Sad Boy Radio

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Sad Boy Radio

A new podcast that discusses everyday problems through the universal language of music. Viewers are
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11/07/2025

Sad Boy Radio CCXI: Chasing Perfection?

Chicago Singer, , slides to to discuss performing the national anthem at “Derrick Rose night,” learning to let go of relationships, chasing perfection & more!

In the song, “Prayers,” Khaliyah sings, “God if you’re hearing me now / I need some answers please / i’m trynna figure this all out / but it’s not working for me / you’re supposed to catch me when I fall.” Khaliyah reflects on a time where it felt like everything was falling apart, and she didn’t understand why it was all happening. Forced to overcome failure, Khaliyah let go of the idea of what she though life “had to be.”

Also discussed: Relationship with Chelsea B, Letting go of relationships that no longer serve her, and former pageant life.

14/02/2025

Sad Boy Radio CXCII: “Everything HAD To Change?“

Chicago rapper, , slides to to discuss working with TVMG, growing up in the streets, surviving 4 four separate shootings, and turning his life around once his daughter was born.

In the song, “Controlling me,” Zippa says, “Where I’m from can’t leave the crib unless that pole on me,” reflecting on the neighborhood that shaped his mentality. Zippa talks about the area with a bittersweet tone; from core memories of Fefes to tragically losing his best friends at 12 years old. Zippa has experienced more pain in life than most; however, he hasn’t allowed it stop him from his purpose. Zippa continues to push forward for those he’s lost along the way & the family he’s created.

Also discussed: Being a product of your environment, expectations we place on our parents, wanting to give daughter everything he didn’t have.

07/02/2025

Sad Boy Radio CXCI: “Living For Me?”

Media Personality, , slides to to discuss her media journey. From hosting “CRU LUV Radio” in Carbondale, to WGCI, Bree has done it all! Additionally, we discuss healing from past relationships, expectations of being an only child, & overcoming periods where it feels like the world is against you.

In the song, “Lonely,” Justin Bieber sings, “What if you had it all / But nobody to call? / Maybe then you’d know me / ‘Cause I’ve had everything / But no one’s listening / And that’s just lonely,” often times as a media personality, the world looks at your life as “perfect.” There’s this expectation to be happy & that nothing in life could be wrong. However, in 2023 Bree’s life took a sudden turn, leaving her to contemplate on if radio was still in her future.

Also discussed: Being a key part of , booking large interviews, infidelity, and the support of her close circle.

24/01/2025

Chicago Artist, , slides to to talk about his latest album, “Moments In Desire,” the impact of his father’s drinking, trauma from witnessing death, learning to love again, and realizing everything he ever desired was peace.

In the song, “God Is Crying,” Cassius says, “Just know I desired fame to feel worthy to be around / and then desire you / which is lust so they love me now / and then desire more / got it all then I finally found / I only desire peace in me & I see it now,” Tae reflects on all the things he’s desired at certain points in time; however, this often stemmed from things he was missing. He searched for fame & love to fill the emptiness he felt from not feeling like enough for those around him. Leading Tae to realize, all of the things he searched for were components of inner-peace.

Also discussed: Modeling in , “Toxic,” video, working with Gold Haze, missing moments he’ll never be able to relive.

17/01/2025

Sad Boy Radio CXC: “Playing By My Rules”

Music Executive, Ashley Nicole, slides to PVTSTCK to discuss her career in music as a manager, A&R, performer & much more! Additionally, we discuss healing long-lasting emotional wounds, finding self-love, and providing support for those who need it.

In the song, “Lost Loverboy,” Demetri Wiley says, “Wondering what it’s like / if the world could know my name / would it be love or a drug / that I’m using to soothe the pain / trying to cope with the fact / that this s**t has made me insane / needing people to love me / is the bump that derailed the train,” reflecting on the need for reassurance from people who, oftentimes, only love you for what you provide for them.

Ash learned early on, that being a performer in the spotlight was solely a chase in a game she didn’t want to play. Ash then pursued artist management where she commanded respect from her music peers, and remained true to her values.

Also discussed: Working Relationships with John Monopoly, RecoeChi, IceHaus Events, King B & more! Push from family to pursue music, and being forced to miss monumental personal moments in pursuit of music career.

10/01/2025

Sad Boy Radio CL###VII: “Lost Loverboy?”

Chicago Artist, , visits to discuss his early love for music, becoming a cultural voice with his “Lost Loverboy,” podcast, the experiences he’s dealt with when searching for love from others & himself, and overcoming the darkest period in his life.

In the song, “Lost Loverboy,” Demetri says, “I think it’s time I finally try find myself / I been running from love / just trynna hide Fromm all this pain I felt.” Demetri often searched for love from others, due to the lack of love he felt for himself. Constantly pouring into others from a cup that was more than half empty. It wasn’t until he was questioning his purpose in life; when he truly searched for the love he needed, and found it from himself.

Also discussed, the importance of becoming a father, a 10+ year love story that left him heartbroken, and learning to let go of relationships that don’t serve him.

03/01/2025

Sad Boy Radio CL###V: “SUEÑOS?”

In 2024, we completed press work at our first music festival for festival. We talked with & , two prominent DJs in Chicago, who consistently promote both Latino Culture & safety for women in the nightlife industry.

During our conversations we talked about , growth throughout both their careers, goals for the future, & maintaining successful relationships while touring & much more!

📸: .jo

31/12/2024

2024: “heartbreak only makes you stronger” or whatever they said. Guess we’ll find out in 2025

The real paragraph coming at the anniversary

S/O to my friends that stayed outside with me every weekend past 3 AM & the people that kept me going when they didn’t even know it.

📸: (slide 4)
📸: .jo (slide 1,2 & 9)

27/12/2024

Sad Boy Radio CL###IV: “UNITED CENTER?”

My team & I completed media work at the to do media for the FIRST time! Covering Tink’s “Winter’s Diary Music Festival.”

We talked with various artists from the event about what to expect from them in 2025, lessons learned from relationships, most memorable moments throughout their careers & MORE!

Artists interviewed: .warren

📸: .jo

26/12/2024

TINK: “Winter’s Diary Music Festival”
CHICAGO, IL (12/20/24)

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