Afford Anything

#650: Sarah Williamson is the kind of person who shapes the decisions that move trillions of dollars. She earned her MBA with distinction from Harvard Business School and holds both the CFA and CAIA designations, two of the most demanding credentials in finance. In this episode, she helps us understand how investing really works, who the major players are, how capital flows through the system, and why the incentives driving investors, activists, and asset managers often collide. Sarah spent more than twenty years at Wellington Management, where she rose to Partner and Director of Alternative Investments, after working at Goldman Sachs, McKinsey & Company, and the U.S. Department of State. Today she leads FCLTGlobal, an organization dedicated to helping companies and investors focus on long-term value creation. She is also the author of The CEO’s Guide to the Investment Galaxy. She explains why index funds now dominate corporate ownership, how Reddit and retail traders changed the market’s dynamics, and what it means when activists push companies to “bring earnings forward.” She also introduces a framework for understanding the “five solar systems” of investing, a map that connects everyone from day traders to trillion-dollar sovereign wealth funds. Whether you are a passive investor or simply curious about what drives the market, this episode gives you the clarity to see how capital really moves and why it matters. Key Takeaways Reddit and the meme-stock movement permanently changed how individual investors move markets Index funds now dominate ownership, creating both stability and new corporate challenges Activists often prioritize short-term profit over long-term innovation Sovereign wealth funds act like national endowments, investing with century-long horizons Understanding who owns what (and why) makes you a more informed, confident investor Resources and Links The CEO’s Guide to the Investment Galaxy by Sarah Williamson FCLTGlobal, a nonprofit that helps companies and investors focus on long-term value creation Chapters 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) Meet Sarah Williamson: CEO, CFA, Harvard MBA, global finance leader (5:41) The five “solar systems” that organize the investing world (7:55) Reddit and the rise of the retail investor (16:25) Tesla, brand loyalty, and shareholder activism (22:57) How sovereign wealth funds invest for generations (28:57) Inside asset managers and their incentives (41:56) Activist investors and the tension between short and long term If you want to understand the real power dynamics behind modern investing, from Reddit traders to trillion-dollar endowments, don’t miss this episode. Share this episode with a friend, colleagues, and your cousin who is obsessed with latest meme stocks: https://affordanything.com/episode650 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#649: Many first-time buyers feel like they’re watching the train pull out of the station. If you’ve saved for years but can’t afford a home nearby, should you stretch to buy further (maybe hours) away or invest that cash instead? In this episode, we dig into the psychology, math, and lifestyle tradeoffs behind the “buy now or wait” dilemma. Plus, we unpack total return, explain when umbrella insurance is worth it, and share what every teen should learn about money. _______________________________________________ Listener Questions in This Episode Anonymous (aka “Lydia”) (3:26): ”I saved six figures for a down payment, but houses are still out of reach. Do I buy far away, rent forever, or invest the cash instead?” Lydia, an Australian listener, spent eight years saving for a home, only to find that every option feels like a compromise. Sky-high prices close to work, or long commutes for affordability. It’s a dilemma many face: does owning mean freedom, or does it just tie you down? We explore how to separate fear from opportunity, why “starter-home-turned-rental” plans often backfire, and how to measure the real cost of lost time when you move hours from work. Ultimately, it’s about aligning your money with your life, not the headlines. Anonymous (aka “Aristotle”) (29:38): “My ETF is up 10% and yields 3%. Is my net return 13%?” It’s a common question for anyone tracking their investments. We unpack the difference between total return and your personal rate of return, and why those two numbers rarely match. You’ll learn what actually drives performance, and how to read your brokerage dashboard like a pro. Joel (39:44): “Umbrella insurance; do we need it and how much?” If you own a home, drive a car, or rent out a property, you’re exposed to more liability than you might realize. We break down how umbrella insurance works, when it’s essential, and how much coverage makes sense. It’s one of the cheapest ways to protect your wealth. Julia (56:13): “I’m building a high-school personal finance course. Should I cover insurance or credit?” When teaching teenagers about