America’s economy continues to sputter. But stocks are picking up steam and flirting with four-year highs. We’re even seeing new “dot-coms” hitting the market. Last May, the social networking site LinkedIn went public at $45 per share, then leaped to $94.25 in its first day of trading. Internet coupon vendor Groupon opened in November at $20 per share, then jumped 31% on its first day of trading. And earlier this month, Facebook filed registration papers with the Securities and Exchange Commission for what may be the hottest IPO since Google.

Companies typically go public to raise money to expand. But Facebook doesn’t really need cash from an IPO. The company made nearly $4 billion in advertising revenue in 2011. So why go public?

Well, companies also go public to let founders and early investors cash out. Mark Zuckerberg, Facebook’s 27-year-old founder, is already a “paper” billionaire, ranked #14 on the Forbes 400 list of richest Americans. (Not many entreprenuers find themselves richer than Scrooge McDuck while still at an age that they watch Scrooge McDuck.) But Facebook’s IPO will give Zuckerberg and fellow early investors liquidity, converting paper wealth into cash for the houses, charitable gifts, and other spending that new dot-com millionaires historically indulge in.

The IPO will also stick Zuckerberg with a historically large tax bill. (You knew that was coming, right?) In fact, one of the big reasons the company is going public in the first place is give Zuckerberg a way to pay taxes when he exercises options to buy even more stock.

Here’s how it works. For tax purposes, the value of most stock options is treated as compensation and fixed the day you exercise them — whether you actually sell them or not. Let’s say you pay $5 to exercise a share of your employer’s stock, on a day when that stock is worth $25. Your company gets a deduction for that $20 per share, even though there’s no cash outlay. That’s great for the company. But at the same time, you’ll owe immediate tax on $20 of income, even if you hold the stock in hope of future appreciation. (If the stock tanks before you actually sell, you still owe tax on that gain.) That may not be so great for you!

Zuckerberg currently owns 414 million shares of Facebook. He also has options to buy another 120 million shares for — get this — just six cents each. Zuckerberg has announced plans to exercise those options and sell enough shares to cover his taxes. We don’t know yet what Facebook shares will trade for. However, private-market trades have valued shares at $40 each. If Zuckerberg exercises all 120 million options when shares are valued at that price, his taxable gain will be nearly $5 billion. He’ll owe 35% to the IRS, plus 10.3% to the state of California, for a total tax bill of over $2 billion. That’s right, billion with a “b.” Can you imagine signing a return with a billion-dollar tax bill? How about signing a check for that much — payable to the IRS!

The important thing to realize here is that Zuckerberg’s tax bill came as no surprise. It’s actually the result of careful planning. Remember, Zuckerberg’s pain is Facebook’s gain. The strategy will probably give Facebook enough deductions to wipe out the entire tax on its 2011 profit, plus refunds from 2009 and 2010, plus even more to carry forward.

Think about that the next time you click the “Like” button on your computer. And remember, we’re here to bring the same sort of smart tax planning to your business.

Sunday night’s Grammy Awards ceremony illuminated two sides of today’s music industry. On stage, British soul singer Adele cleaned up big time, winning Album of the Year, Record of the Year, and Song of the Year. On the darker side, the night was filled with tributes to fallen angel Whitney Houston, who died Saturday after years of backstage struggles with drugs and alcohol.

When you think of your favorite musician, you probably don’t think about a third side — taxes and tax shelters. But you might be surprised to learn just how much influence tax laws have over the music we listen to every day.

Rock-and-roll fans know “Gimme Shelter” as one of the Rolling Stones’ all-time classics — the opening cut on their 1969 album Let it Bleed, and a dark, brooding meditation on the war and violence that seemed to characterize that era. Surprisingly, it turns out that “Gimme Shelter” describes the band’s philosophy on taxes, too.

The Stones’ troubles with the tax man go back nearly as far as their troubles with the police. Back in 1968, with bandmates Mick Jagger, Keith Richards, and Brian Jones facing drug charges, reports surfaced that they had also failed to observe tax laws. As Jagger reported at the time, “So after working for eight years I discovered at the end that nobody had ever paid my taxes and I owed a fortune. So then you have to leave the country. So I said &@#& it, and left the country.” The “World’s Greatest Rock and Roll Band” literally skipped town, with guitarist Richards renting the Villa Nellcote in Villefranche-sur-Mer on the French Cote D’Azur, where they wound up recording their critically-acclaimed double album, Exile on Main Street.

That lesson scarred them, and the Stones vowed not to repeat that mistake. Jagger put his London School of Economics studies to work, and hooked up with some top-notch financial advisors. They eventually set up a series of Dutch corporations and trusts which helped the band pay just 1.6% in tax over the last 20 years. More recently, they established a pair of private Dutch foundations to avoid estate taxes at their deaths.

“The whole business thing is predicated a lot on the tax laws,” guitarist Keith Richards told Fortune Magazine (with a Marlboro in one hand and a vodka and juice in the other). “It’s why we rehearse in Canada and not in the U.S. A lot of our astute moves have been basically keeping up with tax laws, where to go, where not to put it. Whether to sit on it or not. We left England because we’d be paying 98 cents on the dollar. We left, and they lost out. No taxes at all.” It’s worth mentioning at this point that Richards makes his primary residence in unglamorous but relatively low-taxed Weston, Connecticut.

The Rolling Stones were just the first of many artists to flee the United Kingdom to avoid taxes. Folk singer Cat Stevens left around the same time, moving first to Brazil, where his album Foreigner refers to his move. In 1978, rockers Pink Floyd spent three years outside the country to avoid tax. Glam-rocker David Bowie moved to Switzerland in 1976 (before becoming the first musician to securitize future royalties in the form of a bond offering). British singers Rod Stewart and Tom Jones both moved to Los Angeles to avoid British Prime Minister Harold Wilson’s 83% top tax rate. Even fictional musicians have taken extraordinary steps to avoid tax — in The Restaurant at the End of the Universe, British author Douglas Adams created the galactically-famous rocker Hotblack Desiato, who was “spending a year dead for tax purposes.”

Our job, of course, is to help you pay the minimum legal tax. And we think proactive planning beats fleeing the country. So call us when you’re ready to pay less. We’re here for you, and your bandmates too!