Fresh Air

History for the hardcore. Jokes for jocks. Entrepreneurs are reinventing digital broadcasts

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Holly Andres for TIME

Web-radio host Dan Carlin in his garage studio.

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The companies that have been most eager to advertise on the medium so far are technology firms. Anthony Casalena, founder and CEO of Squarespace, sees podcasts as a natural showcase for his company's services. Another strength: the authenticity of the host. "A podcast is only going to be successful if the host has a strong connection with his audience," says Casalena. Goldstein echoes the sentiment: "You never get somebody grateful to the Ford Motor Co. for sponsoring Two and a Half Men."

Would-be podcast jockeys face plenty of potential pitfalls. For one thing, most of the profit in the industry goes to a small number of the top stars. Rob Walch, a vice president at Libsyn, the largest podcast-hosting service, says just 10% of his firm's broadcasters reach the popularity threshold necessary to warrant soliciting advertising. Fewer still attract the number of listeners that would enable them to make a living from podcasting alone. What's more, because most listeners download shows through Apple's iTunes store, hosts are unusually dependent on good reviews and word-of-mouth traffic from anonymous listeners.

And then there are the growing pains. Carlin, for one, is concerned that success might dilute the relationship he has cultivated over the years with his current audience. "I do get worried that if we ever appear to be this juggernaut, that my audience will think I don't need their money," he says. That would jeopardize his business. He also worries about cluttering his programs with advertisements and scaring away listeners who generously donate to the endeavor. After all, they are paying to hear about the bloodiest battles in history, he says, not product pitches. In other words, appearances matter. Says Carlin: "I don't worry about getting too big as much as seeming too big."

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Due to a transcription error, the original version of this article stated that Entrepreneur on Fire produced yearly ad revenues of $2.4 million and $1.5 million in listener membership revenues. The broadcast's ad and membership revenues are actually $240,000 and $150,000, respectively.

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