Matthew Leibowitz

Matt Leibowitz has been a partner with Plaza Ventures since April 2012. Matt is a seasoned early stage institutional tech investor having originated, managed and completed dozens of equity and debt transactions. He has arranged significant private placement financings in private equity and VC settings. Matt is a frequent public speaker at conferences in the technology and clean-tech VC industries and a regular contributor to business schools, accelerators, incubators, selection committees, etc. Matt earned an LLM from Oxford University, an MSc from the University of New South Wales, and an H.BA from the University of Toronto.



Matthew Leibowitz talks about his family history as survivors of the Holocaust and how it gives him perspective on what matters. He also shares why mental health is just as important as physical health and what it is actually like to be a VC.


Great seeing you again. Thank you for taking the time to talk about mental health.

I learned to deal with my personal mental health when I was around the age of 14. I was able to look at things from a 30,000 ft. purview. I don't know how I was able to achieve this, but I remember the specific moment that it happened like it was yesterday.

I was able to separate other people’s baggage from my own. I immediately took a methodological and scientific approach by learning how to compartmentalize.

Ever since I was a kid, I learned how to be very level headed.  And I don't know how this happened as I was never taught. I never lost my temper. I'm always steady-eddy because I know how to rationalize things.



I've lived on four different continents for extended periods of times for university or work and I was able to seamlessly adapt into the local culture and community in each. And this year I will be celebrating my 40th birthday; I turn 40 in May. Deep breath. The one consistency in my life and I think you and I chatted about this before, has been hockey.

That sounds kind of cheesy, but when I play hockey, which I do somewhere between one and four times a week, I'm not thinking about anything else. Zero. There's nothing in my brain. Zero. There just isn't because it's not possible.


I watch hockey, but it's not the same.

It's not the same.

When you are on the ice, you are moving so quickly and there's so much happening, that if you stop and think, you're in big trouble. When I play hockey for an hour, it's the best medicine. I go to the gym at least six times a week too. Every morning. That physical side has always helped me with the mental side of my life.



I have a family history of mental illness, on both sides. When I was a kid, I was very conscious of that and decided I didn't want to live that kind of life.

The other thing that I do for mental health is read. And I do a lot of crossword puzzles. I learned how to do crossword puzzles from my mother and grandmother. And I probably do three to seven crossword puzzles a day.


Wow, that's commitment. How long have you been doing that?

I probably started in university, give or take. I remember making fun of my mother and my grandmother when I was a teenager about the fact they did crossword puzzles. I used to think, “It's what old people do."

For me, it's one of those moments in the day that I find most relaxing. That's my nightly routine as I fall asleep typically while listening to the Grateful Dead


I would love to ask you more about family. I know we’ve spoken your wife and your two children. I know family is important to you and I would love to learn more about how you see things.

Well, it's everything. My ancestors came from a place where they were not wanted. They were either kicked out of their homes, left somewhat voluntarily, or killed. And I'm not talking about thousands of years ago, I'm talking about my grandparents’ generation.

It wasn't that long ago in the history of the world. When you think about your immediate family, who survived the Holocaust and saw the greatest atrocities that have ever been committed by man, it gives you perspective.

When I'm having a bad day, I think "You know what? Life could be a lot worse." That’s the message that has always been guiding me.  Several family stories about my great-grandfather resonated with me, although he personally never spoke about. But later in life, I came to learn about everything he experienced and sacrificed. He came to Canada to seek a better life, and that is why I am here today in this position.

I'm very respectful and appreciative of what they had to go through and the risks that my family needed to take in order for someone like me to be sitting in this magnificent board room that you and I are right now. This is never lost on me and I think about that consistently.

Unfortunately, I never met one of grandfathers as he was killed before I was born. He was killed while my parents were on their honeymoon, believe it or not. And I'm named after him. Jews don't name people after the living. We typically name babies after relatives who have passed away as an honorarium. I'm named after him and I always thought that he's always been my guardian angel, even though I never met him.

And I always think about how different my life would've been if he was alive. He owned a car scrapyard in Bolton, Ontario. He would compress cars and sell off the scrap metal. A lot of Jewish families were in that business back in the day. He was only maybe 43 or 44 when he passed away, which now that I think about it, is just a few years older than me. Right?



Just pretty crazy to think about.

Had he stayed alive, I would've grown up on a car scrapyard and riding horses, and driving old cars, and fixing up old cars. Having perspective as we said before, I think really motivates people. It's constantly motivating me. That's something I'm really proud of because I want my grandfather specifically and my family to be proud of me.


