When Tax-Loss Harvesting Makes Sense for Your Timeline

#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

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For more information, visit the show notes at https://affordanything.com/episode655

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