Gambling Affiliate Empire

Shaan tells a story about an entrepreneur who made $100M by strategically creating gambling affiliate websites as states legalized online betting.

"We sold the Milk Road to two guys, and one had a fascinating background. He was an affiliate marketer for online poker. When Black Friday came and online poker became illegal in the United States, his business died overnight. While all his competitors went international, he took a different approach.

He waited and watched as New Jersey was rumored to be the first state to legalize online gambling again. While everyone else went international, he decided to be the New Jersey betting affiliate. He created a hyper-targeted website, which sounded really niche at first.

He realized if one state was going to do it, others would follow. He wanted to surf this trend and create all the content for states that were rumored to legalize gambling. He sold the New Jersey site for about $42-46 million to a bigger betting company. Then he did the exact same thing for Minnesota, selling that one for another $40-something million within a 2-year timespan.

The company that bought the sites eventually realized they couldn't let him keep flipping these sites to them for $50 million each. He and one other guy who was doing the same thing merged, and because they owned all the supply, they could demand whatever affiliate rates they wanted because they were the only show in town."