#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 in an index fund or your employer's stock, this conversation will help you figure out how big a drop you could actually stomach before the next real bear market tests you. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:29) Walking into Lehman Brothers the day it collapsed (04:38) The $500,000 in company stock that went to zero (06:57) How cheap living let him start a business instead (19:54) Why buy-and-hold hasn't faced a real crash since 2008 (22:52) The Las Vegas test for your risk tolerance (27:07) A five-way portfolio that fell just 9.8% in 2008 (28:46) The one scenario where this portfolio struggles (29:33) Is 20% cash too much with inflation? (44:45) Why bond yields are the economy's warning light (51:25) Why half of retirees claim Social Security at 62 🔗 RESOURCES MENTIONED BEFORE YOU ADD BONDS OR REAL ESTATE FUNDS, KNOW WHICH ACCOUNT THEY BELONG IN 👉 https://affordanything.com/assetlocation Jared Dillian's website 👉 https://www.jareddillianmoney.com The Awesome Portfolio by Jared Dillian 👉 https://amzn.to/4ART5i4 Jared Dillian on X 👉 https://x.com/dailydirtnap Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 matter more than investing knowledge Whether you're five years from retirement or five years into your career, this episode will help you separate what's truly changing from what never does. 🔗 RESOURCES MENTIONED RETIREMENT WORRIES FEEL OVERWHELMING? SEE YOUR WHOLE FINANCIAL PICTURE ON ONE PAGE 👉 http://affordanything.com/cornerstone Rob Berger on YouTube 👉 https://www.youtube.com/channel/UC9C17-OMxa-7oRSaCtztObw Rob's free weekly retirement newsletter 👉 https://robberger.com/newsletter Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 decide what gets funded first, and what can wait. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (05:30) The real difference between emergencies and expenses (07:28) Why a former planner never said "emergency fund" (13:13) The monthly math that breaks most wish lists (18:36) One question that reveals what you really want (26:37) Why four months of savings is enough for now (33:48) Fund the sabbatical before earmarking a down payment (37:00) Why a career break is prime time for Roth conversions (43:24) How to test if you can handle a 22% drop (1:01:53) Judge politicians on policies, not short-term results (1:09:42) Why focusing on what you control grows your influence 🔗 RESOURCES MENTIONED 👉 Emergency fund, sabbatical, retirement? See which box each dollar belongs in with this free one-page worksheet: https://affordanything.com/cornerstone 👉 Paul Merriman's free model portfolios and investing courses: https://paulmerriman.com 👉 Adventure Capitalist by Jim Rogers: https://amzn.to/4xOaEg3 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 shows what happens when costs keep rising and rents can't. 🔗 RESOURCES MENTIONED 👉 Ready to buy your first rental property, or get more out of the one you already own? Join the waitlist for Your First Rental Property. You'll be the first to know when enrollment opens: courses.affordanything.com 👉 New York Apartment Association: https://housingny.org 👉 Housing New York podcast with Kenny Burgos: https://housingny.org/housingnypodcast 👉 Kenny Burgos on X: https://x.com/KennyBurgosNY ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:44) Why New York's 1969 emergency rent rules never ended (04:58) The surprisingly low rent most New Yorkers actually pay (23:33) Why buildings now sell for $50,000 an apartment (25:12) Costs rose 4.5%. Rents were frozen at 0%. (31:39) The rent-freeze program that actually works (39:38) Who really pays when rents are frozen (47:13) Why 60,000 apartments sit empty during a shortage (01:01:53) Buyout or pressure? The $150,000 question (01:06:52) What Vienna gets right that New York doesn't (01:16:18) Should you buy a rental in New York? Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 financial decision that feels more emotional than mathematical — whether that's a rental property, a career move, or a job you're not sure is worth keeping. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (01:45) Why she wants to sell a rental that's "objectively good" (03:25) When it's actually okay to sell a good investment (10:03) One hire that stops panic-selling a rental property (14:44) The simple math to compare rental returns vs. stocks (17:31) Paula's own confession about hating her first rental property (22:22) Why doing what you're best at beats doing everything yourself (30:11) 100% of last month's labor force drop was women (31:54) The real reasons women are leaving the workforce right now (32:18) Why women got 85% of new jobs created this year (47:00) The industry that could fix jobs and housing at once 🔗 RESOURCES MENTIONED 👉 Torn on selling a rental? Get our free 10-day guide, which includes a deal-analysis exercise to help you decide with the numbers, not just your gut: https://affordanything.com/fiire 👉 Sign up for our newsletter (get the new site first): https://affordanything.com/newsletter 👉 Leave us a voicemail with your own money question: https://affordanything.com/voicemail 👉 Read the BLS jobs report Paula cites in this episode: https://www.bls.gov/news.release/empsit.nr0.htm Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 praise than you expect can make you pull away instead of lean in How to actually process a hard emotion instead of shoving it down Why hitting a big financial goal can leave you feeling strangely empty once you get there How to rebuild your sense of self after losing an identity you were attached to Whether you've ever undermined your own progress right before a finish line, or wondered why reaching a goal didn't feel the way you thought it would, this episode gives you a framework for understanding — and changing — that pattern. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:05) The two very different types of high self-esteem (04:36) Self-esteem vs. self-worth: the real difference (05:37) Why self-worth predicts income more than SAT scores (12:21) Sabotaging your own portfolio right before you hit FI (14:15) The self-fulfilling prophecy behind financial fear (23:36) Why too much love can make you pull away (25:05) How low self-worth blocks promotions and job offers (36:13) The memory trick that can change your brain (46:19) Why self-worth matters most in a bad market (1:06:10) Does self-worth actually drive your net worth? 🔗 RESOURCES MENTIONED 👉 Worth: The New Science of Self-Esteem and Secure Attachment: https://drmarisagfranco.com/worth-the-book/ 👉 Marisa's website (speaking, articles, more): https://drmarisagfranco.com 👉 Marisa on Instagram (for signed copies via Lost City Books): https://www.instagram.com/drmarisagfranco/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 decision) A 4-part test for telling a temporary shift from a permanent one Why a "diversified" portfolio might secretly be one big bet right now This episode is for anyone whose career, portfolio, or plans feel less certain than they used to — a way of thinking that doesn't require predicting the future, just noticing when your old model has stopped working. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 believed that was part of being responsible for his office. When the building was struck, he describes that preparation as a “mindset” that simply kicked in. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Life before September 11 (24:34) The plane hits the North Tower (34:03) Fear takes over in the stairwell (1:04:01) Turning tragedy into a new career (1:28:02) Challenging attitudes about blindness (1:38:01) Supporting guide dog organizations 🔗 RESOURCES MENTIONED michaelhingson.com guidedogs.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 first Why paying off your mortgage can beat investing, even when the math says otherwise How to structure your mortgage term like a finance pro (and why the 30-year can win) Why saving in separate, labeled accounts makes it easier to actually hit your goals Whether you're weighing a big life pivot, deciding what to do with extra cash, or just trying to make saving feel less abstract, this episode offers frameworks — not just formulas — for making the call. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (07:12) Can you afford to quit a job you love? (11:09) Three things that actually predict job satisfaction (17:05) Why this window with your kids won't come twice (22:20) Why retiring often beats retiring early (30:14) Why bad trip experiences count as good data (34:18) Why paying off debt can beat the math (36:49) Why coasting on your current savings pace is risky (44:26) How to think like a CFO about your mortgage (51:09) Why one bucket per goal makes saving easier (53:46) Why your 401k isn't really about retirement 🔗 OTHER RESOURCES 👉 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 👉 Camp Fi, the financial independence retreats Paula and Joe swap stories about this episode: https://campfi.org 👉 Heavy Metal Money, Chris Luger's personal-finance podcast (Joe recorded this episode from his place): https://heavymetal.money 👉 Got a question of your own? Leave a voicemail for Paula: https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 of a more flexible brokerage account, and whether a guaranteed-income annuity is the right move for a retiree who isn't great at managing money on her own. In this episode, we discuss: How to know when to stop maxing out your 401k and start filling a taxable brokerage account instead The real "deal" you're making with the government every time you use a tax-advantaged account Why an insurance company can keep 100% of the money if the annuity holder dies too soon — and how to avoid it The one type of person a guaranteed-income annuity is actually built for A simple daily habit trick for building consistency, borrowed from a world-class choreographer Why doing everything right doesn't guarantee a good outcome, and what that means for your own decisions What Nepal's disaster response reveals about the real payoff of economic development Whether you're mapping out an early-retirement bridge or helping a parent build guardrails around a windfall, this episode will help you think more clearly about the trade-offs each option carries. 🔗 RESOURCES MENTIONED 👉 Not sure which investments belong in your 401k, your Roth, or your taxable account? Grab our free guide to figuring out where each one goes: https://affordanything.com/assetlocation 👉 Morgan Housel on the split-second decision that changed everything: https://affordanything.com/488-gut-instincts-and-big-decisions-with-morgan-housel/ 👉 Our interview with retirement researcher Dr. Wade Pfau on annuities and retirement income: https://affordanything.com/271-retirement-planning-in-2020-with-dr-wade-pfau/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 what your family and your community need from you. Define what "enough" means in dollars, then write the number down. Sahil also walks through anti-goals — the things you refuse to sacrifice on the way to a goal — and Memento Mori, the Roman habit of keeping your own death in view. Two questions run underneath all of it. Think about how you spent yesterday. Would your 10-year-old self be impressed? Would your 90-year-old self? You don't experience all four seasons in a single day. Sahil argues your life runs on seasons too. Some stretches call for financial growth. Others call for family. Find Sahil at the5typesofwealth.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 what history says to do about it Why economic optimism and economic data have stopped matching up Why building more housing is the only housing-crisis fix that's ever actually worked This one's for anyone who feels like the rules of money keep changing under them — because they do, and always have. Understanding that pattern is the first step to building wealth in whatever era you happen to be living in. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (05:18) How a runaway slave built his own legal currency (06:52) How he legally declared himself a crypto billionaire (13:22) Why a fifth of the Smithsonian's money collection is fake (15:52) The bestselling book that told readers to commit fraud (20:10) The decades when bonds quietly beat stocks (26:04) How his grandfather secretly became a bond millionaire (31:09) Why that "$10K in 1929" chart is misleading (48:02) Why wages are up 50% and nobody believes it (1:06:39) Why most Americans once owned one shirt (1:23:48) The rent control law that backfired for renters 🔗 RESOURCES MENTIONED 👉 Build a Life of Financial Freedom with our free workbook: https://affordanything.com/fiire 👉 Joseph Moore's site — his book, essays, and more: https://www.josephmoorebooks.com 👉 Your Money or Your Life by Vicki Robin & Joe Dominguez: https://vickirobin.com/your-money-or-your-life/ 👉 The Latte Factor by David Bach: https://www.simonandschuster.com/books/The-Latte-Factor/David-Bach/9781982120245 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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, and build relationships with What an existential crisis at 29 — and five humbling years training for the priesthood — taught a successful entrepreneur about identity This episode is for anyone who feels the pull between fitting in and standing out — in your family, your workplace, or your online life. Luke offers a way to build an identity solid enough to hold up under pressure, without giving up on real community. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (7:42) Two competing drives wired into every human being (10:11) Why group pressure breaks some people and not others (17:39) Why cutting people off replaced working through conflict (19:39) The real number of close friends you actually need (26:51) Where your beliefs actually came from (32:00) You're not responsible for how someone else feels (36:09) The zero-tolerance workplace rule against passive-aggressiveness (41:22) How to actually tell who you can trust (53:33) The existential crisis that sent an entrepreneur toward the seminary (55:39) The humbling lesson hidden in a vending machine 🔗 RESOURCES MENTIONED 👉 This free 10-day workbook helps you trace your money habits back to whether they're actually yours — starting with your own money mindset — https://affordanything.com/fiire 👉 Luke's website (books, newsletter, and more) — https://lukeburgis.com 👉 Luke's new book, The One and the Ninety-Nine: Forging Identity in the Age of Social Contagion — https://www.amazon.com/One-Ninety-Nine-Forging-Identity-Contagion/dp/1250373034 👉 Paul Graham's essay "Cities and Ambition," on how the place you live shapes what you want — https://paulgraham.com/cities.html Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 retirement Why a former financial planner still won't recommend risk parity investing What four well-known investing philosophies get right — and where they disagree Whether you're hiring your first accountant, staring down an early retirement decision, or trying to make sense of competing investment philosophies, this episode will help you separate genuine progress from comfortable procrastination. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (04:02) Why software can't handle a messy tax situation (08:02) The three types of tax pros — and who you actually need (12:46) How to interview and choose the right accountant (24:42) She hit her $1.4M goal three years early (32:22) The hidden fear behind "one more year" at work (38:29) Why loving your job changes the retirement math (49:39) Why a former advisor won't touch risk parity (53:46) Four investing legends who all disagree with each other (59:35) The historian's warning: history doesn't repeat itself (1:07:57) The cooking analogy that explains your portfolio 🔗 RESOURCES MENTIONED 👉 Not sure which investments belong in your Roth vs. your taxable account? Grab our free one-page guide to where each type of investment should sit: https://affordanything.com/assetlocation Karsten Jeske ("Big ERN"): 👉 "How to Lie with Personal Finance – Part 4: Risk Parity": https://earlyretirementnow.com/2026/07/29/risk-parity-lies/ 👉 "Can We Increase the Safe Withdrawal Rate with Risk Parity? – SWR Series Part 64": https://earlyretirementnow.com/2026/07/27/risk-parity-swr-series-part-64/ 👉 #548: Is Your Retirement Safe in Today's Economy?: https://affordanything.com/548-is-your-retirement-safe-in-todays-economy-with-dr-karsten-jeske-big-ern/ 👉 #643: LIVESTREAM: A Former Fed Economist Reveals What's Really Happening: https://affordanything.com/643-livestream-a-former-fed-economist-reveals-whats-really-happening-with-karsten-jeske-big-ern/ Nick Maggiulli: 👉 #375: The 2X Rule (and Other Wealth-Accelerating Advice): https://affordanything.com/375-the-2x-rule-and-other-wealth-accelerating-advice-with-nick-maggiulli/ 👉 #629: The Wealth Ladder Has Six Rungs (and Most People Never Climb Past Four): https://affordanything.com/629-nick-maggiulli-the-wealth-ladder-has-six-rungs-and-most-people-never-climb-past-four/ Frank Vasquez: 👉 #618: How to Retire at 50 While Supporting Aging Parents: https://affordanything.com/618-how-to-retire-at-50-while-supporting-aging-parents-with-frank-vasquez/ 👉 His podcast, Risk Parity Radio: https://www.riskparityradio.com JL Collins: 👉 #624: JL Collins Part 1 – The Simple Path vs. The "Optimal" Path: https://affordanything.com/624-jl-collins-part-1-the-simple-path-vs-the-optimal-path/ 👉 #625: JL Collins Part 2 – What Happens When You Don't Need to Work Anymore?: https://affordanything.com/625-jl-collins-part-2-what-happens-when-you-dont-need-to-work-anymore/ Paul Merriman: 👉 #550: Paul Merriman – The 4-Fund Strategy That Beats the S&P 500: https://affordanything.com/550-paul-merriman-the-4-fund-strategy-that-beats-the-sp-500/ 👉 #590: Small Cap Showdown! Paul Merriman vs. Dr. Karsten Jeske: https://affordanything.com/affordanything-com-small-cap-value-debate/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 money and time might be the reset you need. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:00) He liked his boss on a dating app (06:57) Two very different ways to spend your twenties (17:56) Why grad school became his built-in sabbatical (19:16) Why 30 gets judged harder than 24 (34:12) The real cause of career apathy (39:20) His best fix for feeling stuck (46:27) Same decision, right at 24, wrong at 34 (01:01:43) What's really keeping you in a job you hate (01:14:12) Why more money doesn't fix stress (01:17:56) Turning $6,000 into $400,000 in a stock bubble 🔗 RESOURCES MENTIONED 👉 Take the free 10-day FiiRE money-mindset workbook: if "I make too much to quit" sounds familiar, this helps you find out if that's actually true. → https://affordanything.com/fiire 👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://jackraines.blog/book 👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039 👉 Freedom, the app Jack and Paula both use to block social media and protect focus time → https://freedom.to Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 side hustle is ready to become your main hustle, or holding a stock that's grown far beyond what you expected, this episode will help you think through the tradeoffs before you act. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Why a winning stock can turn into a tax trap (02:23) A $1.2M portfolio and a plan to retire by 45 (07:45) Why an aggressive portfolio needs a cash cushion first (16:49) The real signal your plan isn't working (24:25) A side hustle that made $5,500 in one day (33:51) Quit now or wait — two strong arguments (39:51) The book that could save a new business (54:09) A $200 stock that grew into $25,000 (01:01:08) The tax rule that blocks gifting stock to your kids (01:12:59) A hidden tax that kicks in above $250,000 income 🔗 RESOURCES MENTIONED 👉 Grab the free Asset Location Made Simple guide to see exactly which investments belong in your taxable, Roth, and pre-tax accounts: https://affordanything.com/assetlocation 👉 Frank Vasquez's risk parity portfolio, explained in depth on episode #618: https://affordanything.com/episode618 👉 Profit First by Mike Michalowicz, the book Joe recommends for setting up your business finances the right way from day one: https://amzn.to/3Sf7Tpo 👉 Julie Wainwright's interview on the Stacking Benjamins podcast, on rebuilding after Pets.com to found The RealReal: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Why the jobs report shocked economists this month (03:24) How jobs can drop while unemployment drops too (08:03) Why Paula just bought her first bond ever (09:35) A crash course on why bond yields are spiking (25:34) Why unemployment claims just hit a 55-year low (27:57) Why young job seekers have it harder than everyone else (35:23) Why mortgage rates just hit a one-year high (51:28) Why gold is rebounding, and who's buying it (57:47) What the new 530A investment accounts mean for your kids 🔗 RESOURCES MENTIONED 👉 Wondering which account should actually hold that bond (or gold, or index fund) you just bought? Grab our free cheat sheet showing exactly where each investment belongs: https://affordanything.com/assetlocation 👉 Chat about this episode with the community: affordanything.com/community 👉 TreasuryDirect, where Paula opened her account to buy the bond: treasurydirect.gov 👉 CME FedWatch Tool, for tracking the market's odds of a September rate hike: https://www.cmegroup.com/markets/interest-rates/cme-fedwatch-tool.html Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 count on This episode is for anyone who assumes hackers only go after big companies — because the reality is scammers are counting on you to think that. You'll walk away with concrete, five-minute changes that close the gaps most people don't know they have. