I think this is a really interesting way of describing how entrepreneurs think. Starting a new business is a risky endeavor where the most likely outcome is failure so you have to believe that you have some additional edge otherwise it’s just not worth it.  As an entrepreneur, I believe that I have a unique insight into how technology is evolving and that gives me an advantage over my competitors. Will it pay off? I don’t know, but I’m willing to try and prove that it will.

So what is your business trying to prove? The easy answer is that all business are trying to prove that there is a market for their product or services, but I think that if you look at truly great companies you’ll see that they tie that thesis into a larger scale argument about society. They have a vision of the future and they are prepared to take risks now so that they will be prepared to take advantage of future trends.

This past weekend, I took part in Ottawa Web Weekend. The event was an opportunity for entrepreneurial minded people in the Ottawa area to get together for a weekend and launch a web product in just 48 hours.

On Friday evening about thirty-five of us got together at The Code Factory collaborative workspace in downtown Ottawa and started brainstorming product ideas. For four hours we pitched, debated, voted and re-pitched ideas until we had something that everyone could agree on; a reservation swapping service targeted at event organizers. I’m proud to be a part of Ottawa’s newest startup, reBookMe.com!

For me, the most fascinating aspect of the evening was to watch which ideas were chosen and how they got chosen.

About a week before the event, event organizer Marc-Andre Plouffe set up a private site where the participants could exchange ideas, track down competitors and discuss the pros and cons of each one. By Friday afternoon, there were ten or so ideas posted on the website with a couple clear favorites including my own location-based idea called “LastSeenAt”.

On top of the ten ideas from the website, we had another ten or so ideas which people came up with on the spot and pitched to the group. By the time everyone had finished pitching their ideas, we had about twenty ideas split among thirty-five people. This posed a difficult problem since, assuming most people would vote for their own idea, no single idea was likely to get a significant share of the votes.

There was a wide range of ideas on how to cut down the number of options and in the end we decided to group together similar ideas. This meant that we could reduce the number of options without throwing out anyone’s idea right off the bat. It also had the unintentional side-effect of taking some of the more specific ideas and grouping them into more generic clusters.

This brought us down to about ten general clusters of ideas. We then went around the room and asked people to defend the potential of each idea or take it off the list. This proved to be a time-consuming process which didn’t do much to reduce our options. Without any competitive analysis, it was hard to say one idea was more likely to succeed than any other idea.

Our next approach was to further reduce the field by doing a round of multi-voting. In this stage, each participant got three votes and had to choose their top three ideas from the ten or so general clusters from the previous round. Luckily, the results of this vote produced two clear leaders: “How green are you” and “Appointment scheduling”. Since both of these ideas were either loosely defined or aggregates of several ideas, we split the group into four parts to further refine the ideas. Two teams tried to refine each idea and then all four ideas were pitched to the group.

Predictably, when you ask people to come up with ideas and then vote on which one they like the most, they’ll often vote for the idea they had a part in developing. So when we asked everyone to choose which of the four products they liked the most, just about everyone stuck with the idea they came up with. This meant that appointment scheduling won by virtue of having slightly more people in their group. In the end, everyone seemed happy with the choice since most people seemed to agree that they were both equally good ideas.

So how did we end up with appointment scheduling? How did such an extremely unlikely experiment in startup incubation produce such an ordinary product? For that, I think you need to look closer at how the ideas were pitched.

It was interesting to note that ideas which seemed popular on the website didn’t attract as much attention in person. In fact, both of the final two ideas were ideas which were thought up and pitched on the spot. Of course, this could be because some people didn’t visit the website beforehand, but I think it has more to do with how large groups choose ideas.

Another clue into how large groups brainstorm was that loosely defined ideas seemed to generate more discussion and therefore more awareness than very specific ideas. This leads me to believe that people don’t want to be presented with complete ideas. They would rather be pitched a general concept and then come up with the complete idea as a group. This gives everyone a stake in coming up with the final idea rather than feeling like they are just implementing someone else’s idea.

Another trend that I noticed was that although two-thirds of the group presented ideas, the ideas pitched by business and marketing people seemed to be received better by the group. Now, you could say that this is because business people are better at coming up with new products and marketing people are better at getting their ideas across but I think there’s more to it than that. Take for instance, the fact that all three organizers of the event pitched ideas which struggled to gain any traction. Wouldn’t an event organizer have some of the same advantages as the business and marketing people?

The key here is to look at what types of ideas people were pitching. While the programmers, designers and organizers tended to pitch more specific implementations, the marketing and business people tended to pitch entire markets. For example, “there’s a lot of money to be made in being green these days” or “anyone who has a limited number of resources could use something like this”. In the end, I think these types of open ideas encouraged more participation and led to a much more involved group because everyone felt that they had a hand in defining the final product.

On Saturday morning, the business and marketing folks further refined the concept so that the designers and developers had a specific concept to work with and by Sunday night we had a working prototype to demo. More importantly, when the question came up on Sunday night about who wanted to stay on and finish the product, we had 100% of the group on board. I think that’s a testament to how well we brainstormed on Friday night and how well we were able to come up with an idea where everyone felt they were part of the solution.

