CURRENT EDITION

Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.
READ MOREA Tax-Season “Cheat Sheet” to Avoid Getting Cheated
Scams lurk around every corner year-round, but tax time is when they seem to flourish. The crooks that come out to swipe cash, credit card info, Social Security numbers and other personal details are nothing if not innovative, always ready to use any tech advancement, disaster headline or snake-oil sales tactic to worm their way into people’s wallets. Part of your role these days as a financial pro is to help protect clients against these cons. Here’s the latest to know.
Read MoreTAX COURT ROUNDUP – March 2025
February brings us Groundhog Day, but there are always new developments in Tax Court, as well as refreshers to keep practitioners current.
Read MoreRenewable Energy Tax Credits: An Opportunity to Sustainably Optimize Taxes
Investment Tax Credits (“ITCs”) and Production Tax Credits (“PTCs”, and together with ITCs, “RETCs”) have existed for decades and reflect the U.S. government’s commitment to incentivizing clean energy solutions in industry and commerce. The availability of RETCs was most recently extended by the Inflation Reduction Act of 2022 (“IRA”), which fundamentally transformed policy in this space by tying such credits’ expiration to the U.S. reaching certain targets for greenhouse gas reductions. While the recent change in Executive Branch leadership casts doubt over the longevity of RETCs, a full repeal seems unlikely given the scope and scale of domestic projects which utilize and benefit from such credits. This article discusses how RETCs may benefit both buyers and sellers in an increasingly uncertain environment.
Read MoreDeFi-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.”
Read MorePig Butchering Can Slaughter Your Clients’ Finances
People use the online space to look for love, make business and financial decisions. And all of these decisions can have serious tax implications. That is why as trusted financial and tax advisors, it is important for us to be aware so we can help protect our clients. In 2024, the Federal Trade Commission released a report showing consumers reported losing $4.6 billion in investment scams. That's only the amount reported, so our clients are at risk if they are online making financial decisions. Today, let's look at a newer player in the online investment scam arena: pig butchering. If you're like me, you're probably thinking “what in the world does this have to do with taxes?” Unfortunately, everything. It leads to taxpayers receiving tax bills for money they withdrew but lost as victims of theft.
Read MorePinterest for Accountants: Curating Inspiring Financial Resources and Building Brand Awareness
As we continue our series of articles on various social media platforms, we will focus on Pinterest. As discussed, social media is an indispensable tool for professionals across multiple industries. Accountants, often perceived as traditional and reserved, can harness the power of these platforms to extend their reach, engage with clients, and establish a solid online presence. Pinterest is known for its easy visuals and use, offering unique opportunities for us accountants to curate boards with valuable financial resources. By strategically using Pinterest, we can attract and engage our target audience, drive website traffic, and build brand awareness.
Read MoreLeaving the United States, Part III: Dual Citizenship
In Part I of this three-part series, we discussed the implications and taxes for American expatriates. In Part II we turned our attention to renouncing citizenship. Here in Part III, we will consider the halfway point of dual citizenship. And as you would expect, taxes are a serious consideration.
Read MoreReflecting 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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CURRENT EDITION

Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.

Structured Installment Sales Making Comeback – How Good A Tool Is It?
Structured Installment Sales (SIS) have been making a comeback. Historically low interest rates starting in 2011 made them go out of favor. Starting in 2018, insurers started coming back into offering them. MetLife expanded its SIS solution to 49 states, Puerto Rico and D.C. in 2022. You need to know about SIS and it deserves a place in your toolbox. You might not be using it as often as the toolmakers imply. I took a look at SIS in 2023 and was a little more enthusiastic about it than I am now. Let’s dig in.

Assessment Statutes and Document Retention Best Practices
When it comes to document retention, my guiding policy is “If I don’t keep it, it can’t be stolen or subpoenaed.” That sounds cynical, but there’s truth in it. The smaller your data “surface area,” the less you have to manage in the event of a data breach (or, if you hold paper documents, in the event of a fire or break in). And, if a client or former client gets really sideways in divorce or criminal court, being able to say “I have a policy in place and I don’t keep records longer than three years” can provide you with a measure of peace. But what should your policy be? It depends, but relevant assessment statutes are a good place to start. This article reviews the IRS rules for assessing tax and provides some best practices for developing document retention policies for return preparation documents in your practice.








