Afford Anything

• Q&A: How to Choose Between Financial Freedom and a First Home

  #655: What would you do if, at the age of 23, you found yourself with $70,000 a year leftover after expenses? Would you pour everything into retirement and coast to financial independence, or stockpile a down payment before life gets pricier with kids, a mortgage, and maintenance costs? This week, we dive into that real-life dilemma and explore how to strike the perfect balance between freedom now and security later. Along the way, we question whether a 0.40% fee for automated tax-loss harvesting is really worth it, and debate if the rise of mega-corporations means small-cap value investing is dead. Listener Questions in This Episode “Julio” asks: How should we split savings between Coast FI and a future down payment, and where should that down payment sit? (01:48) Lindsay asks: Is 0.40 percent worth it for Fidelity’s tax loss harvesting and how do we unwind back to self managed index funds? (32:31) Greg asks: If a handful of giants dominate, should we ignore history and tilt to only the top companies instead of broad markets and small cap value? (50:51) Key Takeaways The right savings balance may depend less on math and more on clarity about what “home” really means to you Building a down payment might be the fastest way to reach Coast FI, but not for the reason you’d expect Parking cash safely is trickier than it sounds, especially when the market tempts you with higher returns That 0.40 percent fee could be either a silent drag or a smart trade-off, depending on one often-overlooked detail The rise of mega-caps might look unstoppable, yet history has a way of surprising even the biggest players True diversification isn’t about predicting winners, it’s about protecting future you from overconfidence today 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) Are we headed for a dystopian future (01:48) A 23-year-old with a $125k income and a big savings gap 08:52) House price, down payment size, and the numbers that drive the split (10:47) The savings snowball case, match protection, and timeline trade-offs (25:14) Where to park the down payment, why cash beats stocks for readiness (32:31) Is 0.40 percent worth it for tax-loss harvesting (36:24) Fees versus claimed tax savings, turnover, and exit options (50:51) Should dystopia change our portfolio (54:36) Small-cap value beyond tech, acquisitions, and global opportunity (1:11:02) Optimism, innovation, and why investing still assumes progress P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• How to Stop Fighting About Money

  #654: Fights about money are common, but they're rarely about math. They're about power, shame, vulnerability, and trust. And no amount of data or fancy spreadsheets is going to fix it. What you need is a better system for fairness, more open communication, and a shared ambition. In this candid conversation with Heather and Doug Bonaparte, we explore how two partners rebuilt confidence, handled their six-figure student loans, and designed a rhythm for money talks that actually works. Together they share how early money stories, law school debt, and the Great Recession shaped their dynamic, plus the tools they used to find fairness at home and in their finances Key Takeaways Why 50/50 isn't always fair and how to do it better The small ritual that turned dreaded money talks into something they actually look forward to How borrowing a strategy from the office made household decisions way less stressful The surprising fix for resentment that had nothing to do with chores or budgeting Why tackling six-figure student loans together became a turning point in their relationship The mindset shift that helped them see debt not as a burden but as a shared opportunity Resources and Links Money Together, the book DoMoneyTogether.com, learn more about the book and project The Joint Account, weekly newsletter on joint finances at ReadTheJointAccount.com Fair Play by Eve Rodsky, a framework for dividing household responsibilities Share this episode with a friend, colleagues, and anyone who is part of a couple: https://affordanything.com/episode654 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Radical Transparency in Real Estate Predictions

  #653: What happens when we actually check our predictions? In this episode we play clips from our 2023 conversation with Scott Trench from BiggerPockets and ask the uncomfortable question: were we right? Two years ago we made some big calls about the housing market. Mortgage rates had doubled. Prices hadn’t crashed. Inventory was vanishing. Everyone had a theory about what would happen next. Now we look back with data and receipts to see which forecasts held up and which ones fell flat. Scott joined us in 2023 to talk about the lock-in effect, the shortage of sellers, and why homebuilders might be stronger than expected. At the time it sounded contrarian. Two years later the evidence is in. Homeowners with low mortgage rates are still staying put. Builders have taken market share by offering creative incentives. Multifamily supply has exploded in some cities, while small residential properties have held their value better than many expected. We revisit our old clips and grade them one by one. What did we get right about the housing market’s resilience and where did we miss? You’ll hear how rate volatility created bursts of demand, how regional migration reshaped supply, and why small investors can still find opportunities even when the headlines say otherwise. This episode isn’t about victory laps. It’s about accountability. If you’ve ever wondered whether experts truly revisit their own calls, you’ll love this one. Key Takeaways The lock-in effect remains one of the most powerful forces in today’s housing market Builders have been surprisingly resilient thanks to incentives and creative financing Multifamily oversupply is pressuring rents in some regions while small residential properties remain steady Market outcomes are more local than ever; national averages hide major differences Real estate predictions matter only if we’re willing to go back and test them Resources and Links Our course Your First Rental Property open for enrollment through October 30 at affordanything.com/enroll 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. (0:00) Why we’re replaying our 2023 predictions (4:24) The strange housing market of 2023 (5:04) The lock-in effect and vanishing inventory (6:03) Builders finding ways to keep selling homes (12:12) How rate dips created bidding wars (14:03) The construction pipeline and what happened next (37:24) 2025 check-in on prices and incentives (55:06) Regional winners and losers (58:27) Small residential versus large multifamily (1:06:08) Final reflections and what we learned Share this episode with a friend, colleagues, and anyone in the real estate space: https://affordanything.com/episode653 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Why High Earners Stay Broke, with Rose Han

