Real Fellowship: Week One

Or: Why I Went Back to Learning Full-Time for 10 Weeks


When I moved back to Canada from London six months ago, I wasn’t exactly sure what I wanted to do next, let alone how to get there, wherever there was. I’d just spent an awesome two years working for Microsoft’s Soho Productions studio in London, doing motion graphics design for interactive projects on Xbox + Kinect, including Kinect Sesame Street TV and Upload Studio. It was an incredible learning experience and I worked with some truly talented people, but it was time to return home (mostly thanks to my Visa expiration…). More importantly, it was time to re-evaluate and really figure out where I wanted to steer my career.

While in London, I came across some really cool interactive projects using a programming language called Processing, which is a language built on Java that was created to help new media / visual design communities learn to program through visual feedback. After doing a Processing workshop, it clicked that I didn’t need to have a Computer Science degree to design and even build experiences that solve a problem or delight someone in a new way (more on that later). I knew I had a lot of learning to do.

With this somewhat vague interaction design direction in mind, I tried learning on my own for the first month or so, but quickly realized that no matter how much I read or how many online courses I took, my overstimulated brain needed a more structured learning environment that would force me to tackle real world problems head-on. I looked into doing short courses like SVA’s Summer Intensive in Interaction Design or CIID’s Summer School, which looked like incredible learning and networking opportunities, but I just couldn’t stomach spending thousands of dollars on things I knew I could learn if I truly put enough dedicated time and practice into it.

So, when I came across a tweet about the Real Fellowship being offered this summer in Montreal, I jumped on it (the opportunity to spend a summer in Montreal had just a little bit to do with it):

The fellowship is a 10 week full time program that gives the web’s emerging makers the opportunity to hone their skills alongside the industry’s finest. You’ll attend workshops & lectures, build out your network, be mentored by veterans and put your skills to the test at a leading Canadian startup.

For me to pivot in this new direction, I needed to not only learn a ton, but to do something and for me, the Real Fellowship felt like a risk worth taking: I’d be working hands-on with a start-up that needs more design skills, I’d be learning about all aspects of launching a start-up through pros that have been through it numerous times, and I’d be connecting with like-minded bright people who’re eager to learn. To me, it felt like a no-brainer.

After submitting my application, a Skype call with Real Ventures’ Director of Special Projects, Alex Lynn, a few chats with Transit Co-Founder/CEO Sam Vermette, two weeks sorting out how I would temporarily move from Toronto to Montreal, and I was all set: I would be working alongside Sam and his small team for the summer and helping them tackle some really interesting design problems.

Alex Lynn, Real Ventures’ Director of Special Projects, outside Notman House in Montreal

Not 24 hours after taking the train from Toronto, I arrived at Notman House in Montreal at 9:30 AM, eager to meet my fellow Fellows and hoping I wouldn’t be ancient at the ripe old age of 26. Luckily, the seven are a great mix: from the fresh-faced university students to recent grads and those a few years out of school. I finally met Alex Lynn in person, as well as Stephanie Saheb, Chief of Staff at Real Ventures, both of whom have an unmistakable passion for helping start-ups succeed.

Stephanie Saheb, Chief of Staff at Real Ventures

After a morning of getting to know the other Fellows, we set off to the companies we’d each be spending the next 10 weeks with. For me, that was a short walk to cool Mile End, where Transit shares an office with Provender, a startup connecting farms and restaurants that has also taken on a Fellow (Jo!) for the summer.

Jake and Sam of Transit, outside Notman House

I learned a ton in my first week with Sam and the Transit team, from filling gaps in my knowledge of UI design to the intricacies of transit systems. Just a few of those things I learned:

