Startup Stage: Go With Rosie aims to simplify family trip planning

Go With Rosie

Go With Rosie just launched this month, offering a recommendation engine to surface destinations and properties for families.

The free platform was founded by CEO Tyler Heilberger.

What is your 30-second pitch to investors?

Go With Rosie is a family travel company that helps parents discover, plan and book trips without the 27-tab research nightmare. We score every venue zero to 100 for actual family-friendliness (not marketing labels), build drag-and-drop itineraries that account for nap times and meltdowns and let families book hotels in one place. Planning is free. We make money from hotel bookings. We're building a data-driven ecosystem for families, from families.

Describe both the business and technology aspects of your startup.

Business: We're reinventing the way families travel by building the premiere family travel platform. Planning tools are free. Revenue comes from hotel bookings. No data sales, no paid placements. We answer to families, not advertisers.

Technology: The Rosie Score is a zero to 100 family-friendliness rating, pulling real data from multiple sources, weighted for what parents actually care about (stroller access, wait times, noise levels, changing facilities). Our itinerary generator is built specifically for families: automatic nap time blocking, drag-and-drop scheduling and a "Replan a Day" feature. When it starts raining and everyone's wet in the car, we help you pivot instead of figuring it out on the fly. Private family-to-family matching connects similar families without public reviews from strangers whose situations don't match yours.

Give us your SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis of the company.

Strengths:

• Family travel is a harder niche with more touchpoints and less revenue per transaction, which means less competition willing to do the work.
• The Rosie Score gives us a proprietary, defensible differentiator.
• Our itinerary generator is built to accommodate families. When it rains and everyone's wet in the car, we help you save the day instead of scrambling.
• Business model aligned with user outcomes: We win when trips go well, not just when bookings happen.
• Bootstrapped, so customer-first decision-making without investor pressure
• Team of parents and technologists who understand the problem firsthand

Weaknesses:

• Pre-revenue; launched early 2026
• Small bootstrapped team with limited resources
• U.S. domestic only at MVP (coverage gap for international)
• Technology partnerships are difficult. Suppliers want to see millions in sales before integration. We're building a technology platform, but proving volume comes first.

Opportunities:

• ~35 million U.S. households with kids, underserved by major players
• Millennial/Gen Z parents over-index on peer recommendations (our model).
• Family travel content is dominated by generic listicles; the quality gap is wide open.
• Booking integrations create expansion paths (activities, restaurants, car rentals).

Threats:

• Incumbents (Expedia, Booking, Tripsdvisor) could add family-focused features
• Customer acquisition costs in travel are brutal
• Dependence on booking partners for revenue
• Economic downturns reduce discretionary travel spending

What are the travel pain points you are trying to alleviate from both the customer and the industry perspectives?

• "Family-friendly" labels mean nothing—there's no way to know if a place actually works for kids.
• Reviews are from strangers whose situations don't match yours. A 4.8-star restaurant might have a 45-minute wait and no changing table.
• Trips fall apart the moment something goes wrong (weather, meltdowns, closures), with no tools help families pivot.
• Travel sites optimize for transactions, not outcomes. A bad trip still counts as a booking.
• Paid placements and data sales create misaligned incentives. Recommendations are about revenue, not fit.
• Family travel is treated as a checkbox filter, not a distinct category worth building for.

Now that the product is built, what's your strategy for customer acquisition?

• Organic content: Useful guides and destination resources answering what parents are actively searching; drives discovery from families already in planning mode
• Trust-first giveaways: Gave away $5,000+ in travel credit before launch. It signals what kind of company we are and builds our list with families who share our values.
• Creator and community partnerships: Relationships with family travel bloggers, parenting communities and aligned brands; genuine collaborations, not transactional sponsorships. We're also exploring partnerships with travel insurance suppliers to provide protection as a value add, not an upsell.
• Word of mouth: Parents talk to parents. A good trip becomes a recommendation at pickup, in the group chat, on the Facebook group. We're building sharing into the product.

Tell us what process you've gone through to establish a genuine need for your company and the size of the addressable market.

• Market size: Approximately 35 million U.S. households with children under 18, representing a significant segment of the $900+ billion U.S. domestic travel market. Millennial and Gen Z parents are the fastest-growing travel segment, and they prioritize experiences and peer recommendations over traditional travel advertising.
• We started by talking to parents. Over 100 interviews helped us understand the real frustrations: the 27-tab research spiral, the meaningless "family-friendly" labels, the reviews that don't account for kids' ages or needs.
• We also spoke with travel agents who confirmed the gap. They avoid families due to high touch, low commission. That's exactly the space we're filling.
• We pitched the concept in multiple settings and consistently received strong audience feedback. We won People's Choice at the Midwest Regional Startup World Cup.
• Then we tested it for real. Our beta generated $30,879 in bookings with zero marketing spend. Families found us, used the planning tools and booked. That signal was strong enough that we closed the beta to focus on building out our integration with booking platform suppliers.

How and when will you make money?

