If you’ve followed me on YouTube, then you may already know that I did something totally out of character and something that people have described to me as absolutely insane! 

Let’s rewind a bit though. So, a few months ago I got an email from some guy named Ali who worked for a UK-based company called Fintech Finance. The subject line of his email read “A crazy idea for you!”

My first instinct was to hit the spam button because usually emails like that end up being “Come to Ethiopia, a relative you didn’t know existed died and left you a $1,000,000 inheritance!” But my curiosity got the best of me and I clicked open.

What the email contained was actually an awesome pitch to take part in the Money 20/20 Payments Race, a race similar to the popular TV show The Amazing Race. It would entail me travelling by myself from Toronto to Las Vegas, with a few checkpoints in between and daily challenges to complete. But to make it even more challenging, all the racers would be restricted to one form of payment to use (either gold, Bitcoin, contactless, cash or chip and pin) and a budget of only £1,500 (equal to $2,500 CDN).

This would be the second time this race would take place, the first one occurring this past June. That race was a bit different though since it was only 3 days and the racers only had to get themselves from London to Copenhagen without any other checkpoints. The race that I would be participating in would be twice the length (7 days), and would have me travelling to 4 different cities (not including the starting line in Toronto where luckily I already live).

Since this really did seem like a crazy idea, to make sure it was legit, the first thing I did was get Ali (the race’s organizer) on the phone. After a good 20-minute conversation, all my worries and questions were erased and I was on board for what turned into the most memorable (and adventurous) thing I’ve done all year.

And best of all, I vlogged my entire journey so you can see exactly what I went through.

Here’s a look at each day of the race (but if you’ve already watched them, scroll down to the bottom for my final review of the race!).

Day 1 – Toronto to Buffalo

This was probably the most stressful day of the race because I honestly had no idea what I was doing. I had never done anything like this. When I travel, I pre-plan everything and typically use Kayak or Expedia to book my travel and accommodation.

Since I was restricted to chip and pin where I had to physically put my credit card into the terminal and type in my pin, I wasn’t able to pre-plan or pre-book anything.

Once the race kicked off and I knew that my first challenge was to get myself to Cincinnati, at first I thought the best route would be to contact a travel agent to see if they could help. They could not. I called three different travel agents and not only were last-minute flights to Cincinnati upwards of $500, none of them accepted chip and pin (and yes, I was still in Canada at this point!).

Scrapping the idea of taking a plane to get where I needed to go, I decided maybe the bus would be a better option. I had overheard some of the other racers thinking of doing the same thing, so I went over to Union Station to see how I could book a bus ticket. Apparently all buses out of Toronto come out of the Greyhound Station right near Yonge and Dundas Square downtown. I hopped in a cab (that thankfully accepted chip and pin), raced over to the bus station and bought my bus ticket.

I ended up bumping into most of the other racers there, so I knew I probably made the right choice. Though, many of them decided to book tickets that would take them close to Cedar City, UT (since that was fairly close to the Grand Canyon, our last challenge). I knew I wouldn’t be able to survive a week living on a bus, so I just bought one ticket to Cincinnati then would figure out my next steps later on.

And it’s a good thing I did, because the bus is the worst! But I didn’t know that until Day 2…

Day 2 – Buffalo to Cincinnati

Day 2 was rough because most of it required me to be on the Greyhound bus, trying to sleep like a human pretzel. I’m telling you, I think my neck still hasn’t recovered.

Luckily, I was on the bus from Toronto to Columbus, OH with the other racers so I wasn’t alone and we kept each other’s spirits up. But what I didn’t include in this vlog was that when the other racers departed and I was alone on the bus from Columbus to Cincinnati, a fight almost broke out.

It was between a man and a woman, they were bickering back and forth culminating in the man telling the bus driver to kick the woman off because she was being verbally abusive. The bus driver (this small woman who was a total badass) got up, looked at both of them in the eyes and talked really calmly about how Greyhound’s policy was to have a safe journey where passengers showed respect to one another. If they couldn’t respect each other, then they would have to get off the bus.

