Afford Anything | Make Smart Choices About Your Money, Time And Productivity

#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now. The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages. The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are stuck around 6.2%. And 80% of homeowners are unlikely to sell because they locked in rates below 6%. The Big Picture: The stock market is outperforming the economy. How It Affects You: I call it "millionaire malaise." Your 401k looks great. Your home equity is through the roof (no pun intended). If you bought before 2022, your assets look good on paper. Yet you're stressed out at the grocery store. Everything costs more – insurance, groceries, everything except gas. Jobs are stagnant. People are stuck. We're experiencing the difference between wealth and income. This is 2026: Wealthy on paper. Broke at the che

#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets? I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people. Here’s my breakdown: Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000 Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62,000 Vanguard Roth IRA: VTSAX $228,000, ISCV $6,000 Pre-tax 401(k): Active stock fund $218,000 (0.01% expense ratio), Equity dividend fund $55,000 (0.01% expense ratio) Russell 1000: $270,000 (0% expense ratio) HSA: $9,000 in the Russell 1000 and Russell 2000 ESPP: $90,000 Savings account: $12,000 I view my brokerage accounts as savings, where I can sell assets if I need cash, as well as sell my company shares. My questions: How far am I from the efficient frontier? How efficient is my asset allocation? I’ve mostly been a “VTSAX and chill” type. If I rebalance, what’s the best way to do it

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth. ____ In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then? Build a startup. Raise capital. Scale fast. Get rich. That was the dominant story. But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture. Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business. He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure. From there, we move into one of the

#674: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market. We tackle the five biggest challenges of investing far from home – from fear of the unknown to managing contractors remotely – and reveal four compelling benefits that make it worth the effort, especially when you're competing in markets where million-dollar properties are the norm. ________ Remember when inflation was high and rates were rising? What were people saying about real estate back then? And with the benefit of hindsight, how much of what we thought at the time proved to be correct? If you feel unsettled, join the club. At this present moment – December 2025 – interest rates are falling, but not enough. Inflation is mostly under control, but not enough. The noise makes everything fe

#673: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we've shared for building wealth at any age. Nick Maggiulli joins us to reveal why most young investors obsess over the wrong metrics — and shares his Save-Invest Continuum that shows exactly when your savings beat your investment returns, and when that changes.  _____ When Nick Maggiulli was in his twenties, he spent countless hours obsessing over his investment portfolio – tweaking his asset allocation, running net worth projections, and building complex spreadsheets.  Meanwhile, he was blowing $100 every weekend partying in San Francisco. It took him years to realize the absurdity. His annual investment returns on his tiny $1,000 portfolio might earn him $100 – the same amount he'd spend in a single night out. Maggiulli joins us to explain why young i

#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever. Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiations and net worth. __________ You've mastered the art of asking for what you want — or have you? Jeff Wetzler, Ed.D., a former education executive, joins us to reveal why most of us fail to extract crucial information from the people around us. Think about it: when was the last time someone told you what they really thought about your work? Or shared that game-changing idea they'd been sitting on? Wetzler discovered four categories of information people routinely withhold — and the cost runs deeper than you might expect. We explore why people stay silent about their struggles, unpopular opinions, observatio

#671: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter F stands for Financial Psychology. And we're diving deep with a conversation that changed how thousands of our listeners think about money. This episode originally aired in November 2022, but the insights feel more relevant than ever. Dr. Daniel Crosby reveals why your brain is your portfolio's worst enemy — and what you can do about it. ______ Money is the number one stressor in American lives. Every single year. Without exception. That's what Dr. Daniel Crosby discovered when he looked at decades of research from the American Psychological Association. In this rerun episode from our Greatest Hits Vault, Crosby joins us to reveal why your brain sabotages your investment decisions. He's both a clinical psychologist and behavioral finance expert. His findings will change how you think about money. Your body hijacks your financial judgment in strange ways. For example: People who need to

#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort. We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple. We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact. We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.” If you want to earn more points (or

