Software Hamilton revamp

I’m Kevin Browne (@hamiltonkb), editor of this website that’s been running since January 2011. I’ve had one crazy last 7 years, especially the last couple years, and especially the last 8 months. Long story… finished a PhD, got married, bought a house, and a lot of other things. Suffice to say this blog has gotten dusty and broken as a result. Mea culpa.

I’m going to be making some immediate changes to the website itself, and some longer term changes as to how it operates. In short, I’m going to be more formally treating it and operating it as an indie media outlet. I have wanted to get to this for a long time… shifting gears takes time itself though.

Here’s what’s changing listed below in terms of website structure and operationally. For a pedantic naval-gazing tome as to why, keep scrolling past the list!


  • Mostly batch updates, mostly on the weekend. Software Hamilton has more or less had one daily update Monday-Friday since 2012. This has been resulted in a major “user behaviour” as most users, 80-90%, check the website daily Monday-Friday, and traffic goes to very little on the weekend. This made sense in 2011 when there were hardly any startups, and maybe 3 regular tech/startup events in the city. This format has increasingly made less sense as time has gone on. So now, expect a cluster of postings on the weekend, and some sporadic postings during the week if some big news happens (e.g. product launch, funding, etc.).

  • “News magazine” front page. The “blog” format of one post on top of the other was great for the earlier daily-update and associated user behaviour, but it won’t be anymore. So expect the new website to look closer to BetaKit and other proper news websites – a wall of stories and happenings that you can click on that take you to an individual page.

  • Automated newsletter updates. There is a plugin for pushing out newsletters that I can use. It’s good for generating a simple list of events, but it would need 5 PhDs and some good machine learning algorithms to turn full-detailed calendar event descriptions into something suitable for a newsletter format (maybe that Reddit-bot that summarizes news stories could do it). As a result, the plan is for the newsletter to only list event titles, dates, locations, and links, and it’ll be on users to click through to find out about each event. I know it makes the newsletter less user friendly, but that’s the nature of a scaling community anyways, and it’s what can be realistically done at this point.

  • Automated calendar updates. The number of events and meetups in Hamilton has scaled ridiculously in the last few years, despite my best efforts I’ve lost track, and it’s become a job to just try to maintain the calendar. There are some ways (plugins, scripts, etc) I can automate 80% of this, and I’ll be implementing those. For the other 20%, see below.

  • Contributor role. Even with some automation, there’s still a lot of updates and churnalism to be done. What I could really use to keep things at the quality-level I’d like to see is a dedicated intern. But I, and maybe you too, have moral concerns with having interns and not paying them (especially not even a stipend). That said, even with a part-time 4-8 hour a week intern, quality and quantity could be much better. Which leads me to…

  • Monetization. I never want to personally make money off Software Hamilton, I’ve lost/spent money, and I’ll release “financials” if this is ever in any doubt. It’s a passion project, inspired by sorta-similar efforts (e.g. Raise The Hammer, The Public Record), I’d die a little inside if it ever wasn’t, and I don’t want to “sell out”. At the same time, if you care to read through the pedantic thoughts below, I’ve come to realize some monetization is better. With monetization, I can pay that contributor, even if it’s only a stipend, it’s at least something. So you might see some advertisements, a Patreon button, or maybe even some fun merchandise. The website and all related features will remain free for anyone reading.


Expect the website update over the next 3 weeks, and the operational updates (contributor/monetization) over the next 3 months.


OK, now for the pedantic naval-gazing I promised you.

Software Hamilton was initially started to act as a community hub similar to other regional websites and initiatives that were happening around Canada at the time (and really the world). I read everything I could, attended everything I could, and talked to everyone I could. But I really didn’t know what I was doing, I was just trying my best to give the community something similar, and my plan was to figure it out as I went.

I’ve had a lot of people tell me exactly what “Software Hamilton” should be over the last 7 years, all great folks, all with wildly different opinions. Some people wanted me to get grants and turn it into another non-profit with another mandate, carving its way into a patchwork of existing non-profits (that I feel is a bit overcrowded already). Some people wanted me to turn it into a member-driven organization (paid or otherwise) that would try to formally represent the sector, and exert political clout. Some people wanted the loose, informal club model that you see at meetups and whatnot.

All of these different kinds of structures can create different kinds of value, there’s nothing wrong innately wrong with them, they can all be forces for good. There’s a few reasons why they aren’t a fit for Software Hamilton though.

For starters, all those things listed above already exist. I have no interest in duplicating them. If you want a non-profit pushing along the sector, Innovation Factory. If you want the member-driven organizations and political clout, there’s the Chamber of Commerce and different taskforces put together by different institutions. If you want the informal club, there’s a ton of meetups and similar things.

I think community building efforts are best when they’re trying to “fill gaps” in the community, and when they try to create new value. Maybe not always, but for the most part, these existing tools fill the gap they should, and create the value they should.

The other, bigger reason is harder to describe properly (…here comes the hardcore naval-gazing). I’m not sure if I’ve stumbled on something in human nature that’s hard to describe, or whether I’m bad at describing.

