D'Arcy from Winnipeg
Solution Architecture, Business & Entrepreneurship, Microsoft, and Adoption

My Startup Weekend Winnipeg Experience!

Monday, August 20, 2012 6:12 PM

I finally have some time to blog about my experience two weekends ago at the Winnipeg Startup Weekend event.


The idea of Startup Weekend is simple: bring together bright people who are interested/passionate about entrepreneurship, stick them in a conference room for a weekend, and review the results.


Friday night people come together to meet each other, socialize a bit, and then get to the pitches. Anyone can pitch an idea and it can be anything, but you only have 60 seconds to do it. Ours ranged from a fishing app for mobile phones to a 24/7 environmentally friendly cleaning product depot.

A pitch being made. 60 seconds to communicate an idea!

Once the pitches are done, they’re written up and posted on the wall. This is where the campaigning begins. In the same way that start-up companies search out the most talented people to get them off the ground, so too did our pitchers try to garner interest and attention for their idea. Attendees could vote for which ideas they liked best based on stickies that they were given earlier in the evening.

The campaigning begins!

Voting is complete!

Once the voting is done, the groups with the most interest are announced and everyone self-organizes. Here’s the interesting part though – you don’t *have* to go to one of the teams with the most votes (although most people will gravitate to them). In my case, I threw out an idea and got 0 votes. By the end of the night though, I had two other guys want to come on board on it with me and voila – our team was created!

So then the work starts, and just like a real life startup its all about getting busy, working hard, and pushing to get a MVP out. MVP in this case stands for Minimal Viable Product – think prototype, think demo, or (as my buddy Steve Rogalsky is a huge advocate for) think a sliver of functionality that provides value and forms the basis for future building.

One of the teams (the winning one it turned out) working hard!

Our team was committed, but we rested up Friday night to start fresh on Saturday. One group stayed up until 4AM on Friday to get a jump start on their idea!


Saturday was a work day, with the conference room transformed into a multi-tenant war room. All meals were provided, so nobody had to leave unless it was to collect market research, get supplies, etc.



Matt and Jonathan, my cohorts and the real brains behind ViceMap


Most of Sunday was a working day, but the evening brought the weekend to an end. This was where the teams would present their hard work and do a final pitch to a panel of judges. The judges would pick an overall winner, which would win a bunch of free services for helping continue their venture forward. It was very kewl to see how far the teams had come over the weekend and what they had created.

Final prep before the big demo!

FastChat being pitched to the judges.

What I Learned

A weekend like this is fun, but many of us came to learn something about business and what it takes to build a start-up company from scratch. I think each team did very well and some got farther with their concepts than others. In the end though, it was about the MVP and learning things along the way. Here’s what I gleaned from the experience.

A Business Is Built on Shared Pain

You could replace pain with need or want, but one thing is for sure – it needs to be a shared pain/need/want. Let me tell you about the idea I pitched.

I hate the fact that so many restaurants have horrible online menus. Restaurants are the worst for either putting up a Flash-based site that makes it unusable on mobile devices, or posting PDF versions of their menus which are a pain in the ass to read on a mobile device. And that assumes they actually have a website. Wouldn’t it be great if we had an app that would identify near-by restaurants and host a mobile-browser friendly version of their menus? I know I’d use it. And I’m sure many others would too! And boy, the restaurants would totally come on board! The more people that can access their menus, the more business they get – its a win/win!

And then reality smacked me in the face. For one thing, while I felt this pain many others didn’t. I put out an impromptu survey on Facebook and got 16 responses (a very small market survey, but still interesting) – out of that 16, 4 said their experience getting restaurant info including menus was “Great” and 8 said it was “Satisfactory”. We also identified that sites like UrbanSpoon and Yelp were go-to resources although word of mouth was still the #1 way people found info about restaurants.

Then I went out on Saturday to talk to some restaurants and get some real-world feedback on my idea. Only problem was that as I drove down Portage I noticed all the restaurants I was going to hit up were closed. If they weren’t closed, they were really busy (unfortunately market research around noon on a Saturday isn’t the best time when restaurants are your target). But I realized something: Restaurants that needed to boost more clientele had bigger issues than just having a menu be available online – they couldn’t even be open on a Saturday lunch! Restaurants that were open were busy enough that while they might be interested in the idea, it wasn’t a pain/need/want since business was good. So then who was our market? Flailing restaurants that needed an influx of orders?

In my mind things started to fall apart with my idea. To me, and for me, this was a great solution. But it wasn’t a business solution. There was no way we could realistically make money. We’d need a few hundred restaurants to sign up on a subscription basis, and the cost to attain those customers would cancel out any profit. Plus you have the other side of it – getting a fan base of users to actually use the app and spread the word about it. You need both though: many restaurants on board, and a huge user base. Both would take tonnes of work to put together for very little return. I was starting to get a bit deflated.

If an Idea Isn’t Working, Try To Pivot

Matt and Jonathan, who were busy coding up the mobile app, had an epiphany while getting a beer at the bar though. In talking with the waitress on duty, she shared that it was tough to find late-night eateries for when she got off work at 2 or 3 AM. Would other people be looking for other late-night establishments as well? What about travellers that were new to the city…would they want to know what bars, restaurants, convenience stores, etc. were available? I bet they would!

So we pivoted – we took the investment we had made in our technology and changed the business domain we were dealing with. Instead of identifying close by restaurants and their menus, we’d provide a service that highlights late-night establishments. And thus, ViceMap was born!

You can try the app out in a browser at http://www.vicemap.co/app/

Here’s what you do:

Type in Winnipeg for the location, then pick your “vice” from the drop down list. You’ll now see a map with icons showing where some downtown bars, restaurants, “performance art studios”, convenience stores (for smokes of course), and hospitals are (in case stuff goes down and you need medical help).

Ok, are we serious about ViceMap? Well lots of people told us it was a great idea, and the fact we’re positioning it with a certain flair definitely makes it unique. Our team has said we’d like to get together to talk next steps, although we haven’t arranged a lunch yet. I also realized that on Android devices they have this nice app called “Local”, which let’s you filter nearby restaurants by “Open Now” – so we may have more competitors out there that we didn’t realize. But still…

Iterating Early and Often is Crucial

This was drilled home to me over the weekend. Imagine if we would have stayed on my restaurant idea. Imagine that we spent a month working on it, without doing any real market research or getting any sales or building a customer base. Imagine that we sunk a whole month of our lives into something that ultimately proved to be useless? The thing is businesses do this all the time! I love Dragon’s Den, and I see season after season people who have poured MILLIONS into a business that’s always failed. One of the reasons I believe is that they didn’t iterated early and often – they didn’t push for the MVP out of the gate. Getting something that can be vetted and used to gather feedback is crucial and must happen earlier than later, and often rather than not. We pivoted mid Saturday, which still gave us time to put some polish on the ViceMap app and have a fantastic presentation (we were allowed to go over time because we were entertaining).

Looking Forward to the Next One!

There’s another Startup Weekend in Winnipeg being planned for November 2012 sometime. I’d encourage everyone to attend, it was a fantastic event and definitely a worthwhile endeavour. While I was one of the organizers for the event, Brad Kendall was the real brains and braun behind getting this event off the ground, so huge kudos to him for a hugely successful event!


To see more pictures from the event, check out my gallery here!

For more info on the Startup Weekend organization, click here!


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