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.

AI isn’t Coming—it’s Here: Why Your Business Needs to be Ready

AI isn’t Coming—it’s Here: Why Your Business Needs to be Ready

AI isn’t Coming—it’s Here: Why Your Business Needs to be ReadyConor K Phillips
Published on: 02/04/2025

If you've been holding your breath for the "AI revolution," you can exhale now - it already happened. And while some businesses are still deciding whether AI is relevant to them, others are out here saving hours a day, responding to customers in real-time, and looking like they've got a 12-person support team - when really it's just Christine and a chatbot named Max.

The Unpaved Road - Chronicles of a Founder
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.

The Unpaved Road - Chronicles of a Founder
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).

The Unpaved Road - Chronicles of a Founder
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.

The Unpaved Road - Chronicles of a Founder

"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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