Kelly Eileen Interview | Respect the Dreamer
Kelly Eileen is a model and podcast host from Staten Island, New York, who is passionate about bringing her own brand of creativity to the world. She is the host of the Spilling Wine Podcast, where she discusses relationships, music, mental health, and other topics. With over 150,000 followers on TikTok and Instagram, she has built a strong online presence, using her platforms to not only spread positivity but to create a space for honest, open discussions. Whether she’s sharing hilarious storytimes, interviewing music artists, or addressing real-life struggles, Kelly’s content resonates with people from all walks of life.
What inspired you to pursue your dream, and how did it all begin?
When I was 2 years old, my older sister, Christi Boland, who was a film student in college, included me in her film projects and encouraged me to start speaking in front of the camera. It always felt natural to me. At age 8, my parents introduced me to modeling, and that’s where I began to explore other film projects. At age 12, my mother, Denise Boland, suggested that my twin sister, Valerie Boland, and I create our own web show on her laptop. We started a YouTube channel, and that’s when I discovered my love for content creation. Around that time, I started working with Kenneth Paul Graham at Hub17, where my career started to progress further. During the coronavirus pandemic in 2020, my videos went viral on TikTok, giving me a larger platform as a social media influencer. Today, I’m the host of the Spilling Wine Podcast and was featured on my first magazine cover in December 2024.
Can you share a defining moment in your journey that shaped your perspective and fueled your passion?
Growing up, I faced intense bullying and struggled deeply with my mental health, often feeling isolated and misunderstood. I didn’t let that stop me from doing what I loved, which was creating content. Content creation and modeling became more than just hobbies; they were my outlets, my therapy, and my voice. Through the lens and in front of the camera, I began to find strength in vulnerability and power in authenticity. My passion not only helped me heal, but it also gave me a purpose to inspire others.
How do you handle setbacks and keep pushing forward in the pursuit of your dreams?
The best way for me to handle setbacks is to remember why I started pursuing my dreams in the first place. I make sure to remind myself that setbacks are a part of the journey. I have a tattoo that says “no rain, no flowers” to represent my belief that in order to achieve greatness, you must embrace the struggles along the way.
Are there specific individuals who have inspired you along the journey?
My biggest inspiration throughout my journey has been my mother, Denise Boland. As I was growing up, I watched her passionately pursue her dreams as an actress and the host of Remember This with Denise Boland. Her endless support and encouragement have guided me on my own creative path. She’s not only been an incredible role model but also the person who’s taught me everything I know. I also couldn’t have done anything without Kenneth Graham, my photographer and studio manager, who has given me all the resources needed for success. He has believed in my potential since the start of my career, and I owe it all to him.
How do you maintain a balance between pursuing your dreams and handling everyday responsibilities?
I have always been admired for my hustler mindset. Since I was 19, I've juggled multiple jobs as a student, determined to succeed no matter the cost. I've attended both makeup school and college while working in retail and hospitality. Despite working 16-hour days, I made time to create content and build my brand on social media, all while sacrificing sleep and my social life. Thankfully, my hard work has paid off, and now I work as a social media manager and influencer.
How do you overcome self-doubt and stay confident in your abilities?
There have been many moments in my journey where I felt like giving up when the weight of it all made me question if it's even worth it. In those dark times, I fight through the self-doubt by reminding myself of how far I’ve come and how proud my younger self would be. I think about all the sacrifices I’ve made—the friends I’ve lost, the relationships that didn’t work out because of social media, and the times I’ve lost sight of who I even was. When I feel like giving up, a voice inside of me whispers, “You’ve come too far to stop now.” This is more than just a journey; it's the path that God has set for me, and I won’t allow myself to turn away from it.
Can you share a memorable success story or achievement that resulted from your determination?
As a young petite model, I was often told that I was too short to be able to walk in a runway show. One day, I randomly applied to compete in a Miss New York Teen USA pageant and ended up getting selected. After competing in Miss New York Teen USA 2020, I got scouted by a designer who asked me to walk in their show at New York Fashion Week a month later. That moment showed me that I can do anything I set my mind to.
In what ways do you stay motivated during challenging times?
My true passion for my craft allows me to stay motivated even when it is difficult. I've come to realize that it is a privilege to be able to do what I love as a content creator, and I try not to take it for granted. I remind myself that I am on this path for a reason, and it is necessary to take breaks when needed.
What dream are you living right now?
I’m currently pursuing a career in social media, something I once thought was out of reach. As the host of the Spilling Wine Podcast, my life has transformed in ways I could have never imagined. Hosting the podcast has helped me overcome my social anxiety, gain confidence in myself, and provided a platform for me to share my journey with my listeners. It has also taught me valuable business skills and opened up countless opportunities to showcase my talents and network with amazing people.
What advice would you give to someone with a dream?
There is no time limit for success, and everyone’s journey is unique to them. The road to success is long and rocky, but it is important not to lose yourself worrying about the destination. Appreciate everything along the way, have fun with everything you’re doing, and you’ll be at your destination before you know it. Every step is a lesson to be learned, and the only person that could hold you back is yourself.
Photography credit
Kenneth Paul Graham
Website
linktr.ee/spillingwine
Instagram
instagram.com/kellyislit
TikTok
tiktok.com/@kellyislitt
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