MicroStrategy Whistleblower Gives Surprising Insights into Michael Saylor’s $25 Tax Fraud Case

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The District of Columbia filed a civil lawsuit on August 31 alleging that Michael Saylor, a major proponent of Bitcoin, defrauded the District of $25 million in taxes. The price of the leading cryptocurrency is yet to be affected by the revelations in the matter. However, they paint a striking picture of the weakness that seems to be his downfall, as the sly publicity stunt becomes so enraged by their plots that he can’t bear to talk about them.

The charges allege Saylor called other wealthy taxpayers in the district “fools” and urged his friends to do the same. The most striking allegation against Saylor is that he recruited his subordinates in a micro-strategy to join forces in a complex scheme to commit fraud. Realizing that Saylor was jeopardizing the company he had built by blatantly dodging millions in taxes, senior executives at the data analytics firm approached the boss in panic.

An earlier hacking case gave birth to the district’s case. The district has historically used the False Claims Act to go after contractors who, for example, overcharged or underpaid construction projects. The District of Columbia changed the law in 2021 to allow private residents to file tax evasion lawsuits against “high-income organizations and individuals” in DC. The first action, in August 2021, accused Taylor of evading a $25 million payment. The lawsuit is unsealed and will remain private until the district files another separate action with similar allegations by the end of August.

It is clear that the informant had extensive contact with Michael Saylor, and given their understanding of the power struggles within the microstrategy, they were probably senior executives. The pointer’s history is deep, actually. In the year From 2013 to 2020, Saylor said she lived in Florida, where there is no income tax, but she spent most of her time in DC. The booklet is filled with fascinating anecdotes that highlight Saylor’s love for the nation’s capital: how Saylor combined three lavish Georgetown waterfront apartments into a 7,000-square-foot mansion he calls the Trigate, as well as the boat and backup craft he often lives in, docked in front of his home at a popular cafe. Milano’s frequent appearances and addiction to flying around the world in Microstrategy’s Bombardier Global Express private jet, for which the FAA maintains “perfectly representative flight records.” Saylor’s journey to the county for the past 20 years.

According to the complaint, Saylor In 2012, he paid $13.1 million for his beachfront Mediterranean villa, Villa Vecchia, in Miami Beach. He soon got a driver’s license, registered to vote and started paying his taxes in Florida. At the same time, he was spending most of his time in Washington, D.C., commuting to MicroStrategy’s offices in Tysons Corner, Virginia, and “participating in the District’s social scene.” According to the complaint, “He even said that his friends from New York, California or the District would be ‘fools’ if they didn’t buy a home in Florida and spend the same amount of time to waive their personal income tax.” Regions”

The informant did extensive research to confirm that Saylor had spent most of the year in Trigate and had spent some time in Florida. Saylor, according to him, has only participated in three Florida general elections using absentee ballots for him from corporate headquarters in Virginia. The district’s lawsuit also includes Saylor’s social media posts from 2012, after he said he was in Florida, proof that he hasn’t moved. He proudly posts pictures on Facebook of the final Georgetown Joy Dome, combining the surrounding units into Trigate. Taylor praises “my future home” in the caption and laments how hard it is to leave the house on a beautiful fall morning.

The whistleblower case gathers evidence from social media posts, FAA flight data and, most shockingly, “witness testimony from his inner circle” to show how many days Seiler spent in Florida and Washington, D.C., from 2013 to 2019. Under DC law, time someone spends traveling for business or pleasure while returning to and from the District is not days left for tax purposes, so you can’t claim half a year out of DC and therefore not owe. It pays there. According to the complaint, Saylor spent between 270 and 331 days in D.C. between 2014 and 2019, including travel to and from the district. He never spent more than 71 days in Florida in a year. So Saylor is a long way from spending the requisite 183 days in Florida to be considered a state resident. Tracking his activity shows that he spent many days physically in DC or in and out of DC. 2012 was the only exception. Still, Saylor spent 70 more days in DC than in Florida, so he was liable for taxes that year.

Saylor was charged with a large amount

According to the district’s lawsuit, Saylor cut the devil’s bargain with MicroStrategy to continue the deception. According to the claim, the CFO In 2014, Saylor tracked down her dates there and in Florida and determined she was living in DC. His residence has been listed as Florida by MicroStrategy for years, even on the CEO’s W-2. Saylor was told by the CFO (who has not been named) that he could no longer “justify” concealing Saylor’s true residence. According to the complaint, “the CFO raised Sayler’s fraudulent tax evasion case as a possible cause of Sayler’s liability for the company.

