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#759: At 19, Jaspreet Singh bought a rental for $8,000. What followed was a nightmare tenant, a lawsuit, and a later house stripped of its copper, and it taught him what the real estate books leave out. Jaspreet is the founder of Minority Mindset, a personal finance YouTube channel with more than 2.5 million subscribers, and CEO of Briefs Finance. He’s also a licensed attorney who chose to build businesses instead of practicing law. Avoid these 7 expensive rental property mistakes → https://affordanything.com/rent In this episode, we discuss: How hiring the cheapest property manager can cost you the most Why skipping a $200 inspection led to his worst deal ever Why an employee who’s just coasting hurts a small team more than a weak one A simple two-list exercise that shows whether your hard work actually pays How the tax code rewards owners and investors over employees How a terrible market timer who never sold still turned $100,000 into more than $1 million Where AI’s ripple effects could create opportunities beyond the AI companies themselves Whether you’re weighing a first rental, a business, or simply investing more consistently, this conversation shows what each path really costs and how to learn those lessons for less than Jaspreet paid. 🔗 RESOURCES MENTIONED JASPREET LEARNED RENTALS, BUSINESS, AND INVESTING THE EXPENSIVE WAY. MAP YOUR OWN PATH FOR FREE 👉 https://affordanything.com/fiire Minority Mindset on YouTube 👉 https://www.youtube.com/@MinorityMindset Briefs Finance and the free Market Briefs newsletter 👉 https://www.briefs.co Learn more about your ad choices. Visit podcastchoices.com/adchoices

#758: Joe says that if you tell an employer you’re not motivated by money, you’re unemployable. Paula says that’s exactly the person she wants to hire. Former financial planner Joe Saul-Sehy joins Paula to answer a question from a 26-year-old whose net worth is already 10 times her annual spending. Then they take on two more: whether target date funds are worth it, and whether a dad of young kids should make a career change that cuts his income by 60%. In this episode, we discuss: Why not being motivated by money can make you a better hire The two traits Paula looks for when she hires How to tell whether a small business is a good place to work, and when it isn’t A quick test for whether you’d actually enjoy your coworkers When a target date fund makes sense, and when it holds you back How to decide whether to make a big career change now or wait Why your savings might be meant for exactly this kind of leap If you’ve saved enough that a paycheck no longer drives your choices, this episode will help you figure out what should. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:32) She’s 26 and no longer motivated by money (07:23) What Paula looks for instead of money motivation (12:54) The hidden risk of working at a tiny company (24:55) The 8-hour layover test for coworkers (33:05) Why Paula put her parents in target date funds (40:24) Joe’s 30-minute alternative to target date funds (51:33) Why your 401(k) target date fund may be junk (58:33) The case for target date funds as harm reduction (01:08:01) Should he take a 60% pay cut to switch careers? (01:13:37) Why waiting “one more year” rarely helps 🔗 RESOURCES MENTIONED 👉 Building your own mix instead of a target date fund? See which account each fund belongs in: https://affordanything.com/assetlocation 👉 Episode #709, planning for a child with special needs, with Keith Wargo: https://affordanything.com/709-the-financial-reality-of-developmental-disability-with-keith-wargo/ 👉 Stacking Benjamins, Joe’s podcast: https://www.stackingbenjamins.com/ 👉 Strategic Coach, the entrepreneur coaching program Joe recommends: https://www.strategiccoach.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney. At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Steve Jobs to hire him to build the Apple Store. Years later, he took over JCPenney and watched it fail for a reason that had nothing to do with his vision. Ron Johnson created the Apple Store and worked directly for Steve Jobs for 12 years, after bringing designer products to Target. He later served as CEO of JCPenney and is the author of Shop Different. In this episode, we discuss: How to weigh a lower-paying job that teaches you more How to set goals big enough that people work harder How to persuade a team whose top priority is not getting fired How to change a strong-willed boss’s mind Why a bold plan fails without trust, and how to build trust first What a rush of early customers can hide about a new business How to get out of your head when you’re overthinking a decision Whether you’re weighing a career risk, building a business on nights and weekends, or trying to get people behind a bold idea, this conversation shows what it takes, and what it costs to skip a step. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:14) Why a few columns made Steve Jobs furious (08:44) How he talked Steve Jobs into shopping malls (15:33) Why he turned down $120K to unload trucks (22:10) Why big goals beat small improvements (29:24) How to sell a risky idea to cautious coworkers (37:02) The $30 tea kettle that caught Steve Jobs’ eye (46:02) Why a record-breaking opening day was misleading (56:26) How a hotel inspired the Genius Bar (1:14:40) Why JCPenney failed: trust, not vision (1:35:54) How to escape analysis paralysis 🔗 RESOURCES MENTIONED 👉 Would you turn down $120K for work you love? Find out what’s really driving your money choices: https://affordanything.com/fiire 👉 Ron’s Book, Shop Different: https://amzn.to/4yFA1SH  👉 Ron’s website: https://ronjohnsonshopsdifferent.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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