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:41) Why you're an easier target than a big bank (06:46) Why cryptocurrency theft is nearly impossible to reverse (10:59) How one password can move half your savings (17:35) The fake unpaid-toll text that's made scammers millions (21:55) Why paying the ransom is sometimes the smart move (29:05) How AI clones your kid's voice for scams (37:58) The one thing to never hand a child (54:57) Why you should mask your location online (01:16:18) The setting that blocks almost every account hack (01:18:45) The bank alert that can undo fraud fast 🔗 RESOURCES MENTIONED 👉 See your full financial picture — income, debt, safeguards, and goals — in one place with our free one-page worksheet: https://affordanything.com/cornerstone 👉 Dr. Eric Cole's firm, Secure Anchor Consulting: secure-anchor.com 👉 Signal, the encrypted messaging app Dr. Cole recommends for sensitive conversations: https://signal.org Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 market Whether you're just starting out or already feel behind, this episode makes the case for the boring, unglamorous plan over the tempting quick one — and explains why that plan still works. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Why today's 20- and 30-somethings have it harder than any generation Beth's covered (03:04) The consumer sentiment reading that's worse than the pandemic and the Great Recession (05:14) Why record-low unemployment doesn't mean what you think for new grads (10:23) Why the median first-time homebuyer is now pushing 40 (13:36) The real reason behind the boom in crypto, sports betting, and meme stocks (15:52) The "giving up" factor economists say is driving risky bets (17:15) Why a tiny sliver of prediction-market bettors take home most of the winnings (23:26) Is the "avocado toast" spending story about young people even true? (43:44) How tapping your phone quietly makes you spend more than a credit card (01:04:13) Why financial optimism is rising in countries poorer than the U.S. 🔗 RESOURCES MENTIONED 👉 A free 10-day workbook to work through your money mindset and your next move: https://affordanything.com/fiire 👉 Get Beth Kobliner’s book Get a Financial Life: https://amzn.to/3Ty9tTJ 👉 A Random Walk Down Wall Street by Burton Malkiel, the index-fund classic Beth and Paula both referenced: https://amzn.to/4bq9IGC Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 worth it before you spend the money Why paying a fee to a financial company might actually be doing you a favor How to tell a resilient money habit from a fragile one This episode is for anyone caught between what the math says and what they actually want — whether that's a wedding, a retirement date, or a fee you're tempted to cut. If you've ever done the "mathematically wrong" thing on purpose, you'll feel understood by the end of this one. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:36) Can this couple retire together in 12 years? (07:15) Why his college savings look thinner than expected (26:15) The two retirement levers you can actually pull (26:46) A little-known tax-free account for kids (34:18) Is a $60,000 wedding a smart money move? (41:21) The math behind what that wedding money could grow into (45:44) What every big purchase question really comes down to (57:51) Pay the fee, or invest it yourself? 🔗 RESOURCES MENTIONED 👉 Figure out your own money mindset — free FiiRE Playbook: https://affordanything.com/fiire 👉 Steve Stewart and Sean Mullaney's free webinar on ACA subsidies and the Subsidy Cliff August 4th - no RSVP needed: https://SteveStewart.me/subsidycliff 👉 Hear Paula, OG, and Jesse Cramer react to the Diary of a CEO episode on AI's future, on the Stacking Benjamins podcast: https://youtu.be/wppwRxGtFD4 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 out which ones are actually worth your time — and which ones to let go of. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Meet Cody Berman (03:27) Two paths to FI (05:51) Big piles feel scary (07:09) Cody's FI numbers (08:12) Hustling on the train (11:58) The side hustle graveyard (14:56) Four side hustle types (19:47) The rich own assets (37:17) Biking Uber Eats in Australia (44:20) Skills are future currency (45:33) AI makes doers stronger (52:36) The gap is everything (58:54) Valentine's printables pay off (1:07:54) House hacking slashes costs (1:12:45) Life after FI 🔗 RESOURCES MENTIONED 👉 Grab the free 10-day guide to figuring out which side hustle is worth building next: https://affordanything.com/fiire 👉 Retire by 30 by Cody Berman: https://amzn.to/4gwGSYm  👉 The Financial Independence Show (Cody's podcast): https://podcasts.apple.com/us/podcast/the-financial-independence-show/id1434155196 👉 The 4-Hour Workweek by Tim Ferriss: https://amzn.to/4vXfsj6 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 taxable account Why taking a 30-year mortgage (and paying it off fast) can beat a 15-year mortgage How to decide whether to pay off a mortgage early or invest the difference instead Whether you're trying to make sense of housing headlines, tidy up a portfolio that's grown out of control, or figure out what to do with extra cash each month, this episode will help you think more clearly about the trade-offs. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (01:41) Is America's housing shortage actually real? (06:29) The real numbers behind the housing shortage (14:29) A stunning stat on building permits vs. new jobs (24:32) A simple way to add housing and earn more (28:23) A caller's plan to retire in 15 years (33:01) Which accounts should hold which investments (40:22) Why more funds can beat fewer funds (52:19) A costly bias that skews money decisions (58:46) Should a 26-year-old rush to pay off his mortgage? (1:09:04) A gut-check for choosing between two paths 🔗 RESOURCES 👉 Free cheat sheet: which investments belong in which account: https://affordanything.com/assetlocation 👉 7 Expensive Rental Property Mistakes to Avoid (free guide): https://affordanything.com/rent 👉 Practical Investing and the Efficient Frontier, with Joe Saul-Sehy: https://www.youtube.com/watch?v=Tz59b5H5puw 👉 Submit your own question for a future episode: https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 what it costs, this episode gives you a clearer read on how the venture world actually works. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (03:41) How venture capital actually works, in three tiers (06:09) The fee formula nearly every venture fund runs on (10:30) Why fund managers get paid before they invest anything (14:19) The surprisingly low bar to invest in risky deals (26:52) What to ask before trusting any fund manager (29:27) How investors make an all-or-nothing bet on one company (34:33) The red flag hiding in an eager fund manager (42:16) What separates a great fund manager from a mediocre one (48:10) How outside money quietly changes what a founder optimizes for (55:47) Why kids today may never remember life before AI 🔗 RESOURCES MENTIONED 👉 The free FiiRE Playbook breaks down all seven entrepreneur types — from bootstrapper to funder — so you can see which game you're actually playing: https://affordanything.com/fiire 👉 David Bell's website: https://www.davidbell.co 👉 Lost and Founder by Rand Fishkin: https://www.penguinrandomhouse.com/books/547217/lost-and-founder-by-rand-fishkin 👉 Burn Rate by Andy Dunn: https://www.penguinrandomhouse.com/books/653309/burn-rate-by-andy-dunn Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 understand why people really open their wallets. