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Afford Anything | Make Smart Money Choices

Cumulus Podcast Network

You can afford anything, but not everything. We make daily decisions about how to spend money, time, energy, focus and attention – and ultimately, our life. How do we make smarter decisions? How do we think from first principles? On the surface,...

Location:

United States

Description:

You can afford anything, but not everything. We make daily decisions about how to spend money, time, energy, focus and attention – and ultimately, our life. How do we make smarter decisions? How do we think from first principles? On the surface, Afford Anything seems like a podcast about money and investing. But under the hood, this is a show about how to think critically, recognize our behavioral blind spots, and make smarter choices. We’re into the psychology of money, and we love metacognition: thinking about how to think. In some episodes, we interview world-class experts: professors, researchers, scientists, authors. In other episodes, we answer your questions, talking through decision-making frameworks and mental models. Want to learn more? Download our free book, Escape, at http://affordanything.com/escape. Hosted by Paula Pant.

Language:

English

Contact:

707-728-5202


Episodes
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Q&A: The Goalposts Moved — Is That Actually a Problem?

5/26/2026
#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

Duration:00:41:41

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The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy

5/22/2026
#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

Duration:01:05:37

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Q&A: Your Kids Just Inherited $350,000 Each. Now What?

5/19/2026
RSVP for Paula's Open House to Your First Rental Property TONIGHT (May 19th): ⁠https://affordanything.com/openhouse⁠ #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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:13:35

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Mrs. Dow Jones: Your Childhood Is Running Your Bank Account

5/15/2026
#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:09:16

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Q&A: Should I Sell One Property to Pay Off Another?

5/12/2026
#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. Resources: TONIGHT, May 12th: "Can You Still Buy a Profitable Rental Property in 2026?" webinar. Register for free here: https://affordanything.com/rental2026 Share this episode with a friend, colleagues, and your Uber driver! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:00:55:59

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BONUS: The Economy Added 115,000 Jobs. Consumer Confidence Just Hit a 74-Year Low. Let’s Unpack This.

5/11/2026
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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:00:24:16

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Why Smart People Still Sabotage Their Own Money, with Tiffany Aliche

5/8/2026
#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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:14:13

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The Rental Strategy That Survived Every City Crackdown, with Jeff Hurst

5/5/2026
#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

Duration:01:32:49

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Is a Computer Science Degree Still Worth the Debt?, with Ron Lieber

5/1/2026
#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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:00:07

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Q&A: He Wants to Die With Zero – Here’s How to Spend $1M Without Running Out

4/28/2026
#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:12:37

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The Financial Reality of Developmental Disabilities, with Keith Wargo

4/24/2026
#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

Duration:01:00:50

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Q&A: My Mom Is 73. She Has a House — But It Doesn’t Pay the Bills. Now What?

4/21/2026
#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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:09:17

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Q&A LIVE from Texas A&M Texarkana

4/17/2026
#707: Joe and I traveled to the campus of Texas A&M University-Texarkana for a very special live recording. We were joined by Jay Davis, the Executive Director of Financial and Entrepreneurship Engagement, to answer questions from an incredible audience of students. Whether you’re just starting your career or looking to "reset" your habits, this episode covers the essential transition from the classroom to the professional world. Student Questions Hannah (Psychology Major): How do I navigate the trade-offs between passion, a paycheck, and peace of mind in my 20s without having regrets later? Hannah (Second Student): As I move from a student budget to a professional salary, how do I prevent "lifestyle creep" from eating my first big raise? Gabriel: How do I find the middle ground between being responsible for "Future Me" and actually enjoying my life while I’m young? Stephano: When is the right time to start investing, and how do I balance that with paying down student loans? Valarie: How do I build a solid credit score as a student without falling into the trap of high-interest debt? Thomas: What are the most important "marketable skills" I should be developing now to ensure financial security later? Key Takeaways Follow Curiosity Over Passion: Passion is often a side effect of mastery, not the starting point. Follow your curiosity into deep learning; the fulfillment (autonomy, mastery, and purpose) will follow once you become an expert in your craft. Build Your "Bravery Fund": High marketable skills and a solid emergency fund give you the freedom to take risks. If you have a financial cushion and low fixed costs, you have the "bravery" to pivot careers if your first choice isn’t the right fit. Automate Your Success: The most effective way to beat lifestyle creep is to "hide" your raise from yourself. Set up automated transfers to retirement accounts or debt repayment for the same day your paycheck hits your account. Beware of High Fixed Costs: Avoid the "new grad" trap of heavy car payments ($700–$1,000/month). These high monthly obligations are the biggest inhibitors to your future housing flexibility and career mobility. The 24-Hour "Fun" Rule: To balance current enjoyment with future savings, create a deliberate "yes" list. If you want to spend on a hobby or experience, wait 24 hours to ensure it’s a conscious choice rather than an impulse. Resources mentioned: Don’t miss the YFRP Webinar on May 12th! ⁠https://affordanything.com/rental2026 A&M University Website: https://www.tamut.edu Grab a copy of Deep Work by Cal Newport: https://amzn.to/4truxs3 Receive our newsletters https://affordanything.com/newsletter Don’t miss the YFRP Webinar on May 12th! https://affordanything.com/rental2026 YNAB for students: https://www.ynab.com/college Chapters Note: Timestamps are approximate and may vary across listening platforms due to dynamically inserted ads. (00:00) The Abridged Live Performance from Texas A&M Texarkana (01:19) Hannah’s Question: Passion vs. Paycheck (06:31) The "Bravery Fund" & Your Freedom to Pivot (13:35) Hannah’s Question: Defeating Lifestyle Creep (20:43) Gabriel’s Question: Future You vs. Present You (30:57) Stephano’s Question: Debt vs. Investing (41:55) Valarie’s Question: Building Credit Responsibly (50:15) Thomas’s Question: Developing Marketable Skills Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:00:50:21

