Michael Saylor Crypto Holdings 2023, Predictions & Tweets

  • May 17, 2023
  • 5 Min Read

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Key Takeaways

  • Michael Saylor co-founded enterprise software company MicroStrategy in 1989 and went on to be one of the most successful tech founders of the '90s.
  • In 2020, MicroStrategy began accumulating a large position in Bitcoin, and they now hold more Bitcoin than any other publicly traded company.
  • Saylor is a respected authority on Bitcoin and he doesn’t hesitate to weigh in on all things crypto.
Crypto Opinion👍 "Bitcoin is the ultimate inflation hedge."
Crypto ProjectsPlanned Bitcoin Lightning Network SAAS solution (under MicroStrategy)
ProfessionExecutive chairman and president of MicroStrategy
Net Worth$1.6 Billion
Country of ResidenceUnited States
Companies OwnedLargest holder of MicroStrategy class B shares

Michael Saylor is the co-founder and former CEO of US software company MicroStrategy. Founded in 1989, MicroStrategy provides enterprise software. In 2020, MicroStrategy began an aggressive buy-up of Bitcoin as Michael Saylor, the CEO at the time, viewed the cryptocurrency as the best long-term store of value.

Since their initial purchase of $250 million of Bitcoin, MicroStrategy has become one of the largest holders of the digital asset. As of the end of 2022, their holdings stand at 132,500 Bitcoins worth around $2.25 billion. Michael Saylor has emerged as the pre-eminent Bitcoin proponent, becoming a known crypto whale, some even dubbing him the “Bitcoin CEO.”

Saylor’s Cryptocurrency Predictions

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Bold predictions are not new for Michael Saylor. He strongly believes that Bitcoin is replacing gold and will eventually be the world's reserve currency. He believes the bear market is temporary and is “more bullish than ever on Bitcoin”.

Michael Saylor is known for his cryptocurrency predictions. Here's a timeline of his most famous predictions:

  • In a famous 2013 tweet, Saylor actually provided a negative appraisal of Bitcoin, saying that its “days are numbered”. When asked about the tweet in 2020, Saylor said he did not remember tweeting it.
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  • In September of 2020, shortly after MicroStrategy made its first purchase of Bitcoin, Saylor explained his rationale for the decision. He said Bitcoin is the ultimate inflation hedge and that it is potentially “1000x better than digital gold”.
  • In November of 2021, Saylor said, “It’s pretty clear digital gold is going to replace gold this decade,” citing institutional demand for a digital store of value. He went on to say that he expects Bitcoin to be a $100 trillion asset class. “When we get there,” Saylor continued, “it will be 5% to 7% of the worldwide economy. The U.S. dollar will probably replace 150 currencies. Maybe there will only be two to three left. There might be the euro, the CNY, and the dollar. Everything else is probably going to disappear. And then Bitcoin will be the world’s monetary index. If you simply want to keep your money, and you don’t want to express a credit sentiment, or an equity sentiment, or some property or real estate sentiment.”
  • In December of 2021, Michael Saylor said, “Once upon a time, gold was the most desirable store of value. Now Bitcoin is taking its place.” He has also said Bitcoin will eventually reach $6 million dollars per coin.
  • At Bitcoin Miami in May 2022, Saylor said he was “more bullish than ever on Bitcoin”. He commented on U.S. President Joe Biden’s executive order directing federal agencies to research digital currency by saying, “Bitcoin has been embraced. The administration has given a green light to Bitcoin. Politicians are now competing (over) who’s the most pro-Bitcoin.”
  • Saylor addressed the market downturn in September 2022, saying he expects Bitcoin to rebound to its previous highs “sometime in the next four years”. Saylor also discussed MicroStrategy’s role in developing the Lightning network, a payment protocol for Bitcoin that enterprise businesses can use. He commented on the bearish price movements of Bitcoin, saying a market-bottom price of $20,000 for Bitcoin is “stable”.

Saylor Weighs in on the Crypto Industry

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The Bitcoin King has shared his opinions on Ethereum — he thinks it’s risky and unstable, FTX — he thinks SBF is “ethically broken”, and Elon Musk — he wishes Tesla held more Bitcoin.

Michael Saylor is one of the biggest Bitcoin “maximalists” in the crypto space. This means that he believes Bitcoin’s unique properties make it superior to all other cryptocurrencies, and he is interested in how Bitcoin performs to the exclusion of the rest of the crypto market. As a large figurehead in the space, however, he still weighs in on most major news and scandals. Below are some of his comments:

Ethereum: In December 2022, Saylor tweeted out a warning that the Proof-of-Stake (POS) nature of the Ethereum ecosystem makes it “unstable, inefficient, opaque, and risky”. He contrasted this to the Bitcoin network, which he deemed “increasingly secure & efficient over time-based on Proof of Work and ASIC technology advances”. The post included an image with the text “Will Ethereum break like Terra Luna?” referencing the unprecedented collapse of the TerraUSD stablecoin in May of 2022.

