Chronicles of a Founder Blog:

The Unpaved Road

The road isn’t always smooth,

but it’s always worth the journey

Welcome to

The Chronicles of a Founder:
The Unpaved Road

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.

Why I Started Thinking About Discoverability as Infrastructure

Why I Started Thinking About Discoverability as Infrastructure

Why I Started Thinking About Discoverability as InfrastructureConor K Phillips
Published on: 14/08/2026

One of the biggest shifts in how I think about Roamlii came when I stopped seeing discoverability as a marketing problem.

Chronicles of a Founder: The Unpaved Road
The Economic Development Conversation We’re Missing

The Economic Development Conversation We’re Missing

The Economic Development Conversation We’re MissingConor K Phillips
Published on: 07/08/2026

The moment a project touches visitors, destinations or local experiences, it often gets pushed into the marketing category. Then the conversation turns to campaigns, impressions, promotional reach and whether there’s a tourism budget available.

Chronicles of a Founder: The Unpaved Road
Pushing Pebbles and Looking Three Lights Ahead

Pushing Pebbles and Looking Three Lights Ahead

Pushing Pebbles and Looking Three Lights AheadConor K Phillips
Published on: 31/07/2026

I often describe entrepreneurship as pushing several pebbles up a hill at once. Some move faster than expected. Some seem promising, then stall. A few crest the hill and create real value, while others roll straight back at you.

Chronicles of a Founder: The Unpaved Road
The Dog on the Nail

The Dog on the Nail

The Dog on the NailConor K Phillips
Published on: 24/07/2026

People want things to improve, but the familiarity of today's frustration often feels safer than the uncertainty of changing it. We're funny creatures that way.

Chronicles of a Founder: The Unpaved Road

"The best way to predict the future is to invent it" — Alan Kay

"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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