Back Home


A decade of TWG – Part I.

Last week, as I left the studio, in the early dark of a December night,  I was looking around the studio with a poignant mix of astonishment and gratitude .. Out loud, I asked myself  ‘Well.. how did I get here?’

It’s been an incredible decade for TWG. We’ve seen a couple macroeconomic cycles of boom and bust,  we’ve watched the mass movement online, from brochure web to social media web, to software on the web – systems that now run billion dollar companies. We’re now watching mobile computing become mainstream and I’m pretty sure we’re only a couple more years from the Tricorder.

TWG is short for The Working Group. We’ve always been about the technology, the code, the nuts and bolts of making things *Work* online. But it’s also been very much about the *Group* – the people we’ve been fortunate to work with through the years, each putting their unique mark on who we are.  Together, from the backstage we got to watch the internet grow into its adolescence. Here’s part I of the story of how TWG came about, and who was involved.

Part I – The wonder years.

TWG began 10 years ago, deep in the ‘I told you so’ period following the first tech boom and bust. It was mid 2002, and despite it seeming like a bad time for technology, three optimistic, and somewhat naive thirty year-olds decided that they had worked long enough at their crappy jobs at the bank, the tech firm, and the book store. They decided that it was time to join forces to create something amazing and new, a post-modern, post-corporate, post-business, magical utopia built from each according to his ability, and providing for each according to his need. Yes, still very idealistic, and armed with a few self-help books on how to start a business, Derek, Cam and Dom began planning their sure-fire assault on the business world, with their one great idea.

And despite our best laid plans, supreme confidence, and all the energy in the world, the only thing that seemed to be constant in those first couple years were our failures. Failures to convince people to take us seriously, failures to get paid when we did the work, and sometimes things like failure to renew the domain name .  Yet from the failures we learned some great lessons such as the value in humility, the need for proper project planning, and the ability to adapt. In fact our very name ‘The Working Group’ came out of our failure and subsequent need to adapt.  After months of weak response, we were desperate to get our customers (academics) to open and respond to the emails in which we pitched our services.

Sitting around the apartment over drinks, we surmised that academics might sit up and take notice if they saw email directed to them from a ‘Working Group‘ – common parlance in the academic and research world for a “bunch of people trying to direct things and get shit done“.  Our friend Ben Jones came up with the insight and company name in a moment of blazing simplicity, and we instantly agreed to go with it. Lo and behold, our response rate rose tenfold. It was our first implementation of lean customer development (change your business name till people answer you). Now if only our services had been as effective.

Well. As luck would have it, our initial ‘great idea’ wasn’t so great after all, but rather than being stubborn, we decided to adapt. That’s one of the great benefits of youth. The time invested in one thing is rarely so great that it will block one’s willingness to shift course and try something new.  Asking someone to change something they’ve done for forty years can be far more challenging – ask Kodak.

So we made our first ‘Pivot‘ in 2004 — but at the time we just called it survival. We decided to move away from providing web based services solely for the academic research world, to providing web-programming services to small business, and the not-for-profit world, who at that time were the only people desperate enough to take a chance on our rag-tag bunch of programmers.

St. Christopher House was our first major win. We parlayed the sad truth that our office (otherwise known as the front room of my apartment) was a block away from their ‘Meeting Place’- a gritty drop-in centre for the homeless, addicted, and downtrodden, at the corner of Bathurst and Queen. I think they saw the earnestness in our pitch, and believed that whatever the cost, we would work to understand their needs, and create something that they could use. Turns out they were right, and about nine years later, they are miraculously still using that php and duct tape system that we created for them. It sure ain’t pretty, but I challenge you to find anything online created for so little, serving so many, for nearly a decade.

Rant alert – I’ll stand on the soapbox for a moment and hope that the federal, provincial and municipal governments perk up and listen (we’re optimists). The grants that they provide to small community agencies like St. Christopher House, enabling them to hire staff for their outreach programs, or to build web and mobile based systems to serve their communities, have a powerful spin-on and multiplier effect. These programs help communities, they spawn careers, and help small and emerging companies just like TWG to move out of the basement and into the real world, hiring other young people, building the industries of tomorrow. Don’t stop funding that. Do stop subsidizing large, entrenched, and already massively profitable industries that pollute the planet far more than is sustainable. </rant> back to the story..