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (00:00) Introduction: the invisible forces behind your spending (02:08) From Wharton professor to venture capitalist: meet David Bell (07:32) The Warby Parker origin story: born in office hours (11:27) The "preference minority": why location shapes what you buy (23:12) Beyond necessities: targeting discretionary spending online (31:00) Getting creative offline: postal routes, school buses, and neighborhood showrooms (43:37) Where AI actually fits into consumer innovation (50:49) Touchland: how a "boring" category became a status symbol (55:13) Building a business — and an AI board of directors — from scratch (57:32) Recap: three key takeaways, and what's coming Friday  🔗 RESOURCES MENTIONED 👉 Not sure which kind of entrepreneur you are? Our free 10-day guide helps you find your path — and add the emotional layer that makes people pay more: https://affordanything.com/fiire 👉 David Bell's work at Idea Farm Ventures: https://www.davidbell.co 👉 David Bell's book, Location Is (Still) Everything: https://amzn.to/4aUO3Gh 👉 Touchland, the hand sanitizer brand: https://touchland.com👉 Brad Stone book The Everything Store - Jeff Bezos and the Age of Amazon https://amzn.to/4w6ZT8I Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode732 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 using these tools How to protect your job in your 50s and 60s as companies push AI adoption on everyone Where Marchand thinks the next wave of entrepreneurial opportunity is actually hiding (hint: it's not another app) Whether you're building a team from scratch, trying to decide if a toxic job is worth fixing, or just trying to use AI without losing your edge, this episode gives you practical takeaways you can put to use right away. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:00) – The team breakfast test: how one CEO used a shared meal to hire the right people (17:38) Should you try to fix a bad culture, or start looking for a new job? (26:29) Why people follow good bosses, not companies (28:26) Networking advice for people early in their career (30:25) What heavy AI use might be doing to your memory and thinking (31:06) AI job displacement and the skills worth building now (50:56) Using AI as a thought partner to build emotional intelligence (58:23) Advice for workers in their 50s and 60s worried about AI and ageism (1:06:00) Building a team of humans and AI "agents" — including an AI board of directors (1:14:43) Where Marchand sees the next wave of entrepreneurship and innovation heading 🔗 RESOURCES MENTIONED THE SIMPLE THREE-STEP PROCESS THAT CHANGES HOW YOU THINK ABOUT EVERYTHING 👉https://affordanything.com/turnitaround  Landit – The AI-powered interview and communication prep tool mentioned in the episode 👉 https://www.landitinterview.ai/ Lorraine Marchand's website 👉 https://www.lorrainemarchand.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 eventual estate, she's looking for guidance on how to split the inheritance fairly with her siblings. Share this episode with a friend, colleagues, and your dog sitter4: https://affordanything.com/episode730 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 since 2023, responding to a 10.9 percent surge in energy prices. The Bank of Japan hiked rates to their highest level in 31 years. Australia, Norway, Indonesia, the Philippines and Israel joined in. Brazil was the only country to cut rates – down to 14.25 percent. We cover China's consumer spending decline, the first since the pandemic ended, driven by a 16.1 percent drop in auto sales and a real estate crash that drained middle-class wealth. We end the episode with a deep dive into NYC's rent freeze – who gets the benefit, and who pays the price? ⏱️ Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. (00:00) US Job Market Cooling Off (04:52) Fed’s Stance on Interest Rates (07:29) New Fed Chair Kevin Warsh’s Priorities (17:21) Global Interest Rate Hikes (21:47) Impact of Stable US Rates & Global Trends (26:24) Inflation Data and Predictions (30:38) Consumer Sentiment: US vs. China (40:00) NYC Rent Freeze: History, Policies, and Today Share this episode with a friend, colleagues, and your landlord: https://affordanything.com/episode729 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 stakes are high. When should she ask? How should she ask? And should she be saving differently right now just in case they say no? Mentioned in today's episode: Interview with Family Law Attorney Aaron Thomas https://affordanything.com/episode582 Full show notes at https://affordanything.com/episode728 Download the Four Cornerstones worksheet to see exactly where every dollar belongs https://affordanything.com/cornerstone Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 loops (39:26) Habit 2: Risk — why comfort is killing your courage (54:59) Habit 4: Receive — why you can't hold onto wealth you don't feel worthy of (01:01:41) Habit 5: Repurpose — seeing worth where others see waste __________ 🎧 NEVER MISS AN EPISODE Apple Podcasts: https://affordanything.com/applepodcasts Spotify: https://affordanything.com/spotify __________ 🤗JOIN OUR PRIVATE COMMUNITY: https://affordanything.com/community 🤗STAY IN THE LOOP: https://affordanything.com/newsletter __________ 🛠 TOOLS AND RESOURCES: Check out The 5 Habits of Hope, a book by Dr. Julia Garcia - https://amzn.to/4oUzoRj Dr. Garcia’s Bio - https://www.linkedin.com/in/drjuliagarcia __________ 👀 WATCH THIS VIDEO NEXT: https://youtu.be/TdiyOHkAGiY __________ 👋 SAY HI ON SOCIAL: Facebook: https://facebook.com/affordanything Instagram: https://instagram.com/paulapant X: https://x.com/affordanything #FinancialPsychology #BehavioralFinance #MoneyAndMindset #FinancialGoals Watch the video of this episode https://youtu.be/hx1fJcok6Mk Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 possibility of massive special assessments, aren't discussed more often—and what prospective buyers should know before purchasing in an HOA community.” We'll dig into that in today's episode. Resources: Download the Four Cornerstone Worksheet: www.affordanything.com/cornerstone 7 Expensive Mistakes Real Estate Investors Make: http://afforanything.com/mistakes Video: Japan's Soccer Fans with Blue Bags Video: Norway's Vikings Fans on Escalator Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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" problem. Many people have a financial advisor, an estate planning attorney, an accountant, and an insurance agent - but those specialists never talk to each other. Without someone coordinating the full picture, opportunities get missed and risks go unseen. We also talk through what happens when people try to manage everything themselves, why having multiple investment advisors can actually backfire (think: wash sale rule violations and hidden concentration risk), and why a revocable trust matters even if you don't think you're wealthy enough to need one. Lustig explains the three Ps a revocable trust protects against - probate, incapacitation, and privacy - and why even people in their 30s and 40s should consider setting one up now. The conversation closes with advice for small business owners on how to think about a business that might not be sellable - and how to plan around it anyway. