Pandora has never had a more pivotal moment than this one. The 75 million user-strong service is synonymous with Internet radio, but a growing list of competitors ( which now includes Apple ) and its royalty dance with the record industry loom large.

It’s a classic tech business conundrum. The world looks at Pandora as a new standard, but its position is actually much more precarious: To keep thriving, Pandora needs to ink major deals inside and outside the U.S. This is the kind of stress that would crush a lot of founders, but Tim Westergren says he’ll fall back on an old standby: naiveté.

“The only reason I did [Pandora] was because I was naive,” Westergren says. “I would say that entrepreneurship in general requires naiveté. Were you not naive, it could be so daunting that you would either not try it in the first place or you’d give up if you began to see things getting difficult.”

When he was trying to sell the idea of Pandora to investors, he kept hitting a wall. Indeed, he pitched the idea 348 times before securing the company’s second round of funding.

Westergren heard the same criticism again and again: It doesn’t scale. That is, having trained musicians sit down at a computer and punch in descriptive attributes one by one–effectively building a recommendation engine by hand–might be a culturally smart way to do things, but it would never scale enough to cover all the music in the world. This was, after all, the early 2000s when automation and algorithms were shedding their academic labels and starting to transform industries. You want to use humans to do this? You can’t be serious.

“People thought I was out of my mind to do something that was so retro and slow,” Westergren says. “It was contrary to all the trends in technology. There was a strong belief that you need to build scalable models and that technology was the only way to tackle big data problems. There was a lot of naiveté that I needed to buck that institutionalized belief.”

And yet, like a gambler at the blackjack table, Westergren just kept trying. And trying. And trying.