  • GTFS: stands for General Transit Feed Specification (originally known as Google Transit Feed Specification). This is a set of data files provided by transit agencies that allow developers to write applications for trip planning using the data. This includes things like stop locations, routes (a group of trips that are displayed to riders as a single service), route types (ie. 1 = subway or metro or 3 = bus), trips (a sequence of two or more stops that occurs at specific time) and a ton of other specifics that are outlined in Google’s GTFS reference. Basically, the amount of data that these guys wrap their heads around is incroyable — I’m surprised I haven’t seen their heads explode yet.
Only a short snippet of the stops data in the Toronto Transit Commission’s GTFS feed.
  • I’ve only been with the team for a week, but already I can see the many complexities involved in designing for not just one transit system, but dozens and dozens around the world, each one riddled with unique problems and details. Details like the trip headsign, which tells the passenger where the route’s destination is. Some are quite simple, like the 97 bus here in Montreal, which goes Est (East) or Ouest (West), and has one final destination for each direction. Others are more complicated, like the 501 Queen Westbound streetcar in Toronto, which has numerous different route destinations along the same line. 501 Queen towards Long Branch. 501 Queen towards Humber. 501 Queen towards Roncesvalles. It’s important for a passenger to know which one specifically is arriving soonest, in order to make a quick decision about whether it’ll take them where they need to go. Once you’re on the right streetcar, it’s up to you to pray to the TTC gods that it doesn’t short-turn at Bathurst.

On Wednesday, the Fellows stopped by the office of local start-up PasswordBox. We were met by PasswordBox’s ‘hype girl’ Maeghan Smulders, Director of Product Marketing & Communications, who gave us a tour of PasswordBox’s sweet office digs and ended on a Q&A with a wide range of the PasswordBox team, from members of the networking, machine learning, web and mobile development teams to COO Magaly Charbonneau and Co-Founder and CDO Marc-Antoine Ross, who gave us great insight into the challenges of maintaining company culture while growing so quickly. Marc also touched on the importance of hiring the right people, a process for them that requires any new hire to be interviewed by a handful of team members across different roles, as well as the all important question: “Would I want to have a beer with this person after work on a Friday?”. If it’s a unanimous yes, they’re likely a good fit.


On Friday, the crew returned to Notman House, where we met with Beth Thouin, partner at Montreal marketing agency Brendan & Brendan. Beth talked about customer validation, a crucial first step when solving a problem and/or delighting a customer/user in a new way. No matter how good you think an idea is, you need to validate your problem hypothesis through testing. One of the easiest ways to do this is to use Steve Blank’s tip: get out of the building. Go out onto the street and talk to potential customers to prove or disprove your assumptions about the idea. When doing these interviews, it’s important to be totally neutral — no leading questions. For example: Tell me about this process. Why does it take X minutes? Have you tried alternative methods? Why or why not? Would you tell your friends about it?

Over lunch, Omar Dhalla chatted with us about his transition from working in the corporate world at McKinsey & Company to working with startups in his new role as a Venture Partner at Real Ventures, helping to build Real’s presence in Toronto and Waterloo. It was a transition that I can relate to: going from a large corporate environment like Microsoft to a very small start-up team, where’s it’s imperative to take initiative, to add value to the company wherever and whenever possible and to constantly be learning from your failures.

In the afternoon, Gabriel Sundaram, Director of Platforms at Real Ventures, broke down the oft-misinterpreted inner workings of venture capital funds, beginning with the difference between an angel investor (an individual investing their own money) versus a VC (a partnership investing other people’s money). LPs (Limited Partners) are those that provide the initial funds. General Partners are those that manage the money and make the investments on everyone’s behalf. There are multiple stages of VC funding, including pre-seed, in which startup accelerator programs like FounderFuel provide initial capital for startups to increase traction and continue to grow alongside mentorship.

Real Ventures is a seed stage investor. This means that they are one of the first investors in a start-up company, allowing founders to build out their product. At this point, only 30% of the start-ups are expected to succeed. This means that during the 10 year shelf life of the fund, 70% will return close to $0 to investors. If all goes well, at least 1 company will hit a home-run and get a huge return at the 10 year mark. Alex summarized the sign of a good investment with this equation: the ultimate potential of an idea multiplied by the likelihood that the people in front of you are those that will bring it there. This is only the tip of the VC iceberg!

In just one week, I think I’ve learned more and made more meaningful connections than I had in the span of two months in Toronto. Needless to say, I’m looking forward to Week 2!