Successful Small Business Start-Up

Kirk Simpson, Co-Founder/CEO, Wave

As Co-Founder/CEO of Wave, Kirk Simpson is always looking for new ways to make tools work for small business owners. He has headed up business development and advertising sales, and has built tech teams for some of Canada's largest media brands, corporations and financial institutions. Wave is his third start-up.

Q: Have you always had the entrepreneurial spirit in you?

A: I've always liked taking risks and was never patient enough to learn well in a classroom. I think the combination of these two things has led me to drop out of university twice and start a total of three businesses.

Q: What inspired you to finally make the leap and start your own company?

A: I started two companies before Wave. Neither was a roaring success but I learned lots of lessons along the way.

In between founding those businesses and Wave, I worked in the media industry for about 10 years. It just got to a point where both James Lochrie (my co-founder) and I were sick of working for someone else. We really wanted to innovate and be around smart people who were committed to making the exceptional happen.

Q: Were there ever times when you had doubts about whether you would be successful? How did you stay positive during the lean times?

A: I'm lucky that my co-founder James is often very positive when I am having tough times and vice-versa. That's a real advantage. And bottom line is that as an entrepreneur you have to be incredibly resilient. If you're not naturally resilient and positive you're not going to be successful. It's really that simple since you're going to get a lot of curveballs along the way.

Q: When did you know you were ready to expand?

A: Good question. When we started seeing thousands of business owners sign up every month we knew that we were on to something. And once we knew we could raise significant capital - especially from our second round onward - we knew we could be aggressive in going after the market.

Q: What new challenges have you experienced now that you are an established and expanding company?

A: It's an amazing feeling to be so tightly tied to the success of hundreds of thousands of small business owners but it also brings a unique set of challenges as well. Two things come out of this in our industry:

1. We need to be as close to 100% uptime as technology permits. Wave is critical for our customers to get paid, or for them to pay their employees, and we take this challenge very seriously.

2. We also need the software to be fast and responsive. Since we are now tracking well over $100 billion in income and expenses on behalf of our customers, we have a lot of data running through our servers every second. Again, it's a nice problem to have since it means you have earned the trust of your customers, but it does mean we spend a lot of time and thought ensuring that our application is as fast as possible.

Q: If you had the chance to do it over again, what would you do differently?

A: To be honest I don't think about things like that right now. I believe those lessons can only truly come with a bit of time and space. You need the luxury of a bit of downtime to reflect on some of the macro lessons that were learned. I think you have to be removed from the day-to-day pace. Right now all of my energy is driving towards being a better CEO each and every day. That takes a commitment to being in the moment and not looking too much in the rear-view mirror.