#713: Tiffany Aliche spent her 30th birthday in her childhood bedroom, $300,000 in debt, unemployed, and freshly foreclosed on. Sixteen years later, she's generated over $50 million in gross revenue as a business owner. She joins us to talk about what actually happened in between. Aliche - known as The Budgetnista - built her personal finance platform almost by accident. After a friend stole $35,000 from her and the 2008 recession wiped out her condo's value, she started helping friends navigate their own financial messes. That side hustle became a business. By 37, she was a millionaire. By 40, she had her first eight-figure revenue year. But the money didn't fix everything. We talk about what she calls "post-traumatic broke syndrome" - the way your scarcity mindset from the hard years keeps quietly running your financial decisions long after your bank account has recovered. For Aliche, it showed up as years of refusing to buy herself a vacation home she could easily afford, while simultaneously buying…

#712: Jeff Hurst, CEO of Furnished Finder, joins us to break down what midterm rentals are, who they're for, and why now might be the best time to get in. A midterm rental is a furnished unit rented for 30 days or longer - longer than a hotel stay, shorter than a traditional lease. Cities have been regulating Airbnb-style short-term rentals out of existence, leaving a wave of furnished properties with nowhere to go. That supply is now shifting toward the midterm market, driven by three primary tenant types: corporate and skilled trade workers, traveling healthcare professionals, and relocating families doing a "try before you buy" neighborhood test run. We get into the specifics of what it costs to furnish a midterm rental (about $7 per square foot, compared to $30 to $40 for a short-term rental), where owners typically overspend (treating it like a leisure destination), and where they underinvest (quality mattresses, blackout curtains, kitchen functionality). Jeff also explains how to model out your…

#711: A computer science degree used to feel like a sure thing. Job placement rates topped 90 percent. Starting salaries cleared $80,000. You could do the math on your student loans before you enrolled. That math doesn't work the same way anymore. New York Times "Your Money" columnist Ron Lieber joins us to walk through what families actually need to know before borrowing for college. He covers how to use the federal College Scorecard to look up earnings by school and by major. He explains why the scariest student loan headlines are almost always about graduate school rather than undergraduate debt. And he makes the case that liberal arts majors tend to catch up to their STEM peers by mid-career - even if the early numbers don't show it. Lieber also makes a case that the financial return on college extends beyond salary data. Alumni networks, mentorship, and lifelong friendships all factor into the equation. He suggests asking schools pointed questions about reunion attendance and alumni giving rates as a…

#710: What does it really look like to balance financial optimization with real-life tradeoffs—whether that’s choosing meaningful work, spending down your savings, or deciding where your next dollar should go? Mike is planning to retire at 60 with $1 million saved and a clear goal: spend it all during his lifetime. He wants to know how to structure his withdrawals so he can maximize income now while still covering the decades ahead. Kip was planning to retire after feeling burned out—until a chance conversation led him to a completely different role within his company. Now he’s happier than ever, but he’s also curious about whether real estate syndications are a smart next step for investing. Jessie and their spouse are about five years away from early retirement and trying to decide where their next savings dollar should go—keep maxing out Roth IRAs, or shift toward a taxable account for more flexibility? We’ll get into all of that—and how to think through each of these decisions—on today’s episode.…

#709: Keith Wargo has spent decades navigating one of the most daunting financial planning challenges a family can face: raising a child with a developmental disability. He joins us to share what families need to know. The financial stakes are significant. Keith, who is the CEO of Autism Speaks, estimates lifetime care costs for a person with a developmental disability can run between $1.4 and $2.4 million - and that figure may be conservative. Yet many families put off financial planning because the day-to-day demands of caregiving leave little room for anything else. One of the first things Keith walks us through is the federal benefits system. Medicaid and SSI are the primary lifelines for many families, but qualifying takes time - for Keith's family, it took three years of meetings and paperwork. There's also a critical detail: SSI requires the individual to have no more than $2,000 in assets in their name. A well-intentioned inheritance from a grandparent can wipe out eligibility overnight. That's why…