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Starting in the late 90s, Kevin Ham built a portfolio of 300,000 domain names in less than a decade. The result was a $300 million empire, generating $70 million in estimated annual revenue.
From a 2007 article in Business 2.0 Magazine:
Ham’s cleverest play may have been striking a deal with the Cameroon government to “typo-squat” all non-registered .cm domains.
From the same article:
By 2007, Ham’s days were numbered as companies like Google, Microsoft, and Yahoo began to crack down on domain and typo-squatting.
In October 2017, Ham reportedly sold 100,000 of his domains to GoDaddy for some portion of $50 million.
As per that 2007 article, Ham was apparently generating $70 million in annual revenue at his peak.
To be clear: the golden age of domaining seems to be long gone.
Ham started into it way back in 1998, as per the aforementioned article:
According to our framework it was primarily a referral business, which would be considered a Level 3 online business.
These kinds of businesses don’t own the end product or service themselves. Instead, they connect buyers and sellers and usually collect a commission or finder’s fee.
In Ham’s case, it seems he was earning most of his money by setting up landing pages on the domains he owned. Those landing pages were filled with ads, and Ham would make money from visitors clicking on those ads.
Ham’s typo squatting technique could also be considered a “weird” way to make money online.