Jay-Z had it easy. He faced few restrictions in his quest for money and stardom. Unapologetically driven by material desires and founded on a platform of social Darwinism, Jay-Z’s ascent to mogul-hood represents capitalism in its purest form.

Like most rappers, Talib Kweli wants what Jay-Z has—money, esteem, an audience—but in his pursuit of these goals he’s been held to a much stricter standard than Jay-Z. Long ago labeled a conscious rapper by his fans, Kweli is expected to be above the perceived vanity of mainstream rap. While rappers like Jay-Z can play anything-goes, Tammany Hall politics, Kweli must adhere to restrictive campaign finance regulations or risk alienating his idealistic fans.

This is Kweli’s unique conundrum: how to find commercial success when a healthy chunk of your following cries foul at the slightest whiff of commercialism.

“It can be hard on your pride,” Kweli admits. “You’ll read a review of your album that says you sold out, and then you’ll start second-guessing yourself. ‘Well, did I sell out?’”

But Kweli says he’s learned to move beyond pride. Instead, he’s devised pragmatic ways to reconcile both factions of his target audience—the masses that devour slick, poppy rap, and the more vocal contingent that accepts only the intelligent, beats-and-rhymes hip-hop that Kweli has been best known for since his 1998 debut with longtime friend Mos Def as Black Star.

His solution is to provide something for everyone. Last year, for instance, to cushion the blow of Eardrum, his most explicitly commercial album—one anchored by appearances from Justin Timberlake, will.i.am and Norah Jones—Kweli tossed his underground fans a bone in the form of a free (and, for that matter, freeform) online album called Liberation, an uncompromising collaboration with alternative-rap producer Madlib.

“Trends don’t affect the music that I make, but they do affect the way that I put it out,” Kweli explains. “I could make an album like Liberation all day, but it doesn’t make sense to pay for all those samples and to try to market and promote an album like Liberation in the way that you’d market and promote a Jay-Z or Rick Ross album. But with an album like Eardrum, where there’s slicker production, there’s more money spent on it, and there are other major artists who are involved, you have to market it more aggressively.”

The strategy worked. Eardrum was Kweli’s highest charting album yet, but it sparked little backlash from underground hip-hop circles, which were too busy fawning over Liberation to take umbrage over Kweli’s commercial concessions.

In many respects, Kweli provides a down-to-earth business model for all rappers. While the music industry spins out around him, Kweli has continued to thrive, maintaining a steady buzz through online promotions, free mixtapes and—perhaps most importantly—his live shows. He does roughly 200 a year.

“The artist who is not doing shows right now is floundering,” Kweli explains. “You need to be able to develop a live act and a stage show to cement your fan-base. The idea that you can just put out a record and have it be a hit on the radio works if you’re just trying to sell ringtones or hit a certain number of downloads, but it doesn’t really sustain your career.”

Talib Kweli headlines a 7:30 p.m. concert at MarquetteUniversity’s Varsity Theater with the Rusty Ps on Tuesday, April 22.