Dylan Carollo

Dylan Carollo has worked at the intersection of media, entrepreneurship, and operations — building brands from the ground up and helping small teams grow with structure and purpose.

He founded D100 Media, a creative production company that partners with universities and organizations to produce podcasts, digital content, and experiences that tell meaningful stories. The company began as D100 Radio, a student-led station that grew into a national platform — covered by major news outlets and now collaborating with leading radio distributors across the country. What started as a small side project evolved into a full-service media group with multiple brands, clients, and distribution channels — all built through consistency, care, and collaboration.

Beyond D100 and 50/50, Dylan works on the Transformation team at a leading healthcare company, where he focuses on process improvement, data-driven decision-making, and operational efficiency across large-scale teams. This experience provides firsthand insight into how thoughtful systems and communication can drive real results.

Before launching 50/50, Dylan worked with a private investment firm that acquires and scales service-based businesses. There, he learned the ins and outs of small business acquisitions — from sourcing and diligence to post-acquisition operations — and saw firsthand how thoughtful ownership transitions can preserve legacy while unlocking new potential.

Today, he collaborates with a group of experienced investors and operators from the software and technology space who share his long-term approach to ownership. Together, they bring both operational expertise and capital to every deal — ensuring a strong foundation for growth while maintaining the legacy that matters most.

That blend of creative, corporate, and operational experience shapes how Dylan approaches every opportunity. He understands both sides — the pride of a founder who’s built something, and the responsibility of the operator who steps in next.

At 50/50, his goal is simple: to continue the work others have started with the same care, respect, and long-term vision that got it here.