money, where do you start? We explore why understanding decision-making (opportunity cost, compounding, and spotting bad financial advice) matters more than memorizing credit scores or insurance terms. Key Takeaways Don’t buy from FOMO; let lifestyle goals—not market panic—drive your choices. Total return includes price changes and income, but your broker’s “personal rate of return” shows the truest number. Umbrella insurance offers millions in protection for relatively little cost; bundle it with home and auto. Teach teens the “why” behind money choices before the “what.” Understanding tradeoffs beats memorizing rules. Chapters 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. (4:14) Anonymous Lydia’s question: should I buy now or invest my down payment? (8:23) The emotional trap of FOMO and rising prices (11:45) Why “live there now, rent it later” rarely works (22:14) The hidden cost of long commutes and lifestyle tradeoffs (29:38) Anonymous Aristotle’s question: how do I calculate my true investment return? (39:44) Joel’s question: Is umbrella insurance worth it and how much should I buy? (56:13) Julia’s question: what high schoolers should learn first about money Learn more about your ad choices. Visit podcastchoices.com/adchoices

#648: The U.S. government is shutting down. Bitcoin just hit a record high. Inflation whispers are back. And Wall Street is buzzing with speculation. What does this all mean for your money, your portfolio, and your long-term financial freedom? On this First Friday episode, we unpack the economic headlines you can’t ignore — and help you separate signal from noise. In this episode, we cover: Government Shutdown: What happens when Washington goes dark, and how it could ripple into the markets, interest rates, and your daily life Bitcoin at Record Highs: Why crypto is rallying, what history tells us about speculative manias, and whether this time might be different Jobs Report and Inflation Watch: The latest labor market data, its implications for the Fed, and how it could shape borrowing costs Investor Behavior in Uncertainty: Why volatility can make us overreact, and how to stay grounded in your long-term strategy Key Takeaways Government shutdowns create noise, but historically their long-term market impact is minimal Bitcoin’s surge reflects both speculation and broader demand for decentralized assets — but extreme volatility remains The labor market remains resilient, keeping inflation risks on the radar and Fed policy in focus Emotional investing is costly: staying calm during uncertainty is one of the best ways to protect your wealth. This month’s headlines feel dramatic — shutdowns, soaring crypto, inflation fears. But the timeless principles of money management still apply: diversify, stay disciplined, and don’t let headlines dictate your portfolio. Key moments: (00:00) Jobs Reporting from ADP (08:28) Interest Rates and Mortgages (18:07) Social Security Age (25:36) Consumer Spending and Inflation (31:56) Bitcoin and Gold reach new highs (34:31) Quarterly Reporting for Publicly Traded Companies may go to twice-a-year Learn more about your ad choices. Visit podcastchoices.com/adchoices

#647: What if you and your partner want to take a few months – or even a year – off work?  How do you handle health insurance once you leave your jobs?  And how do you make sure the time off isn’t wasted, but becomes a launchpad for what’s next? In this week’s Q&A, we dive into those questions.  We also cover three more listener questions: what to do with a leftover $125,000 in a 529 account, how one listener landed a fully remote job with a 30 percent raise, and whether you can amend your taxes after a FEMA-declared disaster. Listener Questions: Danielle (04:35): “We want a mini-retirement. What should we do about health insurance – and how can we make the most of the time off?” Danielle and her husband want a break, but don’t want to go uninsured, and they also don't want to squander their mini-retirement. We look at what happens when you leave a job, where to find coverage, and how to design a mini-retirement that sparks discovery instead of regret. Lee (32:17): “We have $125,000 left in a 529 account. No one needs it for school. What should we do?”A six-figure leftover balance sounds great, but it comes with tricky rules. Can you roll it into a Roth IRA? Use it for other programs? Withdraw without a tax hit? We explore the surprising flexibility inside a 529. Pedro (44:06): “I followed your job search advice – and just landed a new role!”Pedro once struggled with dead-end applications. Now he’s celebrating a fully remote job, a big raise, and better alignment. How did he do it? By targeting the intersection of his skills and industry, instead of casting a wide net. Melanie (53:35): “I spent $45,000 after a FEMA-declared disaster. Later, Congress passed retroactive tax relief. Can I benefit?”Disaster tax relief is confusing, especially when laws apply after the fact. Melanie asks if she can amend her return to capture new benefits. We talk timelines, amended return rules, and why professional help matters. 