The Hollywood Version

I needed a change of scenery. So I had a brilliant idea: move to Los Angeles. Why not right? I bought a one-way plane ticket, booked an Airbnb, and was ready for a new adventure.

Every morning I would wake up, go to Runyon Canyon, and run in the Hollywood Hills. I always stopped at the top to gaze across at the Hollywood sign and out over the massive expanse that is the city of Los Angeles all the way out to the ocean — with my iPod blasting City of Angels by Thirty Seconds to Mars. So surreal. It gave me goosebumps every time.

I was determined to learn to surf, this had long been high up on my bucket list. But I definitely didn’t want to settle for the lame commercialized lessons. I was in LA after all — surrounded by surfer dudes — surely one of them could show me? I wanted the real deal. But it wasn’t so simple.

Fortunately I had nothing but time, so I resorted to wandering the streets until one day I met a surfer dude happy to share his favourite hobby. I had the most incredible experience — he knew all the best spots, was a super cool dude, and had great tips and stories to share.

And not only was the surfing amazing, but this led to many other unique experiences: riding a motorcycle down the 101 into Malibu, shooting at the LA gun club (after almost accidentally walking through Skid Row), and much more. You couldn’t ask for more authentic experiences — with the coolest, realest, people in LALAland.

When I shared this on Facebook (proof of life for my mother not to worry) the response shocked me: people I hadn’t heard from in years sent messages asking how the hell I was doing all this. They were jealous. I felt guilty. I believe everyone should have access to this. I found my mission.

I was in LA for about 5 months — during which it rained for a grand total of about 3o minutes [aka drought] and was pretty much 95f and sunny every single day. I loved it. But I knew I could only stay in the US for one more month before getting in serious trouble so I started thinking about Visas.

I decided to fly home for a quick visit to see friends and family and ended up crashing at my buddy Craig’s place (PageCloud Founder & CEO). He kept bugging me to tell him what I was up to — I mentioned I had this crazy idea but I didn’t want to tell him because I knew he was a tough critic and I assumed he would crush my startup dreams.

Finally I caved and told him, bracing for the worst. His response caught me completely off guard: ‘You have to build this. Wait. What? He told me I could stay as long as I needed as long as I worked on this — and mentored me every evening after working at PageCloud all day. Which makes for a funny story when people ask me how I found my advisors…

Then I met Daniel (Shopify Co-Founder) for the first time. He generously agreed to a 30 minute coffee. We talked for 3 hours. When he asked what I do I told him my idea. He asked if I was fundraising. Uh ya…? I mean, yes, totally fundraising. As of now. He said he was interested in investing on one condition: I build this in Ottawa — not run away to LA again. Ok fine.

So I just left my stuff in LA and raised a quarter million dollars with nothing but a dream. XPR was born.

Kinda sounds like a movie screenplay doesn’t it? I go to LA and magically figure out what to do with my life [so cliche]. I have a startup idea that gets funded. Wow, how inspiring. At least that’s what I tell people — cause everyone wants a blockbuster origin story.

Thing is, there’s two sides to every story. That’s the Hollywood version—ironically literally straight from Hollywood.

Next up I tell you the other side of the story.