Giffy Pluggo of Southside on Life, Lessons & Legacy

Giffy Pluggo shared their story and experiences with us recently and you can find our conversation below.

Giffy , it’s always a pleasure to learn from you and your journey. Let’s start with a bit of a warmup: What are you most proud of building — that nobody sees?
My confidence. For years, I was apprehensive about putting music out publicly but doing this has made me more confident in my abilities and has made me more willing to try other things I’ve never done.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Giffy Pluggo — an artist, storyteller, and visionary from Chicago blending real-life grit with luxury ambition. My music reflects duality — the grind of survival and the mindset of elevation. I built my name on authenticity and lyricism, connecting street realism with introspective growth. Beyond music, I’m an educational leader and consultant helping others transform their narratives and communities. What makes my brand unique is the balance — I move like a CEO but speak like an artist who’s lived it. My last project had a song produced by the legendary Scott Storch. That song/project was called “Luxury Manifesto”.Right now, I’m releasing my new single “Mortgage” featuring The Game and finishing my project Douda Deluxe, a reflection of what it means to earn peace and power after pain.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What did you believe about yourself as a child that you no longer believe?
As a child, I believed I had to blend in to survive — that my dreams had to fit inside what other people could understand. I grew up thinking success meant stability, not expression. But over time, I learned that my voice and vision were my real security. The things that made me stand out — my creativity, my leadership, my storytelling — were never weaknesses; they were the foundation of my purpose. Now I move with the understanding that standing out is the assignment.

Was there ever a time you almost gave up?
Yeah, there was definitely a time I almost gave up. I was pouring energy into both my career and my music, but it felt like nothing was breaking through. The industry politics, the personal stress — all of it had me questioning if the vision was worth the grind. But sometimes the breakdown is just the setup for the alignment. That’s when I started reshaping everything — my sound, my focus, my energy — and that rebirth became the foundation for Douda Deluxe and my new single Mortgage.

Those projects aren’t just music, they’re proof that pressure can polish you. Mortgage especially is personal — it’s about ownership, resilience, and turning pain into property, both mentally and spiritually. I realized I wasn’t chasing attention anymore — I was building equity in my purpose. Once that clicked, I knew giving up was never an option.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Is the public version of you the real you?
The public version of me is real — but it’s not the whole story. What people see is the polished reflection, not the process. The real me exists somewhere between the music, the silence, and the moves I don’t post. I give the world enough to feel me, but never enough to figure me out.

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. If you knew you had 10 years left, what would you stop doing immediately?
If I knew I had ten years left, I’d stop shrinking to make other people comfortable. I’d stop second-guessing divine timing and treating my purpose like it’s optional. I’d move with full conviction — speak the truth louder, love harder, and build without hesitation. Legacy isn’t about how long you live, it’s about what still moves when you’re gone. If the clock was ticking, I’d make sure every bar, every word, and every move echoed beyond my time here.

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