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. Key Highlights How to get health insurance during a mini-retirement. Why treating time off as a “science experiment” can reshape your career. Smart options for a leftover 529 account (including new Roth IRA rollovers). A real listener’s success story: from stalled applications to a remote job with a 30% raise. What to know about amended returns for FEMA-declared disasters. Resources Pedro's original question on Episode 605 Healthcare.gov — ACA marketplace for insurance enrollment The Power of Fun by Catherine Price Digital Minimalism by Cal Newport Freedom app — tool for blocking distractions Learn more about your ad choices. Visit podcastchoices.com/adchoices

#646: What if you didn’t have to choose between grinding full-time until retirement or quitting work altogether? By 40, Andy Hill and his wife had built a $500,000 portfolio and paid off their home. Instead of racing toward early retirement, they chose a third way: scaling back to part-time work, becoming equal partners in parenting, and reclaiming their time. In this episode, recorded live at FinCon, Andy shares his 10-step framework for building a “Coast FIRE” lifestyle — where your investments can coast toward retirement while you focus on living today. __________________________ The Middle Path Beyond FIRE Most of us think of retirement as a cliff: one day you’re working, the next day you’re not. Andy challenges that binary. He and his wife structured their careers to work 20–25 hours per week each, creating a rhythm that gave them more time with their children, each other, and their health. He breaks down the mindset shifts and tactical steps — from eliminating debt and protecting your family with insurance to stockpiling FU money and designing a three-day workweek. Along the way, he explains how Coast FIRE frees you from mandatory retirement contributions and opens doors to a flexible, meaningful life. __________________________ Key Takeaways: Balance beats extremes. Neither full-time grind nor full-time stay-at-home felt right; designing a flexible, part-time work life created the equilibrium their family needed. Cash buffers change behavior. A 3–6 month emergency fund reduces stress and scarcity thinking, making it easier to parent calmly and make better money decisions. Choose time over trappings. Fancy upgrades aren’t worth trading away presence; prioritizing family time beats lifestyle escalation. Resources mentioned: Andy Hill's book on Amazon: Own Your Time Marriage, Kids, and Money Podcast (4:01) Why the shift (5:35) What their life looks like now (9:08) Why extremes didn’t work for Andy and Nicole (14:45) Step 1 Dream and define your ideal life (18:21) Step 2 Commit to living without high-interest debt (20:38) Step 3 Protect your family (insurance, estate plan, emergency fund) (27:04) Step 4 Invest to reach Coast FIRE (30:29) Step 5 Pay off your home (or optimize if renting (36:21) Step 6 Stockpile FU money (47:53) Step 7 Design a three-day workweek (57:02) Step 8 Plan your intentional four-day weekend (1:02:39) Step 9 Simplify to avoid lifestyle creep (1:08:56) Step 10 Teach your kids the path to time freedom Share this episode with a friend, colleagues, or with your neighbor with the tricked-out basement : https://affordanything.com/episode646 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#645: Mike (02:50): After 15 years of intentional living, Mike is 80 percent of the way to financial independence. Now he’s trying to help friends take control of their own financial future. But what happens when one spouse is eager to learn and invest, while the other isn’t interested? Michael (27:07): For two years, Michael has tracked his net worth monthly. So far, growth has been driven almost entirely by how much he saved. But when will investment returns begin to take over and shift that steady line into an exponential curve? Alvaro (34:00): After 15 years of investing in U.S. and European real estate, Alvaro has a big decision to make. Should he leverage a commercial loan to build an ADU for short-term rental income, or take on more personal debt to expand their family home? Jonathan (58:50): After hearing Paula and Joe discuss the efficient frontier — and then listening to Big ERN, Paul Merriman, and JL Collins — Jonathan can’t help but wonder: has Joe’s perspective evolved? Is the simple path still enough, or is there merit in a more complex approach? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it ⁠here⁠. Resources Mentioned: JL Collins Part 1 and Part 2 Karsten Jeske (Big Ern) Episode 643 Paul Merriman Episode 550 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. Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode645 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#644: Why do we both crave money and resent it? Why do some people sabotage their financial futures in the name of short-term comfort? And why is your brain — not the stock market — the biggest threat to your wealth? In this conversation, we explore the surprising ways that psychology and money intertwine. Our guest, Dr. Daniel Crosby, is a behavioral finance expert, psychologist, and bestselling author of The Soul of Wealth, The Behavioral Investor, and The Laws of Wealth. His research dives into how our emotions, childhood scripts, and personalities shape the financial decisions we make every day. Dr. Crosby shares why investing is an act of optimism, why income matters more than coupon clipping, and how our spending reveals truths about who we really are — even when we don’t realize it.. Key Takeaways Money is a mirror. The way you earn and spend reflects your real values, not just your stated ones. Tracking your money reveals gaps between who you say you are and how you actually live. Income drives wealth. Frugality matters, but once the basics are handled, your long-term financial future is determined more by growing your income than by cutting costs. Short-term comfort is costly. The biggest threat to your wealth isn’t the market — it’s the temptation to prioritize momentary relief (panic-selling, stress spending) over your long-term goals. Resources & Links Dr. Daniel Crosby on LinkedIn Standard Deviations Podcast Books by Dr. Crosby: The Soul of Wealth The Laws of Wealth The Behavioral Investor Personal Benchmark Closing This episode reminds us that building wealth isn’t just about math — it’s about mindset. The markets may fluctuate, but the greatest risks and rewards often lie within our own psychology. If you enjoyed this conversation, share it with a friend, subscribe to our newsletter at affordanything.com/newsletter, and connect with our community at affordanything.com/community. You can afford anything, but not everything. Choose wisely. 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. (03:24) Does money really buy happiness? Rethinking the $75k income myth. (08:48) Our conflicted relationship with money: Love, resentment, and the paradox of wealth. (10:32) Childhood money scripts: How early beliefs still drive adult financial behavior. (16:10) Personality traits & money outcomes: Why agreeableness and neuroticism matter. (24:15) Investing as an act of optimism: Human progress, markets, and long-term growth. (30:39) AI, work, and the future of wealth: Why EQ may outpace IQ in tomorrow’s economy. (39:46) Habits vs. willpower: Why automation and environment beat discipline. (44:28) Frictionless spending: How Apple Pay and subscriptions fuel overspending. (47:32) Offense vs. defense in wealth: Why income matters more than extreme frugality. (1:03:16) Chronic vs. episodic mistakes: Small leaks, lost compounding, and long-term damage. (1:06:24) The pre-mortem exercise: A Stoic-inspired tool to prevent financial failure. Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode644 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#643: Picture this: you're at the Federal Reserve years ago. The chairman literally hangs up a conference call, waits 30 minutes, then calls back — suddenly everyone agrees on the rate decision.  That's the kind of insider story Karsten Jeske (“Big ERN”) shares when he joins us to break down what's happening with the economy right now. Karsten worked at the Federal Reserve Bank of Atlanta for eight years, then spent a decade on Wall Street at Bank of New York Mellon.  Today he runs the popular Early Retirement Now website, where he applies his economist background to help people understand money and markets. You'll hear Karsten explain why the Fed is about to start cutting interest rates. The futures markets are pricing in a 90 percent chance of a quarter-point cut, with more cuts likely through the end of the year.  But why? After all, inflation just ticked up in the latest CPI report, yet the Fed is still planning to lower rates. We dive into how this affects real people. If you're thinking about buying or selling a house, Karsten suggests acting sooner rather than later.  He explains the "buy the rumor, sell the news" principle – the bond market may have already priced in the good news about rate cuts, so waiting might not help you. The conversation covers some surprising economics too. Did you know that high interest rates can actually cause housing inflation?  When mortgage rates are expensive, fewer people build new homes, which drives up prices. It's the opposite of what most people think happens. Karsten walks through the recent jobs report revisions that caught everyone off guard. The government had to subtract nearly a million jobs from their previous estimates. He explains how this happens – it's not that officials are making up numbers, but tracking new businesses is genuinely hard to do in real time. You'll also learn about two Fed tools most people haven't heard of: the dot plot and R-star. The dot plot shows where Fed officials think interest rates should go over time. R-star represents the theoretical perfect interest rate when the economy has no problems — currently around 3 percent. The interview wraps up with Carsten's take on Fed culture. The consensus-building era under Greenspan is giving way to more dissenting votes, which actually makes the central bank more like it was decades ago under Paul Volcker. Enjoy! 