  #652: What if you did everything “right”, earned the degree, landed the six-figure job, and still felt broke? That’s exactly where Rose Han found herself. Fresh out of NYU with a finance degree and a Wall Street paycheck, she had a negative net worth, mounting stress, and a sinking feeling that traditional success wasn’t the path to freedom. In this conversation, Rose shares how she broke out of that cycle and built a seven-figure business that gives her time, independence, and peace of mind. We explore how she reframed her relationship with money, learned to scale her income, and built a life that aligns with her values. Key Takeaways When a “side hustle” becomes just a second job How your uniqueness is your greatest asset The slow season that led to a million-dollar leap Resources and Links Rose Han on YouTube Add a Zero by Rose Han 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. (0:00) Rose Han’s story begins: doing everything right yet still ending up broke (5:45) The Cancun moment that sparked Rose’s financial awakening (9:12) Discovering the three types of income and why some buy freedom while others don’t (13:45) How Rose Han built her “Add a Zero” framework for lasting wealth (21:30) From employee mindset to entrepreneur mindset (25:15) The three levels of leverage and how to scale your income (28:55) Why not every side hustle creates freedom (31:45) Overcoming the fear of selling (39:16) How to build a business while working full-time (47:10) Rose’s real estate lessons and the myth of passive income (53:55) Knowing when to walk away from an investment (1:10:15) What financial freedom really means and how to find your own version Share this episode with a friend, colleagues, and anyone who is interested in entrepreneurship and investing: https://affordanything.com/episode652 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Everyone Says Don’t Hold Bonds in Taxable Accounts. They’re Wrong

  #651: Many who reach CoastFI find themselves in a strange in-between: financially independent enough to stop saving, but not ready to fully retire. When you’re living off a taxable brokerage for decades, does the “never hold bonds in taxable” rule still apply? This episode explores how traditional asset location advice meets real-life spending. We unpack how to balance growth, taxes, and stability when your taxable account becomes your paycheck. Then we shift to two more listener dilemmas: helping a parent retire through shared home ownership, and using covered-call strategies to earn income from a stock-heavy portfolio. Listener Questions in This Episode Brandon (1:28): “I’m CoastFI and will withdraw from my taxable account for the next 20 years. Should I hold bonds in taxable, or keep it all in stocks?” Brandon’s retirement accounts can grow untouched, but his taxable brokerage will fund two decades of living expenses. The classic rule says avoid bonds in taxable, yet Paula explains why that advice isn’t universal. When your taxable account funds your life, it needs to act as a complete portfolio. We discuss how to balance risk, prioritize liquidity, and plan your glidepath into CoastFI life. Andrew (22:07): “My spouse and I co-own a home with my mother-in-law. How can we help her retire without creating family tension?” We explore fair, flexible ways to support an aging parent while keeping relationships healthy. Paula explains how to design a win-win deal and why seller financing can help balance cash flow and peace of mind. Chandan (49:16): “Can covered-call ETFs help me generate income from my stock portfolio and RSUs?” We explain how covered calls work, what “covered” really means, and the tradeoff between steady income and limited upside. For those with concentrated stock positions, Paula shares when covered calls make sense—and when simpler plans win. Key Takeaways The “no bonds in taxable” rule isn’t universal. When you’re drawing solely from taxable accounts for many years, that account needs to function as its own mini-portfolio, including bonds or cash for stability. Asset location follows purpose, not dogma. Tax efficiency matters, but liquidity and risk management take priority when the account funds your life. Think in terms of buckets. Your retirement accounts can stay growth-oriented while your taxable account carries the ballast for spending. Plan ahead for rebalancing. When taxable balances decline, know how and when to refill your bond/cash sleeve from other sources to keep your glidepath intact. The transition to CoastFI is a mental shift. You’re no longer optimizing for maximum returns, you’re designing for peace of mind and steady withdrawals. Chapters Note: Timestamps are approximate and may differ across listening platforms due to dynamically inserted ads. (01:28) Brandon’s CoastFI question: bonds in taxable when withdrawals start now (03:56) Why “no bonds in taxable” is a rule of thumb, not a law (12:42) How to treat taxable as a stand-alone portfolio (18:31) Balancing tax efficiency with cash-flow reality (25:26) Helping a parent retire through shared property ownership (01:05:40) Options: Buying or selling with Options (01:07:07) Covered calls explained simply, income with a ceiling Resources & Links Asset Location Cheat Sheet (free): affordanything.com/assetlocation Guide to Double-I FIRE (free): affordanything.com/fiire Share this episode with a friend, colleagues, your the person you buy garbage bags from: https://affordanything.com/episode651 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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