#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K brokerage account and plan withdrawals to make the transition financially smooth. David (21:50) - David has a high school senior and is deciding how to pay for college. Should he tap the $60K 529 plan now or the $200K 457(b) from his wife’s former employer to maximize tax efficiency and preserve future growth? Graham (37:52) - Graham loved the episode on holding bonds in a taxable account, but he’s curious about a tax-efficient twist. Can an asset swap strategy let you rebalance and pull cash without triggering capital gains? Share this episode with a friend, colleagues, and your family at the holiday part: https://affordanything.com/episode669 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#668: We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his last big launch as he heads into retirement. Together, we wrestle with a problem our listeners know well: what happens when you’ve built the habit of saving, investing, optimizing … and then feel weirdly unable to spend. We talk about mini-retirements, the psychology of “spend and enjoy,” and why waiting to touch retirement money can be its own kind of risk. Key Takeaways Think about retirement as a series of deliberate mini-retirements, not one finish line you might reach with less energy than you expected. If you’re a dedicated saver, build a plan for the “spend and enjoy” phase so you do not accidentally optimize away the years you wanted freedom for. Run the numbers on “small” spending habits, not to guilt yourself, but to see which choices actually buy future optionality. Treat withdrawals, ben

#667: Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk. In this episode we sit down with Karsten Jeske, PhD, CFA from Early Retirement Now, a former Federal Reserve economist known for forensic financial modeling. Together we walk through when a 50-year mortgage might make sense, when it clearly does not, and why the math is rarely as simple as “higher payment versus lower payment.” We also dig into how ultra-long mortgages could push home prices even higher, and what this means for today’s buyers and tomorrow’s retirees. If you’ve wondered whether extended loan terms offer real affordability or just disguise the cost, this conversation gives you a clearer lens. Key Takeaways Why stretching to a 50-year mortgage can look affordable on paper yet leave you with f

#666: In this First Friday economic update, we explore the paradox defining our current economy: record-breaking retail numbers alongside plummeting consumer confidence. In this First Friday economic update, we explore the paradox defining our current economy: we're spending more than ever, while feeling worse about money than we have in years. The Bureau of Labor Statistics hasn't released jobs data for two consecutive months. The Federal Reserve must make a critical interest rate decision flying blind. Meanwhile, private sector data reveals troubling trends. Small businesses are hemorrhaging jobs while discount chains like Dollar General see their stock prices soar 44%. Americans are spending differently this holiday season. They're shopping earlier, using AI to find deals, and turning to buy-now-pay-later options. Households are spending less than last year, yet total spending increases because more people are participating. This K-shaped recovery benefits luxury retailers and bargain stores while

#665: If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when your net worth is growing and your risks are shifting. In today’s episode, we dig into a listener’s dilemma about soaring liability and umbrella insurance costs, and we explore how to think clearly about protection, exposure, and the parts of your portfolio that may already be shielded. Along the way, we unpack how shifting household risks, driver ages, and asset location change the insurance strategy year by year. From there, we take questions about Roth choices, future tax brackets, and whether it’s worth giving up investment flexibility to build a stronger tax triangle. These conversations get to the heart of how we balance risk, taxes, and long-term planning in the FI journey. Listener Questions in This Episode Andy asks: How can I protect my $2 million net worth without paying nearly $950 a month for incre

#664: Have any of these thoughts ever crossed your mind? If I had more willpower, I’d achieve my financial goals. I’m doomed to fail with money. Budgets suck. They only show me what I did wrong and make me feel horrible. If so, you’re not alone. It’s not that you lack willpower. It’s not that you’re doomed to fail with money. It’s not that you’re a horrible person for blowing your budget. It’s that you’re human. And humans make emotional decisions all the time. Decisions that often defy logic. But making emotional decisions doesn’t have to be a financial death sentence. Money management is a skill, which means we can improve. When we understand the “why” behind our decisions, coupled with the marketing tactics that retailers use, we can guard ourselves against cognitive biases and sales strategies. That’s what today’s guest is here to discuss. Jeff Kreisler, co-author of Dollars and Sense and Editor-in-Chief of PeopleScience.com, joins us to talk about common money mistakes people make and h

