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 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
Lessons in Grit and Grace...The Good, Bad, and Ugly of Entrepreneurship

Lessons in Grit and Grace...The Good, Bad, and Ugly of Entrepreneurship

Lessons in Grit and Grace...The Good, Bad, and Ugly of EntrepreneurshipConor K Phillips
Published on: 14/05/2025

Entrepreneurship isn’t all wins and highlight reels. This blog shares the real-deal journey—grit, grace, and the glorious mess in between. From lessons learned to leadership earned, it’s a look at what building something meaningful really takes.

The Unpaved Road - Chronicles of a Founder
When Life Gives You Lemons, Build a Lemonade Empire

When Life Gives You Lemons, Build a Lemonade Empire

When Life Gives You Lemons, Build a Lemonade EmpireConor K Phillips
Published on: 07/05/2025

Plans go sideways, funding falls through, and perfect hires flop. But that’s where the magic happens. This blog explores how setbacks fuel growth, and how building forward (not just bouncing back) is how you turn lemons into a full-blown empire.

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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