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. (1:04) Carsten’s career path from Fed to Wall Street (1:57) Current economic growth limbo state (4:04) GDP formula and tariff impacts (5:10) Trade efficiency and comparative advantage (6:04) Supply chain threats from protectionism (8:20) Fed meeting and rate cut expectations (9:35) Market pricing in multiple rate cuts (12:19) Real estate timing and mortgage rates (13:55) How Fed rates affect treasury yields (18:50) Buy the rumor, sell the news strategy (22:13) Fed transparency and decision telegraphing (25:56) Fed consensus culture versus dissent (30:48) CPI data shows inflation ticking up (34:32) Transitory versus persistent inflation confusion (38:56) Fed behind the curve on rate cuts (40:00) Major jobs report revisions explained (44:24) Methodological issues with new business tracking (46:00) Dot plot and R-star concepts explained (52:29) Bond allocation strategies by age (57:25) Current bond yields look attractive Learn more about your ad choices. Visit podcastchoices.com/adchoices

EXCLUSIVE: Is your money safe in today’s economy? In this bonus interview, Paula Pant sits down with financial expert Rob Berger to unpack the latest on inflation, interest rates, market valuations, and the future of Social Security. Together, Paula and Rob dive into the tough questions: Is the American Dream dead for Gen Z? Will there be another market crash? How should you invest when stocks feel overpriced? Can you still retire comfortably if Social Security gets cut? Rob also shares his insights on asset allocation, diversification, and long-term investing strategies — advice that matters whether you’re in your 20s saving for a first home or in your 60s planning for retirement. Don’t miss this conversation between Paula Pant and Rob Berger — a deep dive into money, markets, and the decisions that shape your financial future. Timestamps: (04:19) CPI Numbers, Mortgage Rates, and Market Outlook (05:05) Inflation, Jobs & the Fed’s Dilemma (05:46) Stagflation Concerns (06:38) Interest Rate Predictions (07:29) Stock Market Valuations & The Magnificent Seven (09:46) Diversification & Index Fund Concerns (10:53) Rules of Thumb for Asset Allocation (12:07) Bonds: TIPS vs. Nominal Treasuries (13:04) The Future of Social Security (14:41) Retirement Planning for Ages 55–60 (16:59) Should You Invest More Aggressively Near Retirement? (18:52) Gen Z, Millennials & the American Dream (21:08) Action Plan for a 25-Year-Old Buyer (22:45) Predictions for 2026 (and Why Predictions Fail) (25:12) Closing Thoughts & Where to Find Rob Berger Resources mentioned: The Rob Berger Show on YouTube Free Asset Location Cheat-Sheet For more information, visit the show notes at https://affordanything.com/robbergerhttps://affordanything.com/robberger Learn more about your ad choices. Visit podcastchoices.com/adchoices

#642: Curious about how individual stock picking could sharpen your investing skills—even if you’re an avid index fund investor? Paula sits down with David Gardner, co-founder of The Motley Fool and author of Rule Breaker Investing, to delve into the world of contrarian stock strategies and the mindset behind picking standout companies. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Sports team investing analogy (4:20) Individual stocks vs index funds (7:12) Values-based investing approach (13:16) Starbucks pick criteria (13:28) Six rule breaker traits (20:41) Why overvalued works (26:44) Market timing philosophy (32:20) Traditional metrics miss key factors (39:18) When to sell stocks (45:26) Winners vs losers math (48:32) Portfolio allocation rules (55:10) Sleep number concept (1:00:00) Adding to winners strategy (1:05:16) Evaluating unfamiliar companies (1:09:15) Dot-com bubble lessons (1:16:24) AI investing parallels (1:20:18) Sports betting critique Resource: David Gardner's book: Rule Breaker Investing: How to Pick the Best Stocks of the Future and Build Lasting Wealth Learn more about your ad choices. Visit podcastchoices.com/adchoices

