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Bitcoin has a number of personalities, equal components cash, freedom, resistance and hope.
MicroStrategy chairman Michael Saylor sits under all of them as bitcoin’s id — its rawest instincts, personified.
Thursday marked the twenty fifth anniversary of Saylor shedding $6 billion in sooner or later ($11 billion adjusted for inflation) because the dot-com bubble burst. That occasion was among the many greatest single-day private losses in human historical past till that time.
That is his comeback story.
Premium domains
Saylor was not at all times the apex Bitcoin bull. He did, nevertheless, perceive digital shortage lengthy earlier than the primary block was ever mined: in domains.
After founding MicroStrategy in 1989 and spending years constructing it up as a knowledge mining and enterprise intelligence operation, Saylor within the ‘90s had the brilliant concept to start out shopping for up “premium” domains: easy, single-word domains with doubtlessly common attraction and, ideally, over 500 million hits on Google Search.
Angel.com. Alarm.com. Knowledge.com. Emma.com. Speaker.com. Alert.com. Voice.com. Hope.com. Just one individual might ever personal every separately, and MicroStrategy spent $2 million total buying these kinds of premium domains — at a median of round $100,000 every — alongside 1000’s of much less invaluable secondary domains.
“I purchased all these domains as a result of I assumed, ‘Wouldn’t or not it’s nice to personal part of the English language?’” Saylor stated on the My First Million podcast. He personally owns Michael.com and one for his nickname, Mike.com.
“I imply, [as to] proudly owning ‘hope’ or proudly owning ‘voice’ — ultimately, there’ll be a Google Voice, or some telecom firm will need to launch a service. And what a fantastic area to launch on — a phrase like ‘Voice.com.’”

Alarm.com and Angel.com had been later commercialized with actual firms, respectively spun up by Saylor and MicroStrategy’s analysis and growth division.
MicroStrategy ultimately bought Alarm.com and its related enterprise for $27.7 million in 2009 to enterprise capital agency ABS Capital Companions. In 2013, software program firm Genesys acquired Angel.com with its enterprise for $110 million money, and rapidly rebranded it below its personal company umbrella.
Saylor, in the meantime, was adamant that Voice.com was price $1 billion to the best purchaser.
It was round this time, in December 2013, that Saylor first publicly commented on Bitcoin: “Missing a reputable sponsor, Bitcoin is in imminent hazard of being regulated out of existence,” Saylor tweeted.
He posted once more one other week later, after bitcoin had fallen by as much as two-thirds from an all-time excessive of $1,242:
Sunk value
Saylor wouldn’t actually return to Bitcoin till mid-2020, not less than publicly, and going by the timeline of occasions, a premium area sale to a crypto startup may’ve been his lightbulb second, with a capital ₿.
In Could 2019 — one 12 months earlier than MicroStrategy first confirmed intent to purchase bitcoin — the corporate behind upstart blockchain EOS, Block.one, had introduced a brand new social media app within the type of Voice, which promised to pay token payouts to customers for posting and sharing content material.
Block.one was beforehand calculated to have raised $4.1 billion in ETH throughout a year-long preliminary coin providing that began in mid-2017 and ended round a 12 months earlier than Voice was revealed.
“They [Block.one] contacted us, one in all their area brokers, they usually requested, ‘Do you need to promote it? We’ll offer you $150,000.’ I stated no. I assumed nothing of it, as a result of I simply couldn’t see the purpose,” Saylor recounted.
“They arrive again and say, ‘They doubled it to $300,000.’ I stated, ‘Inform them no.’ So a pair days later they [Saylor’s colleagues] go, ‘Nicely the dealer’s actually insistent; they went to $600,000.’ I stated no. In order that they stated, ‘Nicely, what ought to we are saying?’ I stated, ‘Don’t inform them something. Inform them we’re not . It’s obtained to be one thing severe.’”

MSTR returned to all-time highs final November after greater than 20 years — because of its Bitcoin plan. EOS is down 75% previously 5 years. Supply: TradingView.
