During his time in Japan, Freedman opened his own outdoor advertising firm, Pacific Media, in 1988. He eventually sold control of the company to Catalina Marketing Corporation in 1996 and returned home to the United States in 1993, commuting back and forth between Tokyo and the U.S.
In 2003, Freedman sold his remaining stakes in Pacific Media, and two men, Seth Lippert and Sergio Fernandez De Cordova, created Fuel Outdoor, an outdoor advertising agency. One of the company's board members, Joel Rudenstein, approached Freedman and asked if he would be interested in investing in the startup company.
Having started his own media company at a young age, Freedman said that he saw himself in the two young men and agreed to be an investor in their company, albeit not a passive one. Lippert and De Cordova eventually struck a deal with a large institutional-asset manager that wanted to buy Fuel Outdoor...but only if it was under what Freedman called "adult supervision," meaning supervision by someone who had done it all before and had experience running a company. That someone was none other than Freedman, who took over the company as CEO in a time of rapid growth for the outdoor advertising industry.
"[Outdoor advertising is] a hot area these days, an important area, one of the few areas where you can't TiVo the medium," Freedman said. "If you look at where the flows are going in the advertising industry today, it's either going into the Internet or going into outdoor."
The company itself has gone from advertising in New York City to advertising in eight of the top 15 designated marketing areas (DMAs): Boston, Chicago, Los Angeles, Miami, New York, Philadelphia, San Francisco, and Washington, DC.
"What we've done in the last 18 months is we've gone from being a small one-point shop based in New York, and now we're a nationwide concern with almost 4,000 assets nationwide," Freedman said.
With the creation of TiVo and advertising-free satellite radio, Freedman feels that the face of advertising is changing drastically. He believes that in order to get their messages across, advertisers do not necessarily need to be more creative; they need to be smarter.
"Like anything else, you need to be smart about the message you are delivering and how you deliver it. Five years ago, no one ever thought about advertising on pizza boxes. Now pizza boxes have advertising. Three years ago, nobody thought about advertising on coffee sleeves, but now every coffee sleeve you see has advertising on it, whether it's Starbucks or somebody else. So at the end of the day, do you need to be more creative? No. You have to be more intelligent about how you spend your money," Freedman said.
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Outdoor advertising has come a long way from its humble beginnings. Freedman said that when he first started out in the industry, only a handful of companies were "doing 30 to 50 million dollars of business a year nationwide," while today there are three major companies earning several billion dollars each and a handful of second-tier companies (including Fuel Outdoor) that "are powerful in the midsections." He also said that the methods employed have come a long way. Billboards were once a predominant medium, whereas advertisers now use almost anything people walking or driving down the street will see, such as the sides of buildings and construction scaffolds.
"The outdoor space has expanded greatly from the highways and byways to any available place where advertising can be delivered to the consumer who is walking or driving by," Freedman said. "There has been a much, much broader definition of what is now considered out-of-home media. It's not just billboards anymore; out-of-home is a much broader category."
He said that the serious rise of outdoor advertising began about 15 years ago, after the creation of digital printing. Before, advertisers paid a local artist in each city they targeted to create a billboard. For example, if a company wanted an ad in Houston, it would pay one artist, and if it wanted one in San Francisco, it would have to hire another artist. Once digital printing hit the scene, agencies could print larger, more uniform campaigns for cities across the country.
"Technology has been a catalyst for the consolidation of what was a local and regional business into a national business—and an international business, as well," said Freedman.
Originally from Central Massachusetts, Freedman now resides in West Port, CT. Married in 1994, he and his wife have two children: a 10-year-old girl and a 12-year-old boy.