#641: Cristina has a $1.2 million portfolio and hopes to make work optional within the next decade. Is she invested in the right way? Or should she change up her asset allocation? Anonymous and her husband plan to retire in 5 years. They have 10 rental properties and a $2.75 million portfolio. They dream of slow travel, generosity, and family time. How should they structure their assets to support the lifestyle they want? Paula (the caller) and her husband are planning for three kids, private school, and possibly college down the road.  Should they front-load a 529 plan with a large lump sum, or take a different approach? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. Resources mentioned in the show: Interview with Frank Vasquez Risk Parity Cheat Sheet Caller Christina's original call on https://affordanything.com/episode463 Afford Anything Episode 618 https://affordanything.com/episode618 Risk Parity Portfolio Blueprint https://affordanything.com/riskparity Joe's episode SB 1698 https://www.stackingbenjamins.com/create-your-retirement-spending-plan-1698/ Run The Line half marathon with Joe: https://runsignup.com/Race/TX/Texarkana/RuntheLineHalfMarathonTXAR SavingForCollege.com Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (01:42) Christina (16:42) Anonymous (33:40) Paula the Caller Learn more about your ad choices. Visit podcastchoices.com/adchoices

#640: The jobs report came out this morning and it was a painful one. The US added only 22,000 new jobs in August, according to the latest BLS report. And unemployment ticked up to 4.3%. What does this mean? Find out in today's First Friday episode! 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. (01:48) ADP vs BLS Jobs Data (04:33) Mortgage Rates & Their Impact on Homebuyers and Sellers (11:30) Fed Chair Jerome Powell’s Remarks (12:54) The Fed’s Dual Mandate Explained (15:58) The Fed’s Changing Approach to Unemployment (18:13) Implications: Rate Cuts on the Table For more information, visit the show notes at https://affordanything.com/episode640 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#639: Aisha is excited to share how some life-changing advice has played out for her career. She wonders now: what limiting beliefs has Paula and Joe had to overcome in their businesses? Lesley is attracted to community bonds as a way to build collective wealth for the underserved. But do the same risks exist as they do in the traditional bond market? An anonymous caller is intrigued by the promise of Employee Stock Ownership Plans. Is this the answer to a smooth exit from her business that also leaves a legacy for her employees? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. Resources mentioned in the show: Aisha's original call in Episode 473 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#638: Fifty dollars. That's how much this couple transferred to their "Trip to Europe" savings account each time they cooked dinner instead of going to a restaurant. By year's end, they had funded their dream vacation — not through budgeting or willpower, but by hacking their habit loop. This story illustrates how James Clear approaches habit change. Clear joins us to explain the four-stage cycle that drives every behavior: cue, craving, response, and reward. You see a restaurant (cue), predict it will be convenient and tasty (craving), eat out (response), and satisfy your hunger (reward). Repeat this loop enough times and the behavior becomes automatic. Clear translates these four stages into four laws for building good habits: make it obvious, make it attractive, make it easy, and make it satisfying. Want to break a bad habit? Flip the script — make it invisible, unattractive, difficult, and unsatisfying. We explore practical strategies like habit stacking, where you attach a new behavior to an existing routine. Clear suggests saying "After I make my morning coffee, then I will review my budget for two minutes" rather than relying on motivation alone. He explains temptation bundling — pairing something you need to do with something you want to do, like only listening to your favorite podcast while meal prepping. The conversation covers why most people focus on outcomes when they should focus on identity. Instead of saying "I want to save 10,000 dollars," Clear suggests thinking "I want to become a saver" — then asking what actions a saver would take daily. Clear addresses the challenge of delayed gratification with money habits. Saving feels unrewarding in the moment because the benefits come later. He shares techniques for creating immediate satisfaction, like the couple's Europe fund or using habit tracking to mark small wins. THIS EPISODE IS FROM OUR “GREATEST HITS” VAULT, AND ORIGINALLY AIRED IN 2018. ____
 Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) James explains four habit stages (5:22) Cue and craving examples (8:47) Four laws of behavior change (11:05) Making habits obvious through environment design (14:56) Habit stacking with existing routines (16:12) Travel and changing contexts (18:58) Temptation bundling strategies (25:21) Motivation rituals and triggers (29:52) First ad break ends (33:11) Habits of avoidance challenges (39:10) Social reinforcement and tribes (41:09) Making habits easy through friction reduction (44:03) Delayed gratification and immediate rewards (54:16) Second ad break ends (57:16) Making habits satisfying (1:03:01) Commitment devices and accountability (1:08:35) Identity-based versus outcome-based habits Learn more about your ad choices. Visit podcastchoices.com/adchoices