#663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And how do we use it without falling for hallucinations or built-in optimism? In this episode, we dig into the practical, real-world ways AI can strengthen our investing process while avoiding its biggest pitfalls. If you’ve ever wondered how to blend old-school fundamentals with new-school tools, this conversation will open up an entirely new mental model. Our guest is Brian Feroldi, an investor who has spent more than twenty years doing classic, deep-dive fundamental research. He reads SEC filings for fun, and he’s embraced AI not as a stock picker, but as a force multiplier that can turn days of research into minutes. We talk about the specific guardrails that make AI useful for fundamental investors, including restricting sources to trusted filings, designing step-by-step instructions, and assigning the AI

#662: Most teams hire for skills. The best teams hire for wiring. What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, processing style, or sense of mission than their résumé? This episode dives into the hidden patterns that shape how people work, make decisions, and handle pressure; the clues we often overlook, and the tiny tells that reveal who will thrive. We’re joined by William Vanderbloemen, whose firm has completed nearly 4,000 executive searches. After reviewing years of candidate data, he discovered why some people create momentum everywhere they go and others struggle, even when they look perfect on paper. We explore what “fast thinkers” and “slow thinkers” bring to a team, how to spot agility before you hire someone, and why some workers need a mission while others need a measurable win. Along the way, we reflect on our own tendencies and how understanding them can change the way we build teams, manage energy,

#661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how do you rebuild when you’re overwhelmed and out of margin? Once we work through her path forward, we shift to a listener on the opposite end of the spectrum. Daniel has maxed his Roth IRA, HSA, 401(k), and 457, and now sits on growing surplus cash. We talk about where extra money belongs when you’re aiming for early retirement and wondering whether to invest, save, or crush a low-interest mortgage. And to close, we take on a question dominating every financial feed right now, what if AI stocks really are in a bubble? We break down what it means to short the market, whether put options are actually a “safe” bet, and how to position a portfolio if you’re worried about te

#660: Caring for an aging parent can morph into a second full-time job, and even the most financially savvy adults get blindsided. Bank accounts freeze, home sales stall, and family savings disappear faster than anyone expects. In this episode, we dig into what really happens when you take over a parent’s financial life, from the first power of attorney to the final tax return. We explore the emotional and logistical realities of dementia care, Medicaid, trusts, probate, and why a single smartphone setting can determine whether you can access the information you need. Veteran financial journalist and certified financial planner Beth Pinsker joins us to share the hard lessons she learned while managing her parents’ money, housing, and estate. She opens up about the “you don’t know what you don’t know” moments that hit even experts. We look at why almost every caregiver reaches a breaking point, the two documents that can save a year of stress and tens of thousands of dollars, how a forgotten zero-

#659: Imagine that you’re at the absolute peak of your career. You’re the CEO of a prominent advertising company at the age of 36, but you feel like you’re driving in the wrong lane. It’s wrong.Then you make a hard career pivot and it works out beautifully.My guests today know exactly what that’s like. We’re joined by James Patterson, the author who has sold more than 425 million copies of his books. He has co-authored books with President Clinton, Dolly Parton, and now his latest co-author is Dr. Patrick Leddin, who also joins us to talk about disruption. 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) Defining disruption versus gradual change (5:20) Positive disruption mindset and overcoming fear (8:12) Process for uncovering personal passions (10:25) Patterson disrupts publishing with six books per year (13:45) Research reveals 16

#658: An unusual First Friday episode because we don't have a jobs report. However, we do know that in October, U.S. companies announced more job cuts in a single month than they have over any single month of the last 20 years. In other words, October was peak job cut month. By contrast, private payrolls, as reported by ADP, rose by 42,000 in October, so we have a little bit of conflicting data. Some pessimistic, some optimistic. We're going to take a deeper look at that in today's episode. 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) Conflicting Job Market Data (03:40) Youth Unemployment and AI’s Impact (10:16) Fed Rate Cuts and Housing Market (20:23) New Job Postings Lowest in 4 Years (20:54) Consumer Sentiment (22:04) Social Security Payments Increase in 2026 (23:33) Rising Car Costs and Repossessions (24:46) Good New