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.

It’s Time to Talk About the ‘Fragile Generation’… I Think They Might Be Onto a Few Things

It’s Time to Talk About the ‘Fragile Generation’… I Think They Might Be Onto a Few Things

It’s Time to Talk About the ‘Fragile Generation’… I Think They Might Be Onto a Few ThingsConor K Phillips
Published on: 21/11/2025

They’re called “soft,” “fragile,” and “too sensitive.” But what if that’s exactly what the world needs right now? This blog explores how Gen Z and Gen Alpha’s empathy, awareness, and emotional intelligence could be the antidote to a hardened world.

The Unpaved Road - Chronicles of a Founder
You’re Not Lazy - You’re Exhausted

You’re Not Lazy - You’re Exhausted

You’re Not Lazy - You’re ExhaustedConor K Phillips
Published on: 14/11/2025

Let’s talk about the invisible mental load of building something. This blog explores how to recognise burnout before it sneaks up and how to build with better fuel.

The Unpaved Road - Chronicles of a Founder
Not Every Mentor is a Match: Why Guidance Should Come with a Fit Check

Not Every Mentor is a Match: Why Guidance Should Come with a Fit Check

Not Every Mentor is a Match: Why Guidance Should Come with a Fit CheckConor K Phillips
Published on: 07/11/2025

We’re told every founder needs a mentor or coach. Maybe. But not all guidance is created equal. This blog explores how to separate real insight from overpromised advice, and why the wrong fit can cost more than money.

The Unpaved Road - Chronicles of a Founder
Say No (Even If You Could Say Yes)

Say No (Even If You Could Say Yes)

Say No (Even If You Could Say Yes)Conor K Phillips
Published on: 31/10/2025

Not every opportunity deserves your energy. This blog explores how saying “no” to good things creates space for the right things...and keeps your direction clear.

The Unpaved Road - Chronicles of a Founder

"Everything you ever wanted is on the other side of fear." - George Adair

"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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