What I learned from Rogers, and how it took working at early stage companies to realize it.

It’s been 10 years since I graduated university, and holy shit did things turn out completely different than I expected. Like really, really different.

I am pretty ordinary, and yet I still manage to shock the hell out of most people (including myself). I’m a nobody in the startup world. But I am currently working for a somebody company — Shopify. You may have noticed, its been making a lot of headlines these days.

I’ve found myself out of place on more than one occasion. I’m a quick study, and always try to find a way to fit in. Generally speaking when I’ve found it hard to fit in, it had nothing to do with me. Honing the skill of not letting other people’s shit distract me, and focusing on doing good work is what I hope to get better at in my thirties. Let me save you some time trying to figure this out for yourself, the hardest part about working, is never the work. Don’t let others suck you down the rabbit hole.

My first real job was working as a receptionist on Bay Street (that’s like Wall Street in Canada). It only lasted about 8 months. I can’t be entirely ungrateful for the experience, it gave me the executive (assistant) experience I needed to qualify for making killer power-point presentations, file and fetch coffee at for executives at Rogers.

It was 2007, I was finally all grown up living the dream— working as an administrative assistant. Rolls off the tongue nicely doesn’t it? Womp, womp, womp. I had bills to pay, and got a discount on my wireless services. We all know that Canadians pay way too much for their wireless services, amarite?!

While working at Rogers I ran into a few cool people like Ted Rogers, Alan Horn, Phil Lind and Dermot O’Carroll. The best part is these guys probably don’t even remember me. The more Rogers’ history I learned, the better my questions became when I ran into them. I’m pretty sure I was the only Rogers employee that read the bible-like, gigantic unauthorized biography ‘Ted Rogers, and the Empire that Debt Built’ released about a year before his death in December 2008.

Getting mere moments to gush over how Rogers came to be, was one of the best memories I have from my time spent working there. Each of them had a signature chuckle, and I could always count on getting a better version of the story right from the horse’s mouth. This is when I first learned having a thirst for learning, and asking questions is a good thing. Also never be afraid to talk to the most senior of people, they’re human not gods. They got to where they are because they too have a thirst for learning. Knowledge, ambition and tenacity together make for the Jamba Juice entrepreneurs love to snack on.

Aside from learning the best Jamba Juice recipes, I learned that Ted Rogers did a few things right when Rogers was an early stage company. Number one, he built his company on debt. It was all about timing and when you have a good thing and time isn’t on your side (and when is time ever on your side in tech) you gotta move. And by move I mean, find market fit and start making revenue — fast. Rogers in the 1950’s was very much like a start-up is today. Like Kayne, he was trying to hit up Mark Zuckerberg and Larry Page up for millions on Twitter. Ted went to every bank and even begged Roy Thompson to help him with his ideas.

This is the part where everything starts to look a bit different than some of the start-ups we see today. Number two, if you’re going to do something make sure you do it right. So right, that it makes your competitors feel the burn for decades. What am I talking about? I am talking about Netflix and the iPhone.

Ted was a strategic thinker, one of his biggest payoffs was his cable empire. He didn’t want to just squash his competitors, he wanted to keep them on their toes for the next 20, 30, 40 years. Why did this matter? Every other cable co was only taking fibre to the node, and then connected a smaller capacity cable into the home. I think this is what one could call “cutting corners”. Ted took fibre right into your living room, not cutting corners or cord. Ted described it best and that his competitors took Niagara Falls to the node, then from there, hooked up a garden hose into your home. Ted knew back then that for us to enjoy Netflix today, we’d need fibre right to the home :P

Ah, yes more about how the iPhone changes everything. Wireless definitely wasn’t one of Ted’s love affairs, and he was always pretty transparent about that. Radio and Cable, those were his darlings. But Ted invested in a great team. Number three, when you hire smart people you should know when to listen to them. You cannot be all things, all the time.

