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 Digital Economy Playbook - How to Thrive, Not Just Survive

The Digital Economy Playbook - How to Thrive, Not Just Survive

The Digital Economy Playbook - How to Thrive, Not Just SurviveConor K Phillips
Published on: 11/06/2025

The digital economy isn’t coming—it’s already here. This blog breaks down how modern tourism businesses can boost discoverability, build trust online, and grow through automation, smart strategy, and human-first tech.

The Unpaved Road - Chronicles of a Founder
Build a Team That Cares (And Knows What They’re Doing)

Build a Team That Cares (And Knows What They’re Doing)

Build a Team That Cares (And Knows What They’re Doing)Conor K Phillips
Published on: 04/06/2025

Hiring isn’t just about skills—it’s about heart. This blog breaks down how to build a high-performing team that believes in your mission, owns their work, and sticks around because they actually give a damn. Smart hiring. Real culture. Big results.

The Unpaved Road - Chronicles of a Founder
The Confidence Myth: Why Most Leaders are Making it Up As They Go

The Confidence Myth: Why Most Leaders are Making it Up As They Go

The Confidence Myth: Why Most Leaders are Making it Up As They GoConor K Phillips
Published on: 28/05/2025

Think all great leaders have it figured out? Think again. This blog unpacks the confidence myth, the power of self-trust, and why the best leaders don’t always have all the answers—but they show up and lead anyway.

The Unpaved Road - Chronicles of a Founder
Why Popping the Champagne for Small Wins Fuels Big Dreams

Why Popping the Champagne for Small Wins Fuels Big Dreams

Why Popping the Champagne for Small Wins Fuels Big DreamsConor K Phillips
Published on: 21/05/2025

Setbacks aren’t the end—they’re the setup. This blog explores how turning small wins into celebration moments fuels your momentum, boosts morale, and keeps the dream alive (and growing). Cheers to the builders who toast the tiny triumphs!

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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