History Lessons for the Modern Investor
History Lessons for the Modern Investor Podcast
💲What Price Should Investors Be Willing To Pay?
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💲What Price Should Investors Be Willing To Pay?

September 4th, 2025

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As seen on: CNBC.com

Trump’s Big Beautiful Bill: Roth Conversions Enter a New Era of Complexity

Thinking about a Roth conversion? President Trump’s “One Big Beautiful Bill” may have just turned a familiar tax-saving move into a trickier maze for retirement savers—and their advisors.

What’s New and What’s at Stake?

The Bill makes Trump-era lower tax brackets permanent—giving Roth conversion fans a longer runway for favorable rates. But, here’s the rub: the law also layers in a patchwork of temporary deductions (for seniors, tipped workers, and more) that phase out as your income rises. Move too much money via Roth conversions, and you could lose access to these new breaks or bump into a higher bracket, blunting the intended payoff.

🎯As I shared with CNBC, the game is still about “tax bracket management,” methodically converting just enough each year to “fill up the lowest brackets” without triggering unnecessary tax charges or inadvertently increasing future Medicare premiums and other costs. Lower brackets are permanent—but temporary bonus deductions only last through 2028, and often phase out once income passes certain thresholds (e.g., $150,000 for married couples). Converting at 22% or 24% rates might cost you a deduction, but could still be wise if it protects you from 30%+ brackets later due to mandatory withdrawals. Each Roth conversion now demands careful scenario planning around your current and future income, tax bracket, Medicare premiums (IRMAA), and the timing of these new-but-vanishing tax breaks.

The Roth conversion playbook isn’t dead—it’s just more nuanced. The door to tax-savvy conversions is wide open, but the path runs through a thicket of new rules. Now, more than ever, work with a financial planner to manage bracket creep and optimize not just your taxes, but your whole retirement income strategy.

Don’t let tax law whiplash or “bonus deduction FOMO” derail your long-term planning. The smart move is, as ever, making intentional, well-coordinated decisions—never letting the tax tail wag the retirement dog.

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On September 4, 1972, The Price Is Right Premiered on Daytime TV.

American households tuned in to CBS for the first episode of The Price Is Right—a game show that would become a cornerstone of daytime television. Hosted by the endlessly affable Bob Barker, The Price Is Right wasn’t just about luck; it was about knowing the market, making calculated choices, and keeping your cool under pressure. Contestants bid to guess the actual retail price of everything from lawnmowers to luxury vacations, weaving basic economic sense with the drama of possibility. In its first decade alone, the show revolutionized the genre—proof that success isn’t always about dazzling innovation, but about doing the basics brilliantly (and with a bit of sparkle). Today, half a century later, The Price Is Right continues to thrive, teaching generations about the perils and potential of making decisions with incomplete information, and reminding us that sometimes “coming closest without going over” is the surest route to a win.

Here are four lessons for Modern Investors from The Price Is Right’s enduring appeal:

💲 Know the Real Value—Not Just the Hype

The central challenge of The Price Is Right is separating sticker shock from substance. Wise investors face the same dilemma: is that surging market—or that hot stock—worth the price you’re being asked to pay? Chasing trends or ignoring fundamentals (i.e., the “retail value” of a company or asset) can leave you at risk of overbidding. Discipline and research—not just enthusiasm—help ensure you don’t wind up paying more than an investment is truly worth.

💲 Success Is About Edges, Not Extremes
On the show, the winner is often the cautious participant—one who bids closest to the actual price without crossing the line. In markets, the same logic applies: risky bets and maximalist moves make headlines, but portfolios are built for stability. A diversified, measured approach (rather than betting the farm or chasing the penny stocks) tends to outperform wild speculation over time. Being “right enough” beats being wildly right one day and wrong the next.

💲 Adapt on the Fly—But Keep Your Anchor
Contestants on The Price Is Right are constantly adapting—reading cues, watching competitors, adjusting their bids. Modern investors, too, need to stay agile: markets move, economic landscapes shift, and new information emerges daily. But don’t lose sight of your core strategy or let noise dictate every decision. Adaptability matters, but only if tethered to an anchor of sound principles and clear goals.

💲 Enjoy the Game—But Don’t Be Ruled by Emotion
There’s plenty of cheering, heartbreak, and drama when that last price is revealed, but the best players—and the best investors—know the difference between excitement and reason. Emotional investing, like emotional bidding, leads to regret. Celebrate your wins, learn from the losses, and, as Barker himself would say, “help control the pet population”—in this case, the stray impulses that can wreak havoc on your portfolio.

A Final Thought
In the end, The Price Is Right’s secret wasn’t just giving away new cars—it was making sound strategy entertaining and rewarding humility as much as bravado. In investing, as on the big stage, fortune tends to favor those who do their homework, respect the rules, and know when to leave room under the price tag. Next time you’re tempted to chase the next “showcase,” remember: true wealth is less about guessing correctly once, and more about playing the long game—wisely, patiently, and with a smile.


This episode is sponsored by Victory Independent Planning. Ready to take the stress out of your retirement? At Victory Independent Planning, we put you on the right trajectory with our exclusive VIP Retirement Glidepath™️!

Schedule an assessment now: https://freebusy.io/victoryindependentplanning-VIP-Booking/phone-consultation

🎯Patrick Huey is a small business owner and the author of three books on history and finance as well as the highly-rated recently-released fictional work Hell: A Novel. As owner of Victory Independent Planning, LLC, Patrick works with families and non-profit organizations. He is a CERTIFIED FINANCIAL PLANNER™ professional, Chartered Advisor in Philanthropy® and an Accredited Tax Preparer. He earned a Bachelor’s degree in History from the University of Pittsburgh, and a Master of Business Administration from Arizona State University. Patrick previously served as a Naval Flight Officer from 1996-2005, earning the Strike Fighter Air Medal during combat operations and two Navy Achievement Medals. 👉🏻 Reach him at 877-234-8957 or schedule a time to talk using this link:

https://freebusy.io/victoryindependentplanning-VIP-Booking/phone-consultation

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