The Cul-de-sac is a slow steady decline that ends in failure; a dead-end job, a death-march project etc. The Dip is trickier though because it represents both successful and unsuccessful projects where you encounter a major setback mid-way through the project (which Godin argues happens more often than not) . This dip can either break you or give you a significant push ahead of the competition depending on how you handle it. So what differentiates the ‘good’ dips from the ‘bad’ dips. Well according to the book, its all about picking the right size of dip and making sure that you have the time a resources to completely overwhelm the problem rather than just scraping by. This means quitting other side-projects and committing fully to dip that offers the greatest pay-off.

We live in a culture that values success more than almost anything else so building a series of overwhelming successes can give you the momentum to take on bigger dips. I think Steve Jobs has demonstrated this concept quite well by using the many successes of the iPod line to break into the extremely competitive cellphone market with the new iPhone.

The front cover of the book says “A little book that teaches you when to quit (and when to stick)” which is a pretty bold, if not impossible, promise to make. So how does it deliver on that promise? Well, at 80 pages long its hardly a definitive source on when to quit or stick but that’s not really why I bought it. The Dip is much more valuable as an overview of a common trend in project management and possibly in life. By understanding the trends that all successful projects go through, you’re much more likely to make informed decisions when dips arise rather than panicking and quitting or going down with the ship on a doomed project. All in all, its a great little book that’s well worth the cost ($12 CAD) and time (an afternoon) if you read it with the right expectations in mind.

UPDATE: If you read the book or are thinking of reading it you should check out this podcast with Seth Godin where answers questions about The Dip.

Monday night was DemoCamp 5, the last camp of the the season here in Ottawa until the fall. All in all it was a great event with some new and innovative products being shown for the first time. The presenters where:

• Steve Lecomte – Lead to Close – Lead Management/Asterisk
• Darcy Whyte – JumpSocial – Event Sharing System
• David Nadeau – YooName – Unsupervised Named Entity Recognition
• Aydin Mirzaee – bOK Systems – Who will you bOK today?
• Jerome St-Louis – ECERE Corporation – Cross Platform SDK/GUI/3D/New Prog. Language
• Scot Lemieux – Gizmo Logic Studios Inc. – Education, Bilingual Children’s Video Series

The one presentation that really stood out for me was YooName by David Nadeau which does Named Entity Recognition in English text. Basically what that means is that it will read through a page of text that you give it and it will pick out all the “things” like people, places, products, events, etc and classify each one for you so that you know which terms are events or which ones are products. What makes YooName unique is that it can classify 100 different types of entities where most system only group the entities into 5 or so more general groups.

Recently, I also started my own consulting company, Shawn Simister Consultant, to formalize all of the contract work that I’ve done over the past couple of years and to provide a platform for some of the contacts that I’ve been making over the last couple of months. Right now, I’m working on some very cool projects that I can’t wait to write about. So as soon as they’re ready for the masses I’ll post some more details up here.

Last month I attended the Mesh 2007 conference in Toronto and I had an amazing time meeting a lot of really passionate people who were all interested in the potential of Web 2.0. While I was at Mesh, I ran into Jeff Parks of I.A. Consultants and he showed me their new design for the web site, blog and the podcasts that he does. Seeing everything that Jeff and the other conference attendees were doing helped give me the kick I needed to get back into blogging and start building up my profile online.

Also from Mesh…

• An impromptu podcast about user experience and community that I sat in on in-between sessions.
• For those of you who missed the conference mDialogue has some high quality videos of the keynotes.

This past Monday, I was checking my RSS feeds and I noticed some amazing time-lapse photography of downtown Toronto on Sam Javanrouh’s photo-blog Daily Dose of Imagery.

At first, I was really startled by the black lines and drop shadows that he had used to separate the different parts of the composition but as I looked closer I started to understand why he had chosen to do it that way. Black lines or not, the image was bound to have obvious seams, especially in the sky where there were some really dramatic clouds.

Still, I was really curious what it would look like without the separation and I had done enough monkeying around in Photoshop to know that it could be done. So to scratch that itch, I downloaded each of the images separately and layered them together in Photoshop. Immediately, I noticed that by reversing the order of the shots I could easily stitch together the clouds and then the buildings merged together pretty seamlessly.

After about an hours work I had a pretty snazzy looking shot that combined all six images into one without any discernible seams. I thought it looked pretty cool and I was really happy to have been able to scratch my Photoshop itch without taking too much time away from all the work I have to do. I sent off an email to Sam to show him how he had inspired me and he said that if I posted it on Flickr he would link to it off of his blog (sweet!).

So now it’s been on Flickr for a couple days, it has been linked off of DDOI and then just today Sam’s time-lapse (and by extension my remix) got Dugg so the picture has been getting thousands of hits and some really nice comments too. All in all it’s been a lot of fun and a great excuse to update my blog.