Emma Grede, the host of the Aspire Show, recently sat down with Steve Stoute, a powerhouse music executive, marketing genius, CEO, and founder, to dissect his career, which spans bridging hip-hop culture with global brands and defining breakthrough success. Stoute, whom The New York Times calls the CEO that other CEOs turn to for advice, shared his core philosophy: Your background isn't baggage, it’s the key to unlock everything you’ve been chasing.
Grede sought to understand the essence of Stoute’s success, particularly his unique understanding of culture. Stoute explained that growing up in Queens, New York, as the son of Trinidadian immigrants, he had "vivid memories" of watching the emerging hip-hop culture firsthand. He saw influential figures like A Tribe Called Quest, Russell Simmons, Run DMC, and LL Cool J within a five-mile radius, witnessing LL Cool J perform at block parties for 25 cents and battle guys in the mall. This immersion meant hip-hop "reigned supreme" and was "in my DNA," providing him with an early perspective on culture's power, even though he didn't know it would become a business.
Early in his career, Stoute faced the obstacle of trying to bring hip-hop culture to white corporate CEOs who "didn't give a shit" about his perspective. This situation forced him to develop relationship skills, as he realized successful black figures before him, such as Clarence Avant, Quincy Jones, and Benny Medina, often had a "Jewish counterpart" who acted as a segue into larger financial opportunities, distribution, and capitalization. Stoute identified his own necessary counterparts, including Jimmy Iovine, Tommy Mottola, and Peter Arnell, to advance his career. His strategy was to "translate" the culture so brands could see how it was "accretive to what your intentions are". He noted that his best "way in" was often finding a CEO with a teenager at home, as the child’s validation of his pitch would often secure a return phone call. Grede noted that she "totally understand that so much".
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The discussion turned to Stoute’s philosophy on mentorship. Grede noted that the word "mentor" has become popular, but Stoute called the idea of people asking others to be their mentor "insane" and "so fucking fake". He declared, "You can't just microwave a fucking mentor man". Instead, Stoute advises people not to ask for a mentor, but to ask questions. He encourages people to emulate successful individuals and borrow from what makes them successful without shame, suggesting they look at the constellation of successful people and pull from different places. He cited Jimmy Iovine as his mentor but noted that their relationship was never formalized: "I didn't realize that dance was happening until 10 years after the dance".
Grede was also curious about Stoute’s leadership style, which he attributes to telling the truth and adopting the value of "challenge and respect". Challenge and respect means having a disagreement and resolving it without anyone feeling disrespected. Stoute shared that businesses need conflict to grow, and he has gone back to a 4-day work week because "Zooms hinder conflict resolution". He asserted that the hardest part of telling the truth is finding the person inside a company, typically the CEO, who is willing to hear it. Stoute noted that the greatest artists—such as Eminem, Nas, 50 Cent, Lady Gaga, and Beyoncé—always want to hear the unvarnished truth, unlike less talented artists who prefer to be lied to. Grede agreed, stating, "I think the best people always want the truth".
Regarding entrepreneurship, Stoute drew a stark distinction between those who should pursue it and those who should not. He warned that most entrepreneurs fail and are "fucked up," citing Uber’s founder Travis Kalanick failing and being back at his mom’s house at 33. Stoute advises against the path unless you have a dream in your head that you "can’t get out of your head". Furthermore, he critiqued the concept of "work life balance" for early-stage entrepreneurs, noting that it is a luxury few can afford. Grede also emphasized that if you want to be a founder or truly ambitious, the idea that you can decouple "extraordinary effort and extraordinary results is farcical".
Grede concluded the discussion by acknowledging that Stoute's companies, such as United Masters and Carol’s Daughter (the first African American beauty brand in Sephora), were built to "put a dent" in the world. Grede is the co-founder of Skims and Good American. Stoute praised her work, stating, "You guys are killing it," and listed Skims as a company that is currently killing it at the intersection of business and culture. He stated that his primary motivation is leaving a legacy defined by cultural impact, acknowledging the time taken away from his family.