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By agreeing to let MicroStrategy disclose his true residence, Saylor displeased his CFO. Instead, he devised a plan to enlist the company’s help to cover up the fraud, the lawsuit alleges. He agreed to take a modest salary of $1 per year. According to the plan, such a situation will not attract the attention of the DC tax authorities. MicroStrategy’s benefits to Sailors for private air travel, car and driver use, and safety specifications have risen dramatically at the same time. Federal taxes paid on these benefits are paid by the corporation. The risk of misrepresenting Saylor’s tax status was offset by the fact that he received no salary but additional benefits, much to the CFO’s relief. It is said that the chairpersons of the Audit and Compensation Committee have approved the arrangement.

In the district, these non-monetary items are often treated as fees and subject to full taxation. However, Saylor said she is a Florida resident so the benefits were not disclosed in DC. Apparently, Saylor and the CFO thought that replacing the fringes with cash would ensure that the fraud remained undetected. The complaint alleges that the agreement concealed defendant Saylor’s continued failure to pay district taxes.[enabled] Defendant Saylor is fraudulently evading his obligation to pay district taxes.

The circuit response is more extensive. He claims Saylor misrepresented his residency in Virginia for years before moving to Florida. The AG wants Saylor to pay $25 million in indefinite back taxes, 10% annual interest and various penalties. Because the new fraud statute includes treble damages, Saylor must pay triple the taxes, interest and penalties if he loses. The exact amount of Saylor’s debt was not disclosed in the complaint. Additionally, MicroStrategy has been sued for an unspecified amount. In the year According to an August 31 press release, the AG estimated that Saylor and the business would spend a total of about $100 million to settle the allegations. Saylor will no doubt carry the brunt of the load. The treble damages would total $75 million in delinquent taxes alone.

If the district wins the lawsuit, the whistleblower, who allegedly saw Saylor bragging about his intelligence, could be awarded up to 25% of the settlement, or about $25 million, paid by Saylor and MicroStrategy.

Responding to the lawsuit, Saylor said, “Ten years ago, I bought a historic home in Miami Beach and moved my family from Virginia. Although MicroStrategy is headquartered in Virginia, my personal and family lives in Florida, where I vote, serve on juries, and live. I disagree with the District of Columbia’s position and look forward to a fair legal outcome.
In a statement, MicroStrategy said the lawsuit involved Mr. Saylor’s personal tax matters. The company was not in charge of its day-to-day operations and did not control its individual tax obligations. Furthermore, the company did not assist Mr. Saylor in evading his personal tax obligations.

The price of Microstrategy shares has fallen

As of mid-afternoon on Sept. 2, MicroStrategy shares had fallen from $245 to $217 per share since the lawsuit was filed, a roughly 9% drop. But given Bitcoin’s bad luck and weak fundamentals, that’s not really that bad. The business reported a shocking $918 million operating loss for the second quarter on Aug. 2, which included a $903 million impairment charge against roughly 130,000 bitcoins collected. The fact that the main software platform is currently in the red is very worrying. Interest payments on $2.4 billion in debt raised to buy bitcoins exceeded operating profit margins. Due to his terrible performance, Saylor resigned as CEO and took on additional executive responsibilities, chief among them Bitcoin recovery strategy.
At the coin’s current price of less than $20,000, MicroStrategy has spent a total of $4 billion in bitcoins, bringing the company’s war chest to around $2.6 billion. This expenditure was financed by both new equity and debt. So Saylor’s crypto venture cost him $1.4 billion. The holding is $200 million more than the $2.4 billion in bonds currently used to finance the acquisition. The first payment on the debts will be made in 2025. The only possibility to repay the loan of Saylor is if the price of Bitcoin increases, said Ryan Ballantine of the company Berem Capital, which is shorting MicroStrategy. It values ​​the business at just a few hundred million dollars. It’s tempting to argue against his analysis: The software company is losing money and has bitcoin holdings with a net worth of less than $200 million. With $40 million in annual interest on Bitcoin debt, even a positive operating profit is eliminated, the software company is unlikely to be profitable in the future. The stock has become very risky because of Taylor’s high leverage and the company’s side, despite months of declines, the price of Bitcoin could rise.

Surprisingly, MicroStrategy still has a market value of $2.5 billion after suffering significant damage from the controversy. By mid-August, it was selling for a staggering $4 billion. Even now, I believe that the company is being valued more than it really is as a profitable business. So why does it defy gravity? Simply put, MicroStrategy is a meme stock—especially strong because of Saylor’s cult following. I have not yet ruled out the ensuing controversy. However, Saylor turned a concurrent business into one of the riskiest significant investment vehicles in history. The truth about the prophet who once pretended to be a visionary pushing Bitcoin may soon come out. It’s the same carnival barker who was accused of evading his taxes, believing he couldn’t be arrested, then got off the stage bragging to the hacker. Micro-strategy can eventually fire from the markets as well.


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