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Intro (04:52) Three types of financial advisors explained (07:11) Fiduciary vs. best interest standard (13:21) Dangers of dually registered advisors (17:26) Why you need a planning quarterback (22:42) Risks of using multiple investment advisors (35:10) Who benefits from holistic wealth management (38:50) The three Ps of a revocable trust (42:19) Returning to the blind spots overview (45:40) Risks of managing money yourself (55:13) Key questions to ask a new advisor (1:03:34) Index funds vs. active management (1:10:04) Asset allocation and rebalancing strategy (1:19:10) Legacy planning for small business owners (1:25:54) How to spot your own blind spots Resources: Book: Legacy on the Line: Overcome Blind Spots to Grow and Transfer Your Wealth by Andrea Baumann Lustig Free download: The FiiRE Playbook Share this episode with a friend, colleagues, and your estate attorney: https://affordanything.com/episode725 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 than smoothing over disagreements to keep the peace. We also talk about what individual employees can do when they work inside slow, tradition-bound organizations. The short answer: find the people who share your interests, build a coalition, and work your way up - not by chasing the most powerful person in the room, but by starting with whoever cares about the same problem you do. The conversation touches on AI and what it actually takes to stay relevant as a knowledge worker. Linda and Jason both land on the same answer - the ability to build trust and relationships in low-trust environments is one of the hardest things for AI to replicate. Linda and Jason can be found at geniusatscale.com Download the FIIRE playbook: affordanything.com/FIIRE 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) Innovation leadership and the ABC framework (02:19) Architect, Bridger, and Catalyst roles (04:18) Studying Pixar and innovation cultures (06:14) Co-creation versus consensus thinking (07:12) Creative abrasion and productive debate (08:41) Bridgers connecting teams and partners (10:50) Delta biometric boarding pass example (12:56) Relationship skills in the AI era (15:40) AI, trust, and human judgment (18:50) Rio collaboration across government silos (22:53) Innovating inside traditional organizations (25:18) ANA teleportation project and coalition building (30:49) Power of questions for innovation (32:42) Shared purpose versus top-down purpose (43:27) Better decision-making through clear criteria Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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, brings "restaurant freedom."  Level 4, the $1 million to $10 million range, unlocks "travel freedom." Getting beyond Level 4 — into the $10 million-plus territory — requires business ownership or extreme patience. Maggiulli calculates that even saving $100,000 annually after hitting $1 million takes 23 years to reach $10 million, assuming 5 percent annual returns. The data shows income matters more than frugality, especially in the early levels. The median household income in Level 1 is $32,000, but in Level 4 it's $197,000, and in Level 6 it reaches $4.3 million. We discuss why homeownership dominates wealth in Levels 2 and 3, how investment assets become crucial in higher levels, and why many people in Level 4 choose "Coast FIRE" over the grinding path to Level 5. Resource Mentioned: Nick's book: The Wealth Ladder: Proven Strategies for Every Step of Your Financial Life Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Introduction to wealth ladder concept (1:35) The 0.01% daily spending rule (3:43) Six wealth levels breakdown (7:35) Level 1 survival mode focus (11:21) Six levels population data (13:02) Level 1 bad luck amplification (15:08) Level 2 skills development priority (17:55) Income and wealth correlation data (25:28) Level 2 education strategies (28:05) Income opportunity heuristics discussion (32:24) Level 2 mobility statistics (36:38) Asset composition shifts by level (39:28) Level 3 to 4 progression (46:52) Level 3 and 4 similarities (50:14) Level 4 to 5 math (53:29) Business ownership requirements for Level 5 (56:07) Level 5 and 6 non-monetary focus (59:07) Wealth movement bidirectional data (1:04:09) Key takeaways summary begins For more information, visit the show notes at https://affordanything.com/episode629 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 mentioned: Charlotte's original call: affordanything.com/episode352 Paula interview on Emma Chamberlain's podcast: youtube.com/watch?v=VOP7S4w8s0I Midterm Rentals with Jeff Hurst: affordanything.com/episode712 Interview with Brad Klontz, Ep127: affordanything.com/episode127 Interview with Brad Klontz and Adrian Brambila, Ep551: affordanything.com/episode551 Share this episode with a friend, colleagues, and your AirBNB tenants: https://affordanything.com/episode722 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 (33:04) Prescription drug prices drop (39:24) SpaceX IPO plans and demand Resources: JP Morgan article: https://am.jpmorgan.com/us/en/asset-management/adv/insights/market-insights/guide-to-the-markets Free download: Asset Location Made Simple https://affordanything.com/assetlocation Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Join the Afford Anything Community: affordanything.com/community Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 specifics — morning light, circadian rhythm, deep sleep, and why 10 minutes outside before you check your phone can improve focus, sleep quality, and even how big the world feels. Dr. La Puma explains why "just get outside more" misses the point: light has a dosage, a timing, and a location, the same way a financial strategy has specific mechanics. For knowledge workers in cities, we talk through the real-world friction — Manhattan apartments, extreme heat, early wake-ups before sunrise — and what to do when those conditions make outdoor time inconvenient. There are practical workarounds, and Dr. La Puma covers them. The episode closes on a reframe: health and productivity aren't in conflict. Better sleep, more natural light, and regular time outside don't slow you down. They make the hours you do work more effective. Resources mentioned: John La Puma MD's book - Indoor Epidemic: 93% Inside Steals Sleep, Focus & Years—The 7% Outdoor Rx Restores Them Dr. John La Puma's website https://www.drjohnlapuma.com f.lux screen spectrum app https://justgetflux.com Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Your Office Is Making You Sick (03:01) Health cost of indoor living (04:58) Digital obesity