My Leap (a career 180)

Eric Janssen
Feb 5 · 12 min read

I always wanted to be rich.

I grew up in a middle class family, living a good life, going on the occasional family vacation to Disneyland every four years, presents fully stocked under the tree at Christmas. But my parents had to make choices: vacation or new washing machine. New muffler for the car, or fix the fence. I never wanted to be like that. I wanted to be able to do it all whenever I wanted. Complete freedom. Fancy car. New clothes.

Growing up, my parents always told me that the rich people were doctors and lawyers and so, if I wanted to be rich those were my options. I had always hated going to the doctor, so as much as I wanted to drive fast cars, I knew that path wasn’t for me. At the time, my best friend’s dad was a successful lawyer, so by process of elimination, I decided that I would do that.

I taught myself to love the idea of researching a case and presenting a compelling argument to a judge or jury. I watched A Few Good Men once a week, participated in moot court trials, and worked extra hard to win the speech competition almost every year. (My best friend was so mad when my speech on playing football beat out his on Prohibition — BORING!)

Classic.

For an additional resume builder, I decided that doing an internship at a law firm would help build my profile so I ended up actually working at my best friends dad’s law firm in my last year of high school.

Turns out that maybe actually trying the thing that you think you might want to do for the rest of your life is a good idea.

To my surprise, I hated it. After assisting several partners in preparing cases, and doing a ton of paperwork at the office, turns out I hated the actual work that those lawyers did 99% of the time. Great. Now what?

With the only two options that I’d ever known to ‘get rich’ exhausted, I had no idea what to do. I took a summer job at a local private golf course in the backshop (best job ever) — and continued to contemplate my life.

One day, a guest at the club had finished his round of golf and drove his golf cart to this shimmering black Porsche 911 Turbo. I raced over to him knowing that the rich people always tipped well and asked ‘How’d it go out there’? He replied, “Amazing, I just made $100,000”.

Inner Monologue: $100,000! When I thought I was going to be a lawyer, that was like 600 hours of work at ~$150/hour! How the…)

I had to ask: “Did you win a huge bet!?”

“No,” he replied. “I just closed a big deal.”

A DEAL? What was a deal?

Turns out this guy was an entrepreneur, but mainly focused on sales. His company sold software to large enterprises and while on the golf course, he’d had a call with a client and had received a verbal go ahead on a big deal he’d been working on.

As I cleaned my drool off of his golf clubs, he peeled off a $100 bill for me as a tip, loaded his clubs in the car, and ripped it down the road. Wow.

Sorry, I’ll clean that right up.

It was around this time that the idea of going into ‘business’ sounded appealing — and seemed like a much more ‘practical’ (read: easy) way to get rich.

This desire to be rich drove me. It influenced the school I went to, and the things I chose to invest my time in (starting companies).

In my first year of university, I took a first year business course called Business 1220: a fundamentals of business and accounting course taught using the case-based method of learning which was unique to a handful of business schools (like the Ivey School of Business, and Harvard Business School. My prof. was young, a new Ivey graduate, and was a huge inspiration to me. He brought a passion into the classroom that I hadn’t really seen before, and connected with his students so naturally.

Inner Monologue: That looks so AMAZING but don’t you dare think of doing that, there’s no way to get rich being a TEACHER!

The first company I started in university was an online network linking young entrepreneurs with business partners, mentors, and other resources (shout-out to those early days Natalie MacNeil!).

We researched, compiled content, and drafted our own original content pieces. Some of the materials I assembled on the basics of start-up sales got picked up by a local organization who asked us to come and present on this topic to a group of other local entrepreneurs. It was thrilling. I loved condensing my own learning, and finding a way to deliver the content in a compelling way.

Inner Monologue: Okay, well that WAS fun. Maybe you should find more stuff like this to do, but again, stay focused Eric — we know that the way to get rich is starting companies! Don’t get too side-tracked by doing this thing you actually love to do.