#637: Nick wants to set up an investment account for his nephew to contribute annually, creating a nest egg for college since the parents are already opening a 529. He's unsure whether a standard brokerage account, IRA or other options work best when you're not the parent. Diana asks whether she needs TIPS in her portfolio to protect against inflation. Or can she just rely on other investments that outpace inflation? She's also wondering about the tax implications of TIPS ETFs. This matters during her peak earning years. Prethive asks whether he should switch from Roth to Traditional 401(k) contributions. When he retires, he wants to move to a tax-free state. Or maybe move abroad. He wonders if moving to avoid state taxes in retirement would save more money long-term. Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here. For more information, visit the show notes at https://affordanything.com/episode637https://affordanything.com/episode637 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#636: Behavioral economist Etinosa Agbonlahor joins us to discuss "money scripts" — the unconscious beliefs we inherit or develop about finances.  Agbonlahor, CEO of Decision Alpha and former Director of Behavioral Science Research at Fidelity Investments, is the author of "How to Talk to Your Parents About Money."  She studied financial management at Cornell University and explains how these hidden biases create problems when we try to discuss finances with family members. You might assume everyone thinks saving money makes sense, while your parents operate under completely different beliefs. These conflicting scripts can derail conversations before they start.  Agbonlahor shares the story of a single mother who became so anxious about money after her divorce that she refused to buy her teenager expensive shoes. Years later, she realized she was trying to teach extreme frugality to protect her daughters from the financial insecurity she experienced. The key to productive money conversations lies in three principles: care, curiosity and cooperation. You approach with empathy rather than judgment, ask open-ended questions to understand their situation, and work together toward solutions instead of trying to be the financial savior. The conversation covers specific topics you should address with aging parents: debt, retirement planning, long-term care preferences, and estate planning. Agbonlahor emphasizes starting these discussions early, before a crisis hits.  You want to understand their vision for retirement — whether they prioritize security, adventure or leaving a legacy — and then assess the gap between their goals and current reality. When parents refuse to discuss finances, you might need to involve trusted friends, spiritual leaders or professional advisors who can have these conversations instead.  Resources Mentioned: Book: How to Talk to Your Parents About Money, by Etinosa Agbonlahor The Humble Dollar Forum 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) Introduction to money scripts (00:56) What behavioral economics studies (03:03) Hidden money beliefs (04:34) Money script examples (06:16) Adult trauma responses (09:32) Personality and money (11:57) Trauma changes personality (12:55) Protecting future habits (15:17) Debt conversation approach (22:03) When to start conversations (27:53) Using "I" statements (29:51) Sample conversation scripts (33:36) Handling resistance (43:35) Parents' money frameworks (56:46) Long-term care planning (58:02) Stepparent conversations For more information, visit the show notes at https://affordanything.com/episode636 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#635: Arielle’s head is spinning from the seemingly contradictory advice she hears about the best investments to hedge against inflation and a possible recession. What’s she missing? Dave is curious about private investments after listening to a recent First Friday episode. What are they, and should he consider them for his portfolio? Abbey is stoked about the raise she negotiated for her first job out of school. But she’s worried about liability risk related to her new position. How does she protect herself?  Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! P.S. Got a question? Leave it here For more information, visit the show notes at https://affordanything.com/episode635 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#634: Picture this: you're 26 years old, fresh out of Wharton, and you decide to start a business with two friends. You spend years building a digital marketing firm that eventually works with Dollar Shave Club and Madison Reed. You bootstrap the entire thing without taking a dime of venture capital funding. That's exactly what one Wharton graduate did — and his story represents the reality of entrepreneurship that most people never hear about. Lori Rosenkopf, a management professor at Wharton Business School and head of Venture Labs, joins us to shatter the biggest myths about starting a business. The Mark Zuckerberg college dropout story? It's not just rare — it's misleading. Research shows that the most successful entrepreneurs, those in the top 0.1 percent of venture-backed firms, average late 30s to early 40s when they start their companies. Many continue launching businesses into their 50s and 60s.  