We acquire owner-led businesses built on trust, skill, and reputation.
You’ve created something special — we’re here to continue it.
That’s what 50/50 means: growth without losing the legacy.
What we look for.
We acquire profitable, owner-led businesses built on craftsmanship, reputation, and relationships — companies that matter to their communities and teams.
We’re especially interested in trade schools, media, audio-visual, hospitality, and other service-based companies with loyal customers and recurring work. Typical businesses generate $1-10 million in revenue and $500K-$2M in annual cash flow, though we’re flexible for the right fit.
Ideal partners are founders ready for succession or retirement who want their people and legacy protected. We focus on U.S. businesses with strong local roots, steady demand, and room to modernize or grow.
We complete full acquisitions or majority buyouts, often with collaborative transitions and seller financing to make the handoff seamless.
In short: we look for good businesses run by good people — steady, respected, and ready for their next chapter.
About 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 spacewho 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.