Having enjoyed this experience, I applied to a teaching project through my school to teach business fundamentals and entrepreneurship-related content in Europe for three weeks with a handful of other MBA students. I ended up getting the role, and travelling to Tolyatti, Russia (Western Russia) to teach other young entrepreneurs.

This was an incredible experience. I was an expert. The students loved me. And I forged deep connections with my students and colleagues over those weeks that were inspiring and exciting.

When I returned home from Russia, I made the decision not to apply for any other full time positions except for an open position to teach Business 1220, the same class that I had loved so much in my first year of university.

Inner Monologue: Okay, apply to do this job. The presentation skills you learn will be so valuable to one day pitch your company on Dragon’s Den, and the flexibility will allow you to keep working on some side projects so that you can get rich! Let’s not forget: we want to be rich so don’t get distracted doing all this ‘fun’ stuff!

I worked hard, students seemed to enjoy my classes, and I had two incredible years as a Lecturer at Ivey. (Plus, my grandparents were really proud). I’ve stayed connected to many of my students to this day. Talk about meaning, and impact.

Aw, thanks Raza.
Stop…
STOP IT…(says with huge smile eager for more compliments)
Thanks Julie!

I think part of what made me successful in the role was my ability to bring in real life examples that I’d gone through as a student entrepreneur, and make the content highly relevant to my students. I had learned some hard lessons building my own business and had a few scars, and stories to tell.

I also remembered what it was like not to know all this stuff. I was only one degree of separation away from my students — having been in their shoes just years before. Often, ‘experts’ are so experienced that they forget what it’s like not to understand the concepts they’re teaching.

While I loved the experience, I told myself that it was time to re-focus. I needed to go hit a home run, learn way more things and that one day I’d be back in the classroom — maybe when I was older and more successful.

I went on to join several early-stage startups, always in a sales capacity.

I have a strong opinion that in early stage companies, there are only two things that matter: building and selling.

I’m no programmer, or builder so I took to selling.

I became quite good at building out sales and marketing collateral, pitch decks, refining messaging, and ultimately getting traction for early and growth-stage companies.

These companies took me from Toronto, to New York, and San Francisco, and I learned a ton in the process. I spent time at Mobiroo, Wrapp [acquired by Meniga], and Intellitix — where I earned a decade-long start-up/sales MBA.

Cool story, bro.

At Intellitix, I became a partner and Chief Revenue Officer. I had a ton of fun, work with stunning, and brilliant colleagues, and have had the opportunity to see the world, while getting to befriend the organizers behind some of the world’s most sought-after events like Coachella, Bonnaroo, Tomorrowland, Boots & Hearts, and The Crossfit Games.

Tomorrowlandddddd — unsa, unsa, unsa…

By 2015, travel was taking it’s toll. In my peak, I was travelling 250,000 miles a year and there was a stint where I had an apartment in New York, and in Toronto. It seemed glamorous, but was too much.

On a flight back from London England, my wife and I wrote out the things that would need to happen in order for us to be able to move back to the small town that we grew up in. We made a 12-month plan, and had committed to action — and when we found out we were pregnant with our first child (Jack!) we turned that 12-month plan into a 6-month plan and moved out of Toronto and back home to Windsor.

Local news was happy to share our story.

While we’d loved living in other parts of the world, and appreciated our time in Toronto, we had no family in the city, which would make raising children challenging.

Making this decision to move, on our own terms was something we were really proud of. It wasn’t logical to everyone, but it made so much sense to us. We were able to move back to a smaller town and buy a massive dream home in the most desirable location in town.

It was amazing to be close to family, and I had an office about 60 minutes away so I spent about 70% of my time travelling, and 30% of my time split between commuting to the office and working from home.


Intellitix had grown substantially to about 120 people and I was overseeing a team of ~20 sales people. We were doing business in 15 countries, and growing on all fronts.

