The Unpaved Road: Chronicles of a Founder

The road isn’t always smooth, but it’s always worth the journey

Welcome to

The Unpaved Road: Chronicles of a Founder

Starting and building a business is much like exploring uncharted terrain—challenging, unpredictable, and often rewarding in ways you never expected. Through this blog series, I’ll share my experiences as the founder and CEO of Roamlii, navigating the twists and turns of running a startup in the dynamic worlds of tourism and technology.

Here, you’ll find reflections on entrepreneurship, lessons learned (sometimes the hard way), thoughts on the Canadian economy and its impact on small businesses, and a behind-the-scenes look at what it takes to build something from the ground up.

My hope is that these chronicles inspire, inform, and connect with anyone blazing their own trail—whether you’re building a business, championing a cause, or simply looking for insights on resilience and innovation.

The road isn’t always smooth, but it’s always worth the journey.

Let’s get started.

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

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

How I Turned “What If” Into “Watch This” - Roamlii’s Origin StoryConor K Phillips
Published on: 19/02/2025

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.

The Unpaved Road - Chronicles of a Founder
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Provincial Pals - How Crossing Borders Builds Bigger Tourism Wins

Provincial Pals - How Crossing Borders Builds Bigger Tourism Wins

Provincial Pals - How Crossing Borders Builds Bigger Tourism WinsConor K Phillips
Published on: 12/02/2025

Canada is a big country. Like, really big. You could start a road trip in British Columbia, drive for what feels like forever, and still be in the middle of the Prairies with days to go before hitting the Maritimes. One fun fact that absolutely nobody asked for is that Luxembourg can fit inside the Prince Albert National Park approximately 1.5 times. That means the park is about 50% larger than the entire country of Luxembourg! How fun. And yet, despite all this space and endless possibilities, our provinces often act like separate little islands when it comes to tourism. And don't even get me started on our interprovincial transportation situation. Why don't we have high speed trains by now! Omfg I'll save that for another blog though.

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Support Local or Go Home - Why Tech is Small Towns’ Best Friend

Support Local or Go Home - Why Tech is Small Towns’ Best Friend

Support Local or Go Home - Why Tech is Small Towns’ Best FriendConor K Phillips
Published on: 05/02/2025

Small towns are the beating heart of Canada. They’re where you find the best butter tarts, the friendliest people, and those quirky little businesses that give a place its charm. But let’s be real—running a business in a small town isn’t easy. Foot traffic isn’t what it used to be, and let’s not even talk about how tricky it is to compete with big-city marketing budgets and e-commerce giants. Enter: technology. Not just any tech, but smart, accessible, small-business-friendly tech. It’s the game-changer that’s helping small-town businesses not only survive but thrive. And if you’re not on board yet, it’s time to grab your double-double, shove a timbit in your mouth and listen up.

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The Economy, Eh? How Canada Shapes Tourism (and Vice Versa)

The Economy, Eh? How Canada Shapes Tourism (and Vice Versa)

The Economy, Eh? How Canada Shapes Tourism (and Vice Versa)Conor K Phillips
Published on: 29/01/2025

If the Canadian economy were a house, tourism would be the sunny window seat everyone underestimates. Sure, the big-ticket items like natural resources and manufacturing get all the attention, but tourism quietly brings in billions, strengthens communities, and puts Canada on the map—literally. But it’s not a one-way street. Just as tourism supports the economy, the economy shapes how tourism develops, thrives, or struggles. From currency fluctuations to public investment, the relationship between Canada’s economy and tourism is as intertwined as maple syrup and pancakes. In this post, let’s unpack how the economy influences tourism and how tourism gives back in ways you might not expect.

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"Roamlii is headquartered in Saskatoon, Saskatchewan, on Treaty 6 Territory, and the traditional homeland of the Cree, Saulteaux, Dene, Dakota, Lakota, Nakota, and Métis nations. We pay our respects to the First Nations and Métis ancestors of this great land, and reaffirm our relationship with one another."

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