Tax Planning Posts

March 14, 2018
St. Patrick's Day dog

IRS Investigates Pot of Gold at End of Rainbow

IRS Investigates Pot of Gold at End of Rainbow St. Patrick’s Day is here, and every “Irish for a day” tippler in your social circle will take advantage of this convenient excuse to haul grandma out of the house for a little day-drinking. (It seems unnecessary on a Saturday, but whatever.) Faux-Irish saloons across America are tapping kegs of Guinness, pouring shots of Jameson, and covering their walls and ceilings in every Celtic cliche they can find: the shamrocks, the hats, the green beads, and of course, the leprechaun jealously guarding his pot of gold at the end of the […]
March 7, 2018

$11,100 Tip?

$11,100 Tip? The three-martini lunch has a long and mostly honorable history as a deductible business expense. As former President Gerald Ford once said, “Where else can you get an earful, a bellyful, and snootful at the same time?” Ford’s successor, famed buzzkill Jimmy Carter, tried (and failed) to cut the deduction from 100% to 50%. The Tax Reform Act of 1986 succeeded in that goal, and today’s business diner has probably switched from martinis to white wine. But old habits die hard — check any happening lunch spot and you’ll find happy diners eating partly on Uncle Sam’s dime. […]
February 28, 2018

If You Think the Income Tax Is Bad…

If You Think the Income Tax Is Bad… We Americans have fought with our internal revenue code since 1913. But slicing and dicing income, deductions, and a dizzying array of business and personal credits is hardly the only way that Uncle Sam could raise the money he needs to pay for guns and butter. State and local governments also use sales taxes, payroll taxes, property taxes, excise taxes, and “gross receipts” taxes to fill their hungry coffers, too. And then there are the more exotic taxes, the kind that sometimes live only in philosophers’ heads. The nineteenth-century economist Henry George […]
February 21, 2018

Free App Avoids Taxes

Free App Avoids Taxes Traffic apps have revolutionized how many of us get from Point A to Point B. They started with in-dash navigation systems that needed updates every time a new subdivision or interchange appeared. Then they migrated to the phone with Google Maps and real-time traffic updates. Now, apps like Waze tell you where to get off the highway to avoid traffic jams altogether — and terrorize quiet residential neighborhoods in the process. At this point, your kids probably wouldn’t recognize the vintage navigation tool known as the “folding paper map” if you used it to smack them […]
February 14, 2018

Even Love Is Taxed

Even Love Is Taxed It’s February, and love is in the air. Restaurants have been advertising intimate specials for two. Florists have rolled out the red carpet. And in the greeting card racks across the country, Hallmark’s most accomplished poets have presented their new verse. We’re talking about Valentine’s Day, of course. 62% of Americans celebrate the occasion. (Of course, that means the rest of us will just try to keep our heads down and pretend it’s just another blah February day.) But with all those Cupid’s arrows flying around, shouldn’t the tax man get a little love, too? The […]
February 7, 2018

Country Singers v. IRS

Country Singers v. IRS Country music embraces a long tradition of songs about sadness and ruin, heartbreak and pain. It just makes sense, then, that country sometimes runs afoul of the tax system. Most famously, Willie Nelson found himself on the wrong side of a $16.7 million tax bill. And outlaw country icon David Allen Coe, who penned Take This Job and Shove It, drew three years probation and $980,000 in restitution for failing to report his income, which he insisted on taking in cash to hide from the IRS. Joy Ford probably never expected she would become a part […]
January 30, 2018

Obscure Laws and Roller Skates

Obscure Laws and Roller Skates When you think of “federal crime,” you probably think of big-ticket offenses like mail fraud, identity theft, and tax evasion. But our criminal code is also full of, shall we say, lesser offenses. For example, according to the Crime a Day Twitter feed, “18 USC §1854 makes it a federal crime to cut, chip, or chop a government-owned tree to get turpentine out of it.” 7 USC §8313 “makes it a federal crime to bring an imported camel’s blanket into the United States without the permission of the port inspector.” And 8 USC §1865 “makes […]
January 24, 2018


iTax In 2016, SyFy debuted a new show called Incorporated about a dystopian future where corporations, not governments, rule the world. If that nightmare ever comes true, we all know which real-world corporation will rule them all. It’s Apple, of course, which just took the shrink-wrap off their $5 billion ring-shaped headquarters in Cupertino, CA and is on the verge of becoming the world’s first trillion-dollar company. Odds are good that you’ve got an iDevice of some sort in your home, office, or pocket. Apple’s product design geniuses use crack-like design and technology that keeps users hooked like heroin addicts, […]
January 16, 2018

Pop Stars and Taxes

Pop Stars and Taxes In 2012, the singer Whitney Houston died suddenly, drowning in a hotel bathroom after years of battling drug addiction. Yet the world will always treasure her musical legacy. The Guinness Book of World Records reports that she was the most awarded female artist of all time, with two Emmys, six Grammys, 30 Billboard Music Awards, and 22 American Music Awards, among 400+ awards. Rolling Stone listed her debut album as one of the 500 greatest albums of all time. And VH1 put her number three on their “greatest women of the video age” list, behind Madonna […]
January 11, 2018

Taxes for Touchdowns?

