Celebrating 20 Years of Growth and Success at My IT Guy

September 2024 marks a significant milestone for My IT Guy as we celebrate 20 years of dedication, innovation, and growth. Over the past two decades, My IT Guy has transformed from a solopreneur venture, into a robust, people-, process-, and data- driven organization, guided by our commitment to excellence, and we couldn’t have done it without the support of our incredible team, loyal clients, and valued partners.

Reflecting on Our Journey

old business cards reflecting the changing branding are laid atop a printout of one of My IT Guy's first websites

2004-2010: Old business cards, a “New Ventures” newspaper feature in The Record, and a printout of one of My IT Guy’s first websites reflect the evolving brand & services.

In the beginning, My IT Guy was just me, Adam Smith.

I was 21 years old when I registered “my-it-guy.ca” on Feb 13, 2003. I got the “MYITGUY” license plate soon after. However, it wasn’t until the first “My IT Guy” invoice was sent on Sep 21, 2004 that I internalized that I was building something real.

That first invoice was sent to “Sparrowhawk Industries”, a company specializing in accessible vehicle adaptations for mobility needs. I’d first met the owners, David and Mark, shortly after leaving high school while I was working at “The Computer Edge”, a PC retail & repair shop in Waterloo. I stayed in touch with them at my next (and last) employer and when I set out on my own, they were happy to know that they could still count on my help when they needed it. My team and I continued to support Sparrowhawk years after David and Mark’s successful sale and exit from their business.

Sparrowhawk is special to me for being the first, but there are countless other examples of wonderful clients like you who I am eternally grateful for who have remained with us through thick and thin.

Longstanding relationships like these are a big part of why I love my work.

Dec 5, 2012: Adam and Don at the My IT Guy exhibit booth for the Greater Kitchener-Waterloo Chamber of Commerce Business After 5

Dec 5, 2012: Adam and Don at the My IT Guy exhibit booth for the Greater Kitchener-Waterloo Chamber of Commerce Business After 5

I started My IT Guy with a simple idea of “fixing computers”, but in those early days any paying work was work I was willing to do. As a fast and intuitive learner, I picked up more and more skills and broadened the services that My IT Guy offered. There’s now a much longer list of things we don’t do any more than what remains as our focus today. Website development was one such side-quest that took up an increasing amount of my time, until, between that and all the tech work, my business administration duties slipped, and around Christmas of 2008 I realized that I was rather cash-strapped because I hadn’t sent a single invoice since sometime in October!

I learned that lesson, got caught up, and in February 2009, I had my first hire – a part time bookkeeper – one of my friends I’d made in high school, who is to this day still one of my closest friends. Later that year, My IT Guy was incorporated, officially becoming My IT Guy Corp., and the side-quest services were soon left to the wayside (though several of those websites are still in use today).

Over the years, we have stayed true to our core values of building relationships based on trust and exceptionalism in our work. Through every challenge and success, it is our collective strength in relationships, determination, and expertise that has carried us forward.

Milestones on the Path

Photo of My IT Guy street signage in front of the My IT Guy Office at 177 Victoria St N in Kitchener

Nov 17, 2020: The My IT Guy street sign was installed by Westmount Signs at 177 Victoria Street North, Kitchener

As you know, My IT Guy has been “more than Adam” for a long time now. Over the course of our journey, My IT Guy continued growing up in stages:

Obstacles to Navigate

It wasn’t always an easy path of course. There have been plenty of challenges faced by nearly all businesses over last 20 years. Recessions and a pandemic led to the demise of many, yet My IT Guy learned, adapted, and persevered through it all.

On a personal level, I started to reach peak burn-out in 2022. It was a scary time for me. Pandemic-era demand for our services increased the workload, while my techs had to give more of their time to their families’ life-at-home needs. I largely carried the surge of work myself, while also trying to balance and navigate my new role as Chair of the Board of Directors for the Greater Kitchener-Waterloo Chamber of Commerce – a role that I had stepped into in March of 2020, and a role which I wanted to give my absolute best to. I didn’t feel prepared for any of it, and I learned so much through all of it.

