Mapping My Future

Startup job shadowing

Where to learn right

Even today, in 2016, the prevailing attitude around what people my age should be doing with their learning time is lining up for university or college. We’re told it’s the best course of action for us, it opens the most doors, it’s a great foundation.

But, next we’re told to differentiate. We should set ourselves apart with a specialty or a unique experience that makes us really hireable, like an MBA, a CFA. Grab a supporting college diploma, they say, put time into an internship, work abroad. We’re told to conform at first – only to strike out into a new direction on our own afterwards. I didn’t want to do it that way.

Me, I wanted real-world experience first. I had my own online clothing store running on the side and I needed a practical education experience I could throw myself into. I just needed to convince my “personal stakeholders” of family, teachers and friends that challenging this model was a viable path for my learning.

So, I joined a startup for a day.

How I recruited a startup

In the beginning I didn’t know what to expect, but I was determined to contact enough startup founders until one gave me a chance. I started ambitiously: asking Toronto’s brilliant CEO’s and CTO’s for an unpaid internship without even a high school diploma to show. I had almost talked myself out of it – there was no way any busy startup would devote time to teaching a 17-year-old student business basics for free. I contacted them anyway.

Fifteen minutes after my first few emails I get a reply notification from Latif Nanji, the CEO of Roadmunk. Not only did he say, “Yeah! let’s chat!” (with a few more exclamation points), but he was pumped. I’d learn later that Latif sees the world of learning in a similar way I did and constantly challenged the norm.

After an email back-and-forth we’d struck a deal. I wasn’t getting an internship; that was a pretty big investment from Roadmunk, but I was going to job shadow Latif for a day. I was going to be surrounded by a team of bright, spirited entrepreneurs from the Roadmunk team and watch how a SaaS company hit the market hard.

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Call me Ferris

One week later and I’m skipping school to hang out at the Ryerson Digital Media Zone. The ‘DMZ’ was Roadmunk’s home until November 2015 when they acquired their own office, graduating from the business incubator. They would stay in close contact with many of their friends from DMZ startups long after moving.


I took the elevator up to the sixth floor where I was greeted by Latif. He’s wearing a faded tee from one of the other startups, jeans, sneakers – and he talks faster than anyone I’ve ever met before.

We made our way past dozens of startups towards the Roadmunk office. The scene was intense. It was a culture of execution and trial-and-error, very distant from what’s taught in school. Every soul passionate about their project. Stickered-Macbooks were everywhere. Friends working together to make something great. Would I prefer this lifestyle over a standard corporate job? A thousand times yes.

I just needed to convince my “personal stakeholders” of family, teachers and friends that challenging this model was a viable path for my learning.

My startup education started right away. I had just taken my seat – I took the desk of Roadmunk’s sales director, Jalil, who was out on a customer call  – and I listened as Latif planned his day in Google Calendar:

  • Days start with the company stand-up meeting: everyone squeezes into the frame of a web camera to dial into the Waterloo development office. It was the fastest-paced company update I’ve ever seen – tweet-length updates on projects, challenges and successes. It was over in six minutes and the team scattered back to their stations.
  • A call with an important VC at noon. Roadmunk was still raising capital at this stage and Latif was connecting the dots for investors who all demanded product updates, financial spreadsheets and customer data points. For anyone else this could have taken all day; Latif would prepare over lunch.
  • A three-hour product design session with his own product manager, Sameena. They were on the cusp of a breakthrough for a flagship feature and Sameena asked for some perspective.
  • Four hiring interviews – one with a marketing candidate and three for developers – a very typical breakdown, he said. I’d sit in on the marketing interview.

There were a dozen more appointments on his calendar that I’d have to miss as I met with other members of the Roadmunk team. He said this was quiet for a Monday…

Real lessons from real experience

Anything that Latif faced today was a real, surmountable business challenge he had to put down. In the first few hours of the morning it felt like I’d learned more about running a small business than I would from a week’s worth of school. Lessons like:

  • The biggest expense in most tech startups will be payroll.
  • Even CEO’s report to someone: their team, investors and customers. So much for being my own boss.
  • MRR is the kingpin of nearly startup metric in SaaS, but it’s influenced by a myriad of factors. Everybody plays a part. Sales doesn’t own it independently.
  • Churn is evil, but it’s also natural. Customer success teams grind hard to reduce it. Support teams are as influential a brand experience as any marketing campaign.
  • Hiring great people is a critical part of running a great business. It’s also one of the most difficult to get right.

On the other hand, this visit challenged a lot of what I thought about running a small business.

