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 MOREAvoiding Life Insurance Tax Mishaps
Life insurance is such a great income tax deal that it really disturbs me when people manage to create income tax nightmares with it. The build-up in value of a whole life policy is not currently taxed if the policy is properly structured. And even better, except for the insured, the proceeds are totally income tax free when paid because of the death either actual or clearly coming soon of the insured. Of course one of the greatest pieces of marketing genius ever was calling it life insurance, as it is in its pure form, actually death insurance. Here are some stories of life insurance tax nightmares and we’ll see if we can draw a moral from them.
Read MoreRemember, Influencers, the IRS Follows You Too!
The influencer marketing industry was able to grow during Covid as many advertisers had to adjust or cancel their marketing campaigns. This was because more people were sitting at home consuming content on social media. This new opportunity for smaller influencers has created a new group of taxpayers who need to know their new filing obligations. They’ll also be open to tax planning strategies that you have to help them reduce their tax liability.
Read MoreHobby Loss Regulations And Loper Bright
For me, the most exciting Tax Court opinion of 2025 was Judge Joseph Goeke's supplement to his 2024 opinion in the case of Gary M. Schwarz. With a $1,851,878 tax deficiency, it is the largest hobby loss opinion since 2019. (The really big dollar cases tend to settle.)
Read MoreConsult, Don’t Convince: Turning Discovery Calls into Advisory Opportunities
The most successful accountants aren’t the ones who pitch the hardest, they’re the ones who listen the most. When you ask better questions, you can diagnose problems that clients didn’t even know they had, which then helps us clarify outcomes instead of listing services. When we shift from “convincing” to “consulting,” discovery calls stop being “sales” conversations and start becoming advisory conversations. And advisory conversations naturally lead to advisory engagements.
Read MoreTAX COURT ROUNDUP – March 2026
A short but busy month in Tax Court, with the non-shutdown, new wrinkles in law and regulation, and, as always, problems arcane and mundane; so let's jump in.
Read MoreContracts, Signing Bonuses, and the Substantial Presence Test
In tighter job markets, recruits are often offered signing bonuses (and sometimes moving expenses) to join a firm. Sometimes construction workers temporarily relocate to jobs in other states while they are employed by the company that hired them in their home state. This article reviews some of the foundational tax concepts to consider when evaluating sourcing of income for state tax purposes.
Read MoreHelp Clients Rebuild Tax Records After Disaster
Tax pros help clients with a lot of catastrophes: wrangles with tax authorities, paltry nest eggs, more wrangles with tax authorities. More frequently, your clients might face a more tangible and cinematic disaster. These days, there’s always a storm comin’. Swept away in that destruction, for many people, are physical tax and financial records. A few precautions could have prevented such loss and made life at least a bit easier for victims. Here’s how to help clients head off trouble – and recover after it hits.
Read MoreGeorge M. Cohan’s Tax Triumph: The Rise and Erosion of the Cohan Rule
The Cohan rule is named for George M. Cohan. George Michael Cohan (1878 – 1942) was a theatrical producer. In the decade before World War I, he was called the “man who owned Broadway” and is considered the father of American musical comedy. In 1940 he was awarded the Congressional Gold Medal for his contribution to morale during World War I with his songs “You’re a Grand Old Flag” and “Over There,” the first time the medal was awarded to someone in an artistic field. But his most enduring legacy may be the tax rule that shared its name.
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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.








