Darryl Stewart, 48, a mechanical engineer, is co-owner and 'head of the herd' of Winnipeg-based Ibex Payroll, a nationwide payroll software company that focuses, in large part, on organizations helping adults with intellectual difficulties.
I was a geek. I was into computers and introverted, so I read tons of books. I always had a very independent streak. I started my first business before I left university as an engineer, which is not a faculty where you're encouraged to be an entrepreneur.
I was forever pushing too hard at work. My biggest problem was [that] I wanted to just get things done and do interesting things. I had been very successful, but I also knew that I was self-limiting, the way I acted. I was driven and pushy.
But I've also learned by making mistakes. You need to try lots of things and then keep moving. You can't be afraid to try things. That's where the excitement comes for me.
I've had this big-picture learning from other entrepreneurs and business people. Lesson No. 1: focus on one thing. The ones at the table who were the most successful had already made that transition.
We chose this world of payroll outsourcing, doing payroll for other companies. I sold the engineering business, I closed down the staffing business and said 'Okay, this payroll business is what I want to do.' With a business like that, I could create value for people that they would pay me on a recurring basis. I could see – from both my own lifestyle and supporting my family and not having to work 80 hours a week for the rest of my life – the benefits of having a business like that.
We had entered a very competitive world dominated by big companies. The simple solution, from what we read, was if you find yourself in a horizontal market – meaning you're trying to do the same thing in a big market for lots of people with no specialization – just carve out a vertical niche in there. Be a big fish in a little pond instead of the small fish in the big pond.
We can take an organization that's struggling to help a bunch of people with intellectual disabilities. There's a bunch of managers going crazy trying to manage all that [administrative] chaos when all they want to do is love and support all these people. We can jump into that situation, help them and get just as much reward as them.
Our purpose as a company is to empower and inspire great workplaces. The empowering is the software; the inspiring is the kind of culture we try to exude and share that with our customers. And it comes back to us: How do we inspire ourselves? Having those organizations as our main client base has been just wonderful.
I used to think the goal as an entrepreneur was to work 30 or 40 hours a week and [have] it just be the same, steady and normal. But I've come to realize that a part of the freedom of being an entrepreneur is that I can really go hard at it when I want to. I can indulge the desire to work really hard – work 60 or 70 hours in a week because I'm really into something – and then go to Thailand for 10 days. That's not for everybody, but it is for me.
Maybe all the friction in the past was that I didn't like being told what to do, how to fit and how to do the same thing every week. Having some success in business as an entrepreneur has allowed me to be more of the person I think I was meant to be.
I've been with very technical companies where you do amazing work for people, but it's just a project. So everyone's excited about the project … but then, 'Here's your cheque. Goodbye and thank you.' And you're 'Okay, now what do we do?' That was fun while we did it, but we don't have ownership of it and we're only as good as our next project. It's tough to motivate people and yourself when you just keep doing that over and over again.
As told to Robin Summerfield. This interview has been edited and condensed.