We plan to keep all of the tech parts free (for now and hopefully forever) and use that as a customer acquisition tool to convert bookings. However, we have been told our technology would be worth paying for as well.

What are the backgrounds and previous achievements of the founding team?

We're a team with deep tech experience across multiple startups that reached unicorn status. As the founder, I hand-picked the starting team from people I've worked with who were above and beyond in their skillsets. These aren't strangers from a job posting. They're people I've built with before and trust completely.

Our backgrounds are primarily in the property and casualty insurtech space, where we've been extremely successful across multiple initiatives. Insurance and travel share similar challenges: complex data, multiple stakeholders, trust-dependent transactions and customers who need guidance through unfamiliar territory. We've solved these problems before. Now we're applying that experience to travel.

We're parents and technologists distributed across the U.S.—not VC-funded, not Silicon Valley, just people who got tired of spending 20 hours planning five-day trips and decided to build something better.

How have you addressed diversity and inclusion within your business?

We're early stage and haven't formalized DEI programs yet. What we can say: Our product is designed for all families, not just affluent ones.

Our technology is free because we want to support any family. Not just the ones booking a 14-day cruise but the ones planning a road trip, a one-night stay, a budget weekend getaway. Every family gets the same tools and the same honest recommendations regardless of how much they're spending.

We're also building for the full diversity of what "family" looks like: single parents, multigenerational households, families with different needs. The product reflects that range.

Even our giveaways are structured so anyone can win. We want to help the families who help us, not just the ones with the biggest travel budgets.

Formal initiatives will follow as we scale.

What's been the most difficult part of founding the business so far?

Bootstrapping. Building a tech company can cost hundreds of thousands of dollars, which I didn't have. Instead of motivating the team with money, I've had to motivate them with the mission, the vision and feedback from users.

My background is in product management, so I understood what to build. But to get our beta testable and in front of users, I taught myself backend and frontend development. That meant doing 90% of the work myself to prove the response. Once we had real traction and real validation, I used that to bring the team together and prepare for a full launch. It's slower than writing checks, but it's built a team that genuinely believes in what we're doing.

The second challenge has been technology partnerships. As a new player in this space, integrations are hard to secure. Not being able to book through our flow was the number one negative feedback from our beta. Users weren't seeing us as a family travel platform if all we could do was provide an itinerary. They wanted to add hotels, flights, everything in one place.

That feedback was tough to hear, but it was also clarifying. We proved the point with beta, then made the decision to shut it down. I built everything myself, and we believe strongly in data security. We wanted real engineers to rearchitect our beta into something that's safe from a cybersecurity perspective and built properly to support the booking integrations users were asking for. It would have been easy to keep pushing forward, but scaling on a shaky foundation isn't how you build something that lasts.

Generally, travel startups face a fairly tough time making an impact. Why are you going to be one of the lucky ones

Most travel startups fail because they try to out-Expedia Expedia. They compete on price, inventory or ad spend against companies with billions in resources. We're not doing that.

We're building an ecosystem that helps families thrive. The value isn't in being another booking engine. It's in sifting through the noise of advertisers, aggregators and algorithms to be there every step of the way. That's how we win from a customer support perspective. We're not optimizing for transactions. We're optimizing for trips that actually go well.

We also believe strongly in starting slow and scaling appropriately. We're not chasing carrots on sticks from advertisement dollars. We're building something sustainable, not something that looks good on a growth chart but collapses under its own weight.

Even our giveaways reflect this. We give everyone a chance to win a trip of a lifetime, no matter their budget. No payment required. Using the app, sharing it, booking through us increases entries. We're building a community of families who help us because we help them first.

Will we succeed? We believe so. But more importantly, we're building something worth building regardless.

A year from now, what state do you think your startup will be in?

We expect to be focused on U.S. domestic travel with hotel leisure sales as our core revenue driver. That's where we're proving the model and building trust with families.

We'd love to start adding additional product lines. Our roadmap includes features like road trip planning from point A to point B, activity bookings and more. But we're not chasing features for the sake of features.

The beauty of building for families is that our initiatives come from user requests, not from chasing additional revenue streams. If families tell us they need help booking restaurants or rental cars, we'll build that. If they want better road trip tools, we'll prioritize that. We're not a company that builds something and then convinces users they need it. We listen first.

A year from now, we want to be the place families go when they're planning a trip. Not because we advertised our way there but because we earned it.

What is your endgame? (Going public, acquisition, growing and staying private, etc.)

We wanted to stay bootstrapped forever. We want to avoid the VC game and the pressure that comes with it. Building for families means making decisions that are right for families, not decisions that look good on a quarterly report to investors.

But the cost of time has been a huge hindrance to our vision. Moving slowly while bootstrapping means families wait longer for something they need now.

We're hoping our launch will create enough revenue to stay the course. If it does, we'll keep building independently. If we need to move faster, we might look for a strategic partnership to raise funds that aligns with our mission rather than compromises it.

The end goal is clear: Become the premiere family travel platform. Not some cash grab play. Not a flip to the highest bidder. We're building something that matters, and we want to be around long enough to see it through.