Sheboygan entrepreneur Tyler Heilberger has launched Go With Rosie, a family travel planning platform.
The platform is now live at gowithrosie.com.
After returning to Sheboygan County and working remotely during the COVID era, Heilberger noticed how valuable personal travel recommendations were and saw an opportunity to scale that experience through technology. Go With Rosie leverages real experiences from real families.
The platform allows families to quickly build itineraries, evaluate destinations using a family-friendliness scoring system, and book accommodations without hours of research. The platform is free to use, with revenue generated through hotel booking commissions rather than subscriptions or paid rankings.
“We’re helping create the conditions for meaningful family memories,” said Heilberger. “When we take the stress out of planning, parents can focus on being present, and that’s where the real value is.”
Go With Rosie represents the type of high-growth enabled entrepreneurship that Accelerate Sheboygan County was designed to support. Through pitch competitions, mentorship, and programming, the Innovation Council helped Tyler refine his concept, while additional support came through an Accelerate Sheboygan County Technical Assistance Grant and Product Development Loan, helping move the business from idea to launch.
“Go With Rosie is exactly the kind of company we want to see come out of Sheboygan County,” said Justin Vannieuwenhoven, chair of the Sheboygan County Innovation Council. “It’s a scalable, technology-driven idea rooted in a real-world problem, and Tyler has done an exceptional job taking it from concept to launch. This is a great example of how our local ecosystem can support entrepreneurs building solutions that reach far beyond our region.”
“The SCEDC, Small Business Development Center at UWGB, and the Innovation Council gave Go With Rosie something you can’t buy: honest feedback, real support, and people who genuinely wanted to see a local company succeed,” said Heilberger. “They helped turn an idea into a business.”
The community seeks support through user engagement, encouraging families to share travel experiences and help strengthen the platform’s recommendations.
