Love Hollywood Celebrities? We have photoshoots and exclusives of Sexy Actresses, Models, Singers and Sports stars.

How Katy Perry Became America's Top Pop Export
Yet their attempts to jump-start her career went nowhere. Perry struggled to make ends meet, often getting smacked with overdraft fees by her bank; at one point her leased Volkswagen Jetta was repossessed, and her managers had to start advancing her money for rent.

Finally, in 2007, Perry found a home at Capitol Records. Despite her inexperience and desperation, she displayed uncanny business savvy–with the encouragement of her managers, she insisted on a music-only deal that left her in control of her touring and merchandise revenue. She also turned down a six-figure music publishing advance, electing to keep the underlying rights–and the potential for a greater payday down the line–for herself. In 2009 her strategy paid off with the release of “I Kissed a Girl,” her first chart-topping single.

“People were talking about bisexuality a lot that year and also talking about sexuality being fluid,” says Perry of the first of many songs her parents would surely not approve of. “It was zeitgeisty. It was me taking everybody’s conversation and funneling it into a song. I also knew it had that ‘ooh, ahh’ factor. I knew I could open the most doors with that first, but I wasn’t going to let that define me.”

Other top-ten singles from her first album with Capitol included “Waking Up in Vegas” and “Hot N Cold.” Then in 2010 she put out Teenage Dream, which has sold almost 6 million copies in the U.S. alone and launched five singles to No. 1 on the charts–a feat pulled off previously only by Michael Jackson.

Many of Perry’s songs started taking off right around the time she launched her next tour. She played the 7,000-capacity Nokia Theater in Los Angeles before striking out for Europe and eventually Australia, all the while building up a following by playing intimate venues. By the time she returned to Los Angeles she was playing the 18,000-seat Staples Center, eventually sharing her life on the road in a 2012 documentary Part of Me, which served as a big-screen promotional video–and a profitable one at that (it grossed $33 million on a $6 million production budget).

Along the way Perry started to receive offers for all sorts of endorsement deals. She accepted a handful of seven-figure pacts, sticking to products she actually used: Proactiv, CoverGirl and Adidas. She released two fragrances, Killer Queen and Royal Revolution, for Coty (her next, Mad Potion, is due out later this year). She also took a page out of Ashton Kutcher’s book, electing to take ownership positions instead of flat fees for shilling brands like Popchips. ”One thing I’ve been able to do is know the power of having equity deals,” she says. “I don’t ever like to do things unless I’m really a part of them.”

That long-term approach is already paying off, especially when it comes to touring. Perry returned to Australia last November and grossed $40 million from 23 shows before moving on to the world’s next great live market: China, where she played five concerts. “People appreciate when you come. … They know how hard it is,” she says. Indeed, China’s National Orchestra invited her to a performance of “Roar” played on traditional instruments; the event was broadcast on state-run CCTV, which boasts a viewership of more than 1 billion people.

While many acts treat their burgeoning international legs as logistical burdens, Perry, whose formal education ended with a GED at age 15, tries to turn her tours into education extensions, whether the Colosseum in Rome, the British Museum in London or the Renaissance paintings of Florence. “I’m not one that stays in my hotel room,” says Perry. Adds Cobb: “She wants to learn. And she doesn’t care if it’s an embarrassing question.”

The underlying insecurity that comes when your educational credentials don’t match up with your inherent smarts can be a compelling motivator. It can explain why she sits through business meetings and sifts through the professional minutiae other stars would delegate and why, despite her swagger and success and sex symbol appeal, she can seem the most flattered when people talk business with her. “You’re calling me interesting,” she says to me at one point. From the softness of her tone you’d think I’d just given her the greatest compliment she’d ever received.