Welcome to THINK OUTSIDE THE TAX BOX, the premier on-line publication for tax reduction information!
Here at TOTTB, we produce in-depth, easy to understand, exhaustively cited, essays on the topic of tax reduction for our subscribers! And, every two weeks, we add more articles and more features like our live webinar events, private Facebook group, downloadable “Client Alerts” and Infographics, features like our blog, Around the Tax World, an aggregator of all the news happening in the tax world!
If you aren’t a subscriber yet, please understand that this blog is a very small part of what we do. If you really want to dig in, SUBSCRIBE! (We offer a 30-day money back guarantee, you have nothing to lose!)
Around the Tax World- May 7, 2026
In The HeadlinesThe S&P 500 stalls as the war in Iran continues and the Federal Reserve meets on interest rates.
What's New In The Tax World?Republican lawmakers look to woo voters with lower capital gains taxes
State-By-State-UpdatesCalifornia’s “billionaire tax” makes it a step closer to the November ballot.
Tax Planning TipsWho can benefit most from the IRS’ free tax withholding tool?
READ MOREAround the Tax World- August 7, 2025
In The HeadlinesTech stocks may be making a comeback as design tool Figma sees a 250% gain on its IPO day.
What's New In The Tax World?The end of Direct File, leadership investigations, and staffing shake-ups: What is the future of the IRS?
State-By-State-UpdatesFlorida’s hurricane season is also a tax-free season this year.
Tax Planning TipsSummer means tax-free holiday season! Which states can save consumers the most money?
Around the Tax World- July 24, 2025
In The HeadlinesCould your caffeine consumption take a hit with the increased tariffs on Brazil?
What's New In The Tax World?Will the newly-passed tax and spending plan help or hinder Republicans in 2026?
State-By-State-UpdatesGeorgia makes moves toward eliminating the state income tax.
Tax Planning TipsHow could the new tax exemption for tips and overtime pay affect employers?
Around the Tax World- July 10, 2025
In The HeadlinesU.S.-Canada trade talks continue as Canada opts to drop its digital services tax.
What's New In The Tax World?Trump’s megabill continues to prove controversial—including forceful pushback from Elon Musk
State-By-State-UpdatesIllinois sees a slew of mid-year changes to its taxes and other laws.
Tax Planning TipsHow might the new tax and spending bill change your income tax bracket?
Around the Tax World- June 24, 2025
In The HeadlinesHow could ongoing tariffs impact the Federal Reserve interest rate?
What's New In The Tax World?The Senate is proposing changes to the House’s tax and spending bill: What stayed and what’s going?
State-By-State-UpdatesAlaska hits a roadblock in solving problems with state oil tax collections.
Tax Planning TipsSolar stocks plunged in response to the Senate’s revised tax bill.
Around the Tax World- June 10, 2025
In The HeadlinesSteph Curry’s collection of brands hit $173.5 million in revenue last year.
What's New In The Tax World?Will Congress deliver on tax reform by President Trump’s July 4th “deadline”?
State-By-State-UpdatesIllinois’ grocery tax is set to expire in 2026—but the mayor of Chicago is pushing back.
Tax Planning TipsThe Child Tax Credit would face a new restriction under the federal tax bill: What could this mean for families?
Around the Tax World- May 27, 2025
In The HeadlinesElon Musk is stepping back from DOGE and from hefty political spending.
What's New In The Tax World?Trump’s tax bill centers on extending the 2017 tax cuts—but the cost may be too high for some Republicans
State-By-State-UpdatesMaryland’s latest bill brings significant tax increases.
Tax Planning TipsWhat can the entire U.S. Senate agree on? Apparently, no tax on tips.
Around the Tax World- May 8, 2025
In The HeadlinesCould Tesla be seeking a replacement for Elon Musk?
What's New In The Tax World?What could make it into the next budget bill? SALT and staffing are the next big conversations
State-By-State-UpdatesOver 400,000 Florida taxpayers will get a check through the Hillsborough County Sales Tax settlement.
Tax Planning TipsThe federal government may flip the script on electric vehicles by introducing an annual EV registration fee.
Around the Tax World- April 24, 2025
In The HeadlinesCould Harvard and other universities lose their tax-exempt status?
What's New In The Tax World?The renewal of Trump’s 2017 tax cuts is facing pushback from within the Republican party
State-By-State-UpdatesFlorida lawmakers weigh the pros and cons of two budget bills, both proposing over $5 billion in tax cuts.
Tax Planning TipsCould the federal tax on Social Security income actually be eliminated?
NOT A MEMBER YET?
SUBSCRIBE TO GET ALL OF OUR
GREAT ARTICLES AND RESOURCES!
CURRENT EDITION
Small Mistakes With Huge Costs for Your Client’s Tax Returns
We’ve all been there. A client walks into your office and, somewhere in the conversation, you realize that a seemingly minor oversight, a missed deadline, a form nobody filed, an election nobody mentioned, has spiraled into a five- or six-figure tax problem. In my years of practice, some of the most expensive mistakes I’ve seen weren’t the result of aggressive planning gone wrong. They were small, quiet errors. The kind that happens when a deadline slips, an election isn’t made, or a form gets overlooked entirely. The tax code is unforgiving in these situations, and the IRS has little sympathy for “I didn’t know.” This article walks through some of the most common, and most costly, small mistakes that can devastate your client’s tax situation, along with practical guidance for avoiding them.
When Debts Go Bad: The Challenges of Deducting Delinquent Debts
It is painful when you finally realize that the money you expected to be repaid is never coming back. The tiny silver lining in that cloud might be the tax benefit of “writing off” the debt. Unfortunately, that silver lining may well be eclipsed by an even bigger cloud. Writing bad debt off is not that easy, and there’s probably no silver lining to that cloud. Ironically, you might find that the mistakes that caused you to be holding a bad debt might be what prevents you from getting a usable deduction.
Building a Partnership the Right Way: Tax Strategies From Day One
Setting up a partnership is a lot like getting married. It’s exciting, full of promise, and if you do it right, it can be incredibly rewarding. Do it wrong, and you’re setting yourself up for years of headaches and potentially significant financial loss. The decisions you make at the formation stage of your partnership will impact your tax situation for years to come, and in some cases, these decisions can be difficult or costly to undo later. In this article, we’ll explore the critical steps in setting up a partnership and the tax implications of various contribution strategies. You’ll learn how to establish a foundation that maximizes tax advantages from day one.