  • For starters, this startup wasn’t small. At the time this team of nine was constantly hiring – a time-sink challenge for Latif – who needed at least three more developers, an office manager, quality specialist and a content manager immediately. Roadmunk would double in size inside of six months.
  • A product’s success really doesn’t come from a genius, disruptive idea like Hollywood likes to fantasize. Success comes from execution. Capitalizing on the product-market fit takes sweat and exhaustive effort.
  • No one goes alone – Latif and Tomas are Roadmunk co-founders and they met years earlier while working at Waterloo-based Miovision. They compliment each other’s strengths and lean on one another for decisions. Virtually nothing is decided without consultation and friendly debate.
  • I always thought a CEO would naturally be the brightest person in the room. I grew up watching business giants like Jobs and Branson represent their business, but Latif completely opposes that idea. “I hire people smarter than me. It’s the only way this works.” He laughs when he says he’s hiring a team to put himself out of a job.

From theory to practice

The proof that this learning experiment was worthwhile couldn’t be any clearer than during the hour I spent with the Roadmunk team. I’ve always been interested in marketing, but learning the basic 4 “P’s” in a high school class wasn’t the most engaging way to do it. I wanted to understand online human behaviour and what precisely leads to a successful online sale. Me, I needed to see it in action.

Latif sat me down with Rhys Mohun, Roadmunk’s Marketing Director. Rhys spent an hour helping critique my online store’s e-commerce strategy. I have no clue where he found the time in his day, being willing to coach a complete stranger. Just goes to show you how helpful the Roadmunk team is. (Rhys told me to pay it forward, and I will someday.)

He taught me about reducing friction and displaying actionable elements like the “Buy” button above the fold on a product page. He explained to me how and why users interact with webpages and role-played with me as a customer. We talked about running tests to conclusively prove one hypothesis over another, and connected sales principles to user behaviour online.

Even CEO’s report to someone: their team, investors and customers. So much for being my own boss.

After my visit I would implement many of these web strategies into my online store. I don’t think I’ll get that level of one-on-one support from a college class. My mind was leaning further and further away from the idea of undergrad.

Peer-to-peer learning

Shortly after lunch it was time for The Pragmatic CEO roundtable. Coordinated by Latif, it’s a 20-CEO roundtable dismantling the challenges encountered running a startup using sensible and realistic solutions. If it was overwhelming listening to Latif thinking/talking at his pace, imagine a room of 20 like-minded founders.

Groups discussed real-world, relevant problems ranging from recruiting top talent to onboarding new customers. It was my type of learning. The craziest part was the intimate collaboration between very different-sounding startups: you’d have a shipping technology business (hey Fr8nex) discussing social media with a designer temporary-tattoo company (Inkbox, who would share the future office with Roadmunk a month later). Everyone was very close. I crammed notes into my Mac taking full advantage of their experience. It was literally over 150 years of combined learning and experience crammed into a 10 x 10 room huddled around a large poker table. Unreal.

Staying startup late

Copyright © 2016 Roadmunk Inc.

Latif and I spent more of the day together. He shared the outcome of an investor call in which he was asked to produce a measure of the size of his potential market. I sat in on the marketing interview and saw first-hand how tricky it is to identify the correct blend of traits, experience, talent and personality in a person who will ultimately control a portion of the dream that’s 3 years of sweat equity in the making. Finally we talked about customers and product-market fit, how it’s dangerously possible to build the wrong product really well – missing the mark entirely. Don’t do that. listen to customers first.

Witnessing a real-life version of what I hope to achieve myself 5-to-10 years down the line was an impactful experience that helped me not only visualize my goals, but understand the amount of work and learning I needed to stand a chance.

The long day take-away

That wasn’t the lesson I left with. At the end of a late day, Latif and Rhys took my temperature on my education decision. After everything I’d seen today I was pumped to start something amazing and tackle school afterwards. They didn’t exactly agree.

They would stay in close contact with many of their friends from DMZ startups long after moving.

Sure, I could learn a lifetime of valuable business lessons in half the time by running my own business, but I could start that anytime. What I couldn’t do anytime was live the unique experience of going to university, meeting new friends and building my own network of support around me. This was the common thread I’d missed the day I shadowed Roadmunk.

The idea of not going to university came up a lot over the past five months I’ve been speaking with founders and mentors. Not until today could anyone explain a perspective that’s lingered in my mind: going to school to make close friends. Avoiding school costs me an opportunity to create new relationships with like-minded, entrepreneurial individuals and even my future co-founders. What I realized I needed to do was find a balance between institutionalized education and experience while maintaining and feeding my ambition to create something great.

The evidence was all around me. Look at the founders in the Pragmatic CEO, sharing stories and collaborating on common problems. The Roadmunk team, meeting for a handful of minutes to support each other in standup meetings every single day. The friendships between startups at the DMZ persevere well beyond graduation, into their own stories as they pursue the big payday from the Valley.

School would be the perfect environment to bone up on those networking skills; getting along with a variety of A-type people, sharing openly, being vulnerable and willing to ask for help, and even settling disputes when views don’t quite match up. I saw every one of these skills in play today and I nearly missed the lesson right under my nose. I guess that was the point all along.