Conversations with Andrew Messam

Today we’d like to introduce you to Andrew Messam.

Hi Andrew, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Absolutely. My story starts with me being a creator before anything else. Music and film were always my first languages — producing, writing, directing, building ideas from scratch. Over time that passion grew into what people now know as DrewStar Productions LLC, the home of everything I do in entertainment.

I built my name in the DMV by being hands-on and versatile. I’ve produced for and worked with artists across the spectrum — from Wale, Shy Glizzy, Fat Trel, WillThaRapper, Simba, Black Fortune, all the way to recently directing a major video with Boosie. I also run my own platforms, where we’ve played 84+ artists on mainstream DMV radio (WPGC 95.5) and conducted 28 live on-air interviews through my “Real Live” platform.

At the same time, I created something that surprised even me — a youth creative arts program called High School Cypher. What started small grew into a movement:
• 1,000+ students, principals, & administrators served
• 80–100 schools across the DC–Maryland–Virginia area
• Partnerships, grants, Fox 5 features, and recognition from state leaders

That program showed me how impactful music and film can be when you use it to inspire and develop the next generation.

Everything I’ve built over the last decade — the artist brand, the production company, the youth program, the radio platforms — created a full ecosystem. Today my work spans youth and adult entertainment, from developing young creatives to producing for established artists to launching my own music and film projects.

Where I’m at now is really the result of consistency, reinvention, and building something that represents the whole me — not just one lane. I’ve been behind the scenes for years helping others win, and now I’m stepping back into the forefront as an artist with a more mature, polished vision. And honestly, I still feel like I’m just getting started.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Not at all — nothing about my journey has been smooth. But every challenge shaped the artist and entrepreneur I am today.

In the beginning, I was doing everything myself. Producing the music, engineering, filming videos, editing, running programs, managing artists, building platforms, handling business, and still trying to grow my own career. It taught me the entire industry hands-on, but it was a heavy load for one person.

Another challenge was balancing my impact in youth programming with my presence in adult entertainment. High School Cypher grew fast — over 1,000 students, 80–100 schools, national attention — and sometimes people tried to put me in a “youth-only” box. Meanwhile, on the other side, I was working with big artists, running radio platforms, producing for DMV talent, directing major videos, and building my own sound. It took time to get people to understand I’m not one-dimensional. I’m involved in every level of entertainment.

There were also moments where the business side almost overshadowed the creative side. Building systems, keeping things funded, learning hard lessons, losing resources, rebuilding teams — it wasn’t pretty, but it forced me to grow up as a CEO, not just a creator.

But honestly, the struggle is where I developed my discipline, consistency, and vision. Every setback pushed me to level up, restructure, and build something that could actually last. The reason I’m still here today is because I didn’t let the challenges stop me — I used them to sharpen me.

I’m proud of the scars because they built the blueprint I’m standing on now.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I wear a lot of hats in entertainment, but they all come from the same foundation — I create, I develop talent, and I build platforms that move the culture forward.

I’m a music producer, artist, filmmaker, and the founder of DStar Productions LLC.
My work spans across production, filming, artist development, youth programming, and community entertainment. I specialize in creating full systems — not just making a song or shooting a video, but building entire platforms that help artists grow.

On the creative side, I’m known for my sound, my visuals, and the versatility of what I produce. I’ve worked with and created content for artists like Wale, Shy Glizzy, Fat Trel, WillThaRapper, Simba, Black Fortune, and most recently directed a video with Boosie. I also run platforms that have put 84+ artists on WPGC 95.5 and hosted 28 live on-air interviews through my Real Live platform.

On the community side, I’m the creator of High School Cypher, a 13-week creative arts program that has served over 1,000 students, principals, and administrators across 80–100 schools. It’s one of the largest youth creative programs in the DMV, and it’s been featured on Fox 5, recognized by the Maryland House of Delegates, and supported by multiple grants.

What I’m most proud of is the balance.
I’ve built something that serves all ages — from developing the next generation of young creatives to producing for established artists to releasing my own music. Most people only do one side. I do all of it at a high level.

What sets me apart is my ability to build full ecosystems — not moments.
Artists come to me because I don’t just give them a beat or a video. I give them:

A platform,

Exposure,

Development,

Strategy,

Radio access,

Visuals,

Systems that actually help them grow.

And now, as an artist myself, I’m bringing that same level of structure, creativity, and execution to my own brand. Everything I do is intentional, and everything feeds into something bigger.

At the end of the day, I’m not just creating content — I’m building an entertainment infrastructure that will outlast me.

We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
I don’t really look at my journey through the lens of luck — good or bad. For me, everything has come from consistency, timing, and being prepared when opportunities showed up. If anything, the “luck” I’ve experienced is the kind you create by staying in motion.

There were times things went left, deals fell through, people disappeared, resources dried up — and you could call that “bad luck.” But every setback pushed me to build smarter systems, depend on myself, and structure my business so it can’t be shaken by one situation or one person.

On the flip side, the biggest breakthroughs in my career happened because I was prepared. Meeting the right people at the right time, getting calls for big opportunities, being invited into rooms I wasn’t even expecting — those moments only worked because I had already put the work in for years. To some people that looks like good luck, but it’s really alignment.

So in my world, luck is just the intersection of preparation and opportunity.
I don’t rely on it, but I respect it. And I try to keep myself in a position where if “luck” does show up, I’m ready to capitalize on it immediately.

At the end of the day, I’ve learned that the less you depend on luck, the more it seems to show up for you.

Pricing:

• Music Production & Beat Licensing: Custom production and exclusive licensing are available, typically ranging from mid-tier to premium rates depending on project scope, rights, and turnaround.
• Film & Video Production: Includes directing, shooting, and editing services. Packages vary from basic visual content to full-scale cinematic productions for artists and brands.
• Artist Development & Creative Direction: One-on-one or team-based development, including branding, content strategy, recording oversight, and rollout planning. Pricing is project-based.
• Youth Creative Arts Programming (High School Cypher): Schools, nonprofits, and agencies can book 13-week or full-year programs. Rates depend on the district, schedule, and level of service.
• Live Performances, Hosting & Appearances: Rates vary based on venue size, travel, set length, and event scope.

Contact Info:

• Website: https://www.drewstarproductions.com
• Instagram: @drewstar1100 @_dsproductions
• Facebook: @drewstar1100 @_dsproductions
• Youtube: @drewstar1100 @_dsproductions

Image Credits
DrewStar Productions LLC