Club Shay Shay – Hitmaka Part 1 (Feb 11, 2026)

Host: Shannon Sharpe
Guest: Hitmaka (also known as Yung Berg)
Podcast: iHeartPodcasts and Shay Shay Media

Episode Overview

Part one of Shannon Sharpe’s Club Shay Shay interview with super producer and songwriter Hitmaka (formerly known as Yung Berg) dives deep into Hitmaka’s journey from Chicago to international stardom, his complicated family background, gritty industry insights, working relationships with legendary artists, and the real pressures and pitfalls of fame, money, and love. The conversation is candid, raw, often humorous, and peppered with hard-won wisdom.

Key Discussion Points and Insights

Early Success and the Importance of the Journey

• Hitmaka's reaction to his accolades:
  • “I'd be like, ‘Damn, I sold 250 million records.’ … But man, just the journey, man. I think that a lot of people skip over the journey and don't really appreciate the journey. … Look at me now, all them accolades. I ain't got no kids, no wife, no nothing. So shit, it's time to figure it out.” (03:28)
• Longevity’s Key:
  • “The work. Like, I love to work, bro. … I'm just so dead focused on the work.” (05:27)

Chicago Roots, Environment, and the Music Hustle

• Impact of Chicago:
  • “I think it's because like the environment, you know what I'm saying? It kind of builds you to be tough.”
  • "When I was coming out, it was literally Common, Twista, Do or Die, Psychodrama, Crucial Conflict, and Kanye. … So, you didn’t have an opportunity [like New York or LA]." (04:18–05:17)
• On authenticity and playing “the game”:
  • “I be searching for authenticity. But at the same token, it's the music business, so you gotta kinda play the game. But I don't play the game like that.” (05:54)

Navigating Industry Relationships and Betrayal

• Addressing music industry’s transactional nature:
  • “They supposed to use me though, right? Because I provide a service. But when you useless and you can't be used, then they ain't gonna fuck with you no more.” (06:45–07:07)
• Memorable guest quote:
  • Shannon Sharpe, referencing advice from T-Pain:
    • “Ain’t nobody in this business your brother. They your brother as long as they can use you or you got something they want.” (06:12)

Chicago’s “Crab-in-a-Barrel” Mentality & Reality Rap

• Jealousy and street dynamics:
  • “It's crabs in a barrel mentality, my brother. … It's such a clout driven era right now, like a person would rather come and do some harm to you and be famous for doing harm to you than actually express that they truly like you and they fans of you.” (08:30)
  • “People like to see famous people not doing good so they can feel better about where their life going on. …” (09:16)

Experiences with King Von, Lil Durk, and Chicago’s Scene

• On collaborating with King Von:
  • “Von has such a good spirit. … When I work with him … I'll present a beat with a hook already on it to make the job easier for them.” (10:56–11:34)
  • “When I got with Von and he took those records … he like, ‘damn, gang, I'm really supposed to re-say what you said?’ I'm like, ‘Yes, but put your own spin on it.’” (12:00)
• Reality rap’s double edge:
  • “Von is in the era of reality rap. So their thing was to go do shit in the streets and go tell real street stories… and it was just right there. … That's why people fucked with him so much.” (12:45)
• Chicago’s lack of mentorship:
  • "They ain't had no OGs. … They could beat up the OG, like that's the type of time they was on." (17:59)
  • “A wise man learns from others’ mistakes. A fool learns from his own. But you know what my grandma used to say, boy, sometimes you have to bump your own head to realize how much it hurts.” — Shannon Sharpe (18:13)

Upbringing: From Suburbs to the Streets & Family Struggles

• Privileged beginnings & rebellion:
  • “My dad’s 76 ... own like 15 three flat apartment buildings in Chicago. … [But] I was the dumb n**** in school that could have had a Range Rover at 16, but I wanted to go sell crack in the middle of the hood ...” (13:53–14:30)
• Parental divorce and acting out:
  • “My life is really like a movie ... my parents ... normal shit. They get a divorce ... As me being a young kid ... I moved in with my father... But now we in the city now, no more suburbs. So now I'm close to the bullshit.” (32:14–32:47)
• Experience at abusive boarding school (Thompson Falls, Montana):
  • “...it's just a sick, sick place bro. … They up there raping, they up there doing all type of shit...” (61:12, 61:59)