Taxes for Touchdowns? NFL playoffs have begun, and Wild Card Week featured some real competition. On Saturday, the red-state Tennessee Titans barbecued the red-state Kansas City Chiefs, 22-21, and the red-state Atlanta Falcons defeated the blue-state Los Angeles Rams, 26-13. On Sunday, the purple-state Jacksonville Jaguars pounced on the blue-state Buffalo Bills, 10-7, and the red-state New Orleans Saints marched past the purple-state Carolina Panthers, 31-26. Now, if you’re like most people, you’re wondering why we’re polluting your NFL news with red state and blue state political references. You wouldn’t think politics matter on the gridiron! Unfortunately they do, now […]
January 4, 2018

New Year, Better Tax Code?

New Year, Better Tax Code? Welcome to 2018! New Years’ always brings changes to taxes. Key numbers, like tax brackets, standard deductions, personal exemptions, and qualified plan contribution limits, all roll over on January 1. But this year brings more change than any year since 1987. Washington has just passed a sweeping overhaul of the entire tax code, from working individuals all the way to multinational corporations. Tax planners across the country are scrambling to ferret out the opportunities hiding in its 503 pages of typically dense, impenetrable text. (There’s a reason tax lawyers drive Jaguars.) This year’s tax bill […]
December 27, 2017

We Interrupt This Program…

We Interrupt This Program… On Sunday, October 30, 1938, Mercury Radio Theatre fans, who were listening to Ramon Racquello and His Orchestra, were interrupted by a news broadcast reporting an odd explosion on the planet Mars. Soon after, they learned that a cylindrical object had fallen on a farm in Grovers Mills, New Jersey. The radio audience listened in horror as a pulsating Martian emerged from the cylinder and obliterated the crowd with heat rays. Soon, an entire army of Martians had invaded New York, and very real panic had spread across the country. Last week, something a bit similar […]
December 20, 2017

If the 12 Days of Christmas Were Taxed…

If the 12 Days of Christmas Were Taxed… Every year, PNC Bank publishes their “Christmas Price Index” to track the cost of the Twelve Days of Christmas. For 2017, it’s a hefty $157,558. (And you thought your holiday spending was out of control!) The index may not be completely accurate — for example, the ten lords-a-leaping are valued using the cost of male ballet dancers, rather than actual lords, and the eight maids-a-milking don’t include eight actual cows. But still, it got us wondering . . . what sort of taxes are we looking at on the whole affair? Twelve […]
December 14, 2017
Boston Tea Party

Holiday Tea Party

Your kids have finally finished eating their Halloween candy, which means that the real holidays are right around the corner. But before you sit down to open presents, December 16th marks the 244th anniversary of an important holiday in tax history — a pop-up costume ball in Boston Harbor called the Boston Tea Party. From 1698 through 1767, Britain’s Parliament passed a series of laws giving the East India Company a monopoly on the British tea trade, forcing the colonies to buy their tea from British wholesalers, and slapping hefty taxes on it all. But Dutch traders, who paid no […]
December 7, 2017

American Becomes Royalty; Gets Taxed!

American Becomes Royalty; Gets Taxed! Two hundred and forty one years ago, we declared our independence from Mother England — over taxes, of course. But here on our side of the pond, we’ve never completely lost our affection for all things British. We applauded as the Queen celebrated her 70th wedding anniversary. Netflix fans who just finished binge-watching Stranger Things are eagerly awaiting Season Two of The Crown. And now we’ve learned that Prince Harry and his longtime girlfriend, actress Meghan Markle, are getting married in May. Now, Harry may be just fifth in line for the throne, and about […]
November 29, 2017

IRS Loses!

April 15 hasn't always been the way that it is today. Up until the 1940s, you could just waltz into your local IRS office and they would do your taxes for you. But those days have long since passed. You're still welcome to do it yourself, if you need more stress in your life. But how will you know if you're paying too much? Even software like TurboTax
November 22, 2017

Ivy League Tax Problems

They say that "what goes up must come down." But that's not true when it comes to college costs. U.S. News reports the average private college tuition stood at $16,233 back in 1997-98 — roughly $24,973 in 2017 dollars. But the same tuition today costs $41,727. And that's before pricing in luxuries like, you know, meals, and a place to
November 16, 2017
Off Shore

The Rock Star and the Offshore Bank Account

We've all got an image in our minds of who uses "offshore tax havens" to host their business. Let's say you're a junior-varsity Russian oligarch. You've spent a lifetime looting your country's resources like an all-you-can-steal buffet, and now it's time to take some of your chipskis off the table. You buy a flat in
November 8, 2017

Stranger Taxes

The streaming video service Netflix has earned a reputation for providing quality content like Narcos, Orange is the New Black, and The Queen. But Netflix has also upended how millions of people consume television. How have they done that? By dropping an entire season's worth of a series all at once, letting you "Netflix and chill" with a
November 2, 2017
Amazon Box

Talk About “Prime” Real Estate!

Former President Jimmy Carter once called our tax code "a disgrace to the human race," and there's really not a lot to like about it. There's at least some consolation, though, in the fact that we're all stuck with the same maddening rules. If you and your spouse file jointly, and your ordinary taxable income is $100,000, you'll pay the same amount