Investments Archives - Think Outside the Tax Box
By Jeff Stimpson

Another Tax-Smart Way to Save for Retirement

Most clients are familiar with the well-known accounts to save for retirement, such as the 401(k) and IRA. Some clients might be able to supplement those with a lesser-known vehicle as well. A life insurance retirement plan (LIRP) is a type of permanent life policy with a cash value basically funded by overpaying premiums. The money can eventually be taken as a tax-free loan against the policy for anything from medical expenses and long-term care to supplemental retirement income to, for the wealthy, the payment of taxes on large estates.

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An Analysis of the OBBBA’s Trump Accounts (Part 1)

The One Big Beautiful Bill Act, signed into law by President Trump on July 4, 2025, added a new tax saving tool for minors, the aptly named Trump Accounts. In this article, I go over the details of the new Trump Accounts. In part II, I will discuss some of the potential tax planning opportunities and pitfalls related to the new accounts.

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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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Tax Tips for Families Affected by Disability: What More People Should Know

There are a few tax tips for people with disabilities that I think are not as well-known as they should be. They can also be applicable to their parents or others who care about them. This is not meant to be a comprehensive treatment of all aspects of how taxation and disability interact. Rather it is to alert you to some things I think should be more widely known. One thing to keep in mind is that some of the parents and grandparents of disabled adults don’t necessarily share this part of their personal life, so you may be surprised at how this information might be valuable and appreciated by some of your clients.

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Client Alert

Reflecting On Rothing

I have been dissatisfied with most of the articles that I have read about what I call Rothing, i.e. foregoing a deduction for retirement savings with the prospect of tax-free distributions in the future or taking the tax hit on a deferred account to convert it to a tax-free account. The articles generally have a pro-Roth bias. Suze Orman, for example, swears by Roths. They also tend to not have numbers in them. What I am going to do here is to reflect on the idea of Rothing and discuss what I see as some key numbers. I’m not going to dive deep into technical issues.

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2025 Tax Surprises You Shouldn’t Overlook

There are a few tax rules new for 2025 that may catch some individuals and their tax advisers by surprise. These changes have not received lots of attention either because they are overshadowed by related changes that are more significant, or they were enacted a few years back with a future effective date that arrives in 2025. This article covers changes for 2025 that you will want to be sure to share with clients to avoid surprises at a later date.

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Client Alert

Tax Scams: What You Need to Know About “Sovereign Tribal Tax Credits”

Tax scams come in many shapes and sizes. Some schemes aim to steal money or identities, while others present as legitimate-looking investment opportunities with promises of reducing tax bills. These offers often come from law firms, investment groups, financial advisors, and even sophisticated organizations. They tempt taxpayers with strategies like inflated art donation deductions, film investments, and even Native American Tax Credits. The IRS advises taxpayers to consult independent tax or legal professionals to avoid falling prey to aggressive promoters. But as tax planners, how do we determine if a strategy is legitimate? Who do we consult so we can understand the difference between a scam and a scheme? Think Outside the Tax Box of course! One popular scheme being whispered about in tax conferences this year is the so-called "Tribal Tax Credits." It’s been a hot topic, with many professionals asking about its legitimacy. Let's dive into the details to better understand this intriguing yet questionable opportunity.

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The Cryptocurrency Basis Day of Reckoning is Upon Us

Late on a Friday afternoon at the end of June 2024, the IRS dropped nearly 400 pages of new Digital Asset (née Cryptocurrency) Guidance. Most of it related to the forthcoming form 1099-DA. Along with the massive tome of terrible bedside reading, the service also published two new Notices and a Revenue Procedure. The Notices were about boring stuff, like temporary penalty abatement for backup withholding on digital asset transactions. This Revenue Procedure, however, will impact nearly every taxpayer that owned crypto prior to January 1, 2025. This procedure, RP 2024-28, has gone largely unnoticed thus far. On the surface, it seems like a godsend to taxpayers. Below the surface though, it is a ticking time bomb.

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Reflecting On Syndicated Conservation Easements

In late June, IRS announced it would be mailing out a time-limited settlement offer that would allow taxpayers who are haunted by an investment in a syndicated conservation easement to settle. As I write this, the terms of the settlement have leaked. They strike me as overly generous. It does seem that the syndicated easement campaign of the IRS is coming to a close.

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