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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.

As a new iPad user, I’m wondering if this device is making me dumb. Don’t get me wrong, I love this device and know that this, and all the “me too” devices that will follow are going to change mobile computing forever. Still, in my digitally obsessed manner, I’ve decided that I want to do all my reading on the iPad. Why not – I have the Kindle app (I don’t like iBooks and already have kindle books that I’ve read on my iPhone), there are various great magazine apps, Press Reader is awesome and it’s a great device for keeping up with blogs. The problem is, there’s so much there, it’s accelerating an issue I was already worried about – the difficulty staying focused on one thing for longer than a few minutes.

Rather than reading through books from a single, beautifully designed device, I can barely concentrate long enough to get through a blog post. This is not a physical design flaw but rather an issue caused by the access to information and other great apps that are sitting there, asking you to go get them.  I continually find myself jumping around from app to app, website to website, checking/sending email, etc.  I’m sure most of you struggle with this all the time, especially at work where you are pulled in multiple directions throughout the day.  Now, imagine that small amount of time you’ve traditionally held onto for dear life, where you can curl up with a good book, being ripped away and replaced with another device, disguised as something to read on, ensuring you are a total slave to technology.

It’s not completely fair to blame this issue on a device as more and more, I find myself somewhat full of panic that there is so much information I want that I certainly can’t waste my time relaxing with a good piece of fiction.  If I’m honest with myself, this issue was percolating before I started using an iPad.  The iPad has just exacerbated this behaviour.

The funny thing is, I’m not sure I’m upset by this new dynamic in my life.  Instead, I feel completely committed to using my iPad for all my reading and finding a way to control my constant urges to access other things on the device.  I don’t need to describe all the benefits of the iPad – there are tons of sites to tell you what you need.  I want to take on the challenge of figuring out the “right” way to interact with my devices, just like the industry/market is learning as it goes.  In this regard, we’re living in a pretty amazing time.

I’m attending the Web 2.0 Expo this week in San Francisco.  Every year, there are a few themes.  Last year it was definitely Twitter and interestingly, even with the massive growth of Twitter since last year’s conference, it feels less relevant this year (or maybe it’s just yesterday’s news).  The big themes this year are: the lean startup movement, mobile, and platforms (everyone likes to say they are developing a platform).

I attended the lean startup intensive session on Monday curated by the man behind the movement, Eric Ries (check out his blog for all info and material on the movement).  I decided to attend this over other sessions because I’m passionate about startups but also because I truly believe that the lean principles can and should be applied inside larger organziations, like my current employer.  I’d like to think that I can apply some/all of these principles in my job now, developing software products and features for Actuate.  Interestingly, while the philosophies make perfect sense:  Define product/market fit, get close to your customers, constantly validate your product with customers and through data, pivot as much as you can or as much as necessary, etc (you can read them all for yourself – this stuff is all over the web), there is little to no information on how to build these practices inside of larger organizations.  I strongly believe that lean principles make perfect sense for defining and building products, regardless of the size of the organization, but in practice, being “lean” is a difficult challenge when many pre-existing structures, processes and bureaucracy are already well entrenched.  These are challenges at most large organizations, at least any that I have experienced through direct employment and through consulting.  As we all know, changing an organizations culture is next to impossible and needs to come from the ground up and likely from the beginning.  My personal challenge will be to do my best to apply the lessons learned from this movement and effect as much internal change as possible inside my organization to work in this manner.  In a startup, it’s much more straightforward, although the challenges are just different. Continue reading »

Since dumping my blackberry after 10 years of loyal usage for an iPhone one year ago, I have guarded my prized toy at all times, especially from the grimy hands of my two little daughters.  In fact, up until a few months ago, there was no way in hell I would let my kids touch my “other” baby!  Recently though, as my older daughter has become a more mature 3 year old (mature is a very relative term here), and in order to stop her from asking the same question again and again, I allowed some tightly monitored access to my iPhone.

image source: http://www.coneinc.com

I was utterly amazed at how quickly a 3yr old, with absolutely no direction, was able to quickly figure out the interface and operate the phone effectively.  This is a testament to the UI/UX design of the iPhone and the game changing nature of touchscreen technologies in general.  On the flip side, I spend a lot of time thinking about how much difficulty my otherwise capable parents have operating computers .  I suppose the next most obvious test would be to hand over my iPhone to either of my parents and see if they are as productive as my 3yr old from the moment they start using the device.

