Based on a True Story
This is the other side of the Hollywood Version of my story. And though all true — it simply wasn’t the whole story. So now I’ll add a few of the key details I left out.
After just two years my marriage was falling apart. We weren’t right for each other and never would be. I asked for a divorce. It was by far the hardest, most gut wrenching, and heart breaking decision I’ve ever had to make. I needed to get away. So I ran away — to Los Angeles.
Arriving in the so called City of Angels I had nothing and knew no one. I was alone and felt utterly lost. This was way outside my comfort zone. I’d read this quote somewhere: “Outside your comfort zone is where the magic happens.” Kinda corny I know. Yet here I was putting that theory to the test.
I woke up every morning wondering the same thing: what the hell am I doing? Before I could psych myself out too bad I’d throw on my running shoes and head out into the Hollywood Hills to distract myself.
The very first time I got to the top of Runyon Canyon and looked out at the view I was more awestruck then I’d ever been before. How in the world did I end up here? I realized just how hopelessly lost I’d become — and somehow simultaneously felt a strange sense of hope.
It’s a fairly steep climb up Runyon Canyon which on the flip side makes for a pretty precarious descent. Most people hike it. Few people run it. Especially the way down. I knew it was risky. People warned me, told me I was crazy. I did it anyway. It gave me goosebumps every time I felt my shoes skid and almost lose traction — it made me feel alive. Somehow I always made it down in one piece. It was a very effective mind clearing exercise.
I was desperate to try surfing. I needed the challenge; to prove something to myself. The typical tame lessons with big boards on little waves wouldn’t cut it; I stubbornly insisted on the shorter board and taller (up to 10ft) waves.
Mother nature kicked my ass. It was wonderfully humbling. At one point I remember being under water long enough to wonder which way is up?, should I panic?, and how long can I actually hold my breath? Yet I always came out of the water with the biggest stupidest smile plastered on my face. Ha! I didn’t drown — go me!
After days and days of hopelessly wandering Hollywood Blvd and the Venive Boardwalk I was lucky enough to find and get to know a guy who would show me unreal experiences you would typically never have access to. I was so grateful for these opportunities, but also I felt guilty. Why just me? Why not you too? Finally my life re-found some sense of purpose.
I lived out of a suitcase for 5 months. When I flew back to visit home I realized I no longer had a home in Ottawa: my ex got the house and condo in the divorce — as long as he didn’t touch my first business (which I may talk about in a future post if anyone’s interested). Fortunately my awesome buddy Craig (PageCloud Founder) said I could crash at his place.
Craig was the best mentor I could ask for. Daniel (Shopify Co-Founder) wanted to invest. So I prepped a pitch deck and met more investors. Everyone I shared with loved the idea. It was going so well!
One guy loved it so much he suggested he help me by rounding up a bunch of investor buddies of his. Sure, why not? I met each of them and they all loved the idea. This was so easy — life is so good! Or not.
One of the ‘buddies’ started to question my ability to lead: I was young and only had so much experience. At the last moment before the round was set to close, he demanded we change the terms — to give them more equity and control. And if I didn’t accept he, and all the buddies, would pull out.
Another big scary decision. Walk away from a quarter million dollars and hope like hell I can raise it again or get into a business marriage with men I couldn’t trust. Luckily I’d learned something from my failed marriage. And I wasn’t going to make that mistake again. Also, I don’t do take well to bullies. So in more ‘professional’ terms I told them to fuck off — admittedly with tears in my eyes cause at the end of the day I’m still human.
For the next week or so I woke up every morning feeling like I was going to throw up — and no, I wasn’t pregnant. I was thinking of how I’d wasted months of valuable time that might just ruin my chances at bringing this startup [different kind of baby] to life.
Thank god I still had Daniel. He promised he’d still invest — even offered to put in more if needed. But I still needed more. Then a true friend and very special human being named Jeff stepped in to help me find a couple more investors. And with one more guy I met at a poker home game I finally managed to close our first round: I had to raise a quarter million not once — but twice. Stressful as hell.
So yes, from the outside looking in I was living the dream — and in many ways I did. But it wasn’t all rainbows and butterflies. And it sure as hell wasn’t comfortable or easy.
If there’s one thing I truly believe it’s that everything happens for a reason. And it’s making the hard decisions that have led me to exactly where I am today. And there’s nowhere in the world I’d rather be.
