MicroStrategy CEO Michael Saylor is no stranger to criticism. He’s facing it again.

Courtesy of Microstrategy - Michael Saylor, chief executive of Microstrategy.

In one photo, the chief executive grins coyly as women slathered in gold body paint, strings of black pearls and little else stand on either side of him. In another, he shows his sunglasses and gray-tinged facial hair in a selfie snapped on his multimillion-dollar yacht, the royal blue waters of St. Lucia glimmering in the background.

The dozens of pictures posted across Michael Saylor’s social media accounts offer an almost voyeuristic window into the lavish lifestyle of one of the Washington region’s most successful businessmen. It’s a lifestyle many on Washington’s social circuit have heard about, read about or enjoyed firsthand for years.

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But a contingent of large shareholders and former executives of MicroStrategy, the Tysons Corner-based data analytics company Saylor has controlled for a quarter century, are voicing concern in public and private that his party-boy persona has become a distraction from the daily demands of running a business.

Critics primarily cite what they see as a lagging stock price — share value hasn’t crossed the $175 mark in more than 10 years — as evidence that MicroStrategy is undervalued compared with its contemporaries in the software and business analytics industries.

“CEOs have a prerogative to enjoy the fruits of their labor, but not at the cost of running their business,” said Gil Simon, the portfolio manager for technology and entertainment at Apex Capital, a large shareholder that has been critical of MicroStrategy’s performance and has called on Saylor to step aside. “That’s an important distinction.”

The company contends Saylor is the architect who built MicroStrategy in to a profitable, multinational enterprise and that he remains engaged as ever in business operations. Others describe Saylor as a friend who is generous with his wealth, a visionary who spots nascent technology trends and an executive with exacting expectations for employees. He is engaged in granular product and hiring decisions, they say, even if he’s spending less time in the office nowadays.

Any portrait of Saylor is complicated. For a man whose public persona is unapologetically extravagant, Saylor remains comparatively quiet about his day-to-day functions as a chief executive.

He appears on cable news shows to hawk his latest book, but hasn’t attended an investor conference in close to a decade. Much to shareholders’ chagrin, Saylor won’t project future earnings or outline short-term corporate strategy.

He tweets prolifically about technology news. He canceled a scheduled interview for this story. An Instagram account chronicling Caribbean getaways and Miami parties was made private after shareholders became critical and reporters started asking questions.

Still, one thing is certain about Saylor: He has come out on top of critics before. In 2000, scrutiny over the way MicroStrategy records sales forced the company to restate two years of earnings. The stock price plummeted. Saylor himself famously lost $6 billion in a single day.

Many CEOs wouldn’t have kept a seat at the head of the table, but then again, Michael Saylor isn’t a typical CEO.

The executive

In interviews with four former managers, none of whom would comment publicly out of concerns for possible repercussions, they describe a company dominated by a single personality — one that both friends and critics of Saylor admit can be difficult to navigate.

Many agree that Saylor is something of a visionary. He predicted before many that mobile technology was more than just a fad, steering MicroStrategy to make its software accessible through smartphones and tablets.

Saylor notably offered use of MicroStrategy’s software free of charge to Facebook in anticipation that the value in its massive social network would come from data analytics. Today, the companies are close partners, and Facebook CIO Chief Information Officer Tim Campos spoke at MicroStrategy’s World Conference in Las Vegas in January.

But behind that vision is a leader who can be highly emotional and quick to change his mind, the former managers said. Several described a workplace in which it was not uncommon for Saylor to berate an employee one day and praise him the next.

Saylor would also task employees with pet projects that executives and shareholders have said did not fit into MicroStrategy’s core business and, in some instances, did not appear to have much potential to generate revenue.

Ideas might come “from his interactions with celebrities on boats and at exclusive parties,” said one former employee who worked directly with Saylor. “The management team had a hard time squaring current cash flow ideas with Michael’s ideas. They had nothing to do with selling analytic software to Fortune 100 companies.”

Saylor once sent a memo to management with plans to change the company’s name to “Strategy” because the moniker was “100 times more recognizable” and “would fit better on buildings,” said one former manager. “Luckily, someone talked him out of this.”

Brash executives aren’t exactly a rarity. From Steve Jobs to Donald Trump to Paul Allen, some of America’s biggest businesses have been built over the years by bold personalities.

The difference between personality and pariah can perhaps be boiled down to whether investors are making money.

Shareholders who bought MicroStrategy’s stock at depressed prices in recent years are now growing concerned that Saylor and his board of directors aren’t fixated enough on raising share prices .

Led chiefly by Apex Capital, some shareholders are urging the company to buy back stock using the nearly $350 million on its balance sheet. They want the company to resume quarterly conference calls and other communication with investors.

Apex has also objected to the makeup of MicroStrategy’s board of directors. Following the recent departures of Sanju Bansal and imminent exit of Matt Calkins, there will be a dearth of both software and public company experience among the remaining board members. With an average board tenure of about 11 years and following several years of underperformance, there is a need for professional oversight, according to Apex.