I know there have been countless studies on the learning capabilities of older people vs. young children but I’m constantly astounded by the actual divide between these groups.  One way or another, I think that technology, and especially mobile and touch technologies combined with an evolution in UI/UX design principles will drive a new capability between all age groups and demographics over time.  This evolution alone will drive an amazing trajectory of new technology adoption for just about every consumer segment now and in the coming years.

Given that my limited posting to this blog has centered around alternative ways to do a startup and/or support the startup community  I will continue this theme with a few more thoughts for discussion…

I just finished reading a blog post by Brian Link – Entrepreneurs Need to Bootstrap to WIN – and it prompted me to start writing this post, likely because in comparison to similar articles, it is short and sweet, clear, and to the point.

It’s an opportunity to comment directly on some of the messages in the article and perhaps use them to present an alternate view and ask a few questions for debate.  Here we go:

…Bootstrapping is hard. You need to stick your neck out; quit your job; have some money to spend; have a great network to lean on; and have a lot of confidence and guts. It’s certainly not for everyone. But for the brave who have a great idea, the reward can be huge.

Do you always have to quit your job?  What about bootstrapping in your spare time?  I know many will argue that you can’t be successful unless you throw yourself into something and take on the appropriate amount of risk.  Still, I’d like to argue that there can be opportunity to bootstrap on the side.  Granted your project will move more slowly but, a lot of wannabe entrepreneurs could use this approach to get further along  – develop early beta product, find a few customers, maybe even find some revenue.  Using this approach, perhaps boostrapping becomes a great way to get off the ground without all the risk and can help put entrepreneurs in a position to raise their first round from a stronger position and then fully take the plunge.

Let’s move on.  The next bit moves on to Brian’s four major points.

The best practices for bootstrapping can fill volumes of books, but here’s a quick summary of some ideas and strategies:

1. Equity. By bootstrapping, you can control your own stake and your partners’ equity percentages better. Equity is your most powerful tool to attract big talent. But be careful, there’s great need for balance here. Don’t dole out too much too soon and conversely don’t hesitate to share your equity for the right reasons. Many entrepreneurs fall into the stingy founder’s trap – they refuse to give up equity and because of that, they never get the help they need to launch the company. In that scenario, they have 100% of a company that’s worth nothing. Instead, offer equity to those who can dramatically move your business forward, but get advice about what percent makes sense at your current stage of growth. Equity, they say, is the most expensive compensation you can dole out (1% of your company when it becomes a $100MM company will be worth a million dollars!).

Again, nothing here would stop you from bootstrapping on the side and maintaining control of your equity.  Just be careful to understand the details of your current employment contract to ensure that your employer doesn’t have rights to something you might work on independently from your full-time job.

Brian’s point about the stingy founder is an important one.  It is very easy to guard the equity of a company that’s worth exactly zero, and this will get you no where.  Still, the informational resources available to the startup community often create this sort of mindset for new entrepreneurs as they are warned against the evils of bigger investors who will attempt to take too much equity and ultimately, too much control.  While it is fine and good to talk about raising money when you don’t need it, I think this is unrealistic in many scenarios.  Bootstrapping your way to a mature product, a critical mass of customers and revenue is very difficult without a reasonable first or second round investment.  That all being said, there is no single approach to this issue and simply put, the founder(s) need to be careful and strike the right balance to find and motivate valuable  people and resources while ensuring dilution is not too significant now and in the future.  Not an easy task I suspect.  I have to be careful not to come off as an expert on this matter.  In fact, I’m far from that and simply read and write about this subject out of interest and to spur some discussion.  Essentially, and I’ve said this before in other posts, I think a lot of information and advice targeting new entrepreneurs is generic, unrealistic and only speaks to a small audience.  For those reasons, I’m prompted to have a different or expanded dialogue on the subject.

