Dennis Mitchell had always dreamed of the day he’d be scoring touchdowns as a pro football player. But he learned that sometimes in life, much as in football, things can suddenly slip right through your fingers. In Dennis’ case, it was injuries and knee surgeries that put a stop to the football dream.
But he wasn’t prepared to stay thrown down; on the contrary, he swiftly got back on his feet to enter a new playing field: the one of finance.
It began with attending Wilfrid Laurier University for an undergraduate degree, and subsequently completing a Master of Business Administration at York University. Over the course of decades, Dennis has had the Midas touch of success after success, turning mere millions into hundreds of millions of dollars.
Fast forward to 2018, and Dennis corralled a team of diverse and talented professionals to form Starlight Capital, with a focus on investing in listed global real estate and infrastructure securities. Currently serving as Chief Executive Officer and Chief Investment Officer, Dennis spoke with The Edge, A Leaders Magazine about how he tackles challenges in business, leadership, and many of life’s risks.
Can you describe your career path, and how did you come to make such an impact in the finance sector in Toronto?
The defining day for me was the day I was at work as a financial advisor, and Warren Buffett announced his holdings with Coca Cola. So I stopped on my way home, and picked up a copy of a book called Buffettology at Chapters. I read it cover to cover, and I found my new passion: I wanted to manage money for a living. That book gave me purpose. I understood what I wanted to do with my career, where I wanted to focus my energy, and where I wanted to pursue my passion.
I spent the next six years meeting with people, and writing reports, and having interviews until someone finally gave me an opportunity. When I got that first opportunity at Century Investments, I decided that I wasn’t going to let anything stand in my way. I felt like I had been robbed from my first passion through injury. So I wanted to make sure nothing stood in my way; not my grades, not my work ethic, nothing. I was very focused, and I got an opportunity, and that’s all we can ask for in this life. I took that, and with a small $8-million real estate fund, the team and I were able to grow that into $1.5 billion. I eventually took over the Global Equity’s business with $60 million and grew that into $800 million. We had more and more success when I built a bigger and better performing team.
What challenges did you face on your rising journey?
The challenges that I faced were very similar just to anybody who wants to sort of achieve a lot in the finance industry. You have to deal with the market. The problem with our job is that you can absolutely be right, and the market will decide that you’re wrong for very long periods of time. … And then, quite honestly, you just have to deal with the vagaries of life – having children, travel, incidents in the market such as a crash or a financial crisis.
What sets Starlight Capital apart from other financial firms?
At Starlight Capital, what sets us apart is our culture. I know everyone says that, so I’ll start by defining culture. Culture, to me, is the thing that you celebrate, the things you discourage, and the thing you rally around, because that is what forms people’s behaviour. Over a long period of time you attract people who are attracted to those things, and you repel people who are not attracted to those sorts of things.
We try as hard as we can to have a very collegial and fun environment in the office, and I think those things inform our culture. We celebrate people’s birthdays, we celebrate minor achievements, we celebrate just about anything because life is tough, and that encourages people to have a positive attitude when they come to work.
One of the signature hallmarks of anyone you meet from Starlight Capital is they’ll be very animated and very passionate when they talk about this company, this industry, and what they’re doing.
That’s our goal – to find those people who share the belief that what they’re doing is important and that they love what they do. The rest of our culture is being really focused on delivering value to our clients, delivering strong performance, and client experience.
A lot of our conversation is tied to how we do as a team and as an organization, as opposed to how one person individually does.
What insight can you offer to others about how to network effectively?
I think that when people think of networking, they headhunt. They look for CEOs, CIOs, and CFOs. It’s almost like they’re looking for notches on a belt. What I find is that most of the people who have been very successful in their networking, network across.
Most of the key relationships that I have are with my peers, people of a similar age. People who’ve come up in the industry at the same time as me. I think the mistake that most people make is that they’re constantly trying to network up, and I understand why people do that, but the mistake there is that the relationships you’re going to have, and the businesses you’re going to build with, are going to be with your peers. If you’re climbing that ladder of success, it only makes sense that you reach down to help your friends, partners, or colleagues climb their ladder of success at the same time as you.

What is the most valuable advice you’ve ever received?
Without a doubt, do what you love. It sounds very trite and simple, but quite honestly, there is a power in waking up every morning and being excited to go to work. I love managing money, and so that makes it easy to get up every morning, and come to work and stay late, and put in the work necessary to achieve the results we want.
