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#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

#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

#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. Share this episode with a friend, colleagues, and Ryan Gosling: https://affordanything.com/episode706 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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

#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 Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode704 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Share this episode with a friend, colleagues, and your airline gate agent: https://affordanything.com/episode703 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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! Share this episode with a friend, colleagues, and Conan O'Brien: https://affordanything.com/episode702 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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 Share this episode with a friend, colleagues, and your frenemies: https://affordanything.com/episode701 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#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

#699: You've probably heard that mindset matters. But what does that actually mean, and is there science behind it? Nir Eyal, author of Beyond Belief, joins us to break down the research. Eyal, who writes about the intersection between psychology and technology and taught at Stanford Graduate School of Business, opens with a counterintuitive claim: Motivation has nothing to do with rewards, he says. All motivation, he argues, stems from the desire to escape discomfort. That means money management, time management, and weight management are all really just pain management. That reframe sets up a bigger argument about beliefs. Our brains can't process the roughly 11 million bits of information hitting them every second, so instead of seeing reality, we predict it - based on whatever we already believe. That's why two people can face the same circumstances and have completely different outcomes. We dig into why visualization often backfires. Research by psychologist Gabrielle Oettingen found that people who pictured their ideal outcomes became less likely to do the work to achieve them. Athletes don't visualize trophies - they visualize obstacles. Eyal calls the productive version "mental contrasting": imagining what's in your way and planning how you'll handle it. We also cover the difference between limiting beliefs and liberating ones, and walk through a four-question exercise called a "turnaround" - a technique from Byron Katie's inquiry-based stress reduction practice - that helps you examine a belief, test whether it's absolutely true, and consider alternative perspectives. On the topic of quitting versus persisting, Eyal lays out three criteria: Did you hit your checkpoint? Are you still learning? Does persistence actually change anything? If all three answers are no, quitting makes sense. We close on money prioritization. When the math can settle a financial question, run the numbers. When it can't, it becomes a values question - and Eyal defines values as "attributes of the person you want to become." Resources: Download the four question turnaround exercise developed by Byron Katie, for free, at https://affordanything.com/turnitaround Book: Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Breakthrough Results, by Nir Eyal Share this episode with a friend, colleagues, and your florist: https://affordanything.com/episode699 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#698: We explore financial decision-making at different stages of life: A high-earning federal couple debates whether to pause retirement contributions to accelerate a $200,000 down payment.A part-time healthcare provider seeks clarity on balancing a 401k and a traditional IRA.And a longtime listener asks a more personal question: Is there anything we’re still figuring out ourselves? We examine strategy, trade-offs, tax efficiency, housing decisions, and the long-term thinking that shapes financial outcomes. (01:36) Hannah and her husband are in their mid-30s with two young children, and are hoping to upgrade to a larger “forever home” in several years while keeping their current home as a rental. They’re deciding whether to temporarily reduce retirement contributions to speed up down payment savings and how a possible cross-country relocation might affect those plans. (37:15) Amelia is a part-time healthcare provider in New York who earns hourly income and wants to contribute to both her employer’s 401(k) and a traditional IRA. She’s trying to determine how much to contribute to the 401(k) from each paycheck while still maxing out her traditional IRA—keeping the overall approach simple and tax-efficient. (56:12) Lesley praises Paula and Joe’s thoughtful responses to callers and wonders whether they ever seek advice from their audience. After recently undergoing brain surgery that prompted deeper reflection, the listener asks if there is anything in Paula and Joe’s financial, personal, or professional lives where they would value collective wisdom from their community. Share this episode with a friend, colleagues, and your mailman: https://affordanything.com/episode698 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#697: Most people regret the things they never tried. Venture capitalist Bill Gurley says that pattern shows up again and again in research on end-of-life regrets — including regret about the careers people never pursued.  In this episode, Gurley joins us to talk about how people actually discover work they enjoy - and why the cliché to “follow your passion” sends people in the wrong direction. We start with a question many listeners wrestle with: what if you reach your forties or fifties and still do not know what you want to do?  Gurley explains that career changes later in life remain possible. Financial flexibility helps. People who spend every dollar they earn limit their ability to shift paths. People who control their spending keep more options open. Gurley argues that “passion” often appears only after someone spends time exploring a field. A better starting point involves fascination - the subjects that pull your attention when nobody assigns the work.  Gurley suggests paying attention to what you study in your free time. If you find yourself reading about a topic instead of watching Netflix, that curiosity may signal a possible career direction. We also discuss how most successful careers involve several stops along the way.  Gurley studied hundreds of success stories and found that many people move through two or three roles before landing their long-term path. That pattern shows up across industries. Gurley began as a computer engineer working at Compaq. Even though he enjoyed the work, his curiosity shifted toward investing and business.  He eventually left engineering, went to business school and started knocking on doors in New York until he landed a job as a Wall Street analyst. That path later led him to Silicon Valley and a 25-year career in venture capital. Throughout the conversation, we talk about continuous learning, side projects that expand career options and how curiosity often shapes a career more than long-term planning. Resources Mentioned: Runnin' Down a Dream by Bill Gurley - https://amzn.to/4loywlQ The Power of Regret by Daniel Pink - https://amzn.to/4sNwZbQ Designing Your Life by Dave Evans & Bill Burnett - https://amzn.to/47yfeov One Up on Wall Street by Peter Lynch - https://amzn.to/4ruPsIX Atomic Habits by James Clear - https://amzn.to/4bj3cjR Interview with James Clear - Afford Anything Episode #638 Interview with David Epstein - Afford Anything Episode #206 Share this episode with a friend, colleagues, and your postal person: https://affordanything.com/episode697 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#696: (01:50) Jeremy has been a careful budgeter for years, but a surprise car repair has him tapping his emergency fund. With rates falling, he’s wondering if cash is enough or if he should try bonds or a CD ladder to keep up with inflation. (22:22) A listener in Canada has a DIY portfolio but is tempted by Dimensional Funds, which requires a pricey advisor. At the same time, she’s thinking about leaving work and returning to school, but also wants to keep financially supporting her parents. (41:27) Anonymous is navigating the tricky waters of buying a new home while still living in their current one. He is considering a bridge loan to avoid a contingent offer, but he’s worried about the strict timeline and potential financial pitfalls. Is a bridge loan a smart move, or does the risk of being stuck outweigh the convenience? Learn more about your ad choices. Visit podcastchoices.com/adchoices