Relationships, Love, and the Price of Fame

• Skepticism about marriage and trusting women:
  • “Well, I don't trust women at all." (41:47)
  • "I'm damaged goods, Shannon.” (42:00)
• Wealth & relationships:
  • “Yeah. ‘Cause I got money.” (44:50)
  • “You see these young girls ... saying that they don't want a man that don't make over a million dollars a year ... they talking about 5 years, 20 years old.” (45:34)
• On men and women’s motivations:
  • “Men want to accumulate money to take care of others. Women want to accumulate money to become independent.” — Shannon Sharpe (47:32)
• Holiday loneliness and fame:
  • "You know, my most depressing part of my life is the holidays when everything shut down... you wanna cry, you sitting there drinking eggnog, crying and shit, you know what I'm saying? But January 1st hit, New Year's Eve. They back outside, we back outside, we back to work.” (48:24)

Authenticity vs. Image in Rap

• On “living” rap lyrics:
  • "If I'm trying to appease to all these different rappers... the goal at that time was to get signed by… Rough Riders…. I was Pablo Escobar in my raps at 13... I had guns and Mickey Mouse, you know what I'm saying? I'm shooting at Mickey Mouse." (52:14–52:47)
• Vivid storytelling of lost innocence:
  • "[I] lost my virginity to two prostitutes... They sent them in there, and they had they way with me." (56:10)
  • "I started off with smoking, drinking. I think I was drinking and smoking by 11... I took my first ecstasy pill at 13." (57:03)

Signing to DMX as a Teenager & Brush with Fame

• The story of meeting DMX:
  • "He opened up his hand, he had a bunch of weed in it, you know what I'm saying?... I do another one for him, and the whole trailer go crazy. Aaliyah in the trailer… Now he playing my demo out his trailer, blasting my shit.... 'Shorty, I'mma sign you. Not gonna be fast, but I'ma sign you.'" (62:21–64:58)
• Regretful youth and missing out on mentorship:
  • “I wouldn't have let that gun go off in that house ... And deeper than that, I would have just understood what [DMX] was going through.” (65:02)
• DMX anecdotes:
  • “I'll never forget, we in Toronto...he lay on the ground like a dog and start crying like a dog. And he fell asleep on the concrete...for four hours. You can't wake the dog while he sleep.” (68:14–69:19)

Transition to LA, Writing for Eve, and Early Placements

• Being mentored and run-ins with Eve:
  • “I became Shawna Hype Man. I went around the country with her...I ended up meeting Troy Carter and Jay Irving...They moved me to LA...I used to sleep in [Eve’s] dressing room...at the UPN lot.” (71:34–72:43)
• On writing for Eve’s album:
  • “Her last album ... was called Evolution. I end up writing her the title track ... That was like my first real writing placement in the game.” (73:08)

The Birth of "Sexy Can I" and Ray J Stories

• Industry pressure and skepticism:
  • "Charlie Walk, head of Epic...he like, it's gonna be the biggest song of your career...I'm like, ‘Buy me a chain, man.’ ... [I did] the song in Miami at the same studio that I work out of right now." (77:03–77:23)
• Recording session mayhem:
  • “Ray J … he in there. He got a gun on the table...He want porn, he put on vivid DVDs...We finishing the song ... He like, ‘Can I just have some fun?’” (78:51–79:25)
• Arrest on Music Video Set & Shaq’s Rescue:
  • “Police come. ... Put me in jail in Dade County.... Next thing I know, probably like six hours later ... who bailed me out of jail? Shaquille O’Neal!” (79:54–80:49)
• Whitney Houston anecdote:
  • “Ray like, Whitney coming to Compound with us tonight. We gotta show at Compound. ... I'm drinking out the patron. Two hand drinking out the bottle like this, chain smoking cigarettes together, talking shit.... She went in there and she supported us while we was in there on stage.” (84:00–85:23)

Family, Finances, and Industry Advice

• On trusting family as business partners:
  • “… My dad been my business manager my whole time, my career. ... That's one thing I could tell people, man. Like, that was just so beautiful for me. … Who you do have a baby with, who watch them finances.” (100:38–101:02)
• On love, breakups, and money:
  • “I never understood the dynamic to where ... You don't want to be with me and you want to take from me in the process.” (102:07)

