Tyler Heilberger

I'm the founder of Go With Rosie. I was born and raised in Wisconsin, where I still live, and I came to family travel from the technology side — after years digging into the details and reviews behind Yelp, TripAdvisor, and Google.

What I kept running into was a gap. A review tells you a place was good or bad, but not who it was good or bad for. Families aren't one audience. They change at every stage, and each family's makeup brings its own mix of ages, interests, and needs. That makes family travel one of the hardest problems in the space, which is exactly what drew me to it. Getting it right takes iteration, because every family introduces a new set of permutations to solve for.

My conviction is that technology and large-scale data can close that gap. Go With Rosie is built to let families share trusted recommendations securely, and to cut through ad spend, opaque algorithms, AI bloat, and influencer noise. The goal is straightforward: give families real, relevant insight so they can get out into the world and experience it together.

I continue to go deep on the technical side of travel, and I'm building Go With Rosie to lead it.