Wave CEO Kirk Simpson: “Why the most formative experience in my career was dropping out of university”

Fotis Georgiadis
Jan 8 · 10 min read

Honestly, I think the most formative experience in my career was dropping out of university. It wasn’t right for me for many reasons, but it left a significant chip on my shoulder. I felt like I always gave up when the going got hard and I was determined to reverse that tendency in my career. In a way, I needed to prove that to myself and those around me, and it’s given me great returns with Wave.


In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Kirk Simpson. Kirk Simpson is the CEO and co-founder of Wave Financial. Most recently he was named Canada’s Most Admired CEO in the growth sector and Wave was named Canada’s Most Admired Corporate Culture by Waterstone.

Wave is a, free, easy-to-use and secure financial software and service for micro-business owners to move and manage their money and is designed to help entrepreneurs feel empowered to achieve success while giving them tools to do so.

Since launching Wave in 2010, the comprehensive platform is used by 400,000+ small businesses every month, and its innovative platform supports the expanding small business market, which includes 31 million small businesses. In June, Wave marked one of the largest Canadian tech exits following its $405 million acquisition by H&R Block.


Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

From dropping out of university and launching two unsuccessful start-up businesses, to now being the co-founder and CEO of Wave during an exciting growth period — one thing has remained: my passion is to work with amazing people in service of something important.

I first launched Adventurelifestyle.com, a live web-streaming of adventure races, long before YouTube and other streaming services existed. This project was ahead of its time as the market wasn’t ready to support this venture, so I altered my path, and became deeply involved in the evolution and transition from print to online at several major Canadian print media companies.

My second startup, Outdoorsica.com, was a community of outdoor adventure enthusiasts with a user-generated knowledge base. After learning some great lessons in the dedication necessary to achieve success, I sold Outdoorsica to an outdoor adventure magazine.

With the experience of two startups under my belt, I knew it was time to launch Wave.

Wave’s mission is to help small business owners remove the friction from their finances so they can focus on running their business and as a long-term entrepreneur, I know first-hand how difficult this can be. With Wave, small business owners are empowered to put their passions first, while we manage the business of their business — for free, unlike competitors.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

After my first failed dot com company in 2000, I was out of work, in debt. I’d dropped out of college twice, leaving me with no degree, and very few marketable skills. As an entrepreneur, it’s expected you’re a jack of all trades — at that point, I felt I was a master of one.

Carolyn Meacher, President of Key Media — Canada’s third largest magazine publisher, responded to our going out of business email and said, “I hate to be a vulture but what are you going to do next?” I went in and met her a few days later and immediately got a job within a media company that was transitioning from print to online.

The next few years under Carolyn and then under Blair Graham taught me so much about leadership and culture. It showed how you can invest in people and let them thrive under great leadership. When you believe in people, set them up for success and let them run, it can have huge effects on their career, which is my biggest take away from starting my previous companies and working Carolyn and Blair.

When James Lochrie and I started Wave nearly 10 years later, this takeaway inspired the standard of giving our employees the most meaningful experience of their career. If we can do that, we will have been successful.

What do you think makes your company stand out? Can you share a story?

I think there is a remarkable amount of authenticity, kindness and humanity at Wave that I am incredibly proud of. We see it every day in how people interact with each other, how they celebrate people’s professional and personal accomplishments and their deep empathy for our customers. It doesn’t mean we are lacking in drive or a desire to be the best, but it does mean we do it in a way that values people — both those who work at Wave and the customers we serve. I believe that it is our competitive advantage. It makes me excited to come into the office every day and to work arm in arm with this team who serves brave entrepreneurs everywhere.

At Wave, we’re constantly looking for ways to empower small business owners to put their passion first. Over the last few months, we’ve been hard at work preparing to launch the Wave Business Debit Card, another way we’re eliminating the financial friction for small business owners who do not have the time, expertise or desire to manage their finances on a transactional basis. It will be available in early 2020 for Wave customers and I’m so excited to offer small business owners a completely free, no fee option to send and receive payments — and a whole lot more.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There have been around 600 or so people who have worked at Wave over the years and each and every individual has contributed significantly to our success.

Les, Ashira, Paul and Ideshini, who make up the executive team, have been instrumental and contribute massively to the company. Every day they keep the idea James and I had for Wave alive.

