Meet Dylan.
Dylan Carollo is an entrepreneur and operator focused on building and growing businesses with long-term purpose. He has worked across media, operations, entrepreneurship, and small business investing — with experience turning early ideas into structured, sustainable organizations.
Founder of D100 Media
Dylan is the founder of D100 Media, a creative production company that partners with universities, organizations, and brands to produce podcasts, digital content, and media experiences.
D100 Media began as D100 Radio, a student-led station that grew into a national digital platform distributed across major audio channels. Along the way, Dylan helped turn the project into something with real reach and impact — including raising for charitable causes. What started as a small side project evolved into a broader media company with multiple brands, clients, and partnerships, built through consistency, care, and a focus on meaningful storytelling.
"You often don't meet a high-schooler who has an office in the World Trade Center…" — NBC New York
Operating Experience
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.
That work gives him firsthand exposure to how strong systems, clear communication, and thoughtful execution can help organizations operate better and grow with more discipline.
Business Ownership Perspective
Before launching 50/50, Dylan worked with a private investment firm focused on acquiring and scaling service-based businesses. There, he gained experience reviewing companies, understanding owner transitions, evaluating growth opportunities, and thinking through what makes a business durable over time.
That experience shaped the foundation of 50/50: a belief that great businesses deserve thoughtful next chapters — not just transactions.
Why 50/50
Dylan started 50/50 to help bridge the gap between legacy business owners and the next generation of operators. His goal is to partner with owners who care about what happens after the deal — preserving what made the company successful while bringing new energy, structure, and long-term stewardship.
For Dylan, 50/50 is about more than buying or investing in businesses. It is about continuing what owners built, protecting the people and relationships behind the company, and helping strong local businesses move confidently into their next chapter.
Education
Dylan earned a B.S. in Management from Boston College, with concentrations in Finance and Entrepreneurship.
Contact Dylan
dylan@with5050.com
