Mark MacLeod

Mark MacLeod

Mark MacLeod is a twenty year veteran of the Canadian technology industry serving as CFO of Shopify and numerous other high-growth companies. He was a partner in Real Ventures, Canada's most active early stage venture capital firm. He founded Surepath Capital Partners, a successful investment bank. He now advises and coaches some of the most successful CEOs in the industry.

Never one to be constrained by the finance industry, he is also a DJ and founder of electronic music label Deep Down Music.

“In a nutshell, to me this means Be Yourself! Follow your own path. Don't follow convention. Don't do what is expected or conventional. This is how I live my life. I design my life so that every day is happy and fulfilling. I walk how I want!”
Elle: You have had a great career as a CFO, venture capitalist and you most recently decided to change paths after founding and building SurePath Capital Partners, one of the most successful financial advisory firms. Not many people can leave something they built at the height of success but you are not the average man. Tell me about your decision to focus on coaching, advising and investing in CEOs of high growth technology companies. And what does it take for you to take on a new coaching client?

Mark: I went through some big personal changes in 2019. Specifically the end of a long marriage. That prompted much reflection. I have kept a journal for most of my adult life and re-read a bunch of years. I often wrote about work. There was a clear pattern across all my roles: the days I was most excited about were the days when I had a 1 on 1 conversation with a CEO that I felt had impact.

When the first lockdown hit, companies stopped buying other companies for a brief period. This gave me a clean opportunity to wind things down. I now coach several amazing CEOs of high growth software companies and love it. I still manage to sneak in some deal work and helped close $ 580 million of deals last year. But my main focus is CEO coaching.

Elle: Tell me about the record label you founded. Where can we find your music?

Mark: Electronic music is a HUGE passion of mine. Has been since I was a child. I used to DJ at clubs and after hours parties pretty regularly. During the lockdown, I went to the next step and started making original songs.

In everything I do in life I want to do it all the way. So, it was not enough to release songs, I had to start a label. I launched Deep Down Music late in 2021 and we are off to a great start!

“Back when I was running my investment bank, every time we closed a deal I would get a suit or sports jacket made. The suit I wore to this photo shoot was for a deal I did for a company called Uberflip. Their motto is HUSTLE (i.e. move fast, get things done). So, I had the word HUSTLE embroidered into the jacket collar.”
Elle: You have great style. I love your suit and we are both fans of well-crafted garments. Tell me about the suit you are wearing and why you have the word HUSTLE monogrammed inside the collar.

Mark: I have always loved suits. I actually sold them in high school. The first six years of my career I worked on Bay Street and thought I was Gordon Gekko (from the movie Wall Street). I actually wish the world had not gone so casual.

Back when I was running my investment bank, every time we closed a deal I would get a suit or sports jacket made. The suit I wore to this photo shoot was for a deal I did for a company called Uberflip. Their motto is HUSTLE (i.e. move fast, get things done). So, I had the word HUSTLE embroidered into the jacket collar.

Elle: You have a word for this year, what is it and why is this important?

Mark: Yes - my theme for 2022 is Simplify. It can be easy in this go go world to just accumulate more and more. More things. More sources of information. More responsibilities. More, more, more.

The most precious thing we have is our time. Having time that is empty. No to dos. No obligations is vital. For the CEOs I work with, creating this space in their schedule enables them be more creative and effective.

Across all aspects of my life I am looking to simplify. One home, not two. The same recurring schedule with clients vs always scheduling. Eliminating or outsourcing things that I don't want to do or don't love. Creating a stop doing list regularly. Minimizing the sources of information I consume so I can just think on my own. It feels great and is freeing. Highly recommend it!

Elle: What does Walk How You Want mean to you?

Mark: In a nutshell, to me this means Be Yourself! Follow your own path. Don't follow convention. Don't do what is expected or conventional. This is how I live my life. I design my life so that every day is happy and fulfilling. I walk how I want!