I truly believe that the role of co-founder and CEO in a startup gets too much of the hype around a company’s success in this day and age. The reality is that the team around you is the difference between success and failure. The exec team and the team overall at Wave makes up for many of my shortcomings.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

This question has a special meaning to us at Wave because we happen to serve brave entrepreneurs who exhibit this characteristic every day. That’s a privilege for us.

I prefer the word grit in some ways more than resilience. I’m a sports fan and I’ve always been drawn to the players who are willing to do whatever it takes to win. If your shot isn’t falling in basketball, then play better defense, get more rebounds, make better passes, etc. Show your team you’re not going to sulk, but instead you are going to dig in. I view business similarly.

I remember a time when I volunteered to clean the company washrooms for a couple of months. We couldn’t afford a cleaner and I wanted to show I would do whatever it took to help the company. It wasn’t fun but doing that was required. In some ways that becomes learned behavior within an organization.

Small business owners face obstacles every day. You’re going to take a lot of punches. How you react to them often determines how successful you’ll be.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

My mind goes to someone like Nelson Mandela. After being imprisoned in South Africa, he came out resilient — a better man ready to forgive and change the world, rather than angered and withdrawn. Someone like Harriet Tubman also comes to mind. She escaped slavery, and instead of celebrating her freedom she went back to help others at great personal risk.

These are the types of people who inspire you to be better and do better.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

In 2015 Wave was running out of money. We had incredible user growth, but revenue generation was far slower. It was a difficult time. We were struggling to find our next round of finance and were quite frankly weeks away from being insolvent.

We were in discussions with ADP (the giant payroll company) about an investment and a strategic partnership. No one believed that they would come to the table in time and complete the deal. In fact, our board didn’t even believe it was possible.

In the end we secured the investment and the partnership because of the leadership and belief that John Ayala at ADP had in the opportunity. The deal closed, the partnership continues to this day and when Wave was acquired, ADP made a significant profit from the investment.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

I failed twice before launching Wave. At 23, my youthful naivete and a small network led to the demise of Adventurelifestyle.com. A decade later, my second venture Outdoorsica, while more successful, met the same fate with lack of passion as the culprit.

It wasn’t until 2010 I found my niche, working with amazing people in service of something important, which led to helping entrepreneurs feel empowered to achieve success and giving them tools to do so. Like me, nearly 30% of entrepreneurs fail, so I uniquely understand their challenges, and created Wave as a solution to their multitude of money management needs.

Since launching Wave in 2010, the comprehensive platform is used by 400,000+ small businesses every month, and its innovative platform supports the expanding small business market, which includes 31 million small businesses. In June, Wave marked one of the largest Canadian tech exits following its $405 million acquisition by H&R Block.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

Honestly, I think the most formative experience in my career was dropping out of university. It wasn’t right for me for many reasons, but it left a significant chip on my shoulder. I felt like I always gave up when the going got hard and I was determined to reverse that tendency in my career. In a way, I needed to prove that to myself and those around me, and it’s given me great returns with Wave.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

For me what jumps out as I think about it are two things:

First, how can I give back to entrepreneurs to potentially help them avoid some of the mistakes that we made along the way? I love spending time with entrepreneurs and small business owners. I find it impossible to not be motivated by their desire to blaze a path on their own. Through Wave and my own time, I am committed to doing what I can to help as many fellow entrepreneurs as I can.

And second, our son was diagnosed with ADHD when he was 6. Along with it he had some behavioral issues, as well. It’s been incredibly difficult and yet rewarding for my wife and I to invest time, energy and money to give him everything he needs to learn to live his best life and I recognize that we have been incredibly lucky to have the resources we needed to help us find answers. The fact that many parents and children don’t have access to the help and support they need breaks my heart, so my wife and I are actively looking at ways that we can help bridge that divide.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them :-)

Like many people, I would pick Barack and Michelle Obama. I deeply respect them and would welcome the opportunity to meet them. I value their intellect and would enjoy speaking to them not only on today’s world, but how they’ve handled their marriage and the raising of their children in a high-profile environment. They have many traits that I deeply admire.

How can our readers follow you on social media?

You can follow me on LinkedIn and/or Twitter and you can follow Wave on Twitter, Instagram and LinkedIn.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Fotis Georgiadis

Written by

Passionate about bringing emerging technologies to the market

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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