Stop Paying Full Price for Average Hotel Rooms
Freedom favours the informed. What my motorcycle trip taught me about leverage, elite upgrades, and using FoundersCard strategically.
There’s a moment in travel when you realize you’re no longer just looking to book a room, you’re looking to feeling welcomed. That moment usually happens when you open the door and notice the view is better than expected, the room is bigger than what you paid for, and there’s a handwritten note waiting for you, and maybe a welcome cocktail or two - on the house, of course. As I said before, it’s about genuinely attentive service at a beautiful place somewhere far from home.
It wasn’t always like that for me. My first night in a hotel is usually not easy. I feel lost, away from home, and need time to adjust. On most trips, I still do. But for my upcoming motorcycle trip, I’m hoping to accelerate that experience as I only have a single night for most stops on an extended ride. So I need to maximize the experience1, and hopefully skip the first night of discomfort.
For my California coastal trip, I’ve booked a lot of hotels in a short period of time, bouncing between coastal towns and cities, and almost every time I check the confirmation email, something quietly stands out: Complimentary upgrades, resort credits, late checkouts.
None of this was advertised in bold letters. It just, happened.
When upgrades stop feeling like luck
For years, I assumed hotel upgrades were random. A friendly front desk agent, a slow night, or simply being in the right place at the right time. And sometimes that’s still true: you may accidentally score an upgrade by just being nice. But that’s not what I call travel hacking: having a system and being intentional about it. Hotels make money by selling the same room at different rates. The system is being consistently on the “good” side of that equation.
I’ve been a travel hacker for decades, but my motorcycle trip really put it to the test with multiple expensive destinations in a row across multiple hotel brands. This time there were no free flights as I’m spending the entire trip on two wheels. Multiple check-in points where I expected nothing beyond the basics, and yet kept receiving more than I booked: Better rooms, better views, and extra perks that make long riding days feel a little more luxurious after I park the bike.
As someone who values freedom over flash, this kind of luxury hits differently. It’s not about status, but about experience.
Why this matters on a motorcycle trip
When you’re traveling by motorcycle, comfort isn’t optional. After hours on the road, exposed to the elements, the hotel isn’t just a place to sleep. It’s where I recover, reset, and prepare for the next day. A quieter room matters, a balcony matters, sometimes even a late checkout matters when your departure depends on weather and timing rather than a fixed schedule. I don’t often do iron-butt rides and do want to enjoy each destination for a few hours after I park the bike.
Across multiple weeks, those little (complimentary) upgrades compound quickly. They reduce friction, give me space, and save me money. Most importantly: these intentional upgrades make the entire journey feel like an intentional experience rather than rushed.
“Luxury is not about having more. It’s about needing less.”
That’s exactly what these perks provide: less stress, less compromise, and zero negotiating at check-in. It’s feeling welcome. You can’t buy that.
The hidden value most people miss
A lot of people look at memberships like FoundersCard and immediately ask if it’s worth it. I get the skepticism. I had it too. But the math becomes irrelevant when a single booking offsets the cost of the membership. That’s the bar, and I set it high: I just need one meaningful upgrade, one waived fee, one stay where you feel genuinely taken care of - and that should cover my annual membership. By the second perk I’m taking advantage of, I’m making a profit.
Imagine the compounded effect of a multi-week motorcycle trip. What surprised me most wasn’t the savings, but the consistency. Across different cities, different properties, different hotel chains, the experience consistently feels elevated without me having to ask for anything. That’s the kind of quiet advantage I appreciate most, especially when I’m focused on the road and enjoying the experience, not logistics.
This isn’t about luxury travel
I want to be clear about something. This isn’t about chasing five-star experiences or turning travel into a meaningless flex. I still choose routes over resorts and roads over runways whenever I can. I’ve cancelled free business class flights as the timing didn’t align with the experience I was curating - enough said. The places I book reflect my philosophy of maximizing the experience value. Often that means traveling smarter, not harder.
If you’re already investing in travel, especially intentional trips that matter to you, there’s something powerful about stacking the odds in your favour. Letting systems work quietly in the background while you can stay present and just focus on enjoying the experience itself.
Get Into Action
If travel is more than an occasional escape for you, if it’s part of how you structure your life and your freedom, it’s worth learning how these behind-the-scenes advantages actually work. I break this down in my travel book and courses, not as hacks, but as frameworks. Ways to curate trips that feel lighter, smoother, and more aligned with how you want to live.
You don’t need to travel (or spend) more to feel richer. You just need to travel better.
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