Looking Back On… Developing the Mileage Mindset

From now until things get better, I’ll be writing this series to look back on stuff in the past that I’ve never written about here on Prince of Travel, whether it was trips that took place before I started the blog, funny anecdotes from my journeys over the years, “small wins” that helped me develop my keen eye for killer deals, or anything else that shaped who I am as a traveller today.


In this installment, I’m looking back on how I got started hunting for deals, spotting inefficiencies, and pushing boundaries in my everyday life – habits that would eventually set me on the path of maximizing Miles & Points for unbelievable adventures around the world. 

A few years ago, I wrote a series of posts on “The Mileage Mindset”, which walks you through a few examples of the sharp deal-hunting mindset that you need to strive for in Miles & Points if you want to take advantage of killer deals before everyone else.

Those lessons continue to ring true today, and I’d encourage you to go back and give them a read when you have some time.

In this post, though, I wanted to look back on how I personally developed that mindset. What were the first few deals and opportunities I decided to pursue, and how did that translate into an overall opportunistic mindset to spot the potential edge wherever I looked?

Allow me to share this story through the lens of a few real-life examples of the Mileage Mindset in action. 

“Churning” Before It Was Cool

I didn’t apply for my first points-earning credit card until 2014, the summer after my second year of university. But before then, I was already constantly looking for ways in my daily life to “play the game”, “extract value”, “get ahead”, or whatever you want to call it – a mindset that I suppose most of my readers will be familiar with. 

I’m sure everyone will have different motivations for seeking that edge in their own lives, whether it’s in pursuit of financial freedom or simply chasing a cheap thrill. 

For me, I suppose I viewed it as a challenge. As with anyone who’s crazy enough to eventually launch a travel website, I’ve never really bought into the wider society’s idea of how things are and how things should be done, and I’ve always viewed it as inherently valuable to be constantly pushing boundaries and trying out unconventional methods.

“Playing the game”, as it were, was a way to test out that theory – if I profited, then my worldview might just be correct. 

The only problem? I had no idea what was the right game to play.


And so, before I came to learn of the opportunities from maximizing Miles & Points and “churning” credit cards, I “churned” food delivery apps instead. 

Services like Uber Eats, Skip the Dishes, Ritual, and Doordash are household names these days, but five years ago they were just getting started. And in a bid to attract as many customers as possible soon after launch, they didn’t really have the resources to pay attention to things like customers making multiple accounts using different email addresses and phone numbers.

There was one delivery service in particular, which was known as Feast, that seemed particularly lax, and didn’t even care when customers signed up a few times using the same phone number.

And Feast didn’t just deliver dishes from your local Chinese restaurant, either – it offered a rotating menu of made-to-order lunches and dinners using premium ingredients, but was meant to be priced at affordable levels.

Those affordable levels were priced at around $10 per meal, and the thing is, Feast was offering “new customers” a $10 discount on their first purchase, so… you guessed it, I ended up eating delicious meals like seared albacore tuna, flank steak Cobb salad, and polenta with lamb chops, in-between my university classes for a whole month – all for the very affordable price of $0.00 per meal.

All the meals were hand-delivered to my class locations by the same two or three cyclists, who must’ve wondered why I kept adding random periods in the middle of my email address.

Incidentally, it seems that Feast has rebranded itself and has stopped doing online deliveries these days, and instead operates physical locations in partnership with several Toronto coffee shops. I guess they won’t need to invest in better online customer controls anymore!

“Matched Betting” in the UK

Shortly after realizing there was bigger fish to fry out there and signing up for my first American Express card in 2014, I ended up moving to London for a year for my study abroad program.

And while it was a very exciting time, one thing that disappointed me was the fact that I’d have to wait another year before ramping up my credit card game in Canada.

I did wonder if there were similar opportunities in the UK, but alas, I found that the credit card companies were not at all interested in extending credit to a temporary resident with no income. 

But hey, you know who was more than happy to sign up a temporary resident with no income as a new customer? Betting companies. 

Casual gambling, on things like football and horse racing, is very much ingrained in the UK culture, and it’s not uncommon to see half a dozen different betting shops lined up along the local high street. And with online betting becoming more and more mainstream, bookmakers were offering their equivalent of signup bonuses to entice new customers: a concept known as “free bets”. 

The idea is that upon signing up with a bookmaker as as new customer, they’ll give you a certain amount of free money (usually £10 or £20, but sometimes as high as £100) to bet on whatever outcomes you want. If you win the bet, you come away with free winnings, and if you lose, you haven’t really lost any of your own money anyway. Tempting, isn’t it?


