When people hear Michael Saylor’s name today, they picture Bitcoin debates, massive balance‐sheet BTC acquisitions, and fiery social-media rants. What most don’t realize is that, long before he became a Bitcoin evangelist, Saylor was quietly scooping up domain names.
The Early Days of Domain Hunting
In the mid-to-late 1990s, as the internet’s popularity soared, MicroStrategy began acquiring one-word .com domains – simple, generic names such as Alert.com, Courage.com, and Usher.com.
Domain names were the hottest new commodity, and Michael Saylor saw that owning a short, memorable .com was akin to owning a Times Square billboard – except there was no monthly rent, just the promise of future fame.
Reflecting in a 2018 interview, Saylor recalled how MicroStrategy viewed domains as investments rather than marketing afterthoughts:
“So we spent about two million dollars buying domains like Alarm.com, Wisdom.com, Strategy.com, Michael.com, Mike.com, Angel.com, Courage.com, Hope.com,” he recalled. “We turned $2 million into over $100 million of value.”
Unlike speculators looking to flip within months, Saylor’s team played the long game. They acquired a portfolio of generic .coms and resisted early offers, waiting for market demand to drive prices higher. As the dot-com bubble faded and industries matured, more companies realized the value of instantly recognizable domain names. That’s when Saylor’s patience paid off.
Building Operational Value: Angel.com and Alarm.com
Not all of MicroStrategy’s domains stayed dormant. Two standout examples – Angel.com and Alarm.com -evolved into functional businesses before being sold. Angel.com became an interactive voice response (IVR) services provider, leveraging the “angel” brand to convey guidance and support in call-center technology. Alarm.com grew into a publicly traded home security solutions company, tapping into the connected home trend.
By operating these businesses under the MicroStrategy umbrella, Saylor extracted value not just from the domain itself but also from recurring subscription revenues and established customer bases. In 2013, Genesys acquired Angel.com (including its domain) for $110 million in cash.
A few years earlier, in February 2009, ABS Capital Partners paid $27.7 million for Alarm.com. By combining domain scarcity with operational momentum – a premium name plus a proven product – Saylor magnified returns beyond what a simple domain flip would yield.
While Angel.com and Alarm.com proved that spinning domains into businesses could deliver huge payoffs, Saylor’s most spectacular flip was still to come.
Voice.com: The Crown Jewel
The pièce de résistance arrived in June 2019: Block.one, a blockchain-focused social network backed by high-profile investors, purchased Voice.com from MicroStrategy for $30 million in cash. At that moment, it became the largest publicly reported domain-only sale.
Saylor had held onto Voice.com without launching a consumer platform, betting that “voice” would become central to emerging technologies – think AI assistants, podcasts, and decentralized social media. When Block.one’s executives approached MicroStrategy via GoDaddy’s brokerage service, Saylor saw the perfect buyer – one willing to pay a premium for a name that matched their vision.
Rather than selling years earlier for a quick profit, he waited until someone arrived with deep pockets. That patience delivered a windfall, bolstering MicroStrategy’s earnings well before Bitcoin took center stage in the company’s strategy.
As he explained during a DomainSherpa interview,
“I knew that voice was going to be core in the next-generation internet – so owning Voice.com was like owning the main street of a town that hadn’t been built yet.”
Principles of Saylor’s Domain Strategy
1. Spotting Future Trends: Saylor understood that certain one-word domains – especially those tied to broad concepts like “voice” – would become invaluable as technology evolved. He recognized their potential long before AI assistants and blockchain startups prioritized a clean, catchy web address.
2. Holding for Maximum Value: Instead of rushing to flip domains, Saylor’s approach was to wait. By resisting early offers, he allowed demand to grow until industries matured and buyers competed. The longer hold translated into far higher sale prices.
3. Enhancing with Operations: In cases like Angel.com and Alarm.com, building actual businesses around the domains boosted their appeal. Buyers paid not just for a memorable name but also for subscriber revenue and existing customer relationships.
By 2019, MicroStrategy had quietly collected well over $165 million from its portfolio of domain ventures -resources that fortified its balance sheet and gave Saylor the freedom to pivot hard into Bitcoin.
Instead of begging the board for funding, he could confidently declare, “We made fortunes buying .coms when nobody believed in them – now imagine what we can do with digital gold.” In other words, the same instincts that made him a .com pioneer also made him Bitcoin’s most ardent corporate evangelist.