Seeing as both people clearly needed to get somewhere, they both shut up and the bus was silent for pretty much the entire rest of the trip. And this all happened at like 6 or 7am!

When I finally got to Cincinnati, I booked it from the bus station because I had seen enough of them for a lifetime, and even at 10am it was still pretty sketchy. But at that point, I was exhausted and starving, and made my way to Fountain Square where I had to complete my challenge. I went to a CVS and bought a Ohio hat with chip and pin easily, but then it was impossible to find a food shop that would accept it (even Starbucks!).

So, I ended up making my way to a nearby hotel and booking a room. I took a good long nap, woke up and headed straight to the Subway across the street. Thankfully, they accepted chip and pin and I was able to cross off Challenge #1!

The next step for Day 3 would be getting myself out of Cincinnati and to a city close to the Grand Canyon. My first choice was Denver because I knew Michelle from Michelle is Money Hungry lived there, and because I heard Colorado was beautiful.

Day 3 – Cincinnati to Denver

The fact that I had to break Day 3 into two parts should show that Day 3 was absolute hell. Up until that point, the race was a breeze and just a bit tiring. But Day 3 was when some real panic set in and I was pretty much just starving all day.

Luckily I was able to complete Challenge #2 that day (mail something to someone in Singapore) before I even left the hotel, so I’m glad I was able to check that off right away.

After checking out of my hotel in Cincinnati, I asked a nice man (Steve from Florida, originally from Nova Scotia) if I could get a ride to the airport with him. He was headed there anyway and seemed nice and interested in my race (which isn’t a good enough reason to get into a stranger’s car, but it is what it is).

We got to the airport, Steve ran off to catch his flight since he was running late, and I thought it would be easy-peasy buying a flight at the airport with chip and pin. Wrong! It was impossible. So much so that an attendee working for Delta actually laughed when I asked if any airline accepted it in the airport.

My first thought was to see if could convince someone in the airport to buy me a flight, and I was actually almost successful. The only place that did accept chip and pin was the electronics store, and I saw a young man in there looking like he wanted to buy something. So, I approached him, explained my situation and he was eager to help. He said he had some points he could use, but unfortunately after trying to figure it out for 15 minutes or so, he realized he didn’t have enough points to buy me a flight nor had enough cash to just buy one outright.

After that, I decided to see if the personal finance blogger community could come and save me, and luckily Cait Flanders was ready to help and booked me a flight to Denver. As per the race rules, I was only allowed to get someone to buy me something if they didn’t need anything in return or if I could repay them with my payment method. Since me and Cait were roommates at FinCon, I was able to use my chip and pin credit card to pay for our room.

I thought buying a flight was going to be the hard part, but actually the hard part was trying to feed myself. Once I got through security, not one place accepted chip and pin and I only had a few protein bars left in my bag (one of which I ate for breakfast).

After searching the entire area, I discovered that the AAA Members Lounge accepted chip and pin. I shelled out $40 to stay there and snack on their “light lunch” which consisted of chips, carrots, beer and more chips.

That’s why when I got to Chicago for my layover, I almost cried when I found out McDonald’s accepted chip and pin. Finally, I could put something in my belly that was somewhat close to real food.

Day 4 – A Day in Denver

Day 4 in Denver was a dream compared to Day 3. I was able to hang out with Michelle in Denver all day, relax at a coffee shop, and get a local’s tour of Denver which was such a treat!

I was also super thankful that Challenge #3 was an easy one in that I just had to record myself sharing my biggest failure and what I learned from it.

The only hard part about Day 4 was finding dinner. I thought I’d be able to pop downtown, grab some food, and chill out in my room the rest of the night editing footage. Nope! Literally no restaurant, café or shop accepted chip and pin except for good ol’ Walgreens.

It wasn’t exactly how I wanted to cap off a great day of exploring Denver, but when you’re starving, a frozen mac n’ cheese and Gatorade is pretty much your best bet.

I was also able to book a hotel in Las Vegas (though it took me a while because again, NO ONE ACCEPTS CHIP AND PIN), and I got my blogger pal Barry Choi from Money We Have to buy me a plane ticket to Las Vegas and a bus tour to the Grand Canyon (which in hindsight, was my biggest downfall).