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The Collapse of FTX: The collapse of the crypto exchange FTX and the fall from grace of its founder, Sam Bankman-Fried, rocked the crypto world in 2022. In an interview, Saylor commented on the issue, castigating SBF for creating a token out of thin air and issuing loans to himself from customer funds. “There is something ethically broken about being able to issue your own unregistered security,” Saylor said. He also doubled down on his support of Bitcoin, viewing scams as unique to the non-Bitcoin crypto ecosystem.

Elon Musk: Saylor has interacted with the billionaire head of Tesla and SpaceX, Elon Musk, on several occasions. In December 2020, Saylor tweeted at Musk, saying, “If you want to do your shareholders a $100 billion favor, convert the $TSLA balance sheet from USD to BTC.” Saylor then offered Musk direct help in executing such a transaction. In July 2022, after Tesla announced they had sold 75% of the Bitcoin off their balance sheet, Saylor tweeted, “If you sell 75% of your Bitcoin, you will only have 25% of your #Bitcoin left” — apparently lamenting Tesla’s Bitcoin selloff.

Michael Saylor’s Life and Career

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Michael Saylor graduated from MIT in 1987 and co-founded MicroStrategy two years later. He was one of the richest tech CEOs during the dotcom boom, but now focuses on amassing more Bitcoin for himself and MicroStrategy.

Michael J. Saylor was born in Nebraska in 1965 and spent his early childhood years on Air Force bases around the world. After his family settled in Ohio, Saylor was accepted to the Massachusetts Institute of Technology (MIT) where he studied aeronautics and astronautics. He graduated in 1987 and took a job at chemical company DuPont.

Using funds from DuPont, Saylor started MicroStrategy in 1989. The company develops business intelligence software that allows enterprise companies, such as McDonalds whom they counted among their early clients, to utilize big data for insights into their business. MicroStrategy went public in 1998, and, by 2000, the company was so successful that Saylor’s net worth skyrocketed to over $7 billion.

In August of 2020, MicroStrategy purchased $250 million of Bitcoin and made headlines as the first publicly traded company in the US to buy the digital currency. According to Michael Saylor, the rationale behind the purchase was that Bitcoin was a good alternative to holding cash. The company has steadily bought Bitcoin since. At the end of 2022, MicroStrategy owned 132,500 Bitcoins. Saylor himself reportedly owns over 17,000 Bitcoins.

In August of 2022, Saylor stepped down from his CEO role. He now serves as MicroStrategy’s executive chairman.

Investigations and Criticisms

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Michael Saylor has been at the center of several scandals, including an SEC accounting investigation in 2000 which was settled for $11 million, and a lawsuit by the attorney general of Washington DC alleging tax fraud.

Michael Saylor and MicroStrategy have been no strangers to controversy, and even some federal investigations.

SEC Investigation: In 2000, MicroStrategy paid an $11 million settlement following an investigation by the U.S. Securities and Exchange Commission. The investigation uncovered that MicroStrategy had "materially overstated its revenues and earnings" during several quarters after its IPO in 1998. Due to this accounting, the company had reported a profit when it was actually losing money. The MicroStrategy executives named in the SEC investigation did not admit to any wrongdoing following their settlement. Comments from the investigators pointed to new accounting rules that were not followed within the company as the reason for the investigation.

Tax Fraud Lawsuit: In 2022, the attorney general of Washington DC filed a lawsuit against MicroStrategy and Michael Saylor alleging tax fraud. “Today, we’re suing Michael Saylor — a billionaire tech executive who has lived in the district for more than a decade but has never paid any DC income taxes — for tax fraud,” the attorney general announced. According to the lawsuit, Saylor avoided paying taxes by claiming he was a resident of Florida — a state with no income tax — even while spending the majority of his time in DC. Saylor responded to the lawsuit, saying, “​​I respectfully disagree with the position of the District of Columbia, and look forward to a fair resolution in the courts.”

Major Achievements:

  • Led MicroStrategy to become one of the most successful companies during the “Dotcom” boom
  • Accumulated the largest Bitcoin balance of any publicly traded company during his time as CEO
  • Regarded as one of the most influential Bitcoin supporters

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  • Avatar of George Hristov

    George is a tech writer interested in web3 startups and communities. In the dynamic world of crypto, he stays plugged in to the day-to-day headlines, deep dives, and industry commentary.

  • Avatar of Gary Anglebrandt

    Gary Anglebrandt is a US-based editor, copywriter, and communications consultant with a background in business and international news. Beyond the US, he has worked from Seoul and Beijing, and continues to work with professionals based around the globe.

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