Dominic Bortolussi

On the road again

October 20, 2017

Links from this article: Original post by Dominic on Startups & Venture Capital

Originally posted on Startups & Venture Capital, Dominic is the Founder of TWG and a member of Founder’s Only. Dominic and Rajah have been friends for Dominic’s more than half of Dom’s Fourteen Year Journey.

In September of 2016, after fourteen years, I decided to step away from the company I started and love — The Working Group. It was hard to do, but I was grateful to see the company in great shape, and in the expert hands of three amazing partners and a strong management team.

It’s now September 26, 2017, our fifteenth anniversary. It took me a year to reflect on all of this and to write this post. TWG for me was like a lifetime. Here’s how it all happened.. Back when it all began

In 2002, I started a little web services business with two close friends, Dee and Cameron. We called it The Working Group. The name has since been shortened to TWG - as you do in these acronymical times. Between the three of us, we could design, code, and sell well enough to meet the base requirements for any fledgling web services business. Our world headquarters was in the front room of my run down apartment, directly over a Chinese seafood restaurant on Spadina Ave. We didn’t know what would become of our small business, and we didn’t have much time to worry about it. We were scrappy, we worked long hours, and fortunately good things happened for us.

A place to live and grow

There’s a campy jingle from 1967 about Ontario — a place to stand a place to grow, Ontari-ari-ari-o — Jim Carrey and Conan O’brien sang and joked about it here a few years back. It’s from an era of earnest and unbridled optimism, with an eye to the future. When we began TWG, we had similar optimistic ambitions (minus the awesome jingle), and after a number of years we enshrined that early mission — to be the best software studio in the world to learn, create, and grow at. In doing so, we focused on the means rather than the ends for our business, believing that if you build a workplace where people love what they do, and the people they work with, then great things will naturally follow. In those days we couldn’t afford the salaries of the bigger firms, but we always did our best to compensate by cultivating the best environment, focused on the qualities of learning, experimentation, professional and personal growth. We took team trips down south in the winters, and north to the lakes in the summer, where we hacked on our own product ideas and celebrated our victories as often as we could. To this day, we still focus on a great environment — a place to learn, create and grow. It’s a ‘first principle’ at TWG, and describes how we approach work and life. It’s embedded in our DNA.

TWG retreat circa 2007

Storm Clouds

TWG’s first big test occurred when my original business partners, Dee and Cam needed to leave the company and the city, for a variety of good reasons. I spent long nights wondering how I was going to manage a small team, and grow the business without them. I was a capable salesman, a distractible project manager, and a bad coder, and TWG wasn’t generating enough revenue at that time to afford the experienced senior staff who could help me out of this jam.

So I hung on for dear life over the following few years with a small team, and I was fortunate enough to meet and bring on three amazing business partners who helped bridge the management gap and then much more. They each brought their own unique personalities, experiences, and skills in helping transform TWG into what it has become today.

First, Jack Neto joined as an engineer in 2005, and soon after became my business partner. We first met when I was grabbing a loaf of bread at his cousin’s convenience store on Queen West. He was visiting from Portugal and when we were introduced he handed me a crinkled paper resume and told me that he liked to do web work in PHP, and had built some software for the European Space Agency. Suffice to say that I grabbed him then and there, and brought him next door to our office (by then we had moved in the world to a unit above a tattoo parlour). We got to work, and Jack and I have never looked back.

Then in 2007 I was introduced to a friend’s acquaintance, who was running his own small creative agency. His name was Andrés, and we quickly found mutual admiration in our dreams, values and ambition. We spent many hours at Le Gourmand sipping cappuccinos, and munching on their legendary chocolate chip cookies, talking about business, life, guitars, and the future. Things got serious pretty quick, and we dug into the mechanics of how to build business alignment and join forces. I was grateful when Andrés Aquinobrought his formidable vision and people skills to TWG in 2008. Since then, we’ve worked together, travelled together, and along with Jack even played in a rock band together (Les Bonaires .. 4EVR !!).