Day 5 – Denver to Las Vegas

Since my flight to Las Vegas wasn’t until 10pm that night, Michelle was nice enough to take me out for brunch, then take me to Red Rocks (which was absolutely beautiful). We also made a little trip to Boulder which I didn’t include in the vlog, but it was such a cute little town. It really reminded me of Whistler, BC, which also made me get really homesick.

After another fun day out, Michelle drove me to the train station so I could get to the airport. From there, I took my less than 2 hour flight (that cost $38!) to Las Vegas. The only thing I really had left to worry about was getting from the Las Vegas airport to The Mirage where I was staying.

Since I was getting more used to talking to strangers, I chatted up the guy sitting next to me on the flight and wound up getting a free taxi ride with him to my hotel. Thank god for the kindness of strangers!

Day 6 – Las Vegas to the Grand Canyon (and Back Again)

The Grand Canyon was incredible. I’m gonna start there, because the trip to and from there was literally the worst. Yes, worse than my bus trip from Toronto to Cincinnati. What saved me from going crazy on the 16-hour bus ride was the knowledge that I was almost done the race, and the fact that I made a friend (Stephanie) who sat next to me on the bus.

But let’s get back to the good bit. The Grand Canyon was incredible. Photos and video footage just don’t do it justice. It really is something you need to see in person, and I’m so thankful I got to check it off my bucket list!

I was even able to buy a few souvenirs (a magnet for my fridge and a print of a painting) because the gift shop surprisingly accepted chip and pin.

After being in total awe of nature for 3 hours, it was back on the bus for what should have been a 5-hour drive. It turned out to be 7 hours because as luck would have it there was a car accident on the highway, which tacked on 2 more hours to our journey.

Getting back to my hotel after 16 hours, almost no sleep from the night before, and smelling like someone’s worst nightmare, I got back to The Mirage where I handed over my last day’s footage to one of the race’s video editors. It was by far the most anticlimactic finish to the race, but at least I was done. I didn’t have to worry about booking flights or hotels anymore. I didn’t have to ask store clerks if they accepted chip and pin anymore. I could finally wear real clothes again!

But still, I wanted my crossing the finish line moment. And I got it on Day 7 (sort of).

Day 7 – Crossing the Finish Line

I woke up on Day 7 feeling absolutely relieved and a bit in disbelief that I actually did it. I successfully completed the race, although I knew I didn’t win. I wasn’t sure in what place I got, but I knew that long bus trip meant I didn’t get the top spot.

Still, I made my way to The Venetian where the Money 20/20 conference was taking place and crossed the finish line! It wasn’t exactly how I’d imagined, but it still felt good.

After that, I got to check into my hotel room, watched some bad reality TV and took the longest nap of my life. That night, I met up with the other racers for a party hosted by my race sponsor AEVI, and indulged in free tacos, mini-burgers and all the margaritas. It was also a great chance to exchange stories with the other racers, who up until that point I had only hung out with on Day 1 and chatted with in our WhatsApp group.

After hearing some of their stories, I think my trip was actually the least crazy of them all!

Click here to watch the other racers’ vlogs from the race

The next day, we were all brought on stage at the conference to share our journeys and for the winner of the race to be crowned. Surprisingly, Amelie who had Bitcoin won the race! And I say it was a surprise because in the first race back in June, the racer who had Bitcoin couldn’t even make it out of London! In second place there was Ash with gold, then Stu with cash, myself with chip and pin and Jordan with contactless.

My Review of the Race

So, the race is officially over. I’ve had a few weeks to reflect on everything that happened, and my overall feeling is that I’m so glad I did it. I pushed myself and grew as a person because of it. I reminded myself how strong and resilient I am. And most importantly, I had a crazy adventure I’ll never forget.

Not only that, I made some awesome friends from the UK. To watch their vlogs from the race, I’ve compiled them in this special YouTube playlist for you to check out.

Now that the race is over and I was able to do conquer some major fears, there’s really only one thing that remains to be answered…should I do this again in Asia?

I’d love to know your thoughts. Should I do it again, or should I just let it be and let someone else take the reins?