The court filings allege Saylor has been "bragging" to confidants about his tax affairs since at least 2012 — and told friends they were "fools" if they didn't do the same.
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Michael Saylor is feeling the heat over allegations that he has failed to pay millions of dollars in income taxes over recent years.
A lawsuit has now been filed by Washington DC's Attorney General — and a complaint written by whistleblowers has now been unsealed too.
They both contain allegations that shed light on Saylor's lifestyle, and provide evidence that could back up the claims he has evaded tax. Here are seven things we've learned.
1. $25M Owed, But Penalties Could Exceed $100M
According to DC's Attorney General, Saylor avoided paying more than $25 million in income tax by claiming to be a resident of Florida or Virginia.
But new laws allow a court to impose "treble damages" — three times the amount of tax evaded — meaning the entrepreneur could pay substantially more if he loses the case.
When coupled with action that's being taken against MicroStrategy, the Attorney General says it's seeking to recover funds that could exceed $100 million.
Saylor would also have to pay interest on his underpayments and court costs.
2. Saylor 'Bragged' About Avoiding Taxes
The court filings allege that Saylor has been "bragging" to confidants about his tax affairs since at least 2012 — telling them about how he creates the illusion of residing in Florida in order to evade income taxes in DC.
According to whistleblowers, Saylor told friends based in New York, California and DC that they were "fools" if they didn't do the same.
3. He Spent Most of His Time in Washington DC
Newly unsealed court filings from whistleblowers also include calculations about how much time Saylor actually spent in Washington DC. For tax purposes, a resident is defined as someone who is based there for at least 183 days of the year.
Here's the problem: It's alleged that he was physically present in DC for 228 days in 2014, 323 days in 2015, 225 days in 2016, 196 days in 2017, 243 days in 2018, and 251 days in 2019.
And despite the fact that tax forms claimed his address was in Florida, it's alleged that he only spent 28 days in the Sunshine State in 2019.
4. The Evidence He Was Mainly Based in DC
The complaint from the whistleblowers claims that there is evidence to back up their allegations, writing:
"For some individuals, it would be difficult to reconstruct their past day-to-day locations and establish that they spent the majority of their time in the District. Saylor, on the other hand, left a trail of information to reconstruct his movements to and from the District."
It describes how Saylor often tagged his location on social media posts, while articles in local newspapers documented some of the extravagant parties he held in DC.
"He established a regular presence at Café Milano in Georgetown, where his near-weekly appearances for approximately 15 years made him a recognizable figure to staff and patrons. He also hosted frequent open-bar parties at District establishments including Cities, Sequoia, L2, as well as hotel ballrooms at the Four Seasons, both Ritz Carlton hotels, and the Mandarin Oriental, among others."
Saylor's preference for flying in a private jet rather than commercially also means flight information with the Federal Aviation Administration shows "exactly when he left the District and when he returned," whistleblowers claim.
5. Saylor Found DC 'Irresistible'
There's no shortage of color in the whistleblowers' complaint — which said Saylor "found the appeal of the District irresistible, particularly its proximity to power, affluence and women."
It describes how the entrepreneur started spending more time in DC in the 1990s and early 2000s, but was yet to live there at this point.
Saylor was named on local television in 1999 as "DC's most eligible bachelor," was invited to White House events, and hired a radio personality to promote him in "District media and District social circles" as his life became increasingly concentrated there.
6. Bitcoin Interviews Used Against Him
Throughout the court filings, some of his remarks in interviews are also used as evidence. The whistleblowers' complaint says:
"Saylor bragged in a January 24, 2021 interview that Bitcoin is an ideal tool for evading taxes, suggesting that owners of Bitcoin could tell their government to 'go f*** yourself' and claim to have lost their Bitcoin access key, daring the government to 'tax that!'"
7. Whistleblowers Could Get 30% Cut of Recovered Funds
What's especially interesting is that a recently updated law means the whistleblowers who initially made the allegations could end up receiving a percentage of the funds that the District of Columbia recovers from Saylor — up to 30%.