My stress was boiling over in the Summer of 2022, and by the Fall I had begun to accept that I needed to accept more help from others, and that I needed to make myself less accessible for a while.

I have since been on my own path of recovery, self-discovery, and growth. Recognizing my propensity for workaholism, at the outset of 2023 I gave myself some relief by moving to a 4-day work week. This was something I had tried, and failed, to achieve in the two years prior. This time it was different. Michelle was increasingly comfortable in her new role as Chief Operating Officer, and the process improvements we had been working on were starting to come together. I had confidence the business didn’t need me to be perpetually working 60-hours per week.

Despite the additional time I was taking for myself, there were still some significant challenges ahead. I carried on with the support of my team, my friends, and my family, and my recovery continued. By the Spring of 2024 I was finally starting to feel the crushing weights begin to lift from my shoulders, and today I am a much healthier and happier person than I have ever been before.

Improving Communication

Longstanding relationships still are, and always will be, crucial to our mutual success. I recognize that during my recovery that communications with us became more difficult while I was making myself less accessible. I’m sorry for the strain that has put on our relationship, and I’ve been working on rectifying that.

Our new 24/7 live answering service has launched!

Your calls to 519-496-6463, the same phone number you’ve been using for two decades, will be greeted by a friendly group of Canadian dispatchers who will ensure you can reach our team in priority sequence.

Team Photo, Fall 2022

Sep 27, 2022: Team Photo with Michelle, Ali, Adam, Autumn, Spencer, David, & Susan

Friendly Faces Along the Way

My IT Guy’s success over the years was influenced by many people who left their mark and who helped me, and the company, learn and grow for the better. A few of those notable names you might remember who have come and gone: Andrew, Autumn, Don, Mittens*, Steve, and Susan.

Today, I’m still fortunate to work with truly talented professionals, each of whom brings their own wealth of experience and depth of knowledge, and who perform as an impressive, cohesive, and mutually supportive team. Michelle, David, Spencer, and I are The Team at My IT Guy, and we are all proud of what we are capable of and all that we are accomplishing together.

Our Commitment to the Future

As we celebrate this momentous occasion, we are more committed than ever to continuing our legacy of continual improvement and success. Our focus remains on supporting you and providing our expertise in guiding your business through the complex technology landscape that lies ahead, safely around the threats, and confidently towards the opportunities.

Change is inevitable, and you can expect that My IT Guy will continue to grow, adapt, and reinvent itself, as it always has, for the better.

Thank You

I want to extend my heartfelt gratitude to everyone who has been a part of our journey. To our dedicated team, thank you for your hard work and passion. To our clients, thank you for your trust and loyalty. And to our partners, thank you for your collaboration and support.

Here’s to the next 20 years of success and growth! We are all excited to be part of this journey with you!

Sincerely,

Adam Smith

P.S. A small favour?

Consider subscribing to our newsletter, or if you would like to share your experience of our journey together, we would greatly appreciate it if you would leave us a testimonial.


A picture of Sergeant Reginald Mittens III, aks

Sep 12, 2024: Sergeant Reginald Mittens III, enjoying some time outside

*Mittens

In July of 2010, I brought a fluffy little kitten into my home, which at the time was also My IT Guy’s office until the end of 2016. During those 6½ years, Sergeant Reginald Mittens III, “Mittens”, was our unofficial mascot. Always friendly and welcoming, he kept my team and I entertained between calls and happily greeted every client who knocked on our door.

Sadly, in late August I was told that Mittens, at 14-years old, had terminal kidney failure, and on Sep 17, 2024, four days before My IT Guy’s 20th anniversary, I had to say my final farewell to Mittens.

I am grateful for Peaceful Passing making it possible for Mittens to leave this world comfortably in my arms, as we sat under the trees in our yard where we spent so much time together, in the only home he ever knew. He is dearly missed.