As TWG grew, personnel changed. Derek decided to take his strategic problem solving skills and apply them to group facilitation and consulting work with Cap Gemini. He also embarked on a very brave and remarkable personal journey. Through some difficult times we’ve  always remained the closest of friends and Dee has now adapted to her new way of being with a level of courage that I have found inspiring in my own moments of doubt. Cam, left with all of our blessings to follow his dreams with one of the Startups that we were working closely with in California. To this day, we continue to have a mutual admiration society from across the continent, and I look forward to seeing him again soon. Darcy, the perpetually inquisitive php developer with whom we had collaborated extensively, moved on to new and exciting projects on the West coast. TWG grew just like any other business through the years and continued to face the usual set of challenges around cashflow, how to find interesting work, how to land good paying work, how to compensate our team fairly, and mostly importantly how to continue feeling inspired and grateful for what we do each day.

In 2005, TWG had the good fortune of meeting Jack as he arrived fresh off the plane from Portugal, a couple years out of a degree in computer science. It took about two days to realize that Jack was the real deal; a great developer, who took great pride in crafting applications properly, and who had the patience and focus to accept every challenge that a new country and culture threw at him. It took about three weeks for us to realize that Jack was nodding and pretending to understand what the hell we were saying about half of the time. But what was obvious from the start, was that Jack was someone who I wanted to build a company with.

In late 2005 we also made a big move out of the front room of my apartment and into a studio on Spadina, sharing a great address and open concept space with a design firm – Evoke Solutions. I think that their owner, Jeff Howard, took pity on our fledgling startup and offered a chunk of floor-space for us to set up shop. The shiny new studio, the downtown address, and exposure to designers with whom we shared the space gave us the incentive to pick up our own game, and work at presenting ourselves in a light that truly reflected the quality of work we were producing.  The years we spent with Evoke were great years, when we began to grow and meet some of the key members of TWG’s future like Hesham, Sean and most importantly – Oleg and Scott.

Oleg had just rolled into Toronto after a computer science degree, and he somehow found one of our unique job posts online. Just one hour with him and it was clear that he was smart, was interested in building the same kinds of apps that we were, and that he’d be a great addition to the team. For two weeks, Oleg wore his business casual uniform to the office, until he realized that the job really was his, and he promptly switched over to jeans and tshirts like the rest of us. It’s universally acknowledged that Oleg writes some of the cleanest, most maintainable, and well structured code around.. Exacting in character, he’s a good teacher, and won’t shy away from a debate on code, convention, and best practices.

Scott, came in shortly after this – out of the blue, noticing our quirky job posts, wanting to try something new. Scott always had major geek cred, having worked at and led some small startups around Toronto. A veritable almanac of both useful and useless knowledge, Scott’s role is part chief of research, part plumber of the depths and idiosyncrasies of the internet. Scott also has some serious lateral thinking chops, and can be relied upon in a pinch to come up with a hair-brained or genius business idea (but you never know which it is). On one of our retreats down in Mexico he came up with the idea for PostageApp, and very soon after, TWG decided to make a strategic shift in how it operates..Pivot #2.


Stay tuned.. up next in Part II..

The core team of TWG perseveres, through good times and hard times and we begin to actualize our mission to be the best software shop in the world to learn at, work at and create at. PostageApp is born. Oleg builds a comfortable sofa. TWG makes many trips down south, our office moves to the Burroughes building and we bring in a new partner named Andres.

Ten Years Later: The TWG Story from The Working Group on Vimeo.

12 Responses to A decade of TWG – Part I.

  1. Adil says:

    Dom, there are so many points here that inspire me – be it the insights or journey or even just that you’ve taken the time to reflect and do this. Lookin forward to part 2.

    Cheers, Adil.

  2. Andrew says:

    I love these posts. :)

  3. Nael says:

    Great post! love it. Waiting for part 2!

    Congrats folks!

  4. Arati Sharma says:

    Dom, this is fantastic. Also, I love when you’re up on that soapbox. :)

  5. Dominic says:

    Thanks everyone.. I’m excited to post part two and three in the weeks ahead for your holiday reading pleasure :)

  6. Andrés says:

    Great post Dom. TWG was clearly an early adopter of Lean!

  7. Jason Hanley says:

    Great stuff. Eagerly awaiting parts 2 and 3.

  8. Chris Eben says:

    I know what’s going to happen and I still can’t wait to read it. There’s no doubt you’ve got a way with words Dom.

  9. Vivian Hui says:

    I remember sitting in my corner Evoke desk and seeing those first few dudes come in for their interviews… *tears great post dombort <3

  10. I love this story and the opportunity to learn more about our fantastic roommates. I’m excited for what’s next…

  11. Cameron Booth says:

    Great read Dom. Pretty amazing to see you guys grow past us sitting in the front room of your apartment on queen. Also awesome and nuts to see St Chris still on that system!!

  12. Holly says:

    Great post Dom! I really enjoyed reading about the early stages of the TWG journey. LOTR ain’t got nothing on this ;)

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>