explained (09:24) Minimum effective dose of nature (12:10) Why burnout is a biology problem (15:15) Morning light and deep sleep (17:11) Light first, coffee second (28:12) What happens during deep sleep (36:54) Workplace study results (45:23) Pink noise, brown noise, and sleep (54:45) Why blue-light glasses fall short (59:48) Outdoor tips for remote workers (1:04:55) Green exercise as a nature dose (1:10:10) Mental health cost of indoor life (1:14:51) Modeling outdoor habits for kid Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode719 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 later to review it honestly. She was wrong. Equities kept climbing. But having a written thesis let her make a clean new decision rather than doubling down out of ego. We also walk through five investor archetypes drawn from behavioral research on fund managers. Connoisseurs let winners run. Raiders take profits too early. Rabbits freeze — or keep buying into a losing position. Hunters wait and take calculated shots. Assassins cut losses cleanly, without emotion. Most people default to rabbit behavior when things go south. The goal is to be an assassin. Clare's practical rule: don't let any single position drag your overall portfolio down more than 1 percent before forcing yourself to reassess. Her closing advice for long-term investors: ask yourself five simple questions before every major move, write down your reasoning, and go back and check. 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) 5 Ways Investors Behave When Things Go Wrong (05:20) Clare Flynn Levy — hedge fund manager turned behavioral finance analyst (06:50) 2008 crisis — watching screens turn red daily (08:25) Sunk cost fallacy and the endowment effect — why investors hold losers too long (10:25) Index funds — riskier than most people think (17:09) Tech concentration — how indexes got warped (27:52) Algorithmic trading — machines changing the game (29:37) Playing the wrong game — taking cues from short-term traders (31:22) Individual stocks — same behavioral traps apply (35:22) Hit rate vs. payoff ratio — what actually drives returns (44:57) Five investor archetypes — how you behave when winning and losing (50:17) Alpha decay — when to exit a winning position (54:22) Being an assassin — rules for cutting losses without emotion (59:42) Decision journaling — five questions to ask before every move (01:03:22) Quarterly snapshots — simple way to track your own patterns (01:05:22) Closing advice — discipline, patience, and realistic expectations Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 podcastchoices.com/adchoices

#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 your mindset by replacing limiting beliefs, and act. The final step is tactical: a 15-minute timer, one small action, and a monthly money date to review spending and set goals. We also get into the concept of financial energy - the idea that you have a finite amount of mental bandwidth for money decisions each day. Spending it on coupons and skipping lattes leaves nothing left for the moves that actually build wealth: negotiating a raise, automating savings, maxing out tax-advantaged accounts. Haley also breaks down learned financial helplessness - the belief that the system is too broken to bother trying - and why pushing back against it puts you ahead of most people before you've done a single thing. 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) — Your Childhood Is Running Your Bank Account (08:42) — Money beliefs form by age 7 (11:35) — Why financial independence matters (13:00) — The Momofuku story (17:04) — "Financial energy" — and why you're wasting it (24:35) — The IBIZA framework, explained (28:32) — I: Identify your money origin story (31:07) — "If you don't control your money, it controls your life" (32:31) — How pop culture shapes money beliefs (46:51) — I: Interrupt old patterns (54:24) — Learned financial helplessness (55:59) — Z: Zhuzh your mindset (59:06) — The Tyra Banks story (1:02:54) — A: Act — the 15-minute starter move (1:06:18) — The monthly money date Resource: Haley's book - Future Rich Person: The New Rules for Building Wealth (Even if You're Stuck, Broke, and that Billionaire Won't Text You Back...) Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 assumptions behind them, and how to think through each decision. Share this episode with a friend, colleagues, and your Uber driver: https://affordanything.com/episode714 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 full-time work jumped by 445,000 in a single month. Consumer sentiment is at its lowest point in 74 years of University of Michigan tracking - worse than 2008, worse than the inflation of the 1970s. One reason: gas prices. There's a psychological outsized effect to standing at a pump watching the total climb every week, versus an invisible mortgage adjustment buried in a monthly bank statement. The housing market didn't get its usual spring bounce. Existing home sales ticked up just 0.2 percent between March and April. Inventory rose 5.8 percent, but at 4.4 months of supply, the market still needs roughly 30 percent more inventory to reach balance. Median sale price sits at $417,700, up less than 1 percent year over year. Homes are averaging 32 days on market - giving buyers more negotiating leverage than they've had in years. Timestamps: (00:00) April jobs report: 115,000 new jobs, but tech takes a hit (02:38) Jobs data matters more than the stock market (03:14) Where jobs grew: healthcare, transportation,warehousing, retail (05:14) Consumer sentiment hits 74-year low (07:46) Why gas prices hurt more than other costs (11:20) Tech sector down 342,000 jobs from 2022 peak (11:52) Part-time workers up 445,000 in a single month (13:38) Housing market: no spring rebound (15:16) Inventory up, but still 30 percent below a balanced market (16:16) Housing market frozen - not crashing, not skyrocketing (17:13) Golden handcuffs: why sellers aren't selling (18:23) Why buyers have more negotiating power now Enroll in our course, "Your First Rental Property" while the doors are open! https://affordanything.com/enroll Share this episode with a friend, colleagues, and your postal person: https://affordanything.com/firstfridaymay2026 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 properties for her sisters and stepdaughter, neither of whom asked for them. We also get into the emotional mechanics of financial shame - specifically, how shame blocks access to solutions you already have. Aliche says she grew up with a CFO father who taught her exactly how to budget, save, and invest. None of that knowledge was available to her at rock bottom, because shame had walled it off. The fix, she says, was simply saying it out loud to a friend. The conversation covers people-pleasing as an under-discussed form of financial self-sabotage, the current economic disconnect between paper wealth and lived experience, and a practical exercise for figuring out whether you already have enough money to fund the life you actually want. Resource: Tiffany Aliche's book - Get Good With Money: 10 Simple Steps to Becoming Financially Whole Share this episode with a friend, colleagues, and your CFO: https://affordanything.com/episode713 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 returns, estimate vacancy, and use tools like Furnished Finder's market insights tab and AirDNA data to vet a market before you buy. On the question of where to invest, Jeff walks through a layered research approach - starting with population migration, proximity to hospitals and universities, commuter corridors, and school districts. He's bullish on mid-sized cities with data center build-outs and expanding healthcare infrastructure, and argues that markets like those around northwest Arkansas, parts of Texas, and mid-sized Midwestern cities offer better risk-adjusted returns than the leisure destinations that dominated the short-term era. Jeff also covers HOA red flags to look for, how to approach off-market deals, what the regulatory environment looks like for midterm (spoiler: almost no city is restricting it), and why the category today feels a lot like short-term rentals at their peak. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Intro (05:12) What midterm rentals are (07:00) Why cities banned short-term rentals (08:19) Who rents midterm — nurses, corporate workers, relocating families (14:45) Extended stay hotels vs. midterm rentals (16:34) Hospitality expectations for hosts (19:22) How much to spend on furnishings (21:02) Regulatory risk — nearly zero (32:16) How to estimate vacancy and returns (45:58) How to pick a market (52:16) Why mid-sized cities win (57:42) Following extended stay hotel construction as a demand signal (1:13:00) Who owns midterm rentals — older than you'd think (1:14:36) Why midterm feels like AirBNB in 2012 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 way to gauge how connected - and how useful - a community actually stays after graduation. On the debt question, Lieber draws a clear line between federal undergraduate loans, which cap around $31,000, and the more dangerous combinations of Parent PLUS loans and private debt that drive the horror stories you see in the news. He also addresses the community college path in detail - including what it actually takes to pull it off without losing time or credits along the way. The conversation closes with a framework for parents: keep sparking conversations with your kids, stay curious about what they're drawn to, and treat yourself less as an advice-giver and more as someone planting seeds. Share this episode with a friend, colleagues, and your college student: https://affordanything.com/episode711 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) No BLS jobs report today  (01:41) Ron Lieber intro – NYT personal finance columnist, student debt expert (02:41) College still worth it? Ron says yes, despite tough entry-level job market (05:03) How to use the College Scorecard  (06:27) Liberal arts majors often catch up by mid-career  (07:17) The non-financial ROI of college  (15:08) How much debt is too much? Federal undergrad cap is $31,000 (18:31) Community college as a launchpad; savings potential, but requires high executive functioning (21:36) Scary student debt headlines are mostly about grad school, not undergrad (24:39) AI and shifting willingness to pay; colleges facing enrollment pressure (37:00) Financial aid office dynamics  (40:39) Peak 18-year-olds; demographic cliff hits colleges differently by region (45:54) Location matters; urban schools have recruiter and networking advantages (54:11) Framework for parents and students; stay curious Resource: Ron Lieber's book - The Price You Pay for College: An Entirely New Roadmap for the Biggest Financial Decision Your Family Will Ever Make Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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. Resources Mentioned: Listen to Kip’s previous question: https://affordanything.com/episode627 Don’t miss the YFRP Webinar! https://affordanything.com/rental2026 Join the YFRP waitlist:⁠ https://courses.affordanything.com Stay in the Loop:⁠ https://affordanything.com/newsletter⁠ Die with Zero, a book by Bill Perkins: ⁠https://amzn.to/3P1ydBS⁠ Share this episode with a friend, colleagues, and your arborist: https://affordanything.com/episode710 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Keith recommends a special needs trust for most families. Assets held in the trust don't count against federal benefit limits. He also recommends pairing the trust with a "second to die" life insurance policy - one that pays out after both parents are gone - to help fund it. ABLE accounts round out the toolkit. Similar to a 529 plan, they allow tax-free contributions of up to $20,000 per year for a person with a qualifying disability. The funds cover everyday expenses like food, transportation, and entertainment. Unused 529 funds can also be rolled into an ABLE account, up to $20,000 per year. Keith also addresses trustee succession - who manages the money after the parents are gone, and who steps in after that person. His advice: start building a network early, revisit the plan every few years, and bring siblings into the financial conversation sooner than feels necessary. 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) The Financial Reality of Developmental Disabilities (02:00) Caregiving's financial toll on families (03:41) Keith's background (04:26) His son AJ's diagnosis and journey (07:08) Rights and services end at age 22 (08:06) Medicaid, SSI, and SSDI explained (14:12) The $2,000 asset limit for SSI eligibility (14:33) Why special needs trusts matter (16:04) Life insurance as a funding tool (23:08) Planning two retirements simultaneously (25:04) ABLE accounts - the basics (27:06) ABLE account balance limits by state (36:35) Employment opportunities for neurodiverse workers (42:11) Fraud and safety risks to be aware of (51:15) Trustee succession planning (53:22) Rolling 529 funds into ABLE accounts Learn more about your ad choices. Visit podcastchoices.com/adchoices

#708: What’s the smartest way to handle big financial transitions—when the stakes are high and the “right” answer isn’t always obvious? Anonymous “Cyndi Jr.” is helping their 73-year-old mother relocate across the country and needs to decide how to use the proceeds from a home sale to balance long-term housing security with inflation protection. Anonymous is trying to figure out how to handle quarterly estimated taxes on investment income—without relying on safe harbor rules that don’t always reflect market swings. Luz, whose previous question was featured on the show, is now navigating a major job change and wondering what to do with an old 401(k)—while also rethinking how Roth accounts, an HSA, and debt all fit into a bigger financial strategy. We’ll walk through each of these and help you think it through in today’s episode. Resources mentioned: Don’t miss the YFRP Webinar! https://affordanything.com/rental2026 Join the YFRP waitlist: https://courses.affordanything.com Listen to Luz’s previous question: https://affordanything.com/episode583 Stay in the Loop: https://affordanything.com/newsletter Share this episode with a friend, colleagues, and Cyndi Lauper: https://affordanything.com/episode708 Learn more about your ad choices. Visit podcastchoices.com/adchoices