And Apex wants Saylor to step aside.

“At this critical stage in the company’s life cycle, we believe that his skills and expertise are best suited for a chairman or advisory capacity,” Apex Capital stated in a letter to the company. “There is ample precedent where successful technology company founders — among them Bill Gates at Microsoft and Sergey Brin at Google — made a natural progression into these types of roles.”

MicroStrategy has its own executive role models in mind.

“Some of the most successful companies in history continue to be run by their founding CEOs, such as Amazon (Jeff Bezos), Oracle (Larry Ellison), Capital One (Richard Fairbank), News Corp. (Rupert Murdoch) and Berkshire Hathaway (Warren Buffett),” spokesman Warren Getler said via e-mail.

A close friend with business ties to Saylor said Saylor takes the long view as chief executive. He’s not focused on what the market will bring in the next six months, but rather how MicroStrategy can be ahead of trends three to five years in the future.

“When people are trying to rush him with short-term-sightedness ... he finds that ridiculous,” the friend said.

The socialite

Saylor’s reputation as an executive may be surpassed by his reputation for hosting blowout parties and intimate getaways, from St. Tropez to St. Bart’s to his sprawling Florida mansion.

One Fourth of July party at Saylor’s Washington Harbour penthouse — an expansive condo with sweeping views of the Potomac River and quick access to the marina — welcomed guests with a bathtub stocked with ice and Veuve Clicquot champagne.

“It was very opulent and very fun and everyone had a great time,” said Sophie Pyle, a lifestyle writer for In The Capital, who attended the party. “And because Michael paid for everything, there wasn’t much to worry about except tipping the bartender.”

A birthday party during the heavy snowstorm in February 2010 brought guests to the W Hotel for a safari-themed affair complete with exotic jungle animals, including an albino Burmese python that Saylor draped around his neck for photos.

“Everyone [in Washington] seems to be somewhat restrained, but not Michael and not the crew he runs with. They do like to go big,” said Allison Priebe Brooks, a friend.

Among Saylor’s most infamous parties is his annual Rocktoberfest, a pre-Halloween bash featuring dueling bands and guests dressed as rock stars. Saylor himself has gone decked out in leather, face paint and sleeveless shirts.

Mr. Greengenes, a cover band that performed songs by artists including the Beatles, Limp Bizkit and Kelly Clarkson, was a staple at Saylor’s parties in D.C. and New York before the group parted ways last year.

“He didn’t want to be the center of attention at the parties. He wanted his friends to have a great time,” said lead singer Bryen O’Boyle. “Every now and then, if we were playing one of his favorite tunes, he would come to the front row and dance for a couple.”

On occasion, Saylor would even grab the mike to belt out a song, O’Boyle said, mainly karaoke-go-tos such as Cheap Trick’s “Want You to Want Me” or Bon Jovi’s “Livin’ on a Prayer.”

But friends and business contacts say Saylor hasn’t hosted a large event in Washington in at least six months. Instead, much of Saylor’s social life has shifted to Miami Beach, where he purchased a palatial waterfront home for $13.1 million in July 2012.

The 86-year-old mansion , dubbed Villa Vecchia, boasts 13 bedrooms and 12 bathrooms spread across 18,006 square feet, according to property records. His two multimillion dollar yachts, Usher and Harle, dock out front.

Two former MicroStrategy managers said the chief executive has been taking longer and longer trips away from the Tysons Corner headquarters in recent years. They believe that Saylor’s trips have resulted in a disconnect from the day-to-day operations.

“Like many CEOs of companies with global operations, Mr. Saylor travels frequently to meet with customers and partners, and to participate in industry panels and public speaking engagements,” Getler said via e-mail. “Regardless of his location (in the office, at home or on the road), as chief operational executive, he actively oversees the company’s efforts in our global marketplace.”

MicroStrategy amended its company aircraft-use policy in April 2012, regulatory filings show, so that use of jets owned in full or part by the company for nonbusiness purposes could make up 50 percent of total flight hours in a given year. Getler declined to comment beyond the filing.

The friend and business contact said even on vacations Saylor remains plugged into the business through phone calls and video conferences. He also meets with executives and business contacts while away in St. Bart’s and other locales where the wealthy congregate.

“You can make contacts faster there than anywhere else,” said the friend. “In D.C., Michael is probably one of the wealthier people in town, but when you go to St. Bart’s, he’s networking to meet the right people.”

Pictures on the Villa Vecchia Facebook page — which is administered by Saylor and counts more than 2,000 likes — show the home lit up in purple and pink lights for a 2013 New Year’s Eve party. More recently, Saylor hosted a massive halloween bash to benefit Miami’s Little Lighthouse Foundation.

“He’s now partying really hard in Miami because he has a great house down there now,” Brooks said. Socialites there are “all very excited that Michael Saylor has come to Miami and he’s throwing money around Miami. He’s making a big splash down there.”

 
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