My Journey With Points & Miles: Kyle

It was April of 2014 and I had just gotten engaged. I was on an Alaska Airlines flight to Puerto Vallarta with my family on our last vacation as a family of 4 before my wife was added to the family later that year.

Secrets Vallarta Bay Sunset
Secreta Vallarta Bay Pool at Sunset

The flight attendant did her credit card schpeel during the flight and announced that if you handed your application in before we landed that you’d get an extra 1,000 points.

The welcome bonus was now 26,000 points instead of 25,000. That seemed like a good enough offer for me.

I opened the application and noticed one of the requirements was an income greater than $80,000. Uhh, I had just finished college and didn’t have a job.

The next line read “Or a household income over $120,000”.

Well between my brother, my mom, and my dad, we were over that amount. Perfect!

So I filled out the application and then handed in my application as I got off the plane.

When I got back from my vacation I was the proud owner of an Alaska Airlines World Elite Mastercard from MBNA. To this day it is one of my favourite cards.

I thought to myself, “can I have two of these cards?” So, I applied for a second one. Approved. Hmm…

I didn’t bother to push my luck going for any more than that but I later found out that people had gotten up to 8.

For whatever reason, I never bothered to explore this much further since I didn’t realize it was such a lucrative hobby. So, I laid low for a few years just earning Alaska miles one mile at a time.

Then in late 2016, I came across a blog post titled “What It’s Like To Fly In The World’s Most Expensive Airline Seat” or something like that. It’s now titled “What It’s Like To Fly The $23,000 Singapore Suites Class” by Derek Low.

It’s about how Derek used his frequent flier miles for a First Class seat in Singapore Airlines Suites Class (First Class).

That got me really intrigued about this and how could I do something similar with the points and miles I had stashed and how I could earn more.

The problem was, there were no resources out there on how to help. There was one blog that was okay at the time and there was one forum that I found. That was it.

Luckily, the blog provided a decent starting point and I figured the rest out on my own with the help of some friends I made online.

Within one year, I had hundreds of thousands of points and miles and was ready to book a First Class trip.

I made some mistakes along the way, which is part of the reason I wanted to start this business; to help you guys avoid the same mistakes I did because they ended up costing me tens of thousands of points and miles plus cash out of my own pocket.

Then my chance came. It was late January of 2018 when Adam was in Bali and called me to tell me that his travel partner had decided to go home early. He was upset and jokingly through the idea out there that I should go travel with him. I was down; so, I proposed the idea to my wife Sam who wasn’t a huge fan, naturally. We had 2 boys under 2 at home and she didn’t want to do life by herself for the next 10 or so days. I told Adam “no”.

Then my dad called and said “Do you and Sam want to go travel Bali with Adam? I’ll pay for half your flights and we can watch the kids.”

Even Sam couldn’t say no to that offer. I also just happened to have a couple hundred thousand Alaska miles in my account which was enough to get us there in First Class on Cathay Pacific. The route was Vancouver to Hong Kong to Bali. The last leg would be in Business Class since Cathay doesn’t operate First Class to Bali.

When I searched for availability, only Vancouver to New York to Hong Kong to Bali was available. That meant we had to route backwards through New York to get there. But it also meant about 5 more hours in First Class. Poor us…

Cathay First Class Dining
Sitting in the buddy seat so my wife and I can dine together.
Cathay Pacific Caviar
Caviar for 2 please!

That was one of the best trips of my life and flying First Class for the first time was an experience I will never forget.

I was now all in on this hobby. I wanted to do this more. I wanted to take my family somewhere so when we got back from Bali, Sam and I started to plan a family trip to Europe.

So, I started churning really aggressively. I was now on pace to earn over one million points that year, more than enough to take my family to Europe.

We booked a trip to Europe in Business Class for the 4 of us. We planned it strategically so that we would get back just before my oldest son turned 2 so that we wouldn’t have to get him his own seat.

This was our trip:

Vancouver to Toronto where we stopped for several days to visit friends.

Toronto to Istanbul to Paris where we stopped for a week. (We stayed right near the Eiffel Tower in a luxurious 5-star hotel.)

Paris to Zurich to Athens where we stopped for a couple of days before getting on another plane to Santorini where we stayed for 3 nights.

Then we took a boat to Crete for 6 nights where we stayed at a 5-star luxury resort where our “room” was a villa with a private hot tub on our balcony and our own private pool in the “backyard”.

We then flew back to Athens to Zurich to Chicago to Montreal to Vancouver on our way home.

Domes of Elounda Villa
Family time in our “backyard” at Domes of Elounda in Crete, Greece. No need for the hotel pool when you have your own.

If you found this page by taking our email course, you’ll learn more about this trip inside the course. 

If you aren’t signed up for our FREE Crash Course to Luxury where we teach you all about this hobby and how to do what we do, you can sign up below!


This hobby has brought me great joy and I’m so excited to be able to travel more with my family and create amazing memories with them all around the world.

I’ve since got my parents involved and I’m excited to see them experience travel in a way that they wouldn’t otherwise be able to afford.

I continue to churn but not as aggressively as I used to. I have more points now than I know what to do with. My balance across all of my points and miles programs is currently sitting at 3,775,264. 

I can’t get enough time off work nor find people to watch our 3 kids to use all of those points for vacation which is why I don’t need to churn as aggressively as I used to. I plan to travel a lot more once my kids are older so I continue to earn for the future. Though many people, including myself, will tell you that isn’t the best idea since points and miles are a depreciating asset as loyalty programs get devalued somewhat regularly.

ANA First Class Krug Champagne
Unlimited pours of $375 Krug Champange

If I choose to do so, I never have to fly economy again. I definitely won’t be taking any longhaul flight in economy anytime soon but I don’t mind the shorter flights in economy, it’s really not that bad. Some people gasp at economy after being in this hobby and flying First and Business Class; I look at First and Business Class as a luxury rather than my new norm. Plus, economy saves points and miles but it also keeps me humble and reminds me to appreciate the situation I’m fortunate enough to be in.

I plan to help others experience travel in a way they never would have thought possible by giving away points and miles in the future and I think that will bring me more joy than taking another First Class flight or staying in another 5-star hotel like the St Regis Osaka where we got upgraded to the Vice Presidential Matsu Suite with a retail cost of $2,500 per night.

Thanks for reading my story and I hope I’ve inspired you to explore the world in ways you never thought possible and if you sign up as a Points Brothers member I look forward to helping you see the world in ways you never thought possible.

If you are interested in learning more and staying up to date with what’s going on in this hobby, join our Facebook group and follow us on Instagram!

PS. I highly suggest reading Adam’s Journey as well as we are very different travellers