Questlove and Phonte have each enjoyed tremendous success in their careers, both of them emanating from the worlds of underground Hip-Hop to mainstream success. The former is a multiple Grammy-winning cultural icon and Tonight Show bandleader, while the latter is a Grammy nominee who has managed to earn critical acclaim as an MC, a singer, record-label executive, producer, and arranger. Like most successful artists in the entertainment industry, Quest and Tigallo have both dealt with attraction to fame and fortune, as well as the plentiful obstacles (both literal and mental) littering the path to success. But together with an industry veteran, the two shared the blueprint for keeping one’s eye on the prize, in the latest episode of Questlove Supreme on Pandora.

Shep Gordon, whom Questlove calls “the guru of all gurus,” has been managing artists since the 1960s. With a client list that includes Teddy Pendergrass, Luther Vandross, Blondie, and Alice Cooper, Gordon served alongside Phonte as a special guest on Questlove’s new internet-radio program, and the three spent two hours engaging in conversation. Some of the most insightful discussion revolved around the concept of fame and vice, and the correlation between success and great pain. The topic was introduced indirectly by Phonte, after Gordon began describing Alice Cooper as a deeply devout man of faith, an image of the Rock & Roll Hall of Famer that most would find surprising. Phonte, in expressing his admiration of Cooper for being able to remain true to himself despite working so hard at creating an entirely different persona for the world, caused Gordon to rebuff that observation. In fact, Gordon says, Cooper was not able to effectively juggle his private and public identities, eventually becoming an alcoholic and checking into rehab. Similar things, Gordon says, happened to Jimi Hendrix and Jim Morrison. “There always was a link between fame and using crutches that really hurt you,” he says.

When asked by Questlove to explain why Gordon thinks that is, he responds by saying “I think in the live-entertainer world, the rejection is so gigantic to get to a place of success. It’s so overwhelming that if your goal is to just make a living but have a career, you can’t take all that rejection. So normally it’s to fill some hole in you. You think that applause is gonna fill some hole in you, and it doesn’t. And you just get angrier and start using crutches. Most people who hit that level of fame, especially if they’ve done it as entertainers, have to deal with that moment where they’re not being fulfilled. It’s a very few of the number-oners that I’ve come across who don’t need an adjustment somewhere along the way, who don’t fall to something.”

Something in Gordon’s statement clearly resonated with Quest, who goes on to share his own personal story of working with his late manager Richard Nichols, whose style of management wasn’t appreciated by all in his circle. “Everyone around me was like ‘he’s so negative, why do you embrace all that negativity?’ My mom had problems with him and everything. But what I realized he was doing by the first year was he was just preparing [The Roots] to not have any expectations… Richard was like ‘I’m not preparing you for stardom. I want you to have a long-term career, so I’d rather you guys, you know, live better than the average Jazz musician.’ Because we were in Hip-Hop,  you instantly think of this, like, ticker-tape parade, or what Rich called the ‘Bentley moment’…he just wanted for us to sort of just get rid of that expectation. He would always say ‘lower your expectation.’ And maybe the first year we started taking it personal and pointing fingers at each other,” shares Questlove.

He goes on to admit that, all of these years later, he is thankful for Nichols’ stern guidance, saying that it helped Black Thought (born Tariq Trotter) and him maintain focus on what was really important. “I will say that protecting ourselves helped us, helped me and Tariq in the long run. I mean, some of us sorta fell by the wayside and kinda succumbed to different vices and whatnot. But, at least for Tariq and I, it kinda helped us. But then again, like 20 years later, I don’t know it’s made us immune to emotional feelings.” That last thought spurred Phonte to ask Quest “so when you say that, you mean like you don’t feel the good stuff either?” It’s then that Questlove shares one of the most powerful pieces of his own shortcomings as an artist who has reached a tremendous level of fame.

