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.

The Future Called – Travel in 2030 is Closer Than You Think

The Future Called – Travel in 2030 is Closer Than You Think

The Future Called – Travel in 2030 is Closer Than You ThinkConor K Phillips
Published on: 26/03/2025

Let’s play a quick game of time travel. It’s the year 2030. You’ve just booked an immersive culinary tour through coastal Atlantic Canada—via voice command. Your AI travel assistant knows you’re gluten-sensitive, get hangry between 2–4pm, and are weirdly obsessed with historic lighthouses. (Relatable.) It’s planned your full itinerary—eco-conscious, hyper-personalized, and fully synced with real-time weather, accessibility preferences, and crowd levels. Sound far-fetched? It’s not. In fact, the future of travel isn’t lightyears away—it’s basically knocking on our door. Here’s a peek at what 2030 has in store and how it’s already reshaping the way we move, plan, and experience the world around us.

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Micro-Failures, Major Wins: How Iteration Saves Startups from the Big Fail

Micro-Failures, Major Wins: How Iteration Saves Startups from the Big Fail

Micro-Failures, Major Wins: How Iteration Saves Startups from the Big FailConor K Phillips
Published on: 19/03/2025

If you spend enough time in the startup world, you’ll hear the phrase "fail fast" at least a hundred times. And while failure isn’t inevitable, it is everywhere—especially in the micro-moments that shape how a business grows (or doesn't).

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Money Talks, Fundraising Walks - My Rollercoaster of Startup Wins and Losses

Money Talks, Fundraising Walks - My Rollercoaster of Startup Wins and Losses

Money Talks, Fundraising Walks - My Rollercoaster of Startup Wins and LossesConor K Phillips
Published on: 12/03/2025

If you’ve ever seen a headline about a startup raising millions in funding, you might think fundraising is just about pitching the right investor, shaking hands on a deal, and popping champagne. Spoiler alert: it’s not. Not usually anyway.

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Dream Big, Hustle Harder – Juggling Vision and Reality Like a Pro

Dream Big, Hustle Harder – Juggling Vision and Reality Like a Pro

Dream Big, Hustle Harder – Juggling Vision and Reality Like a ProConor K Phillips
Published on: 05/03/2025

Ask any founder why they started their company, and you’ll hear a version of the same thing: I had a vision. A big, audacious, world-changing idea. But here’s the unsexy part no one talks about—having a vision is easy. Executing it? That’s where the real work happens. And along the way, you must maintain a belief in that idea and in yourself. It doesn't have to be a steady belief, you'll definitely bobble here and there, but it does have to be an anchor you consistently return to.

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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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