Episode 474: Planning Around Taxes In Transition, Bitcoin FOMO, Living In A Trailer, And Portfolio Reviews As Of December 19, 2025

Dec 21, 2025

Listeners explore the myth of "never pay taxes" while transitioning to a Golden Butterfly portfolio. The discussion dives into managing taxable gains through strategic account placements and specific-lot sales. Bitcoin's volatility and speculative nature is examined, urging caution with allocations. Portfolio reviews highlight performance and strategies across various investment styles, including leveraged options. Additionally, engaging listener-created content adds a fun twist, enriching the financial discourse.

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ADVICE

Stop Letting Taxes Drive Your Life

Don’t let avoiding taxes dictate your life decisions or prevent you from reorganizing accounts and spending on what matters.
Spread taxable events over years and prioritize building the portfolio you actually want before minimizing taxes.

ADVICE

Rebalance Inside Tax-Deferred Accounts First

Use retirement accounts to adjust allocations first because trades there have no immediate tax consequences.
Move long-term Treasuries and gold into tax-deferred accounts, then minimize taxable-account trades.

ADVICE

Harvest Gains And Use Specific-Lot Sales

Harvest gains in low-income years to exploit the 0% or lower capital gains brackets.
Use specific-lot sales to sell newer lots with smaller gains and reduce tax bills.

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In this episode we answer emails from Jenna, Kevin, and Jack Rabbit. We challenge the myth of “never pay taxes” and show how to transition scattered holdings into a Golden Butterfly framework while keeping taxes manageable. We also examine Bitcoin’s role, review sample portfolio performance, and share new listener-created bonus material on the site.

And THEN we our go through our weekly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.

Additional Links:

Father McKenna Center Donation Page: Donate - Father McKenna Center

Jack Rabbit's Creation re Episode 208 (Advice for Beginning Investors): A Parable for Beginning Investors in the Land of Oz

"Free Steak Dinner" Rant Episode: Episode 321: A Small Rant About Newman Selling Annuities At Local Steakhouses | Risk Parity Radio

Breathless Unedited AI-Bot Summary:

You can optimize a portfolio to the comma and still miss the point if the tax tail is wagging the rest of your life. We dive into a common blocker—fear of realizing gains—and replace it with a better plan: build the mix you actually need, then minimize taxes over years with smart account placement, specific-lot sales, and well-timed gain harvesting. From there we lay out a practical route to a Golden Butterfly structure—growth and value stocks, long Treasuries, gold, and short-term bonds—implemented primarily inside tax-deferred accounts to keep the brokerage account’s changes light and intentional.

Along the way, we tackle a hot question on Bitcoin. Our take is grounded, not tribal: no income, high volatility, and shifting correlation that often mirrors high-beta growth. If you must touch it, keep it tiny so it can’t steer your long-term outcomes. More important, we reframe risk tolerance: being comfortable with swings isn’t a destination. Decide whether your target is maximizing lifetime spending or terminal wealth, then right-size volatility and liquidity to fit that goal. Finance comes first; the personal is how you stick to it.

We round out the conversation with a market scoreboard—gold’s surge, equities’ strength, managed futures’ late-year pop—and a transparent look at model portfolios, from classic all-weather to a measured, levered stack that’s built for accumulators who accept higher swings. We also share a listener-made “graphic novel” twist on a past episode now posted as bonus material. If you’re ready to shed tax paralysis, align your assets with your life, and use diversification that actually works across regimes, this one’s for you. If you enjoyed it, subscribe, leave a review, and tell us: what’s the next move you’ll make to simplify and realign your portfolio?

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