2. Partners. Choose your partners and co-founders wisely. They should complement your skills and pass both the beer and elevator tests. Is this person someone you’d want to hang out and have beers with? If you were stuck in an elevator with this person for 24 hours, would you murder them? You’ll be spending more time with your co-founders than you might with your family, so best to have a great relationship and high level of trust and respect.

This goes without saying and I’m certain is one of the most important steps in the process to have any chance at success.  An interesting aside to this is the concept of co-founders as “good” friends.  In discussions with my wife on the topic, she gets very nervous about the idea of going into a new venture with a friend.  She believes that there is so much risk involved that you have to be willing to accept the fact that you are suddenly putting your friendship on the line.  I, on the other hand, believe that in order to meet some of the requirements listed above to find a good partner, it’s going to be quite difficult to find someone who is not already a close friend of sorts.  Part of the process and agreement has to be to create a strong foundation on a shared understanding of your approach and goals.  Furthermore, you must always remember that this is business and shit happens.  If your friendship going in is strong, then it should weather the many storms that you are sure to encounter during the startup process.  While Brian doesn’t quite say this, I think that a similar belief comes through in his message.

3. Business Plans. Don’t dwell so much on the format and length of your plan, but rather on the concepts of the business, the product or service and your competitive advantage. You should know exactly what your customer looks like, what alternatives they have, what the value is of what you’re offering and where you’re going to find those customers. And if you don’t have all those answers, get yourself some partners or team members who can. An executive summary of 1-2 pages is best. It should explain the big picture as concisely as possible. Don’t drag anyone through the details of your product until you’ve completely nailed it at a high level. Also prepare a Kawasaki 10/20/30 presentation and the two sentence and three paragraph versions. You’ll need those for marketing and email conversations to get people interested in having conversations with you.

Can’t really disagree with anything here.  I certainly take the first point – don’t worry too much about the format but rather, ensure that you’ve covered off the most important aspects of the product or service.  I’ve done this myself and it’s just a waste of time – especially early in the game.  There is plenty of time much later to spend time on formatting and adding information that certain stakeholders might be interested in seeing but aren’t necessarily critical to the concept.

4. Investors. You’re going to need investors at some point. Hopefully later instead of sooner. But as CEO of your company, your role is chief fundraiser, so start building great relationships. Find a trusted few to be part of your inner circle to give you honest and direct feedback. It’s never too early to plant seeds and start conversations. But be sure your message is polished enough before you request the face to face meeting. It’s not as hard as you think to get meetings with investors. But it’s very hard to build a compelling enough story to make them part with their money. Practice your pitch a dozen times on friends and friendly investors before you start talking to your big target investors. Also, do not assume that the big VC is your only option. Angel investors and chunks of $10-20K are extremely viable. It’s a lot easier to find a dozen people or more with $20K than it is to ask for large fractions of a million dollars from any investor.

Again, it’s hard to argue with anything here.  I think Brian’s last point is the most important one, especially if you’re doing your venture in Canada.  The VC industry in Canada is very small and limited and it seems more realistic these days to raise money through angels, formally or informally.  Creating a network would be vital to raising money and there is no reason that you can’t be doing this all the time, whether you’ve quit your job and thrown yourself into the project or are working on it more quietly on the side.

So in the end, I suppose I wrote this post for two reasons.  Firstly, I liked Brian’s article for it’s simplicity and straightforwardness.  There is so much stuff out there and often it’s convoluted and doesn’t really tell you anything.  This, at the very least, is a quick and helpful reminder of some things to think about when going down the path of bootstrapping your startup.  Secondly, I wanted to add my own point around the concept of taking this same approach but doing it in your spare time.  I’m sure that a lot of people already do this and it’s quite possibly the way that most ideas get off the ground.  What I don’t see is a wealth of information and resources that speak more directly to this approach.  Perhaps that’s because most people in the startup community in some form or another don’t believe that it’s effective.  I’m interested to hear your point of view on this.