Of course, that would be too easy! The catch is that you almost always need to place a bet using your own money first before unlocking the free bet. The bookmaker profits off your first bet before enticing you to have another go with a free one, and also hopes that you’ll subsequently place more bets with them in the future.

Now, here’s the thing: while the mathematics behind it is somewhat beyond the scope of this article, it turns out that you can use a concept called “matched betting” – which involves using your free bet to bet on a certain outcome (e.g., England winning their match), while simultaneously using a separate betting website to bet against that outcome (i.e., England drawing or losing) – to squeeze out a guaranteed risk-free profit from these free bet offers, no matter the actual outcome of the event. 

It’s kind of like maximizing credit card signup bonuses, except with betting companies’ free bet offers instead.

And with over 50 registered bookmakers in the UK all offering tempting free bet offers just for opening an account, I ended earning about £600 over the course of two months – which, for a student on a junior-year exchange program, was a hefty chunk of change that translated into a few weeks’ worth of backpacking around Europe. 

Matched betting would be my first experience in gaining a subtle edge by doing no more than accepting marketing offers in a way that may not be appreciated by the companies making these offers, but is nevertheless perfectly legal.

Sounds familiar, doesn’t it? 

Loosely Enforced T&Cs: A Real-Life Example 

Many readers will be familiar with the idea that just because the terms and conditions of a certain program are written in a certain way, doesn’t mean that things will always work out that way in practice. As we know all too well, merely publishing terms and conditions is an entirely separate matter from actually enforcing them.

Well, after returning from studying abroad, I learned this lesson through what was ostensibly a very important program at that time in my life: a summer internship program at a Big 5 bank.

Most commonly, university students choose to pursue an internship in the summer after their third year of university, and indeed, most such programs are geared towards students who will be returning to school in the fall.

But in my case, having spent my entire third year studying abroad in London (read: gallivanting around all of Europe), I had let my career aspirations fall by the wayside, and returned to Toronto as a fourth-year student with little meaningful work experience under my belt.

Facing an uphill battle to secure a job after graduation, I grinded away and set up a few networking chats with professionals working in the banking and consulting industries in Toronto. 

But despite my best efforts to leave a good first impression, the best I could do was to persuade a contact at one of the Big 5 banks to put my name into the pool of potential interns for the upcoming summer, rather than the pool of potential full-time hires (which was presumably guarded much more closely, and usually only drew upon graduating interns from the preceding summer).

And here’s where I was faced with an obstacle in the form of, well, terms and conditions: I was told that the summer internship program was meant for students who would be returning to university in the fall. 

For a moment as I sat there, looking at that checkbox on my screen, I thought to myself, “Well, I’ll be graduating this summer and won’t be returning to university, so I guess that’s me out of the running, then.”

“Aw shucks.”

“Aw shucks.”

And then, of course, my better instincts kicked in, reminding myself that I could always choose to return to university and take a fifth year if I really wanted to. I mean, it’s never too old to learn, right?

The rest was history – I impressed in the interview, earned a four-month summer internship, took a vacation day in the middle of June to attend my graduation ceremony, and then sat down with the program recruiter one day and asked: “So… how strict was the requirement to be going back to school in the first place?”

As I expected, it turns out that the requirement wasn’t very strict at all, and I was free to do whatever I wished after the internship period ended.

Of course, I still needed to secure full-time employment after that, and having relied on a bit of luck to worm my way into the program from the outset, I now relied on my own abilities to get further ahead. I ended up outperforming a colleague on my team over the course of the summer, and was offered to take over his temporary contract in September; after that, another few months of hard work saw me earn the position on a full-time basis.

There’s no denying that I was quite fortunate in how I landed my first job out of university – a fairly cushy one for a new graduate, might I add – and I’m always grateful that things played out the way they did.

At the same time, I also made my own luck in some ways, because it was only through a certain irreverence for the exact letter of the terms and conditions that I had put myself in the running. 

Little did I know at the time that this would only be the first of many instances of deriving maximum benefit from a set of loosely enforced terms and conditions, all in pursuit of a more fulfilling life. 😉


I’ve always said that the art of maximizing Miles & Points to travel the world requires a certain mindset that must be honed over time – a mindset of pushing boundaries, seeking the competitive edge, and questioning whether things truly are as they seem.

My own Mileage Mindset has its origins in my university days, and the process of developing and applying this mindset to my goals and aspirations has shaped my life in ways I never could’ve imagined.

And does this mindset end with getting to travel the world on points? Certainly not. While Miles & Points is undoubtedly lucrative, I remain open-minded to all of the opportunities to be sought in the future, just as I was open-minded back in the days of cycling through food delivery apps.