Getting Robbed & Industry Dangers

• The chain snatching incident:
  • “I got the number one record on radio. ... This big transformer chain ... I feel the energy shift. … Club security ended up just having their way with us. ... And then from there, like, that was kinda like... That kinda put a pause to kinda my rapping career.” (102:51–105:41)
• Advice for young rappers:
  • “People want what you got; like, you a fucking target. ... You gotta be ... on defense everywhere I go.” (107:58–109:02)
• On PNB Rock’s tragic death:
  • “He lost his life by not trying to give it up. Get that shit up ... The only thing that can't be replaced is life.” (109:57–110:04)

Notable Quotes and Moments

| Timestamp | Speaker | Quote / Moment | |-----------|---------|----------------| | 03:28 | Hitmaka | "Just the journey, man. I think that a lot of people skip over the journey and don't really appreciate the journey…" | 06:12 | Shannon Sharpe (via T-Pain) | “Ain’t nobody in this business your brother. They your brother as long as they can use you or you got something they want.” | 08:30 | Hitmaka | “It's crabs in a barrel mentality, my brother. … It's such a clout driven era right now...” | 13:53 | Hitmaka | "My dad's 76 ... own like 15 three flat apartment buildings in Chicago… But I was ... could have had a Range Rover at 16, but I wanted to go sell crack in the middle of the hood..." | 44:50 | Hitmaka | “Yeah. ‘Cause I got money.” | 47:32 | Shannon Sharpe | "Men want to accumulate money to take care of others. Women want to accumulate money to become independent." | 56:10 | Hitmaka | “I lost my virginity to two prostitutes… they sent them in there and they had they way with me.” | 62:21 | Hitmaka | “He opened up his hand, he had a bunch of weed in it… [DMX says] ‘Shorty, I'mma sign you. Not gonna be fast, but I'm assign you.’” | 69:09 | Hitmaka | "Don't nobody wake the dog while he sleep. ... He's laying in the middle of the street. Police with us. … That's how big he was." | 79:54 | Hitmaka | “Police come... put me in jail in Dade County… who bailed me out of jail? Shaquille O’Neal!” | 85:02 | Hitmaka | "Me and Whitney [Houston] drinking out the patron. Two hand drinking out the bottle like this, chain smoking cigarettes together, talking shit." | 109:57 | Hitmaka | “He lost his life by not trying to give it up. Get that shit up ... The only thing that can't be replaced is life.”

Timestamps for Core Segments

| Segment | Timestamp | |---------|-----------| | Shannon introduces Hitmaka | 02:39 | Accolades, success, and the journey | 03:19–04:13 | | Chicago’s unique musical climate | 04:18–05:24 | | Longevity, authenticity, industry relationship insights | 05:27–07:07 | | Chicago’s street dynamics, reality rap, King Von & Lil Durk | 07:35–16:28 | | Upbringing: family, privilege, and rebellion | 31:04–41:47 | | Boarding school trauma | 38:38–61:59 | | DMX signing story, working with icons | 62:21–68:14 | | Eve, LA beginnings, industry grind | 71:34–73:31 | | "Sexy Can I" story, Ray J, Shaq, Whitney Houston | 75:42–85:24 | | Love, women, and money | 41:47–50:21+assorted | | Getting robbed, dangers for rappers, PNB Rock | 102:48–110:44 |

Tone and Style

• Extremely candid, at times raw and confessional; both men show humor, vulnerability, and street wisdom.
• Hitmaka lays out both the harsh and redemptive elements of his journey and the music business, never shying from the darker details or drama.
• Shannon Sharpe blends insight, encouragement, and his signature straight-talking warmth, often sharing advice, analogies, and personal experiences.

Summary for New Listeners

This episode gives listeners an unflinching view into the realities of the rap industry, the destructive and redemptive forces of upbringing and fame, and the personal cost of success. Hitmaka’s stories—his privileged yet troubled home, his street and industry struggles and triumphs, raw stories from studio and street, and wisdom about money, relationships, and hustling—make for a powerful, memorable listen. This is not just a music industry interview; it’s a frank discussion on what drives, wounds, and shapes a hip hop star and how survival often means being wise, adaptable, and always on guard.