“Well, yeah. I don’t feel anything,” he responds. “And, like, it’s to the point where it’s just ‘oh my god Stevie Wonder’s on my show!’ Yeah, it’s cool. That’s the thing, like, I had to numb myself so much to keep myself from forming a drug habit or suicide, or whatever vices artists get into. Now, as a 40-plus-year-old man, like, now I’m trying to get emotions back.” People with drug addiction can also check out iop south jersey as they help people to maintain a healthy lifestyle.

Gordon offers a fascinatingly different perspective, saying “from completely the other side, I’ve come to the same place. People ask me if there’s anything I regret, and I say one of the most satisfying nights of my life was Alice getting in the Rock & Roll Hall of Fame. It was 40 years of hard work and really amazing. And I went home and looked in the mirror and said ‘good work,’ and got into bed and watched CNN, 15 minutes after the [ceremony]. I didn’t go to the party. I wish I could’ve shared in the love. And I said to Alice ‘you know, it’s weird, I’ve always been like this. I don’t know why.’ And he said ‘well I was in bed 15 minutes after watching a movie!’ So we come in from the other side, ’cause I managed them exactly the opposite way. I used to sit them in a room, and I would always tell clients ‘if I do my job perfectly, it’s very possible I’ll kill you, because I’ll make you so famous, you’ll kill yourself.’ I would tell them that, and say ‘that’s what I do for a living. It’s the only thing I know how to do. Other guys’ll make you more money. Other guys’ll do a lot of stuff better than me. I know how to make you really famous.'”

Questlove asks if, based on that, it’s better to go for second place, to which Gordon responds that he tells people he loves who are interested in entering the industry to remember that the ultimate goal is to be happy, and if they’re happy now, they should reconsider seeking fame and fortune. “You’re going to have to unwind a lot of stuff if you’re successful,” he says. “I think, for most people, [the goal is] to get happy, be able to buy dinner. And I think most artists work at it so hard and they get to the end of the road where they can be happy, and they forgot how to be happy.'”

To his point, Phonte says “yeah, it’s literally the dog chasing it’s own tail,” with Questlove adding “there’s also this insatiable thing going on.” After explaining that every few years, he develops a new end-game goal in mind like winning one Grammy, in an effort to achieve contentment and satisfaction. “It never stops…I don’t believe in happy, I believe in satisfied.” Phonte shares that he can certainly relate to that endless search for contentment, saying “my satisfaction would be when I have enough money in the bank to where I can sit still for at least three years and, like, not do shit. I ain’t gotta go to a show. I ain’t gotta fucking write not a song, I ain’t gotta sing one goddamned note.” Questlove then questions whether three years is enough, or if, when Phonte has actualized that goal, whether he’ll wish it was for ten years instead, calling that need for more “part of human nature.” “My thing was,” Phonte responds, “when I first, first started, before [Little Brother] had signed anything, I was working at the call center making $10 an hour. I remember saying to myself specifically ‘if I just get to a point in my career where I’m making $10 an hour rhyming, doing what I love to do, I’m good.’ And so, I got to that point, and my moment of realization was I got to the point where I was makin’ way more than that. But you still findin’ yourself asking for more, so I had to check myself. Whenever I get depressed or overwhelmed, I remember there was a day I was praying for the things that I have now.”

Shep chimes in at that point, saying “I wake up each morning and physically say thank you for all the gifts that I have.”

Further along in the episode, Gordon shares his insights on knowing so many of the musicians who belong to the “27 Club,” navigating the racism he encountered when representing Black artists in a predominantly White industry, launching women-only shows with Teddy Pendergrass, and a truly engrossing story about Luther Vandross’s experience dealing with great loneliness.

Questlove Supreme premieres each Wednesday on Pandora, at 1pm EST, and airs continuously thereafter for 48 hours. Listen here. Heads can learn more about Gordon’s work by checking out the Mike Myers-directed documentary on him streaming on Netflix, Supermensch: The Legend of Shep Gordon.