Ted along with his team moved into the wireless business, and he was sure do it right. He went with an GSM network similar to AT&T in the USA. I believe this is what led to Rogers’ success in the Canadian wireless market when margins started to get thin. During the time the iPhone launched, Rogers leap frogged it’s competitors with a vengeance. The iPhone is the flagship mobile device that really started to move significant amounts of data wirelessly, and early versions of the iPhone could only be enabled on a GSM network. Leaving HSPA wireless carriers in the dark. To this day, Rogers still is the largest wireless provider in Canada with 9.8M subscribers.

If you’re good at reading between the lines, you’d see that by making good business decisions, you can build a business that has the ability to reinvent itself over the course of time.

Lastly, number four, it’s important to get the basics right before biting off more than you can chew and when you get the basic’s right, you’ll likely last for decades. It was the cash provided from Cable done right that fed the build of its wireless infrastructure. The revenue from wireless allowed for Rogers to diversify its asset holdings by acquiring the Blue Jays, parts of TML Sports and various print and media properties. It’s like Craig Miller at Shopify reminded me while we were eating layered cake, that building a solid business is just like baking a layered cake.

I worked at Rogers until 2011, moved on from being an assistant into roles supporting sales & marketing as a specialist/analyst towards the end of my time there. However the role I had as an Assistant taught me the most.

It remains to be seen what the future holds for big red. Ted was one of the strongest entrepreneurs I’ll ever meet. After he died, many of the oldies (and goodies) started to exit the building along with some of the company’s entrepreneurial spirit. I was starting to piss people off with my tenacity, and had to make sure when I got excited about something that I didn’t make my peers feel stupid. Later on, little did I know I’d move on to work at Shopify. Where we openly admit to each other that we often feel stupid, most of the time.

Before working at Shopify, I spent about 4 years at Wave Accounting, building its Advertising and Sales business. Working there taught me more than I ever could have learned working at an established corporation. I learned about what it takes to build a brand, and be disruptive in the marketplace. VC funding, and how it feels to live the highs and lows of money coming in and going out the door. Peaks and valleys are just something you have to get used to if you’re gonna work in an early stage company. You can’t take the heat, get out of the kitchen.

While I was living on the island of advertising operations and sales, the larger business broke its back to build a cloud accounting app for small businesses with 1–9 employees. My time at Wave, is another post entirely. But what I couldn’t have timed more perfectly is my experience at Wave uniquely sandwiched between my time at Rogers and now Shopify. It was Rogers, Wave and Shopify all in this order that has allowed me to better recognize the defining moments of success for a business.

I always knew Rogers was big, profitable and unlike BlackBerry … likely not going anywhere in my lifetime. Let’s just say I met the Jamba Juice, of Jamba Juice at big red, but I never saw how the Jamba Juice was actually made. This mostly took place before I was born.

Working at Wave, gave me a better perspective on the things that you need to make the BEST Jamba Juice. And Shopify, well … working here has made me realize all the reasons why Rogers became the company it did. Why Ted made the decisions he had, and as much as people believe timing and luck have a lot to do with success — Wave and Shopify made me realize the tenacity it took for Ted to build an empire was far from luck and nothing short of hard work, and damn good business strategy.

I came to Shopify because I want to continue to do big things. Here is a place I can drink Jamba Juice until it makes me sick. I am surrounded by too much ambition, too many a-types and too many people that give a damn. It’s a great problem to have, and that’s why we all laugh when we talk about our culture of feeling stupid sometimes. Together we challenge each other, challenge the business’ limits and thus the market.

Tobi, Shopify’s CEO tells us to do things, tell people. It’s written all over the walls at every office. He values different perspectives, ideas and ways of thinking. His motto of default to open is used to fuel everyone’s capacity to act like an owner. Different industry, different business, different time, but it’s easy to recognize a potential empire when you start to realize there is more that makes them the same than different.

Like I said earlier, I am a nobody in the startup world. I’ve simply had the rare opportunity to watch some pretty great entrepreneurs work. I’ve noticed a few things over the last 10 years, and so I thought I’d share.