What’s a professional risk that paid off?
I can’t say Starlight Capital just yet, but that will be my answer the next time I do this interview.
I would say the biggest professional risk I took was that I got married, I bought two new cars, a house, and then I quit my job. The reason I did that is because I was having trouble “breaking in” on Bay Street for my original job as an advisor for the branch network. There’s lots of competition; people are walking in off the street handing in resumes, people graduate all the time, there’s tons of recruiting. I did all of that, and I also quit my job, and I did my MBA at York. The main reason I did that was because I wanted to go through the “Grad Recruiting” process. I wanted companies to come to me with jobs, as opposed to me constantly going to them looking for opportunities. That was a big risk on my part, because I had a job that, quite frankly, I could do in my sleep, and it paid all the bills. I could’ve just kept knocking on the door indefinitely, but I really did take a risk and say, “I want to expedite this and get in as quickly as I possibly can.”
What are the biggest challenges facing young businesspeople hoping to reach your level of success?
The challenge is to really differentiate yourself, so that clients will listen to what you have to say and trust you with their client capital. That’s always the biggest challenge, and one that you never stop facing even when you’ve got $10 or $50 or $100 billion in capital. You constantly have to prove yourself and earn your place. How do you define success?
You think about what it is we’re here to do – we’re here to manage capital on behalf of clients, and they’re expecting support in their own business and returns that justify them choosing you. We’re in the business of helping other people look good; we take capital in from advisors that go to end investors. Success, for us, would be many advisors committing a large amount of capital to us, because they believe in what we’ve done, and they trust us to make them look good to their clients.
What do you believe to be the key to building new relationships, professionally and personally?
Reciprocity is the key to building strong relationships. Many people know what they want, but spend little time listening to what their colleagues or business partners are seeking. The intersection of these two desires/needs is where strong business and personal relationships are forged.
Who are your role models – personally and professionally – and why?
I would say professionally my role model is Warren Buffett. From the standpoint of his personal integrity and his investment success, it’s hard to go wrong when selecting someone like that.
From a personal standpoint, my role model is a gentleman by the name of Gale Sayers. Gale Sayers was a fantastic football player who played for the Chicago Bears. The reason why he’s my role model is because he suffered a similar injury to me, only he suffered his injury in the ‘70s, and there was no orthoscopic surgery or any of that. It was just a matter of working out and getting your legs strong. It required him to be extremely committed and work very hard, and he came back an even better player than when he left. The story really resonated with me and then, after I hurt my knee, it resonated even more with me. Over time, as I think how my past diverged from sports to finance, and how Gale was able to overcome that huge obstacle and continue on his chosen path, I have a great deal of respect for the man.
How do you summon motivation when life throws a wrench into things?
Just recognizing that life isn’t personal.
I like to ask professionals at seminars: “Put your hand up if you woke up this morning and your first thought was, ‘How do I make Dennis Mitchell rich?’” And similarly, I don’t think there are a lot of people out there who wake up and think, “How do I ruin Dennis Mitchell’s plans today?” Well, life isn’t personal.
In this business, we have a habit of saying “the market went up because of this” or “the market went up because of that.” Most of the time, that’s not true. There are several things that drive market activity, stock activity, and similarly, there are several reasons for negative things to happen to a person. My approach is simply to recognize that none of this is personal. The way to deal with it is just to figure out how to overcome that obstacle.
As the leader of the company overseeing many employees, what leadership traits have you discovered are most critical in your position?
Communication is the number one skill. [You can’t have it where] some people know more than others, and other people are aware of less. That can lead to some poor decision making. It can lead to resentment, and so the key is to really communicate.
A close second is holding people accountable. The moment people start thinking that they’re not accountable for their actions, or not concerned with the overall success, is the moment things start to slide out of control.
What part of the job excites you most?
Building that team sort of brick by brick, finding somebody who’s fluent in French but also does marketing, or finding someone who’s going to be your sales coordinator but also has a great network in Atlantic Canada. When you put those pieces together and you build the whole, that’s what excites me.
What does the phrase “define your worth” mean to you?
That’s an interesting one. To me, the one thing you want to ensure is that people won’t take advantage of you. People recognize exactly what it is that you bring to the table, and they acknowledge and respect it.
Jennifer M. Williams | Editor in Chief