Afford Anything

#688: Anonymous: "Anonymous Sheryl" is 38, mortgage-free and exhausted after 15 years of teaching. She’s torn between pushing a few more years toward FIRE or switching to relief teaching now for better work-life balance. How do you trade speed to FIRE for sustainability without blowing up the plan? Anonymous : "Anonymous Ray" hired a bank portfolio manager but isn’t sure how to judge the results after just a few years. With mixed performance, dividend-heavy funds and higher fees, when is it fair to evaluate a manager — and would a simple index ETF outperform? Nathan: Nathan’s 14-year-old just earned his first W-2 income, and Nathan wants to jump-start his son’s investing journey with a Roth IRA. But with household income above the Roth limits, is there a legal way to make this work without sacrificing the child tax credit? Share this episode with a friend, colleagues, your substitute school teacher: https://affordanything.com/episode688 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#687: Your tax refund might be $300 to $1,000 bigger this year, and that's just the beginning of what's changing with your money. The Tax Foundation estimates most Americans will see significantly larger refunds thanks to seven major tax cuts. The child tax credit increased by $200. The standard deduction jumped by $750 for individuals or $1,500 for couples. The state and local tax deduction cap now sits at $40,000. Seniors get an extra $6,000 deduction, and deductions for auto loan interest, tips, and overtime work all increased. Retirement accounts saw major changes too. Catch-up contributions for high earners now must go into Roth accounts, which pushed thousands of employers to add Roth options to their 401k plans between 2024 and 2026. Kevin Warsh, the new Fed chair nominee, thinks the Federal Reserve has been doing it all wrong. The former Fed governor and Wall Street banker believes the Fed focuses too much on backward-looking data and reacts too slowly. He wants strategic, forward-thinking policy instead of chasing lagging indicators. President Trump clarified he never asked Warsh to lower interest rates and wanted to "keep it pure." The labor market shows serious cracks. Job openings dropped by nearly one million year over year to 6.5 million. Unemployment claims jumped to 231,000 last week. January layoffs hit 108,435 people — up 118 percent from last year and the worst January since 2009 during the Great Recession. Big Tech continues its massive AI spending spree. Microsoft, Amazon, Google, Meta, and Oracle will collectively spend over $500 billion on AI infrastructure this year. Google's spending alone doubled from 2025, reaching up to $185 billion focused on data centers and Gemini development. Share this episode with a friend, colleagues, and your tax preparer: https://affordanything.com/episode687 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#686: Rachel: Rachel is new to investing and has noticed the stock market being dominated by AI companies. She wants to make sure her portfolio is balanced without overexposing herself.Should she rethink her index fund strategy to protect against a potential AI bubble? Sarah: Sarah just turned 65, owns her home outright, and has been relying on credit cards since losing her job last year. She’s weighing whether to claim Social Security now, pay off debt, remodel her home, or convert her traditional IRA to a Roth.How should she prioritize these major financial moves while balancing income, debt, and retirement accounts? Anonymous “Julie”: This listener is on COBRA after her spouse took a federal buyout and is exploring starting a small business with her two young kids to teach them entrepreneurship.Will employer-provided health insurance fade away, and how can she test business ideas before fully committing? Resources Mentioned: Books:  So Good They Can't Ignore You by Cal Newport The E-Myth by Michael Gerber Traction by Gino Wickman The Lean Startup by Eric Ries Learn more about your ad choices. Visit podcastchoices.com/adchoices

#685: You're not an investor. You're a saver. That's the first of 10 principles Cullen Roche shares in this conversation about building what he calls "the perfect portfolio." Roche, the founder and chief investment officer of Discipline Funds, argues that when you buy stocks on the secondary market, you're not actually funding companies or making investments in the traditional economic sense. You're just swapping your cash for someone else's stock position – reallocating your savings. This reframe matters because it changes your entire approach. Instead of trying to beat the market, you focus on the boring, prudent work of allocating your savings across different time horizons. We walk through all ten of Roche's principles. He explains why you are your portfolio's worst enemy – not just because fear makes you panic-sell during crashes, but because FOMO during bull markets leads you to chase performance at exactly the wrong time. He breaks down why diversification is the only free lunch in investing, why costs matter more