In 1990, seeing the Internet's commercial potential, Meckler started "Internet World," a newsletter that became a magazine two years later. "I started a trade show in 1993 with just eight exhibitors because there were so few commercial applications back then, but 1,500 people showed up for the conference, so I made about $300,000," he said.
By the time he sold his company, Mecklermedia, to Penton Media in 1998, its revenue topped $60 million. He simultaneously made a deal to buy back 80.1% of the company's Internet assets and founded Internet.com Corp., later renamed INT Media Group.
Ahead of the trends once again, Meckler launched a series of Search Engine Strategies trade shows in 2001. He plans to produce the show eight times this year and probably a dozen times next year.
In 2002, after the bottom fell out of the Internet boom, Meckler saw a deal he couldn't refuse and picked up Jupitermedia, then primarily known for its Internet research, for $250,000. He dramatically expanded the scope of the business, making a big push into digital images with the acquisition of ArtToday Inc. in 2003.
"Since then, I've spent $112 million acquiring image companies, and it's now the largest part of our business," Meckler said. "It's just the most incredible business I've ever seen, and it's quite profitable. There's really no physical inventory, and the distribution costs are so low that you can start to make money after selling an image just once."