“The Events That Truly Make an Impact Are the Human Experiences”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:  How I Travel

Jordan writes How I Travel, which peers into the lives of some of the world’s most interesting travelers through the lens of their favorite travel possessions.  He also writes Yore Oyster, a flight hacking agency which saves corporate executives 20 to 40% on their international Business Class flights.

How and when did you start collecting miles and points?

Late 2014 for travel related miles and points, though I’ve been fascinated by just about any points program since I was really young.  I remember collecting arcade points for months, only to lose them all when the arcade changed their system architecture.  That’s one way to make a young boy cry.

I suppose what I’m trying to say is that I’ve always been good at delaying gratification, which I think is an important trait for collectors of any sort.

Why did you start your blog?  What’s special about it?

I started Yore Oyster by accident; I found 1 small loophole within Aeroplan’s system that no one was talking about, and before I knew it my story was making national news.  From there, I pretty much had to start a blog to keep my newfound followers happy.

It’s special for 2 reasons.  It’s aimed at Canadians, and it’s designed specifically for the everyday person.  And I go through great pains to ensure that anyone can apply the strategies I write about, whether they know something about miles and points or not.

How I Travel was more deliberate, and it came from my own personal dissatisfaction of not being able to find high-quality traveler profiles accompanied by professional photography.  I’d seen a very similar blog model work in some unrelated verticals, so I thought I’d try it out in the area I knew best:  travel.

What’s the one single thing people can do to get more miles?

I’m always surprised by how few people capitalize on status matches.  I wrote a piece for Forbes about how to apply status matches to get elite status on just about any airline in the world, and their readers went bananas for it.  Of course, when you have higher status you earn more miles; the perks don’t stop at priority boarding and a nice lounge.

What’s your most memorable travel experience?

This is extremely difficult.  I’ve been traveling for the past 3.5 years, never spending more than 3 months in a given place, so a lot of experiences come to mind.  The extreme experiences like sleeping under the stars in the Gobi Desert pop to mind, of course, but what’s truly made an impact has been the human experiences.

Meeting old compadres in new places around the world; long conversations lasting deep into the night; the pure bliss of a musical note mixed with a friendly smile; those are the real reasons I continue to travel.

What do your family and friends think of your miles & points hobby?

They love it!  I get requests from friends pretty much every day to help them find the best flights, and in a lot of ways it helps us to stay connected.  I know that when most of my friends think of flights they think of me, and I like that.

Is there any tool or trick which you’ve found especially useful in this hobby?

After some intense research and hacking together my own system, I’ve become pretty astute at fuel dumping (booking certain flight combinations to eliminate fees, like fuel surcharges).  Of course, the fuel dumping world has extremely pursed lips so I can’t give any secrets here, but the fact that I devised my own system from scratch makes me optimistic that others can do the same.  Mine is by no means foolproof, but it works often enough for me to keep using it.

What was the least expected way you’ve earned miles or points?

Never in a thousand years did I think my mom would get The Platinum Card® from American Express (Canadian version) —it’s completely at odds with the modest lifestyle I was raised into.  When I explained the benefits to her, though, and showed her how it was impossible not to profit by getting the card, she came around.  It goes to show that people are much more malleable than we give them credit for; that 25,000-point referral bonus was an extra special one for me.

What do you now know about collecting miles and points which you wish you knew when you started out?

I wish I had known more about the 3 major airline alliances, and that it’s a good idea to choose a favorite airline in each alliance to keep things as simple as possible.  Then, rather than learning the ins and outs of dozens of programs, you only need to learn 3 (at most).

What would your readers be surprised to know about you?

That Yore Oyster was launched completely by accident.  I’m even a bit hesitant to admit that now, since I did everything I could in the early days to make it look and feel like a legitimate business, but it’s the truth.  I had no intention of starting a flight hacking company; it only came into existence because of all the press my first project received.

Any parting words?

Travel will change your life in an infinite number of ways, but like all things, there can be too much of a good thing.  Though I’m obviously a huge advocate of unstructured, spontaneous, no-strings-attached world travel, I’ve been feeling burnt out lately and have decided to consciously slow down and focus on planting roots in one place (Berlin) for the time being.

Jordan – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!