You Can’t Make This Shit Up (Part I)

When I think back to how I got to where I am today I must admit even I sometimes find certain parts of my story hard to believe. When I meet new people who ask me about my past I often surprised myself as I recollect memories. The story of how I ended up is unlikely as it was unplanned.

“In order for art to imitate life, first you must have a life.”

I once read this quote and I absolutely loved it. I’d just moved to LA and why not try writing a movie script? Cause I’m in Hollywood aren’t I? I liked the challenge. But what would I write about? If only I had an interesting life…

Well I thought, to practice why not start writing a script about my idea to start writing a script — based on a true story [my life] up to now, then eventually switching over to my imagined story of what I would do if I were to actually try to sell my script (as a stubborn young entrepreneur). Truth is I had this crazy theory that this could somehow manifest as a self fulfilling prophecy.

So I found an online screen writing software called Celtx, taught myself movie script formatting, and started to write. I decided to set the stage by explaining how my lead character [yours truly] found herself in Hollywood: a series of random events from my past couple years.

The following are the experiences that would impact my entire perspective on life and be instrumental in shaping the next stage of my post divorce life. There are people you meet in this world who truly open your eyes. For the sake of this story there are two men who played a leading role in altering my viewpoint, my mindset, and inevitably my trajectory.

The first scene fades in at StartupFest in Montreal to the keynote speech by Jeff Hoffman (founder & original CEO of Priceline). Nothing had ever resonated with me so profoundly . Not even close. To say I was inspired is an understatement. I dreamed of how unbelievable it would be to have a mentor like that.

Days later I still couldn’t stop thinking about this talk. So I had one of my ideas. Let’s see if I can find Jeff on LinkedIn. To my surprise I did. Without a second thought I sent him a message saying how much of an impact his talk had had on me — and maybe, just maybe, he’d be willing to speak with me?

I have a tendency to do these things rather spontaneously and then almost instantly forget about them because realistically I know how much of a totally unlikely shot in the dark it is. You can imagine my shock when I actually get a message back to coordinate a time for a call.

I was way too excited and honestly don’t remember much of our conversation other than him mentioning he was giving another keynote in Canada in a few months. He asked if Waterloo was far from Ottawa. It’s a 7 hour train ride but I just said I’ll be there. “Lets have dinner then”. Utter disbelief.

When we meet in Waterloo and look for a place to eat we end up settling on this dingy little pub. Looking at the menu he asks “What’s this poutine thing?”. I laugh and explain. “We must have this”. So we shared a poutine as we chatted about startups, life and entrepreneurship.

At one point I said something and he just stopped me. He simply stated that he knew I would be successful. I asked him how he could possibly make such a statement having just met me. He said he could already see my determination and competitiveness — also “It’s not about the money with you, you want to win. That’s why you will succeed.”

What struck was not just the fact that an entrepreneur I admired so greatly saw and identified something in me that no one else ever had, but it was also the very first time in my life I actually felt like someone really understood me. This was the very moment I finally understood why I had never felt like I fit in. Because where I fit in, where I was understood, was with other entrepreneurs. I did not grow up in an entrepreneurial family nor have any entrepreneurial friends — this was a whole new mindset I’d never directly experienced.

The next morning Jeff gave the keynote at Communitech’s Techtoberfest. Of course I was there in the front row. Jeff began his talk and I hung onto every word. All of a sudden his speech took an unusual turn. He says he wants to share a story about someone who was in the audience. No. He wouldn’t…

He did. He told everyone my story: how I’d reached out, jumped on a train, and had dinner last night. To my horror he even called me on-stage so for the rest of the event everyone knew who I was — which is rather intimidating for an introvert like me.

A few hours later Jeff had to catch aflight to DC where he worked with Obama and the White House as Global Ambassador for Entrepreneurship. He made sure to say goodbye before he left and promised we’d keep in touch.

That’s Part I. Cut scene. Part II here.