Story & Lesson Highlights with Dametri Jackson of Kansas City

We recently had the chance to connect with Dametri Jackson and have shared our conversation below.

Dametri, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What is something outside of work that is bringing you joy lately?
My children’s creativity. My daughter designing phone cases to my son drawing and preparing his own comic book

Can you briefly introduce yourself and share what makes you or your brand unique?
Hello! I’m Dametri Jackson (some of you might remember me as Disfunny Guy Robert Jackson). I’m a comedian, actor, and content creator based in Kansas City, MO. My work lives in characters, sketches, and small moments where real life and absurdity collide.

You’ll find me playing characters like Lil RORO, Roman Green, and Mr. Shrugs, each with their own voice, their own energy, and their own take on what we all feel but don’t always say:

I started making content with nothing more than a phone, ideas I couldn’t shake, and a willingness to look silly. Over time, I turned that into a brand around authenticity, humor, and characters that walk that fine line between caricature and truth. What makes my work special is that I don’t just play roles, I channel parts of real life, break them, and rebuild them into something people laugh with and sometimes at themselves.

Right now, I’m developing a mini-series based on my experiences of working in the corporate world.

At its core, I create because I want people to laugh and feel seen. If someone watches one of my videos and thinks, “That’s me,” or “I never saw it like that before,”* then I’m winning.

Great, so let’s dive into your journey a bit more. What breaks the bonds between people—and what restores them?
I think what breaks the bonds between people is pride and not listening. Everybody wants to be heard, but not enough people want to understand. Sometimes it’s not even about being right, it’s about not wanting to look wrong. That ego can mess up good connections.

What restores those bonds is humility, humor, and honesty. When you can admit you’re wrong, laugh at yourself, and speak from love instead of anger, things start to heal. I’ve learned that laughter can break walls faster than arguments ever could. Sometimes you just gotta take a Lil RoRo approach and when things are going haywire and no one wants to listen, give them a ‘Mannnn…come on cuhhhh!!” Then let it go.

Was there ever a time you almost gave up?
Yeah, there was definitely a time I almost gave up. I think it’s easy for anybody. Life gets busy, depression and anxiety creep in, and you start wondering if what you’re doing even matters. For me, it happened when I got too focused on the numbers, the views, the followers, the likes. I lost sight of why I started creating in the first place and was just cranking out content instead of being genuine. When the results didn’t match the effort, it got heavy, and I wanted to walk away.

But what kept me going was remembering my “why” and surrounding myself with people who encourage me. It’s important to have folks who remind you to get back up, but it’s also about reminding yourself that what you create is bigger than numbers. Once I got back to being authentic and having fun with my characters, the passion came back. That’s what keeps me moving now.

Next, maybe we can discuss some of your foundational philosophies and views? What are the biggest lies your industry tells itself?
One of the biggest lies the industry tells itself is that you have to “go viral” to matter. People act as if your video doesn’t hit a million views, you failed when really, the goal should be connection, not clout. I’ve learned that one genuine laugh or message from someone who says, “Man, that made my day,” means more than ten thousand empty likes.

Another lie is that you have to fit a certain look, sound, or trend to succeed. Nah. What makes people stand out is what makes them *different.* When you start chasing formulas, you lose the soul of it. I think creators forget that the most powerful thing you can be is *yourself* even if that means being weird, awkward, or random sometimes.

At the end of the day, I don’t want to be a trend; I want to be timeless.

Okay, so before we go, let’s tackle one more area. Are you doing what you were born to do—or what you were told to do?
I’m definitely doing what I was born to do. For a long time, like a lot of people, I tried to fit into what I thought I was *supposed* to do, what was “safe” or what other people expected. But the more I tried to live like that, the more I felt like a stranger to myself.

Creating characters, making people laugh, telling stories, that’s always been natural for me. It’s how I connect with people, how I heal, and how I help others heal. Nobody told me to be Lil RORO, Roman Green, or Mr. Shrugs; those are just parts of me that found a voice.

So yeah, I’m doing what I was born to do. It’s not always easy, but it feels right. And when you’re in that lane, even when it’s hard, you feel alive.

Contact Info:

• Website: https://dametrijacksonentertainment.com/
• Instagram: https://www.instagram.com/dametridfg/
• Facebook: https://www.facebook.com/DisFunnyGuy/
• Youtube: https://www.youtube.com/user/DametriezH
• Other: https://www.tiktok.com/@dametridfg