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Q&A: The Case for NOT Paying Off Your Student Loans

4/14/2026
#706: When the numbers look straightforward—but the rules, timing, and future are uncertain—how do you decide what to do next? KJ has $90,000 in student loans, a recent inheritance, and a lot of uncertainty around changing repayment policies, and is trying to decide whether to pay down debt now or hold onto cash in case future payments become unaffordable. Anonymous (let’s call her Andrea) is about seven years away from retirement with $1.9 million saved and is thinking about sequence of returns risk, and is wondering whether working part-time could help protect against a poorly timed market downturn or simply delay the risk. Anonymous (let’s call him Andrew Ryan) is a retired homeowner in their early 70s who recently bought a second home to be closer to family and is planning to rent it out part of the year, and is wondering how to structure it and how taxes work for a property that’s both personal and income-producing. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:12:30

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What to Fix First When Everything Feels Stuck, with former Lyft COO and Tesla President Jon McNeill

4/10/2026
#705: Jon McNeill, former president of Tesla and COO of Lyft, starts with a simple problem: his teenage son is about to start driving, and he’s worried about texting behind the wheel. Instead of setting rules, he builds a solution. That idea becomes TruMotion, a company that uses smartphone sensors to track driving behavior. You hear how the app figures out whether someone is actually in the driver’s seat, and how that technology ends up powering programs used by major insurance companies. From there, we zoom out. McNeill walks us through the systems he uses to build and scale companies. He explains how to question assumptions, including a case where his team reduces a 12-page car loan document down to a few sentences after realizing none of it is legally required. We also talk about speed. At Tesla, he learns to make decisions quickly, even without perfect information. He describes how faster decision-making compounds advantage over time. You hear a story from his early days working with Tesla, when he visits multiple stores, signs up for test drives, and never gets a follow-up. That leads him to identify thousands of missed sales opportunities sitting in the pipeline. The fix comes from focusing on the bottleneck, not adding more leads. McNeill also shares how he approaches negotiations at scale, including working with government officials in China and learning how incentives and systems shape outcomes. Throughout the conversation, he returns to a few core ideas: simplify the problem, identify the constraint, and move quickly once you have enough information to act. McNeill’s new book is The Algorithm: The Hypergrowth Formula That Transformed Tesla, Lululemon, General Motors, and SpaceX. 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) Jon McNeill, former Tesla President and former COO of Lyft (06:50) The "First Principles" Mindset (15:05) Managing Hyper-growth at Tesla Solving for "Pain Points" vs. Chasing Profit Autonomous Driving and Electric Vehicles Working with Visionary Founders Building a Culture of Innovation in any Organization Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:27:58

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Q&A: Should I Quit My Job to Be a Stay-at-Home Dad

4/7/2026
#704: How do you make smart financial decisions when you’re balancing debt, investing, and big life changes … all at the same time? Today, Brigham and his wife, ages 25 and 23, wonder: can they buy a $500,000 home AND still support a stay-at-home parent? Next, JVR asks how to balance high-interest credit card debt, student loans, and a large cash reserve while planning for a future home purchase in the Bay Area. Then we’ll hear back from Elizabeth, from Episode 611 (from just under 1 year ago), with an update and a follow-up question on how to approach real estate investing over the next five years when she’s unsure where she’ll ultimately settle. We’ll cover all of that in today’s Q&A episode. Resources: Elizabeth's (formerly Anonymous) original call: https://affordanything.com/episode611 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:00:52:16

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First Friday: Jobs Are Up. So Why Does the Economy Feel Worse?