Finally, in 2010, at one of the Mesh conference after-parties at The Drake, Mike McDerment introduced me to an acquaintance of his, Chris Eben. Chris was back in Toronto, after long stints in San Francisco and London where he worked with some large tech organizations. But now, back in his home town, Chris was trying something new, by getting involved in the Startup space — running Startup Weekend. I remember our conversation; Chris wanted to know if working in a small agency could offer enough growth potential, and enough pay to justify a much desired career move. He envied the self determination that running your own business offered, and he was looking for some straight talk. We spent many months following this encounter, on my front porch sipping beers and working out the mechanisms for his joining TWG. In 2011, despite caution from some of our advisors, we took the plunge. Looking back now we laugh at how much of a ‘win-win’ it was.

In fact, each partner at TWG was a clear win-win. As each joined, TWG’s identity evolved, and what began in 2002 as a company that builds websites, morphed over time into an ambitious international consultancy that now creates software platforms, and drives world class innovation for some of North America’s most successful businesses.

The value of partnership

Nobody knows for certain what further evolutions lay ahead of us, but looking back, partnerships were the key foundation for TWG’s success. When I’m asked what was the key determiner of our success, I point to the partnership. Be willing to bring on partners, but choose them wisely. Great partners help carry the load, great partners keep each other accountable, great partners are with you in the trenches when times get tough, and there’s nobody better than a partner to celebrate your wins with.

A sabbatical

It was with my three partners that I sat down a few years ago and discussed taking a sabbatical, to contemplate what was next for me and TWG. I had reached a plateau, and I wanted to step away for some fresh perspective and inspiration. So I spent nearly five months travelling, writing, thinking, and experiencing life in India and Southeast Asia. Those were some of the most important and unforgettable days of my life.

When you’re uncertain about your direction, do yourself a favour and stop. Find some time to step away, look around, reflect, and understand yourself a bit better.

What are the things that you’d do if nobody was paying you, and what are the things that you can just never seem to finish? A wise friend even suggested to reflect not only what brings you joy, but what brings you rage, as a clue to where to seek greater fulfillment. Keep a journal, and for extroverts like me, learn to be on your own. Don’t expect an epiphany on what you should do next, but the signal will emerge from the noise, if you listen. Morning over the ricefields. Time to step away

“Walker, there is no path. You make the path by walking.”

  • A. Machado

After a lot of searching, thinking, feeling, and writing, I got back to Toronto, and reconnected with the partners. We talked. A lot. We had never been stronger, our client base was growing, the team was flourishing, and we had successfully created an effective management team. Andres and Chris were excited to take the helm, with a more streamlined leadership team and to propel TWG into the next phase of growth. And I was feeling the ‘call of the road’, and a yearning to work with small agile teams, solving new problems. It was a good time to step back from TWG.

Fortunately for our partnership, and TWG, the four of us were very aligned on the values that we would honour through the transition, and I’m happy to say that we were able to make it all happen without teams of lawyers, and with our friendships strongly intact.

Now, as I begin this next phase of my life, you can continue to reach me at I’ll remain active on the TWG ownership board, I’ll continue to drop by the office for the occasional Monday yoga, or Friday demos, and I’m always up for a good coffee and conversation. In the months ahead I’ll be focusing on what gets me excited each morning — the Canadian startup community. I’ll continue to work with a number of Accelerators, and startups around Canada, as well as an organization I’ve launched called Caravan Ventures.

It feels really good to step away with fifteen years of wonderful experiences and friends. I’m tickled that the baby’s all grown up — a healthy, vibrant software agency of 100+ talented individuals, spanning multiple countries and time zones.

With immense thanks I look to my three partners and co-workers past and present for shining some light along this path. I’ll step away now with a glad heart, knowing that TWG will continue to make the world a little bit better each day — by designing and creating the very best software for the world’s innovators.



….but like the tipsy uncle who won’t put the mic down after the wedding speeches… I want to send one last shout out to the old timers who were there through the early days — Jack, Hesham, Oleg, Scott, I shotgun a Pabst for you!

I’ve also bent the ear of many colleagues as I explored my departure, and want to thank them for their sage advice. Mike McDerment, Pete Forde, Mark McLeod, Jonathan Blumberg, Andrew Peek, Adil Dhalla, Gregor Bingham, David Furlong, David Bortolussi, Rob Hyndman, Bill Barbot, Anna McRoberts, Anil Patel, Ronan Levy, Mike Schaus, Rhia Mackenzie, and of course my parents Bob and Michele — a big thanks to you all.


Written by Dominic.