Your age and corporate experience isn't holding you back from entrepreneurship — it's actually giving you an advantage. Rosenkopf breaks down seven different types of entrepreneurs, from disruptors who overturn entire industries to bootstrappers who build profitable businesses using their own resources. You'll hear about a founder who disrupted the hair color industry in her 50s with Madison Reed, and a banker who built an entire financial services division inside Square. We cover the rise of direct-to-consumer brands in 2013, why 80 percent of entrepreneurs are bootstrappers, and how artificial intelligence is creating new opportunities for people to start businesses without massive upfront investments. Rosenkopf explains her "six Rs" of entrepreneurial thinking: reason, recombination, relationships, resources, resilience, and results. She argues that most people already think entrepreneurially without realizing it — even parents who optimize their family routines are solving problems through innovation. We explore the world of "intrapreneurs" — people who build new businesses within established companies — and discuss acquisition entrepreneurship, where people buy existing small businesses instead of starting from scratch. Whether you want to start a side hustle, position yourself for a promotion, or eventually launch your own company, Rosenkopf's framework shows multiple paths to creating value through innovation. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (0:00) Entrepreneurship myths (1:28) Data on successful entrepreneur ages (2:10) Seven entrepreneur archetypes  (3:09) Defining entrepreneurship through value creation (5:27) The disruptor model  (8:13) Direct-to-consumer origins (11:13) Bootstrapper  (14:03) Transitioning from employee to bootstrapper (18:38) AI's impact on entrepreneurship (28:27) Social entrepreneur  (35:31) Technology commercializer  (39:45) The Funder  (43:12) The Acquirer  (58:06) Intrapreneurship  (1:03:12) Finding your entrepreneurial calling (1:14:40) Six Rs of entrepreneurial mindset (1:19:50) More information For more information, visit the show notes at https://affordanything.com/episode634 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#633: Paul is worried the private equity investment he’s about to make could be a scam. How can he do his due diligence and stay protected when there’s a shortage of reliable information? Rob is questioning the purpose of a bond allocation in his eight-figure investment portfolio. Is he on to something, or is there a legitimate case to add them? Dan can retire in a few years, but he’s itching to do it now. Would buying a business be the key to unlocking an earlier exit from his W2? Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode. Enjoy! Resources: Interview with Dr. Eric Cole Interview with Katie Gatti Tassin P.S. Got a question? Leave it at https://affordanything.com/voicemail For more information, visit the show notes at https://affordanything.com/episode633 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Your Next Raise is open for enrollment! ⁠https://affordanything.com/how-to-negotiate-your-next-raise #632: There are 10 conversations that a person should have at work in order to do a better job, have better relationships at work, and make more money. Melody Wilding, Professor of Human Behavior at Hunter College, joins us to talk about how you can get the most out of your boss. Resources: Managing Up by Melody Wilding: managingup.com Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) The 10 Conversations Framework (02:37) Shifting Workplace Dynamics (06:11) Key Conversations for Alignment (10:02) Understanding Your Boss’s Priorities (12:02) Mapping Stakeholder Influence (15:28) Visibility and Proximity Bias (20:31) Managing Shifting Priorities (22:11) Understanding Boss Archetypes (28:01) Navigating Personality Frameworks (32:06) Articulating Your Communication Style (35:03) Taking Ownership and Suggesting Ideas (39:59) Building a Reputation Through Ownership (45:03) Setting and Framing Boundaries (56:01) The Ripple Effect of Unaddressed Issues (59:00) Feedback Conversations (01:03:02) Recapping the Framework Steps (01:11:09) Building Your Story Bank (01:18:01) Advancement and Compensation Conversations (01:25:15) Framing Your Compensation Request (01:29:00) Navigating Policy-Based Responses (01:31:51) Creative Compensation Solutions (01:34:29) Knowing When to Leave (01:36:13) Assessing Future Opportunities For more information, visit the show notes at https://affordanything.com/episode632 Learn more about your ad choices. Visit podcastchoices.com/adchoices