Capital Gain Strategies Archives - Think Outside the Tax Box
By Peter J Reilly CPA

This Is The Only Other Year-End Tax Tip Guide You Need

So as I did last year, I have reviewed a multitude of year-end tax tips articles. One of them is a real standout that you should be sure to check out. If you missed it, you should definitely roll back to the November 15 edition and go over Dominique Molina’s piece, which focuses on what you need to do sooner rather than later in response to OBBBA. It provides more detailed, relevant, actionable advice that you won’t see anywhere else than any of the multitude of pieces I have reviewed. As for the rest, I will give you a basic rundown of what I call the SOSO (same old, same old) and a few suggestions that stand out as different that I will get into a little more along with some thoughts of my own.

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The Corporate Vault: How to Use a C Corporation to Stockpile Cash for the Future

When most people think about saving for the future, their minds jump to retirement accounts—401(k)s, IRAs, maybe even defined benefit plans. But business owners have another option that often goes overlooked: using a C corporation as a strategic savings vehicle. By leveraging the flat 21% corporate tax rate, smart income shifting, and careful timing of distributions, business owners can “stockpile” cash inside a corporation, building wealth for future use without the red tape of traditional retirement plans. Want to see how top tax strategists legally use C corporations as private retirement vaults while avoiding double taxation and IRS scrutiny? Continue reading to learn the blueprint.

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Client Alert

Year-End Tax Planning Under the One Big Beautiful Bill Act (OBBBA)

The One Big Beautiful Bill Act (OBBBA), signed into law on July 4, 2025, doesn’t reinvent the tax code it refines it. Much like its predecessor, the Tax Cuts and Jobs Act (TCJA), it keeps many familiar provisions in play: lower rates, expanded SALT flexibility, and broader deductions. But here’s the real story: While most tax pros are busy memorizing what stayed the same, the planners who will win 2025 are the ones spotting what just became possible. OBBBA quietly opens a handful of powerful new planning windows — each one capable of delivering real, measurable savings for the right client. The key is knowing which changes are worth your time… and which are just political garnish. Below, we’ve curated the most strategic, high-impact moves to make before year-end 2025, the ones that separate the advisors who explain the law from those who leverage it. Most tax pros will stop at what changed. The smart ones will keep reading to learn how to use it.

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Client Alert

An Analysis of the OBBBA’s Trump Accounts (Part 2)

In part one of this series, I went over the basics of the new retirement accounts for minors, Trump Accounts, which were created as part of the One Big Beautiful Bill Act (OBBBA). Trump Accounts allow the Government, Charitable Organizations, Parents, and others to contribute to a child’s savings, usually on an after-tax basis. These accounts then transition to a traditional individual retirement account (IRA) when the child turns 18. Although the contribution limits act like non-deductible traditional IRA contributions and have a contribution limit of only $5,000 per year, they do not have the same earned income requirements that traditional IRA contributions have. This means that children are able to accumulate savings even without earned income. This article presents several scenarios to examine how Trump Accounts may play into an overall savings strategy for children.

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Are There Tax Consequences of The GENIUS Act? It Depends!

The Guiding and Establishing National Innovation for U.S. Stablecoins Act became Law on July 18, 2025. It “establishes a regulatory framework for payment stablecoins,” which are defined in the legislation as “digital assets which an issuer must redeem for a fixed value.”

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Client Alert

The Think Outside the Tax Box OBBBA Quick Reference Guide

The One Big Beautiful Bill Act (OBBBA) marks the most sweeping overhaul of the tax code since 2017, reshaping rules across personal and business income, education, healthcare, and credits. To help you stay ahead of the curve, Think Outside the Tax Box is proud to share our Quick Reference Guide, designed to keep you and your clients informed, prepared, and proactive.

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What You Need to Know About the Proposed Trump Savings Accounts

Tucked inside the narrowly passed “One Big Beautiful Bill Act,” President Trump’s sweeping tax and spending package, is a provision that’s drawing media attention: the creation of a new tax-deferred investment account called a Trump Account. A proposed $1,000 “baby bonus” tied to the account only adds to the intrigue. While the reconciliation bill primarily focuses on extending the 2017 tax cuts and reshuffling federal spending priorities, this unexpected addition could offer new planning opportunities for taxpayers.

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DeFi-nitely Confusing: Final Regulations for Digital Asset DeFi Brokers

Well, at least the treasury department is true to form. They have ruined yet another international trip for me, which is the third time if you’re keeping track at home. This time it was a weekend trip to Toronto, which coming from upstate New York is technically “international,” yet somehow substantially closer to home than New York City. Late afternoon on the Friday before New Year’s Eve, the Treasury released another 115 pages of Digital Asset Regulations, along with a 13 page notice for good measure. As we’ve discussed previously on TOTTB, the last set of regs punted on a number of more complex crypto issues. This most recent release is all about one of those issues, Decentralized Finance, better known as “DeFi.”

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Exploring the Final 1099-DA (Digital Asset) Regulations

One of the IRS’ favorite ways to entertain itself is to release new and important guidance at 5 pm on a Friday. They self-award bonus points if it is the Friday before a holiday. They hit “publish” and immediately shut down the office before anyone can react. When it comes to digital asset guidance, I speculate they also have access to my vacation calendar to release it at the most inconvenient time possible. Last summer, they released the temporary regulations on 1099 crypto reporting while I was on vacation in South Africa. This year, at 4:45 pm on the Friday before the 4th of July, they released the final regulations. I then had to spend the rest of the summer dodging my editors at TOTTB because this article was really harshing on my vacation plans.

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