than you think, and why real returns are the only ones that count after you strip out inflation, taxes, and fees. Roche introduces some concrete strategies most people have never heard of. The 351 exchange lets you swap concentrated stock positions into diversified ETFs without triggering immediate capital gains taxes. The "defined duration" approach matches specific pools of money to specific future expenses—like pairing a six-month treasury bill with next year's bathroom remodel. He also tackles the hardest allocation question: what to do with money earmarked for three to ten years from now. That awkward middle timeframe sits between "keep it in cash" and "put it in stocks," and Roche explains why traditional approaches like sixty-forty portfolios don't always work. The conversation covers everything from why long-term bonds make terrible matches for long-term goals to why thinking in time horizons beats thinking in investment styles. 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) Principle 1: you're a saver, not an investor (04:48) Real wealth comes from direct business ownership (06:43) Principle 2: you are your portfolio's worst enemy (09:58) FOMO during bull markets vs fear during crashes (12:43) Principle 3: beating the market is hard (15:18) The 5 percent "fun money" allocation debate (16:18) What to do when your position explodes (17:18) The 351 exchange tax strategy explained (20:28) Should you rebalance concentrated stock positions (22:18) Principle 4: diversification is the only free lunch (31:03) Gold and stock market both high simultaneously (35:43) When diversification becomes diworsification (40:03) Principle 5: the cost matters hypothesis (44:23) HSAs, 401ks and unavoidable fee structures (47:03) Why ETFs beat mutual funds on taxes (51:03) Principle 6: real, real returns matter most (1:00:58) Principle 7: risk is uncertainty of lifetime consumption (1:06:18) Longevity risk and unpredictable healthcare costs (1:13:03) Principle 8: asset allocation as temporal conundrum (1:24:43) The 3-10 year allocation problem explained (1:28:03) Principle 9: past performance doesn't predict future (1:31:18) Principle 10: set realistic expectations, stay the course Resources: Cullin's website and newsletter: https://disciplinefunds.com Grab the FREE handbook: https://affordanything.com/financialgoals Share this episode: https://affordanything.com/episode685 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#684: Most people search for the perfect portfolio — the one allocation that works in every market, at every age, for every goal. This interview starts by explaining why that portfolio does not exist. We talk with Cullen Roche, founder and chief investment officer of Discipline Funds, about why copying someone else’s portfolio can backfire, and why portfolio design works better when it starts with your own constraints instead of rules of thumb. We walk through real portfolio models. The conversation begins with the classic 60-40 portfolio. You hear where it came from, how it held up during the Great Depression, and why it became so widely adopted. We also talk about its trade-offs — why it feels boring in strong markets and comforting in crashes, and how that emotional balance plays a role in investor behavior. Next, we shift to a Buffett-style portfolio. You hear why the takeaway is less about stock picking and more about structure. The discussion covers why Buffett keeps a small allocation to cash-like assets, how that “dry powder” functions during downturns, and why psychological stability matters as much as returns. The episode then turns to cash management. We talk about high-yield savings accounts, money market funds and Treasury bills. You hear how many cash products are built on T-bills, how banks capture part of the yield, and when managing cash directly may make sense. The concept of “T-bill and chill” comes up — along with when the extra effort may or may not be worth it. Finally, the conversation zooms out to time horizons. We discuss why income from a job functions like a bond allocation, how that changes risk capacity when you are younger, and why the early years of retirement carry the most danger. The episode closes by explaining sequence-of-returns risk and why portfolios need to work not just on paper, but in moments of fear. Resource: Cullin's website and newsletter: https://disciplinefunds.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) Intro  (02:00) No perfect portfolio (03:34) 60-40 portfolio starts (06:38) 60-40 keeps calm (08:00) Buffett portfolio basics (12:11) Stocks vs cash fear (13:34) T-Bill and Chill (18:22) TreasuryDirect is clunky (23:42) Income as bond proxy (25:33) Bond tent buffer (29:12) Sequence risk explained (31:42) Early retirement mindset (32:36) COVID panic calls (42:49) Three-fund portfolio basics (58:41) Get-rich-quick trap (1:18:21) Risk parity and All-Weather Share this episode with a friend, colleagues, your preferred financial advisor: https://affordanything.com/episode684 Learn more about your ad choices. Visit podcastchoices.com/adchoices