Meet Jai Winter

 

We’re excited to introduce you to the always interesting and insightful Jai Winter. We hope you’ll enjoy our conversation with Jai below.

Jai, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

I had to learn over the years that there is nothing in this life that can make me feel less of myself unless I allow it to. God created everyone in his own image, so who am I to dislike any part of me that he crafted? As a kid I was bullied so much because of my height and appearance. I was super short for my age and bald in my youth years. People would tease and call me “Little Bill” everyday of my life. Looking back on it, I definitely did look like little bill, but I learned to embrace it. Over the years I learned to love myself and the unique things about me. People are so quick to call out your flaws but the truth is, your flaws are the most amazing part about you. Your flaws are what set you apart from so many people. That’s something you should embrace and cherish dearly.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I am a musical artist that specializes in the genre of hip-hop. With influences like Kendrick Lamar and the late Nipsey Hussle, I’ve crafted my sound around the West Coast hip-hop scene, blending both melodic and conscious rap. What’s most exciting about being an artist is being able to reach and interact with so many people who enjoy the work I put out. I craft my music in a way that it resonates with each listener regardless of what they may be going through. There are so many people out here going through different seasons in their life and the music has been guiding them through it. Aside from the music, I offer mental health checks every month just to check up on everyone and see where their heads are at and what’s new in their lives. Being able to talk to so many people about their problems or just some goals they’ve achieved recently feels good because a lot of people don’t have anyone in their circle to share that information with. For my listeners, I’ve become the outlet that so many of them have been needing so they have someone to go to when they need to pour out what’s on their mind.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

I had to be self-dependent, open to constructive criticism, and had to be open to learning the roles of a team so I could fulfill roles that weren’t filled. In the beginning of the journey you’re all alone. There’s no one believing in your craft or dream except you. You have to be willing to rely on yourself and learn all that you can as you build your foundation. When I started out I researched the equipment and programs needed to record music. I researched what all an artist manager does so I could manage myself. I researched marketing tactics for music so I could market and promote my work in ways that would work for me so I could reach a wider audience. You have to put yourself in a position to where you fill and operate every role yourself until you’ve found solid people to take on that role for you. My first manager managed 3 of us at once. One artist stopped making music and focused on podcasts, the other artist was already performing at local shows in his city. One day she just stopped responding and focused on the artist already performing, who eventually stopped making music as well. I took everything I learned from her in the small time we worked together and applied it to my work flow so I could continue to manage myself. I learned I couldn’t rely on someone else to help guide my career if we didn’t have the same focus and goals. Don’t let that be you.

To close, maybe we can chat about your parents and what they did that was particularly impactful for you?

My mother and only my mother helped me find the necessary equipment to start out with music. She’s been there since the beginning to keep it real with me. She’d be the first to tell me that most of the songs I made were terrible because I narrowed my audience to people my age when I should be making music that can affect every generation. I was focused on trying to be the next one hit wonder on TikTok until she broke it down to me and said I should be making music we can listen to 10 years from now that people all over will call a classic. That alone made me change my entire brand and the trajectory of my music.

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