How I Turned “What If” Into “Watch This” - Roamlii’s Origin Story

Startup Life: Trials, Triumphs, and Tough Lessons
- How I Turned “What If” Into “Watch This” - Roamlii’s Origin Story

Every startup begins with a what if. Some are small, fleeting thoughts. Others burrow deep into your brain and refuse to leave until you do something about them. Roamlii was one of those.

Back when I was working at Elk Ridge Resort, I kept running into the same, maddening problem—there was no singular place to showcase everything our resort offered. No seamless way to promote the full experience. We had golf, spa services, conferences, weddings, multiple accommodation types, and outdoor activities galore—and yet, there wasn’t a single platform that could effectively house it all.

Sure, there were booking websites, but they only covered bits and pieces. There were tourism directories, but they were scattered and rigid. There were marketing tools, but none of them truly captured the dynamic nature of a business that thrived on variety and experience. It felt like trying to jam a square peg into a round hole—over and over again.

Then came the moment that turned frustration into action.

The “What If” Moment

I was deep in the backcountry, horseback riding with a fantastic family from Luxembourg (because where else would you have life-changing startup epiphanies?). As we rode through Saskatchewan’s untamed landscapes, we started chatting about how difficult it was to fully discover everything to do—not just in the region, but across Canada.

It wasn’t just an Elk Ridge problem. It wasn’t even just a Saskatchewan problem. It was a nationwide problem.

There was no comprehensive platform for discovering all the incredible experiences a place had to offer.

Businesses had no centralized way to showcase what made them unique—especially the ones offering more than one type of experience.

Travellers were left piecing together their trips from a dozen different websites, directories, and scattered recommendations.

Not to mention our critical lack of affordable, accessible inter-provincial transportation (seriously, where’s our high-speed rail?!). But that’s a rant for another day.

So, I asked myself: What if there was a platform that solved all of this?

What if businesses—hotels, adventure companies, small-town shops, tourism operators—could easily showcase everything they offer in one place?

What if travellers could seamlessly discover, plan, and book an entire itinerary without having to search through a mess of unrelated websites?

What if we built something that didn’t just list businesses but actually helped them grow?

What if everything was built onto a super fun interactive map?

Turning “What If” Into “Watch This”

From that moment on, I couldn’t unsee the need for a solution.

Fast forward through a ton of research, saying yes to everything, attending every networking event in the city, a million brainstorming sessions...sometimes just with myself...and an unhealthy amount of pacing, and I launched what was originally called Pathfinder365. At the time, it felt right—a platform to help people navigate their way through the overwhelming world of tourism, 365 days a year.

But as we grew, the name no longer resonated. It was practical, but not inspiring. Functional, but not fun. We needed a name that truly captured the heart of what we were building—something accessible, vibrant, and full of adventure.

So, in August 2024, we made the leap. We rebranded. Pathfinder365 became Roamlii. And with it, the #GetRoaming movement was born.

And let me tell you, launching a full rebrand, a couple years in, is not for the faint of heart. New branding, new marketing, new messaging, updating our profile on almost a hundred sites—everything had to evolve. It's February, 2025 and I'm still unsubscribing my old email from things and resubscribing with the new email. But it was worth it. Because Roamlii isn’t just a name—it’s a movement. It’s a rallying cry for small tourism businesses, a tool for travellers who want to explore beyond the algorithm, and a platform that actually supports the businesses that make travel unforgettable.

The Hustle (aka, How We Got Here Without a Pile of VC Money)

Building a startup isn’t all grand ideas and rebrands. It’s bootstrapping, seed-strapping, and debt-strapping—a never-ending game of financial Tetris to keep the dream alive.

To date, we’ve cobbled together about $415K from a mix of:

✅ Grants

✅ Bootstrapping

✅ Strategic debt

✅ Generous friends and family

✅ Sheer force of will

We’ve also hustled our way through incubators, accelerators, and startup programs, including:

💡 Co.Launch with Co.Labs

💡 WESK's Founder's Table

💡 Startup TNT’s Top 20

💡 Y Combinator’s Startup School

Every single step has been about stretching every dollar, every resource, and every opportunity as far as humanly possible to build something real—a platform that actually solves a problem for tourism businesses and travellers alike.

The Best Part? We’re Just Getting Started.

Roamlii isn’t just a booking platform. It’s not just a directory. It’s a game-changing ecosystem designed to support businesses, destinations, and travellers alike—in a way that’s actually useful (gasp!).

What started as a what if turned into a watch this—and now, we’re building something that has the power to transform how tourism works in Canada and beyond.

And if I have my way, maybe we’ll even get that high-speed rail while we’re at it. 🫡🚄

Yours in tourism, innovation and startups,

Founder & CEO
Roamlii