by Lance Roberts
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| Most people think about taxes once a year. Smart investors think about them every year. RIchard Rosso & Sarah Buenger break down the critical difference between tax preparation and true tax planning, and why that distinction could be worth thousands of dollars to your portfolio over time. We'll walk through real-world anonymous case studies from our client work, including how we helped one client sell nearly half of a concentrated stock position while staying entirely within the 0% capital gains bracket. We also cover Roth conversion timing, IRMAA bracket management, tax-efficient withdrawal sequencing, portfolio migration strategies, and proactive planning for stock options and restricted stock. Whether you are accumulating wealth or drawing it down, understanding how these levers work together is what separates a good financial plan from a great one. #TaxPlanning #WealthManagement #RetirementStrategy #CapitalGains #RothConversion |
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Most investors chase returns and compare themselves to an index that isn’t a real portfolio.
Indexes don’t pay taxes, trading costs, management fees, or deal with withdrawals.
They also replace failed companies without absorbing permanent capital losses — something individual investors can’t do.
That structural advantage makes consistent outperformance extremely difficult.
Because of these differences, obsessing over beating or matching an index can lead to poor psychological decisions. Investors often chase last year’s winners, assuming recent outperformance will continue.
But markets rotate — sectors and themes shift leadership over time. What worked last year may underperform next year. By jumping into what just worked, investors frequently buy high and set themselves up for
2-21-26 What You’re Being Told About Annuities is Wrong
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Richard Rosso & Danny Ratliff tackle one of the most misunderstood retirement tools: annuities—what they are, who they’re actually for, and where investors frequently get trapped by slick marketing and incomplete comparisons. We start with why annuities aren’t for everyone, then walk through three clear use-cases where an annuity can make sense—especially for households prioritizing guaranteed lifetime income and a more stable retirement “paycheck.”
Danny & Rich also dig into the common mistakes: chasing teaser rates, misunderstanding caps/participation rates, overlooking rider costs, and buying a contract that doesn’t match the real goal (income, legacy, or risk transfer). We also cover how Social Security functions like a foundational annuity, and why your claiming strategy can matter
A No Landing Outcome Is Assumed: Should It Be?
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Quite often, investors describe economic forecasts as a hard landing (recession), a soft landing (weak growth but no recession), or no landing (moderate to strong economic growth). As evidenced by the massive rotation toward economically sensitive sectors like industrials and materials and the significant underperformance of interest-rate-sensitive growth stocks, the no landing, or as it’s …
Data Center Debt: Can Oracle Hang With The Big Boys?
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Meta and Google recently borrowed a combined $55 billion in the corporate bond market. As we share below, this debt represents a new source of funding for data center expansion. Further, as shown in orange, Oracle tapped the private market for loans to secure the capital needed to sustain AI innovation and the related data …
11-12-25 December Rate Cut Back in Play
2025-11-12
Soft jobs data and falling rents point to weaker inflation ahead, setting the stage for a potential Fed rate cut in December.
In this short video, I explain why this slowdown may be exactly what the market needs to keep the rally alive.
📺Full episode:
Catch me daily on The Real Investment Show: https://www.youtube.com/@TheRealInvestmentShow
OpenAI Seeks Government Support
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Sarah Friar, OpenAI’s CFO, spoke at a Wall Street Journal technology conference to update the audience on the potential of AI. While her comments were very optimistic, she noted that OpenAI seeks continued capital inflows, highlighting the lynchpin for AI development. Her quote below, courtesy of Bloomberg, takes traditional bank and industry financing a step …
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