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Why I bought a 20-year-old DMC while pregnant

Kaitlyn Dineen · Jun 2026 · 3 min
Why I bought a 20-year-old DMC while pregnant

People love a tidy founder story. Mine wasn't tidy.

I bought a 20-year-old destination management company in the middle of a pandemic. While pregnant. While renovating a house. The events industry had just been told to stand still, and I decided that was the moment to bet on it.

It sounds reckless written down. It felt like the most honest decision I'd ever made.

Buying belief, not just a business

Fifth Street DMC had been trusted since 1999 to design and produce experiences. I wasn't buying a logo or a client list. I was buying the belief that people will always need to gather, celebrate, and remember together. Even when, especially when, the world tells them to stay apart.

A destination management company is the team that turns a place into an experience. Venue sourcing. Staffing. Full-service event design and production. Activities and excursions. Talent and entertainment. When a company brings its people to Austin or Montana or the Carolinas, we're the ones who make the destination do something.

I believed that work mattered. I still do.

The unglamorous truth about founding

The version of founding that gets posted is the win. The RFP you stayed up weeks chasing and finally landed. The version nobody posts is the rest of it.

I've walked into the office on New Year's Day to fire damage from a stray Roman candle that hit our roof overnight. I've read a rough review from a former employee that made my stomach drop. I've been miserably sick for two days of a five-day program and had to learn, the hard way, to build in margin.

Founding a company is not a survival story you tell once. It's a thousand small decisions to keep going, made by a whole person, not a highlight reel.

Building from possibility

Every decision comes from one of two places: fear or possibility. I try to choose possibility on purpose.

That doesn't mean I don't feel the fear. I feel it. I just try to name it before I act from it. Buying a business mid-pandemic was fear and possibility in the same breath. I chose to build.

Businesses don't scale. Humans scale businesses. So I started with the human, then the home that holds her, then the business. In that order.

That order is why Fifth Street DMC exists today, and why it became the first brand in the OMC village. People First, even in the founding story. Especially there.

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