Block.one then provided $1.2 million, which Saylor rejected. Then $2.5 million. Then $5 million. Then round $10 million.
“When it obtained to $12 million, I stated I’d get on the cellphone for half an hour. That decision began with somebody saying, ‘Nicely, how about $22 million?’ And I stated, “Let me clarify. That is like my daughter. I’m keen to marry her off, however solely to a person that values her greater than I worth her.”
MicroStrategy closed the deal in June 2019 for $30 million — 200 instances above Block.one’s preliminary provide. It’s nonetheless the biggest identified pure area identify sale in historical past, almost doubling the earlier file of $17 million, which Qihoo paid for 360.com in 2015.
Block.one went on to sink one other $150 million into Voice.com’s growth over the subsequent two years earlier than shutting it down in late 2023. Voice said that “the continuing uncertainty within the crypto and NFT market will proceed for extra time than we now have.”
Conversely, Saylor and MicroStrategy started shopping for bitcoin, positioning themselves to capitalize immensely on an impending bitcoin rally fueled by anticipation of ETFs from BlackRock, Constancy and others.
The way it began
One 12 months after the area sale closed, in July 2020, Saylor stated in a quarterly earnings name that MicroStrategy might begin shopping for bitcoin over the subsequent 12 months as a part of a brand new capital allocation technique.
The plan was to speculate $250 million over the subsequent 12 months in different property — “which can embrace shares, bonds, commodities akin to gold, digital property akin to bitcoin, or different asset varieties,” whereas shopping for again $250 million in firm inventory from shareholders.
Besides it didn’t take a 12 months. MicroStrategy purchased 21,454 BTC for $250 million in lower than two weeks, and in August 2020 declared bitcoin its major treasury reserve asset.
Bitcoin was then buying and selling for below $12,000, and inside 4 months had damaged its $20,000 value file, which had beforehand held for nearly three years.
Nook the market
By December 2020, MicroStrategy had opened its first debt sale since opting into bitcoin — $400 million with 0.75% curiosity — which it pledged to spend on shopping for extra cash. Then a second increase two months later, and a 3rd 4 months after the second.
So by the point Block.one wound down Voice in September 2023, MicroStrategy was sitting on $4.2 billion in BTC on the very early phases of a monster bull run.
Since then, MicroStrategy has spent nearly $27.8 billion to accumulate a further 340,860 BTC ($28.7 billion). Bitcoin has greater than tripled in value in that point, whereas MicroStrategy has dropped the “Micro” from its identify and solely goes by Technique today.
Technique now holds a complete of 499,096 BTC — 2.5% of the circulating provide — and is effective sufficient to be included within the benchmark Nasdaq 100 inventory market index. Saylor has relentlessly bull-posted all the time, selecting up the place former evangelists akin to Roger Ver left off.
After all, Technique has raised billions of {dollars} throughout 9 accomplished debt gross sales to assist fund the bitcoin acquisition plan.
The way it’s going
Proper now, the agency has $9.3 billion in convertible debt towards $41.8 billion in BTC, and is that this 12 months accountable for 30% of the US convertible market, all “powered by Bitcoin.”
Technique has spent $33.2 billion on bitcoin in whole, and the serviette math places Technique successfully forward by $700 million at time of writing. Saylor’s private web price is estimated at $6.6 billion, and in January, the agency brazenly promised to boost $42 billion over the subsequent three years to purchase an entire lot extra.
Whether or not it’s conviction that Voice.com is admittedly price $1 billion, or that bitcoin is “going up ceaselessly,” Saylor’s profession has been marked by the identical base intuition to nook the market on long-lasting digital property, significantly ones that function foundational buildings for web economies.
Saylor merely expanded from one highly-illiquid digital asset class in domains — a distinct segment area the place he’s additionally thought-about a legend — to at least one deeply liquid digital asset in bitcoin.
Amazingly, what adopted the Voice.com deal doubles as a near-perfect allegory for crypto investing. Block.one sunk 9 figures right into a token mission that pivoted to NFTs, solely to go zero earlier than it even began, defeated by a bear market.