#695: The U.S. lost 92,000 jobs in February, pushing unemployment to 4.4 percent.That result contradicts a different report released two days earlier showing 63,000 jobs added, leaving economists trying to square the circle. Many agree that we're in a "low hire, low fire" jobs environment.We walk through several major economic stories using a three-layer framework: the household economy, markets and policy, and long-term forces shaping the future.First, the household layer. Hiring has become uneven across sectors. Health care and education previously drove much of the job growth, but layoffs in those areas now appear in the data.Job openings have also fallen to 6.54 million, the lowest level since the pandemic began. Workers are switching jobs less often, and the pay bump for job-hopping has shrunk.Mortgage rates recently crossed 6 percent, influenced in part by rising Treasury yields and concerns about inflation. Gas prices climbed about 26 cents per gallon in a week, partly due to tensions affecting oil shipments through the Strait of Hormuz, which normally carries about one-fifth of global oil supply.The episode also looks at household finances. Six percent of workers in Vanguard plans took hardship withdrawals from their 401(k)s in 2025, up from five percent the year before. That increase suggests some households are leaning on retirement savings to manage financial stress.At the end of the episode, economist Dr. Ben Zweig, CEO of Revelio Labs, joins us to unpack the conflicting employment reports and explain why the labor market may look weaker than expected. He also discusses why health care hiring may be slowing and how economists interpret mixed signals across multiple labor data sources. (0:00) February jobs shock(1:02) Three-layer economy framework(2:03) BLS job losses explained(3:12) ADP vs BLS data gap(4:30) Job openings decline(5:39) Layoffs and AI cuts(7:15) Mortgage rates near 6 percent(8:26) Gas price spike(10:02) Markets react to oil shock(16:00) Record 401k withdrawals(19:30) Asset owners vs nonowners gap(21:22) Supreme Court tariff ruling(23:31) AI costs collapse, usage surge(27:03) Fed reactions to jobs report(33:33) Economist Ben Zweig interview Share this episode with a friend, colleagues, and your job recruiter: https://affordanything.com/episode695 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#694: There are about 90 million unique job titles in the U.S. labor market. Ninety million. If you are trying to negotiate a raise, switch companies or launch a side hustle, that number has consequences. If titles do not line up, you cannot easily compare pay, scope or seniority. You might be doing the same work as someone with a higher title and higher salary - and never see it. That problem is the focus of Part 2 of our conversation with Dr. Ben Zweig. Zweig is the CEO of Revelio Labs, a workforce data firm that analyzes millions of job postings and online profiles. He also teaches The Future of Work at NYU Stern School of Business and holds a PhD in economics from the CUNY Graduate Center. His work focuses on how jobs are structured and how they evolve. We talk about taxonomy - the systems used to categorize work. A title acts as shorthand for a bundle of tasks. Trouble starts when the shorthand breaks down. Two people with the same title may do very different work. Two people with different titles may perform nearly identical tasks. Zweig explains how large language models can group job descriptions based on actual responsibilities rather than labels. That approach could make it easier for workers to search accurately and for companies to organize teams. The conversation shifts to management. He argues that managers spend much of their time reconfiguring roles as business needs change. Technology accelerates that reconfiguration rather than replaces it. We close with stories about bank tellers and typists. Their titles remained familiar. Their tasks transformed over time. Resource: ⁠Job Architecture: Building a Language for Workforce Intelligence⁠ by Ben Zweig Share this episode with a friend, colleagues, and your bank teller: https://affordanything.com/episode694 Learn more about your ad choices. Visit podcastchoices.com/adchoices