Though life was busy, I stayed involved at my alma mater, visiting Western to run startup selling workshops at the campus incubator and doing occasional keynotes in the startup community. Every time I ‘performed’ I got a high that I didn’t feel anywhere else. Not when I closed a big deal, or ‘cracked’ a new strategy, or anywhere else professionally.

Inner Monologue: Hey, maybe this was the ‘find your passion’ thing that everyone always talks about.

They say work is either a thing you do to earn the money to have the life you want, or what you do to achieve your mission — or some mix of the two.

My career in the start-up and scale-up ecosystem had been pursuing the former. I had started companies from scratch, turned them around, scaled them, and hired some incredible people — people I’d consider family — but the life I was living wasn’t sustainable. When we had baby #2 (Grace!), things had reached their breaking point.

The balls are all staying in the air! Oh no…

The more I grew the companies, the more I was away from my family — travelling hundreds of thousands of miles a year to dozens of countries but really seeing none of them except for the airports, and hotels. Things that were once important to me: a commitment to fitness, family, playing piano or drums, being thoughtful — those things weren’t things that described me anymore.

I became the ‘busy guy’ to friends and family: always on the road, always on the phone, always travelling. I didn’t like the person I had become. The ‘successful’ people in the startup community talked about not taking their partners on a vacation for years, living for the weekend, and savouring the moments with your kids because before I knew it, they’d be gone. I didn’t want this inevitability.

After delivering several ‘Startup Sales’ sessions at Ivey, I connected well with several of the faculty members. I had been pushing the importance of sales at an undergraduate level for years, and it seemed my message was finally ringing in the ears of the school. Students who attended the sessions made their voices heard that this needed to be taught and I soon found myself considering a full-time position in the Entrepreneurship faculty at the business school.


Inner monologue: Eric, you haven’t had your ‘home run’ yet…your ‘career maker’ or significant exit. Get your ass back out there, you can’t teach yet!

On a bi-weekly basis, I’d return to Toronto to meet with my friends in the tech ecosystem. Several had started companies years before and had seen significant exits. Others were raising millions in capital and taking a run at the ‘next big thing’ in AI, or Blockchain tech.

So what was I really after? We’d proved money wasn’t the prime motivator because we were financially stable and had already decided that, if anything, we wanted to re-prioritize, downsize, and live with less. We wanted to purge things and live below our means.

What I was really after was meaning. I became obsessed with learning how companies went about growth. How they went about acquiring customers, mastering messaging, and the systems and processes they put in place to scale. I wanted to bottle all of this up to bring it to those that needed it: our next generation of entrepreneurs.

I envisioned myself at 85, where I’d say to myself: “Self, what made life worth living?”

It was meaning, friendships, relationships, and ultimately doing things that made me feel the way I did when I was teaching — in my element.

I think of my life as a series of chapters. This chapter is about following my heart, providing more value to my students and the community than I am taking in return, and knowing that following this path, putting myself out there, and doing what feels natural will allow Grace into my life.

How much Grace? THIS much!

I made the leap in the summer of 2018 and it was the best thing I’ve ever done. I cleared my plate so that I could focus on delivering a world-class sales curriculum at Ivey and I’m in the process of doing just that. I wrote out the Principles that I think are important for me to follow as I follow this path.

I even wrote about my decision to start ‘teaching sales’, and a huge nod of support from the community — and received literally hundreds of direct messages from entrepreneurs and senior leaders telling me that this is so badly needed and asking how they could help.

Validation!

I stay connected to the startup community by meeting with sales leaders, and doing consulting work to understand and work through their challenges with them. I then develop my curriculum so that my students are plug-ins for these companies. I also do sales consulting work for high-growth companies and continue to do Business Development and Advisory work at Intellitix so that I can stay sharp, and maintain my ‘practitioner’ side.

You only get to do this one time, and we’re doing it our way. My heart is full and I couldn’t be more fulfilled.

From the beginning, an inner voice told me that this was what I’m supposed to be doing, so go do it. And I finally listened. I finally did.

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Killing the sales stigma & teaching sales @iveybusiness www.hustleandgrit.ca