Michael Saylor Bet Billions on Bitcoin and Lost
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Michael Saylor Bet Billions on Bitcoin and Lost

The longtime MicroStrategy CEO, and perhaps the biggest bitcoin bull, steps down.

By Paul Vigna
Thu, Aug 4, 2022 4:29pmGrey Clock 3 min

If you ask Michael Saylor why he bet the future of his company on bitcoin, he’ll tell you he didn’t have a choice.

In 2020, MicroStrategy Inc.’s stock was stagnant, and the tech company struggled to compete with software giants. “We were either going to die a fast death, or a slow death, or embark on a risky strategy,” he said.

He opted to buy bitcoin—lots of it. That decision backfired, badly. On Tuesday, MicroStrategy announced Mr. Saylor would step down as CEO, a position he has held since 1989, amid mounting losses tied to bitcoin.

His dalliance with bitcoin began on Aug. 11, 2020 when the company announced a plan to take $500 million—half of its corporate reserve—and convert it into bitcoin. It has since doubled down, and doubled down again.

In total, MicroStrategy raised $3.45 billion in debt and loans. It issued $1.44 billion in equity. The company used it all to buy bitcoin.

For a time, the decision appeared to be working. The price of bitcoin rose from about $17,088 in August 2020 to nearly $99,000 by November 2021. MicroStrategy’s stock rose from US$124 the day before its announcement to a record of US$1,273 on Feb. 9, 2021.

But on Tuesday, MicroStrategy announced its seventh quarterly loss in the eight quarters since it started buying bitcoin. This time the loss was big: $1.44 billion, much of that from bitcoin.

The same day, the company announced Phong Le, the company’s president, will take on the additional role of CEO. Mr. Saylor took on the role of executive chairman.

MicroStrategy shares were down 49% year-to-date through Tuesday, and 78% from its record.

The company is sitting on nearly 130,000 bitcoins valued at roughly $4.3 billion at current market prices. Its market capitalisation is about $4.45 billion. Essentially, MicroStrategy has become a bitcoin-holding vehicle with a cash-generating software business attached to it.

MicroStrategy’s losses reflect the volatility of bitcoin. Under accounting rules, the company must assess the value of its bitcoin holdings each quarter and take an impairment charge if the price has declined. MicroStrategy has taken a string of such charges totalling about $3.5 billion.

The bitcoin strategy turned Mr. Saylor into one of bitcoin’s most visible proponents. His Twitter feed, followed by 2.6 million, is a constant stream of pro-bitcoin quips.

He is uniformly bullish in interviews. In one, he advised people to “take all your money and buy bitcoin. Then take all your time, figure out how to borrow more money to buy more bitcoin. Then take all your time to figure out what you can sell to buy bitcoin.”

He similarly advised a conference room full of crypto enthusiasts in Miami to never sell their bitcoin.

It is this very philosophy that has worried some market observers.

“MicroStrategy is not an ideal investment for most traders,” said Oanda analyst Edward Moya.

For one thing, Mr. Moya said, MicroStrategy’s strategy was only to buy and hold bitcoin. There was no profit-taking. There also was no hedging against the inevitable volatility and tumbles. When the selloffs came, MicroStrategy was exposed to the full breadth of them.

Another problem is that the company doesn’t have many more ways to get more money to buy more bitcoin, said BTIG analyst Mark Palmer. “A lot of the levers MicroStrategy could have pulled to create more capacity have been pulled,” he said. “Now it’s just using the cash flow from the software business.”

Still, Mr. Palmer said, the ultimate judgment on MicroStrategy’s bitcoin bet won’t come until some of that debt it borrowed to buy bitcoin starts to mature. If the price of bitcoin languishes, the company is going to have problems paying back its creditors, he said.

“The ticking clock is the maturity of the MicroStrategy debt,” he said.

Despite the risks and the criticisms, Mr. Saylor still believes in his strategy, and bitcoin. In an interview last week, he noted that the stock is still well above its pre-bitcoin levels, and believes the strategy has raised the company’s profile, despite the risks attached to it.

“I feel better about it today than I did on the day we started,” he said.

He says he will continue to head MicroStrategy’s bitcoin investments. He has no plans to sell any bitcoin, and still expects it to gain in value over the years. The company reiterated Tuesday it has no plans to sell any bitcoin.

Mr. Saylor said swapping the CEO roles had been a long-term plan. “The new executive structure means I can even more enthusiastically focus on communications and strategy and bitcoin advocacy and evangelism,” he said.



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Luxury watch collectors showed ongoing strong demand for Patek Philippe, growing interest in modern watches and a preference for larger case sizes and leather straps at the June watch sales in New York, according to an analysis of the major auctions.

