Life, Values & Legacy: Our Chat with D-Win of Downtown

D-Win shared their story and experiences with us recently and you can find our conversation below.

D-Win, it’s always a pleasure to learn from you and your journey. Let’s start with a bit of a warmup: When was the last time you felt true joy?
The last time I felt true joy was when I went back home to Indianapolis to be with my family. Living across the country while chasing my dreams can feel isolating at times, but being surrounded by the people who know me best always fills me with a sense of peace and gratitude. No matter how far I go, being with my loved ones reminds me of where I come from and keeps me grounded.

Can you briefly introduce yourself and share what makes you or your brand unique?
Hello, my name is D-Win. I was born and raised in Indianapolis, Indiana, and my journey has taken me from the Midwest to Chicago and now Los Angeles. I’m both a rapper and a fashion designer—running my record label, Winfield Sound, and my clothing brand, Winfield. At the heart of it all, I’m just a kid from the Midwest chasing big dreams on the West Coast, determined to build a lasting legacy for my family.

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 was your earliest memory of feeling powerful?
My earliest memory of feeling powerful was when I moved to Chicago for college. I came in with the dream of becoming a rap artist, and by the time I left in 2019, I had accomplished everything I set out to do. During that time, I learned the essentials of life—discipline, focus, and resilience and how to apply them to get closer to my goals. The real power came from creating a new version of myself, the version I had always envisioned but hadn’t yet lived out.

If you could say one kind thing to your younger self, what would it be?
If I could say one kind thing to my younger self, I would tell him to stay down, stay patient, and keep dreaming big. The struggles, the setbacks, and the moments of doubt are all part of the process that shapes you into who you’re meant to be. Don’t rush the journey trust it. Every small step you take is bringing you closer to the life you’ve always imagined. Keep God first and nothing is the world can compare to living a christian life.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What are the biggest lies your industry tells itself?
One of the biggest lies the industry tells itself is that success happens overnight. People see the highlights viral moments, big shows, designer collaborations but they don’t see the years of grinding, failing, and rebuilding that go into it. Another lie is that you have to follow a certain formula or compromise your authenticity to “make it.” The truth is, the artists and brands that last are the ones who stay true to themselves, even when the path is slower. Longevity comes from patience, consistency, and vision not shortcuts.

Okay, we’ve made it essentially to the end. One last question before you go. If you knew you had 10 years left, what would you stop doing immediately?
If I knew I only had 10 years left, I would have never stepped away from the church. Faith has always been the foundation of who I am, and whenever I drifted from it, I felt the difference in my spirit and my direction. I’d make sure every day counted by staying rooted in God, because at the end of the day, that’s what gives life meaning and keeps everything else in perspective.

Contact Info:

• Website: https://www.winfld.com
• Instagram: https://www.instagram.com/dalwayswins/