Startup Weekend – Toronto – Lessons leaned

I finally have some time to write about the Toronto Startup Weekend experiment. First of all, I’d like to mention that we launched a product into beta. Yay! By that factor alone I guess we can consider this a success. There has been some buzz in the blogsphere about how the SW Toronto was run and organized. Here’s what’s been floating around so far:

Andrew Hyde: showing disappointment at the way things were organized, feeling that the spirit of the event was trampled.

Steve Poland: Agreeing with Andrew, but more mildly so 🙂

Brill Pappin: Giving his take having been one of the organizers of the SW Toronto event

And now for my take on it. First, my disclaimer, this is my opinion and mine alone. Ok with that out of the way… I was one of the pre-weekend organizers and had the “role” of product development lead.

I think that overall the weekend was a success for the following reasons:

We launched: Well, we did and with two applications not just one. is in private beta and we’ve also created a Facebook companion application that is also in private beta. So… for a bunch of people that ran the weekend “wrong” we didn’t do so bad 🙂

Met some great people: I can’t speak for anyone else, but I did. Andrew, Joe, and Erica were a refreshing addition to the weekend. Although Andrew did not participate much in the weekend itself, I found all of their opinions and insights into the process to be very interesting and I think they brought up some really good points with regards to the detriments of being as organized as we were. I look forward to future SW events (I’m attending the DC weekend) to see how Andrew intends to run it. I think it will have a different flavour and I look forward to being a part of it. I also met some exceptional people at the event on each one of the teams. Once we got into the swing of things (kinda late, around noon on Sat) the team was energized and seeing these people at work was absolutly inspirational. I’m not going to name anyone here as I don’t have their permission, but I could name about 20 people that emerged as stars during the weekend and that I would be honoured to work with them again in the future.

The Energy: I thought the energy and enthusiasm was intoxicating, I loved seeing the will of the team to succeed (and we did). Made all of us want to work hard. I was not at the Boulder event, so I have nothing to compare this to. I will be in DC and look forward to the experience.

Now… what didn’t go so well.

Too organized: I think we might have over organized for this event. How exactly, you ask? I’m not 100% sure, but I got the feeling people felt like they were pegged into a role before even stepping foot in the facility. We had name tags with people’s team assignments on them. I think name tags are a good idea (I’m terrible with names) but I don’t think assignments should be done before the weekend starts. It will allow for a more fluid environment. I think one of the major success of Boulder was that people felt free to move around and contribute where they thought they were needed and where they had skills. I got a feeling like that was a bit stifled in Toronto. I had a badge that said facilitator and was interrupted many times while working on the site’s splash page. At one point I was asked why I was creating the splash page since that wasn’t my “role”. Hmmmm, well, there was no splash page and we need one, that’s why. So… no “roles” on name tags 🙂 I think the organization issue has been at the heart of this debate. Toronto organized as much as we did as a direct result of following the Boulder experiment and seeing what we thought were the biggest mistakes that were made there. I think the major thing to keep in mind is that this is an experiment and a learning experience. I think the natural thing happened, we over organized, the next weekend will most likely be less organized. Andrew has put up his Bill of Rights I think I agree with most of what’s there. What I’m wondering is, will this feel to the attendees that they are forced to be “disorganized” (that might be the wrong word, but I can’t come up with a better one). I think the structure is going to fluctuate from weekend to weekend, some getting really organized and some flying by the seat of their pants. Neither on of these is wrong or right. I think the questions we should ask are:

  • Did it work for those involved?
  • Did we have fun?
  • Did we create a good product that we feel proud to stand behind?

Oh, lets not forget that the culture in Boulder is probably a bit different then the one in Toronto. For example this weekend in Birmingham is WAY more organized then Toronto was (although they’re not using the Startup Weekend name).

My two cents about the whole thing.

I had a great time, met great people (Canadian and American), learned A LOT, and helped launch a great product. I would love to see how the Startup Weekend experiment evolves over time without too much internal influence. After all if we let the local groups do their thing and organize the way they see fit and we learn from each of them, IMHO, the weekend will evolve to a very successful model.

I know that I don’t usually solicit feedback on this blog, but this time I welcome your thoughts and comments…


4 Responses to Startup Weekend – Toronto – Lessons leaned

  1. Andrew Hyde says:

    Great writeup! I had a lot of fun meeting and working with you and the team on the product. Lessons were learned, and every weekend will be stronger from it.

    Great getting to know you.

  2. confusement says:

    @Andrew. Thanks for the comment. I’m really looking forward to seeing you again in DC, working with another great team and putting out another world class product!

    See you in a few short weeks 🙂

    ps. I totally misspelled your last name on the first “draft” of my post. Sorry about that, it’s fixed now 🙂

  3. Steve Poland says:

    Yeah we’re all on the same page. It was an experiment — and this one was very organized; people still went and enjoyed themselves and that’s what counts. I’m a guy that likes to see a fluid flow to things — and that’s me.

  4. Seems to be a fair representation of what most people probably took away from the weekend. I look forward to meeting you in DC as well.

    An example of the difference between the Boulder adventure and Toronto’s: 20 minutes before the kickoff on Friday I asked Andrew if he thought nametags would be a good idea.

    Could some organization have helped, yes. I think by nature you have three types of people attracted to the startup world:

    1) the idea guys – they love the lack of structure, which often breeds problem solving and creativity. Interaction is the measure of success.

    2) the builders – they love to find practical solutions to problems. Structure is a must as is project management and progress management. completion is the measure of success.

    3) the doers – a mix between structure and no structure works best. They want to always be doing something, but not constantly being told what to do. Interaction and completion are measures of success.

    By definition, idea guys and builders tend to have conflicting styles. (And no, one cannot belong to multiple groups.) It seems thats what happened in Toronoto is that exact conflict. But, it seems the doers persevered and got something out the door.

    Boulder was light on builders, which is why we didnt launch on Monday am. The move forward team is a great mix of the three groups above, and in the coming months, we will see a positive refinement of the product. Hopefully, Toronto’s move forward team will experience the same.

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