Divergence, Elephants & Shipping – or How to Get the Most out of Startup Weekend


The third Startup Weekend Okanagan kicks off this Friday and I’m looking forward to playing my part as one of the mentors at the event.

Ahead of that I’d love to share some tips based on my experience as a participant at the first Startup Weekend Okanagan.

1. As with life in general… don’t take it too seriously.

I’m a competitive person by nature. Whether it’s Friday night 6-a-side soccer, poker with some buddies or gurgling competitions with my daughter – I like to win. Probably my only ‘regret’ about Startup Weekend 2012 is taking the event a bit too seriously.

As an entrepreneur I like to have at least a couple of irons in the fire at any one time. Normally that’s my main business (currently Hiilite) plus one or two other sidelines.

Back in March 2012 I had room to work on a new side initiative and was hoping that Startup Weekend may provide that. And what better way to kick start a new initiative than by winning the whole damn thing.

However, if you look at the survival rate and ultimate success rate of startups that are formed at Startup Weekend you’ll see what a long-shot that is. (The linked article is a little old – but seems to be the best info available).

My ‘strategy’ was the equivalent of joining a bunch of people on a ‘fun’ day out at the racetrack and then being the guy that had his head down in the form guide all day, with the sole purpose of turning his $50 stake money in to $5000. It’s damn long shot and you’re going to miss out on the fun.

Startup Weekend is a great opportunity to learn, to form friendships, to develop working relationships, to laugh and to be a bit silly – all while making a solid effort.

2. Separate your thought processes

Startup Weekend involves a lot of brainstorming. From product name, feature set, customer acquisition plan there will be dozens of aspects that require creative thinking.

And most people make one simple mistake with creative thinking: they don’t separate the divergent and the convergent thought processes.

Wikipedia explains this as well as anyone:

Divergent thinking is a thought process or method used to generate creative ideas by exploring many possible solutions. It is often used in conjunction with convergent thinking, which follows a particular set of logical steps to arrive at one solution, which in some cases is a “correct” solution. Divergent thinking typically occurs in a spontaneous, free-flowing manner, such that many ideas are generated in an emergent cognitive fashion. Many possible solutions are explored in a short amount of time, and unexpected connections are drawn. After the process of divergent thinking has been completed, ideas and information are organized and structured using convergent thinking.

I can not emphasize enough how important it is to separate out the two parts of the process. Preferably with a coffee or lunch break in between. Or at least a round of high fives.

Unfortunately what tends to happen is rapid bouncing back and forth between those thought processes. An idea is put forward. It is immediately analyzed & critiqued. Maybe it doesn’t even get put on the whiteboard.

Wrong. Wrong. Wrong.

If your team leader ends up running brainstorms this way stop them. They are killing creativity.

3. Don’t ignore the elephants

Without getting in to details, a team at the 2012 event spent the whole weekend ignoring two elephants in the room. Their ‘idea’ was completely unoriginal. It was also not legal.

If there’s an elephant in your room the first sign will be that you can’t get a balanced team together. You’ll end up with a room full of technical developers, but no business person will go near you… or the other way round.

The second sign is that the mentors will tell you.

If you ignore all that the third sign will be (or should be) the judges ripping in to you on the final evening.

Don’t be those guys.

4. Go hard on night one

Here’s a list of what you should get done on night one:

Decide on the overall idea and what’s it will be called?
Develop an understanding of who the customer is, what their problem is and how can you solve it?
Work out what the simplest version of your idea is – what’s it’s most important feature?
What technology will you leverage and who is working hands-on.
Who’s taking on the other roles? Bear in mind that there’s a lot of hats to be worn.

If you can get through all that on night one, then you’ll be free to start Saturday fresh and focussed.

5. Ship the damn thing

The Startup Weekend judging criteria are public knowledge – not just available to judges.

However Startup Weekend judges are known for being unpredictable, so while you may just win the damn thing by focussing on the business plan, customer validation and delivering a good looking presentation you’ll have missed out on a key objective of Startup Weekend – actually building something to MVP stage.

6. Be thankful

If this were a commercial event, that ticket price would have a zero on the end.

Remember – nobody is making money of this event. Everyone that has worked to bring it to fruition is a volunteer. The organisations that support it are donating use of facilities, prizing and all sorts of other things.

So be positive towards everyone involved. This isn’t a gig. Nobody owes you a performance. You’re as much a part of the event as anyone.

Good luck!

Richard Taylor