4/3/2026
#703: April’s jobs report comes in much stronger than expected, with 178,000 jobs added and unemployment ticking down to 4.3 percent. That headline deserves a closer look, especially when other labor data still points to a slower, lower-hiring environment.From there, we break down what the latest Fed decision means, why mortgage rates remain elevated, and how a sudden spike in oil and gas prices could affect inflation, consumer sentiment, and the broader economy. We also cover recent market volatility and why long-term investors may want to think differently about short-term swings. In the second half: News involving Vicki Robin that has rippled through the FIRE community, proposed changes could expand what 401(k) plans can hold, and major student loan developments — including the end of the SAVE plan and what borrowers should be watching next. Vicki Robin links: Paula’s Newsletter - https://ckarchive.com/b/0vuwh9h9e4289c7mggrmzhv8qo9rqhnh50v Vicki’s Substack - https://vickirobin.substack.com/p/abusers-and-the-women-who-love-them Afforder Community - affordanything.com/community Sources: https://www.advisorperspectives.com/dshort/updates/2026/03/31/jolts-report-job-openings-february-2026 https://www.challengergray.com/blog/challenger-report-march-cuts-rise-25-from-february-ai-leads-reasons https://www.dol.gov/newsroom/releases/ebsa/ebsa20260330 https://myeddebt.ed.gov 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) A busy start to April(01:03) Stronger than expected jobs report(06:06) A softer picture for job openings(07:13) Where layoffs are showing up(10:15) Why the Fed held rates steady(12:05) What’s keeping mortgage rates elevated(21:05) Why gas prices rose so quickly(27:28) How to think about market volatility(30:20) A proposed change for 401k plans(32:37) News from Vicki Robin(40:55) A shift in student loan management(42:37) What the end of SAVE means(45:16) Changes for Parent PLUS borrowers Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:00:40:49

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Q&A: Why 3 Years Is a Weird Timeline for Money

3/31/2026
#702: Olivia is saving for a specific three-year goal and wants to know whether a money market fund is the right place to store that cash, or if a traditional savings account would be safer. Robert is planning to retire early in the next few years and is trying to decide whether to prioritize building taxable investments or continuing to grow Roth accounts. And finally, we’ll hear from a listener with nearly 30 years of experience in social work who wants to open an adult day center in a rural area where services for disabled adults are extremely limited—but isn’t sure whether to structure it as a nonprofit or a for-profit business. We’ll tackle all of that on today’s episode. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:03:10

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What Retirement Planning Gets Wrong, with Jamie Hopkins

3/27/2026
#701: Forget the idea that you need a magic number to retire. Jamie Hopkins is a certified financial planner, professor of taxation at the American College of Financial Services, director of the New York Life Center for Retirement Income, and Top 40 Under 40 financial services professionals from InvestmentNews. His take on retirement planning will make you rethink a few things. We start with the "no magic number" concept. Hopkins explains that fixating on a savings target - whether it's $1 million or $10 million - misses the point. What matters is what income you can generate relative to the lifestyle you want. And that lifestyle shifts. Research shows retirees often spend more than 100 percent of their pre-retirement income in the first few years, then gradually spend less as they age. From there, we get into sequence of returns risk, which Hopkins calls one of the biggest threats to any retirement plan. A market downturn in the first few years of retirement can be nearly impossible to recover from, since you're withdrawing money while your portfolio is declining. We also dig into the well-known "4 percent rule" - which Hopkins prefers to call a "4 percent finding" - and why it only holds up in certain historical contexts. The conversation also covers the topics people tend to avoid. "Silver divorce" - the spike in divorces among people over 60 - is happening at higher rates than most people realize, and it can gut a retirement plan that was built around shared costs and two incomes. We also discuss elder abuse, which Hopkins says is mostly committed by family members or trusted advisors, not strangers - and how AI-generated voice cloning is making financial scams harder to detect. Finally, we end on what Hopkins considers the most important, and most overlooked, element of a good retirement: community. He argues that retirement is actually an ideal time to intentionally rebuild your social circle, choose where you want to live, and figure out what you're retiring to - not just from. Hopkins holds a JD, MBA, LLM, CFP, RICP, CLU, and ChFC. Resources: Jamie’s Book: Your Retirement Sketchbook: 125 Retirement Planning Lessons from Financial Experts Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:31:28

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Q&A: A $30K Promotion Near FI, Learning Put Options, and Scaling a 16-Unit Portfolio

3/24/2026
#700: Today we’re tackling three different financial questions from our listeners. First, we’ll hear from Melanie, who is deciding whether to pursue a promotion that would increase her salary by $30,000 but may add more stress, even though she’s already close to financial independence. Next, Ami wants to learn how options trading works and is wondering how to find legitimate training without falling into expensive or questionable courses. And later in the episode, we’ll revisit Ben who called in six years ago asking how to grow from four rental units to twenty. Today he owns sixteen units and is deciding how to scale from here. We’ll tackle all of that on today’s episode #700!!! Resources: Interview with Rose Han: affordanything.com/episode652 Jeanne_Retired on TikTok (shared by Joe): https://www.tiktok.com/@jeanne_retired/video/7615363778938408223 Ben's original question on Episode 243: affordanything.com/episode243 Share this episode with a friend, colleagues, and your bank teller: https://affordanything.com/episode700 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Duration:01:10:22