But the idea is this… pre-existing power dynamics and interests tend to be re-enforced by many efforts aimed at assembling people together with a structure. I’ve gotten to do a lot of social things in the last 7 years… organized events, own and partner in private sector companies, partner with non-profits to create new programs, chair committees, etc, and this is something I’ve seen everywhere, so that’s why I think it’s a human nature thing.

So for example, if you were to bring together a bunch of mover and shakers in a city to talk about increasing economic growth and related ideas, they’d tend to go for expanding their current industries, rather than trying to create new industries altogether (that they don’t have an interest in and/or don’t understand). This goes doubly so when talking about how to allocate money or resources to anything. They’d describe the existing industries as differentiators and strengths, they’d create programs to grow these industries, and they’d allocate money to them. And a lot of the time, this process is great, and value is created, but only a certain kind. Nobody is a moustache twirling villain in this scenario either, it’s not about “down with the system” or whatever…. it’s just how it is… people have their interests, “they know what they know and not what the don’t”, etc.

What’s interesting is that this process… of pre-existing power dynamics and interests being re-enforced by social activities, applies just as much at things as simple as pub nights as it does at board tables. You’ll get someone coming out to the pub night that does awesome stuff that just doesn’t quite fit with the group dynamics, and poof, even without any ill-intent or malice, they’re left out, and so are there ideas. Whereas if they had another group to go to that fit their interests, they could more likely contribute and create value.

It’s honestly like Nash equilibrium, Prisoner’s Dilemma game theory type stuff. By everyone choosing to re-enforce their own interests and understanding over possible other interests or things they don’t understand, we all lose out on the value that isn’t created by the unexplored paths, and people capable of creating value that we just don’t appreciate or include.

This doesn’t make structures bad. Again, personally I work with all kinds of structures (private sector, non-profit, etc) and at a certain point they are necessary to create and especially amplify creating value (e.g. you get a grant, you hire an employee, and all of a sudden you’re able to reach 3000 people instead of 30). It just means that structures aren’t perfect, especially when it comes to making change happen. This is why people say “real change happens from the bottom-up”, because at the grassroots any sort of social dynamics or interests don’t really matter.

The problem is, a lot of those roads untravelled and a lot of those people capable of creating value are folks we need engaged. To use one example, there’s still a disconnect between McMaster students and Hamilton (though it’s 10x better than a decade ago). The McMaster brain drain was one of my biggest motivations for doing this at all… being a McMaster student for so long, and seeing my friends leave year after year, to create value in other cities.

Anyways, this whole “pre-existing interests being re-enforced” stuff” is why it’s particularly hard to create and grow new things. I remember when I was creating Software Hamilton 1.0, there was a point where I had to tell a mentor who was advising me how bad an idea it was that, “I’m not asking your permission, this is happening, I’m asking whether you will help”. I remember when I was creating a new initiative in the city, a bunch of movers and shakers told me it wouldn’t work, was a bad idea, etc. Nope, they were well-intentioned, but wrong. And I’ve been at the other end of it too… I’ve gotten to watch all kinds of people create things I never thought would work, and few others did either.

The one thing I did with Software Hamilton that I think I did right was to give support to people who wanted to step up into a leader role. So if somebody wanted to start or were starting a new company, or a conference, meetup, co-working space, or whatever other initiative, Software Hamilton gave them publicity and a push how it could. This let people explore those pathways that maybe an organization that is more structured would not see the “interest” in doing so. And some pathways work, and some didn’t. But the point is people could try weird, new stuff and find out for themselves. Many community initiatives don’t operate like this, some people want to control and direct, harness the power of others, or have this notion of turf, etc, and it just doesn’t work at creating an organic, real community.

The approach I’ve tried is what I interpreted as being advocated for by others in further along communities, and I just imitated it as best as I could (they’re better, but I did my best). I think that approach played a positive role in developing a more vibrant community than the type of “community” that is captured or represented by a specific organization, with all those interests and power dynamics. That’s also why it’s important to me that I don’t ever cash a cheque with Software Hamilton on it, I also want to keep my own interest in it such that I’m not ever depending on it for money (though, short of perhaps ultimately unsustainable grants, I don’t think it’s possible to live off something so niche). Personally, I think you can’t really blame someone for bending to prevailing interests if they need something to put food on the table.

That’s why I want to keep Software Hamilton as a lightweight indie media outlet. So when somebody has a crazy, weird new idea, or I have a crazy new idea (as I often do), Software Hamilton can just push it out there, free from any of those “interests”, and let the market decide what has value.

But the other problem is sustainability. In my travels over the last 7 years I’ve come to appreciate that structure can provide value and make things last longer and improve in quality. It’s great to have this indie sort of approach, but how do you make something sustainable longer term? If you want to go fast, go alone, but if you want to go far, go together. That’s where some lightweight monetization and the creation of a contributor role come in. It’s the minimum amount of structure that I can get away with for the project, while making it less dependent on me alone, improving the quality/quantity and especially consistency of content, and keeping it independent.

Anyways, I know this is a tomb, I just wanted to explain the rationale.

I’ve got some crazy ideas left to try that my gut tells me aren’t so crazy. And if you’ve got something you want to try, and your gut tells you you’re right, even if some others think it’s crazy, you should give it a try, and just see what happens. Hopefully Software Hamilton can help you push it out there!


Kevin Browne

Editor of Software Hamilton.