How I
Stumbled into
Entrepreneurship

What’s my story? Why this blog?

For some people, entrepreneurship is a calling – a strong inner impulse that pushes them to pursue exciting and often risky career opportunities.

But for many of us, it just happens.

Let me tell you how I stumbled into entrepreneurship, and my multi-path career. 

In 2012, I had a stable career that fulfilled me – or at least, I thought it fulfilled me. I had been climbing the corporate ladder with industry leader KPMG for over twenty years, looking for the next rung as soon as I landed on the current one. Around that time, my Mum’s failing health meant that my parents needed to downsize. Part of that downsizing exercise led me to discover the tricycle of my little brother Lonny, who had passed away decades earlier after corrective surgery for congenital heart disease. That tricycle had helped Lonny feel ‘normal’ – he couldn’t run like the other kids, but with the trike, he could keep up with them. Inspired by the trike and the memory of my little brother, I decided to start Lonny’s Smile Foundation, a charity to give kids with special hearts the chance to experience what other kids do, such as going to summer camp. Did I set out to start a charity? Absolutely not – and yet that’s what I did, in 2010.

With Dr. Joel Kirsh, Paediatric Cardiologist & Founder and Medical Director of Camp Oki.

Photograph by Isaac Peiris

With this charity as as my passion and second career path in what was now becoming a portfolio, I kept climbing the corporate ladder, until one day I met Murray Foster from the band Great Big Sea and asked him if he’d host the annual fundraising Gala for Lonny’s Smile. I didn’t know much about him – just that he was a talented musician from my favourite Canadian band, and that he had a good heart, because he signed on to host the event without any hesitation. And so our connection began. The day after Murray hosted our second Gala, he reached out to me. “I’m doing a feature film. Would you like to work with me on it?” After falling off my chair, I said yes, without any hesitation or clue what it meant. I just knew with every cell of my being that I could NOT pass it up. As I’ve said to many people since, “You never know who’s watching you and what they’re observing.” Turns out, Murray was watching what I was doing for Lonny’s Smile – how I built relationships, how I raised funds, how I presented myself. And he wanted my skill set to be a part of his movie. After a quick trip the next morning to The World’s Biggest Book Store to buy a couple of books on fundraising for films, I mustered up all of the courage that I could for a role I was convinced I was ill-equipped for (classic Imposter Syndrome) and brought everything I knew and had experienced to the new job at hand. Less than two years later, I had raised the funds we needed through private investors, delivered unforgettable flash mob events, successfully pitched CBC’s Dragons’ Den (gaining exposure to over 2 million viewers), and landed an Executive Producer credit on my first feature film, “The Cocksure Lads Movie.” Most importantly, I had built a lifelong friendship and collaboration with Murray.

As luck would have it (but luck, I’ve found, is just an expression), the Producer of the film was watching me too. After the film wrapped up, he asked me to join his production company, Spiral Entertainment Ltd., as Executive Director of Business Development.

Did I set out to add a career in the film and television industry to my portfolio? Heck no! I had always wanted to be part of the industry, but it wasn’t one of the rungs on my ladder. Guess I hadn’t looked around to realize that there was more than one ladder.

Then one day, SMACK! Someone pulled my ladder right out from under me. Almost twenty-five years into my comfortable corporate career, I found out that the ladder rung I was standing on wasn’t as solid as I thought it was, and my role was eliminated through restructuring.

Truth be told, I had talked to Murray for a long time about making an exit. The chair (paycheque, benefits, routine) was just too comfy, the handcuffs too golden.

So when I met up with Murray right after I got the news, he said exactly what I needed to hear: “That’s amazing! You’ve been wanting this to happen for a long time – and whether you get pushed or you jump, you land in the same place!” He was right. I had been imagining myself somewhere else, usually walking on the boardwalk at the Beach in my jeans (translation – doing what I wanted, when I wanted, how I wanted) ever since I started working with him on his film. I felt like I was “home”– where I was always meant to be.

Since then, my life has continued to take twists and turns, to the point that frankly I can’t see it being any other way now. I still work part-time as an independent contractor for KPMG (an incredible organization that’s consistently recognized on multiple fronts as a top employer). I’m also Partner in Crazy D’s Prebiotic Sodas, a company that’s created a whole new category in the beverage industry, leading our Corporate Social Responsibility Strategy – the perfect fit for my “heart” and the skills and experience I’ve gained through Lonny’s Smile and my work with other non-profits. And during all this, I’ve come onboard as a Partner and helped launch Connectiv Innovation, a technology innovation consulting firm which leverages many aspects of my skill set – my corporate experience, my deep entrepreneurial spirit (which I didn’t know I had) and my experience in and love for the non-profit sector (we’re establishing an advocacy arm focused on improving the lives of Canadians), something I’m deeply committed to.

So, why this blog?

A lot of us look around and say, “Must be nice for people who know exactly where they’re headed – to have that clear vision and focus.” But I only know literally one person who did that – the rest of us are from that unsettling and confusing club that just finds their way as they move along. I’m still finding my way, and I’ve now come to the realization that I probably won’t ever arrive there – I’m now content that this is truly how it’s supposed to be, at least for me.

I’ve also come to the realization that I need a multi-path career – a curated medley of part-time careers that allows me to earn the money I need while doing multiple things simultaneously that interest me, make me happier, and provide me with greater flexibility.

I’m looking forward to taking this journey with you and sharing some of what I’ve learned along the way. I hope I can offer something that’s relevant for you, and that you can tweak it until it helps you move forward down your own path. Maybe it will spark something in you. Hopefully you’ll find something you can take tangible action on. But I also know that I will learn as much from you (and probably much more than I’m even imagining now). Because that’s exactly how I got here in the first place, and if I took the time to credit everyone who’s had a part in that, well … I’d never get around to writing a blog! So, let’s do this. As my pal and portfolio career co-conspirator Isaac says, “I GOT YOU”.