The Road Is Back And Here's Why

It’s been a minute, and I have to apologize.

It’s been a minute, and I have to apologize.

When I launched this newsletter in 2023, I bit off a little more than I could chew. The Maple Leafs site I manage migrated from Sports Illustrated to The Hockey News earlier than expected, and the site took off like a juggernaut. I’ve been told I have an all-or-nothing complex when it comes to my work. It’s a trait that isn’t well-suited for a “jack of all trades, master of none” like me.

But then I realized I actually am a master of something: travelling to every single Maple Leafs game of the season. Aside from one snowy game in Minnesota where a cancelle

d flight ended my “ironman” streak of 440 consecutive games attended, I have been there for every moment. More importantly, I’ve mastered travelling well while keeping costs effectively negligible.

My goal for this newsletter is to help those who cover their own travel expenses, whether you are self-employed or running a business. I’ve learned a ton of travel hacks along the way, and I want you to utilize them to your fullest advantage.

A few things I’ve picked up on the road:

• Wi-Fi Workarounds: Before Air Canada stopped charging for Wi-Fi, I found a hack to bypass their overpriced and underperforming onboard internet.

• Ticketmaster Hacks: I learned a trick that helped me score amazing, cost-effective tickets to see Depeche Mode while I was in Washington, D.C.

• Hotel Stacking: I once stayed in a fancy downtown Los Angeles hotel where, after stacking rebates and offers, the effective savings were like they were paying me to be there.

• Currency Strategy: I discovered why it is almost always better to buy tickets in USD rather than CAD. Even without a credit card that waives foreign transaction fees, American funds are often effectively discounted by an average of 10 percent.

What you can expect in the coming weeks:

• Why I almost never pay for hotel parking and the better alternatives I use.

• How a specific American credit card launched last year cut down my Canadian travel costs through an Alaska Airlines partnership.

• How the journey started through credit cards and discipline.

So, why will this time be different?

I’ve learned what makes a niche newsletter successful—and what doesn’t. I was lacking structure, but that changes now. Every Friday morning, there will be a new post based on a lesson I’ve learned from the road. The road is long, and my list of tips to help you cut travel costs is even longer. Whether you apply these to your business or a family vacation, my hope is that you’ll never feel like you’re breaking the bank.

Thanks for sticking around. I vow you won’t regret it.