Independent and neo-vintage categories, meanwhile, experienced declines in total sales and average prices, said the report from  EveryWatch, a global online platform for watch information. Overall, the New York auctions achieved total sales of US$52.27 million, a 9.87% increase from the previous year, on the sale of 470 lots, reflecting a 37% increase in volume. Unsold rates ticked down a few points to 5.31%, according to the platform’s analysis.

EveryWatch gathered data from official auction results for sales held in New York from June 5 to 10 at Christie’s, Phillips, and Sotheby’s. Limited to watch sales exclusively, each auction’s data was reviewed and compiled for several categories, including total lots, sales and sold rates, highest prices achieved, performance against estimates, sales trends in case materials and sizes as well as dial colors, and more. The resulting analysis provides a detailed overview of market trends and performance.

The Charles Frodsham Pocket watch sold at Phillips for $433,400.

“We still see a strong thirst for rare, interesting, and exceptional watches, modern and vintage alike, despite a little slow down in the market overall,” says Paul Altieri, founder and CEO of the California-based pre-owned online watch dealer BobsWatches.com, in an email. “The results show that there is still a lot of money floating around out there in the economy looking for quality assets.”

Patek Philippe came out on top with more than US$17.68 million on the sale of 122 lots. It also claimed the top lot: Sylvester Stallone’s Patek Philippe GrandMaster Chime 6300G-010, still in the sealed factory packaging, which sold at Sotheby’s for US$5.4 million, much to the dismay of the brand’s president, Thierry Stern . The London-based industry news website WatchPro estimates the flip made the actor as much as US$2 million in just a few years.

At Christie’s, the top lot was a Richard Mille Limited Edition RM56-02 AO Tourbillon Sapphire
Richard Mille

“As we have seen before and again in the recent Sotheby’s sale, provenance can really drive prices higher than market value with regards to the Sylvester Stallone Panerai watches and his standard Patek Philippe Nautilus 5711/1a offered,” Altieri says.

Patek Philippe claimed half of the top 10 lots, while Rolex and Richard Mille claimed two each, and Philippe Dufour claimed the No. 3 slot with a 1999 Duality, which sold at Phillips for about US$2.1 million.

“In-line with EveryWatch’s observation of the market’s strong preference for strap watches, the top lot of our auction was a Philippe Dufour Duality,” says Paul Boutros, Phillips’ deputy chairman and head of watches, Americas, in an email. “The only known example with two dials and hand sets, and presented on a leather strap, it achieved a result of over US$2 million—well above its high estimate of US$1.6 million.”

In all, four watches surpassed the US$1 million mark, down from seven in 2023. At Christie’s, the top lot was a Richard Mille Limited Edition RM56-02 AO Tourbillon Sapphire, the most expensive watch sold at Christie’s in New York. That sale also saw a Richard Mille Limited Edition RM52-01 CA-FQ Tourbillon Skull Model go for US$1.26 million to an online buyer.

Rolex expert Altieri was surprised one of the brand’s timepieces did not crack the US$1 million threshold but notes that a rare Rolex Daytona 6239 in yellow gold with a “Paul Newman John Player Special” dial came close at US$952,500 in the Phillips sale.

The Crown did rank second in terms of brand clout, achieving sales of US$8.95 million with 110 lots. However, both Patek Philippe and Rolex experienced a sales decline by 8.55% and 2.46%, respectively. The independent brand Richard Mille, with US$6.71 million in sales, marked a 912% increase from the previous year with 15 lots, up from 5 lots in 2023.

The results underscored recent reports of prices falling on the secondary market for specific coveted models from Rolex, Patek Philippe, and Audemars Piguet. The summary points out that five top models produced high sales but with a fall in average prices.

The Rolex Daytona topped the list with 42 appearances, averaging US$132,053, a 41% average price decrease. Patek Philippe’s Nautilus, with two of the top five watches, made 26 appearances with an average price of US$111,198, a 26% average price decrease. Patek Philippe’s Perpetual Calendar followed with 23 appearances and a US$231,877 average price, signifying a fall of 43%, and Audemars Piguet’s Royal Oak had 22 appearances and an average price of US$105,673, a 10% decrease. The Rolex Day Date is the only watch in the top five that tracks an increase in average price, which at US$72,459 clocked a 92% increase over last year.

In terms of categories, modern watches (2005 and newer) led the market with US$30 million in total sales from 226 lots, representing a 53.54% increase in sales and a 3.78% increase in average sales price over 2023. Vintage watches (pre-1985) logged a modest 6.22% increase in total sales and an 89.89% increase in total lots to 169.

However, the average price was down across vintage, independent, and neo-vintage (1990-2005) watches. Independent brands saw sales fall 24.10% to US$8.47 million and average prices falling 42.17%, while neo-vintage watches experienced the largest decline in sales and lots, with total sales falling 44.7% to US$8.25 million, and average sales price falling 35.73% to US$111,000.

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