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It started off with a simple tweet and suddenly I’m organizing a huge startup event in Toronto…

Back in April, I was planning my next trip out to Actuate’s HQ in San Mateo and my attendance at the web 2.0 conference when I came across Startup Weekend Silicon Valley.  I started reading and, while I couldn’t stretch my trip and leave the family for an extra few days to attend, I thought to myself, why hasn’t this event come to Toronto yet?  So I tweeted that same question.

Next thing I knew, the folks at Startup Weekend were in touch to let me know they wanted to do a bunch of Startup Weekends across Canada – covering all the major cities.  Now I’m not going to bore you with all the details that followed.  Let’s just say that I met the Startup Weekend crew in San Francisco at web 2.0 and here I am, organizing Toronto’s first (well, not quite but that’s another story) Startup Weekend.

Frankly, I’m surprised it’s taken so long to get here.  Toronto has a vibrant tech and startup community and given that these weekends are going on all over the world and gaining tons of momentum, why didn’t someone jump on this before me?  Perhaps it’s because there’s a perception that we already have these type of events in this city.  If that’s the case, I’d have to disagree.  While we have many great events in Toronto covering this space, there is nothing following quite the Startup Weekend model.

Here’s my plug for the event… I hope to see you all there so please check out the site, register and come out with all your great ideas and skills.

Startup Weekend recruits a highly motivated group of developers, business managers, startup enthusiasts, marketing gurus, graphic artists and more to a 54 hour event that builds communities, companies and projects.

Founded in 2007 by Andrew Hyde, the weekend is a concept of a conference focusing on learning by creating. It is known for its quick decisions, ‘out of the box’ thinking (oh no, the buzzwords are attacking!), unique facilitation technique and letting the founders show what they can do. The program has already met with success in over 100 cities all around the world.

The participants that attend a Startup Weekend decide what they want to tackle over the weekend and come out at the end with several developed companies or projects. Attendees are responsible for bringing desire and passion to the project and walk out of the room with the task at hand, in a short 54 hours. Sound intense? It is.

Startup Weekends continue to build momentum, happening in cities across the globe every week. Toronto is holding its first Startup Weekend September 24-26, 2010 at Ryerson University. The event will be limited to approximately 100 participants and expects to be sold out quickly.

If you read it here and want to attend, use this discount code (lowpostSWTO) to register for a great price.  Yes, there is a cost – the event is 54 hrs long and covers meals and drinks along with prizes and other great stuff.  Startup Weekend is a non-profit and we only look to cover costs and make the event great.

It’s also worth noting here that Startup Weekend has no rights to any ideas, products or companies that come out of the weekend.  We’re only interested in getting people together to build cool stuff and see where it goes.

Follow @startupwkndTO and search #swtoronto for news and updates about the event.

Lately, I’ve read a lot about the local community here in Toronto of tech entrepreneurs, VCs and everyone who falls somewhere in between or on the fringes. Now, I’m certainly no expert and haven’t done all the research to back up my opinions, but I am starting to believe a few things that might be worthy of discussion.

Firstly, the comparisons to the US are problematic on so many levels. While Canada looks and feels very similar to the US, speculative investing and risk taking in general is an area that has always differentiated the two countries. If it doesn’t come out of the ground, the average Canadian investor has no interest until the product is proven and the cash flow is certain. Therefore, it’s not surprising that Canadian VCs have trouble finding Limited Partners and raising substantial funds. Furthermore, the Canadian Government cannot be compared to its more business-friendly neighbour and really, always has much more pressing economic issues around industries and labour markets that need support today. Why would they want to support the privileged, white collar world of engineers and MBAs – even if future success in this area would certainly lead to better economics for the country as a whole.

All this being said, forgetting about the comparisons, what can we learn from our neighbours and our general experiences around this issue? If we recognize that the core issue in building an environment where Canadian entrepreneurs can succeed, is dealing with the question of risk and our baseline of risk tolerance, then I think we might be attacking the real crux of the problem. I was asked the other day what it would take for me to leave my current job to start my own venture and this helped me see that the “risk” of this proposition is the core problem – and that doesn’t mean that I am not a risk taker or that I don’t recognize that the profile of an entrepreneur must be someone who is willing to take on an enormous amount of risk. At the same time, an entrepreneur doesn’t have to be stupid or irresponsible with the risk they take on. This issue becomes all that more important in today’s economy which has completely moved the baseline for what is considered risky.

Because we so often see the world of startups through the stories of overwhelming public success, we get to hear how Mark Zuckerberg dropped out of Havard to make a go of Facebook or how Sergey Brin and Larry Page left their PhD programs at Stanford to take Google to the next level. While we all know that these examples are more representative of winning the lottery than examples or models for statup success, they do end up taking on a place in our minds that might consciously or subconsciously represent the profile of a tech entrepreneur. What if you have this image in your mind, but you happen to be well out of school, have a family to support and you’re just not in a position to start a company out of your parent’s garage? How many amazing products and companies have never been realized because so many of us just can’t quite take the risk, or the capability or idea came to us at a point in life when the risk is that much greater? Now, I might just sound like I’m whining and am afraid to take the startup plunge, but I am trying to get to the point…

What I’m really thinking about is what type of environment needs to exist to push this group of people to explore their ideas in a tangible way. We already have a lot of this in place with the cheap or even free access to technology and infrastructure to really bootstrap a product from concept to production. What we clearly have less of is time and the many other resources required to make a product successful. Take myself as an example. I have ideas and a strong background in technology product management with over 12 yrs of experience but, I’m not a pure engineer and can’t really develop my ideas into working code – or at least something that I think is worthy of putting in front of a customer. The fact is, I’m not a developer. Now, this shouldn’t be a problem in a world where development is becoming (if it isn’t already) a commodity. But, if you’re not in a position to fund the development yourself, where are you left? The days of investing in ideas are over and investors want to see real product, if not customers and revenue to back it up. You can’t get to customers and revenue without the product so how do you get started.

The incubators like Y Combinator are really targeting the 20-something team who have a cool idea but more to the point, are capable of developing it themselves both because they can code and, more importantly, there is nothing whatsoever in life holding them back. In my 20s, nothing would hold me back from trying something new, not getting paid, moving away. In fact I did some of this, but it’s now that I have experience and ideas that I think are worthy of taking to market.

I’m going to think on this some more. I have some ideas about how one might foster a better environment targeted at this group of people, myself included, that can’t work for free in a garage. I’d love to hear your thoughts if you’re reading and have anything to say.