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Wale Opens Up to Rich Kleiman About the Journey From DC to Hip-Hop Stardom

In the latest Boardroom Talks, Wale reflects on his Blog Era rise, industry battles, and 15-year evolution while discussing his new album, everything is a lot.

It doesn’t happen often, but once in a while, the stars align and a group of talented folks emerges together to change the course of an industry. Think about the 1996 or 2003 NBA Draft classes that remade the league with infusions of talent. The last time that happened in rap was 2009, when a kid from Toronto, a kid from Cleveland, a kid from Fayetteville, North Carolina, a kid from Compton, a kid from Detroit, and a kid from D.C. all started popping at the same time. That moment in time is now called the Blog Era, due to the way music was discovered and shared in the early 2000s, but the true markers were the six aforementioned artists who signed major label deals and went on to help transform the game in their image. Olubowale Victor Akintimehin, better known as Wale, was one of those rappers. 

“I wish we were all still cool,” he says in the main room of Crane Club, an upscale eatery on the west side of NYC. He’s here to talk about his new album, everything is a lot, with his former manager, Rich Kleiman, and Boardroom’s head of content, Damien Scott, in the latest episode of Boardroom Talks.

But due to the history Wale and Rich share, the conversation goes in a few unexpected places. The two reminisce about their come-ups, Rich as a manager in music, and then sports, Wale as a burgeoning talent coming out of D.C. Wale talks about the hardships he encountered when he decided to sign with Interscope for $1.3 million after an intense multi-label bidding war, how he decided to then sign with Rick Ross’s Maybach Music Group label, and how he thinks his label drama impacted his career. He talks about his friendship and relationships with the other Blog Era rappers. And strung through all of it are lessons Wale believes he had to learn the hard way through his 15-plus-year career.

And what a career it’s been. Two consecutive No. 1 albums on the Billboard Hot 200. Four gold-certified albums. Five platinum singles and one Diamond record. All-in-all, it’s been a pretty phenomenal run for the D.C. native who broke onto the scene with the regional hit “Nike Boots” in 2008. His obsession with basketball sneakers has come full circle as he’s finally working with Nike in an official capacity, having launched a spot in the lead-up to the release of his latest album in November.

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But if you’ve followed Wale’s career, that shouldn’t be a surprise. This is the same guy who went from making a “Seinfeld”-inspired mixtape to getting Jerry himself to host an album. Wale’s ability to bend and pull culture to his will has been a defining trait over the past decade and a half. 

Now, he’s back with what he believes is his best album yet. everything is a lot finds Wale touching on his doubts, dreams, and fears while still making time for his signature singles that sound just as good on the radio as they do in a lounge at 2 AM. In the lead-up to the album, Wale sat down with Boardroom to not only talk about the new project but to give fans a look at how he views his successes and failures. It’s funny, heartening, and real. Or, as Wale would say, it’s a lot.

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Boardroom Staff