Thanks for sharing that with me. Perspective is so important. I think about the hardships that my parents and grandparents had to go through; war, immigration, poverty. At least in the developed world, a lot of those things have been alleviated.

The problem is that maybe we're too comfortable now. And when you're comfortable, you can get lazy, for lack of a better term. We spent the last 60/70 years trying to build as much comfort and ease into our life with a view to make our lives as better as possible. But sometimes that ‘better’ also comes with consequences.

And if you're left sitting around with nothing to do and nothing to motivate you and if you're not worried about shelter or immediate needs anymore, perhaps your mind starts drifting. Maybe you start making comparisons. The pressure of social media, especially for the younger generation these days, is incredibly intense.


Yeah. It reminds me of what you said about hockey and the impact it had on your life. I imagine when you play hockey, it is a lot like how I feel when I dance. I am just present with life and myself, rather than focusing on what other people have.

Here’s what I’d love to know. What's been the most surprising part of your journey?

Well, it's hard to surprise me these days. As a VC, maybe earlier on in my career, I was much more surprised by people. Now that I'm a lot more experienced and I've been doing this for 10 years, I don't get too surprised anymore. I've seen a lot of interesting situations.

However, the one thing that continues to surprise me is when people make poor business decision as a result of their inflated egos. There is a lot of chest beating, chest thumping.

This ends up being to the detriment of their own profit.  And I've never understood that. I see that constantly where people need to be, dare I say, the biggest man in the room, versus considering what is best for the company at large.



And the other thing that I would share is that as a VC it's not a glamorous world. It's not all it's cracked up to be in the media. We're not all sitting in ivory towers somewhere, controlling the planet with all of our billions and trillions of dollars.

It's immensely hard and challenging work with many different players and actors. If you join a VC or if you become a VC, it's a 15-year commitment minimum. And you won't know if you're successful for probably six or seven years into the job.

If your interest is making money, VC is not the ideal choice. Because there are better and easier ways to make money. Way easier. If you want to make money and be in finance, go into investment banking. You will make way more money and it's a much quicker path.

Also, people have to bear in mind that VCs have investors too, just like a company has investors. I have investors. I have a lot of investors and I am accountable to them. I have a fiduciary responsibility to them. That is my number one focus. My view is that whatever is good for my companies is also good for my investors, which is ultimately good for me and my team. That is my philosophy and how I operate and conduct myself in business.


I feel like founders have a hard time communicating with their VCs. It came up in a lot of conversations I had last year. People saying, "I knew I should've talked to my VC."

Well, here’s the thing: Everything that I do in my life, whether it be personal or in business, comes down to communication. I got over that hump of sharing the good, and the bad, and the ugly, and even the devastating with people up front.

There is typically an answer to a problem. Once in a while, there isn't a direct answer, but you know what? If you get four or five relatively smart people around a table and you put your egos aside, you could probably come up with a decent plan to deal with it.

The foundation of success comes down to communication. It translates to my marriage. How I deal with my kids, my family, my friends. I take that same approach in business. To me, I'd rather over communicate than under communicate.

And I feel that that further translates to mental health specifically. I really do. For people who are struggling with mental health, reaching out to talk to somebody is a great starting point.  It could be a friend or family member, your doctor or mental health professional. I honestly feel that communication helps significantly.

My wife has been there.  She went through a very traumatic accident while crossing the street. She was obeying the traffic laws, and a car hit her.  Beyond her physical injuries, she was diagnosed with PTSD. She was afraid to get in a car again even though she was the pedestrian.  She also suffered from flashback and nightmares.  I was really proud of her when she first said, “You know what? I need to start going to someone and working through this." It made a massive difference in her life. My wife has never had any issues with these kinds of things before. And yet this accident really affected her. My wife's a doctor, and she had the courage to go seek someone else's counsel. And that's something I'm very proud that she did.


That's incredible.

Yeah. And it's helped her. As a result, it helped our family tremendously.

A car accident is a very serious matter. Her body was physically affected by the accident but with time, it healed.  Her mental health issues however, lingered well beyond the date of the accident. She remembers everything about the car coming at her and subsequently seeing herself flying through the middle of a major intersection. And this happened right after she dropped off our daughter at preschool. This really affected her and I totally understand that.


I really appreciate your honesty. There is a lot of fear in the world, fear of taking down the armour. But we need to be real with people in order to get the support we need.

Yeah. I've always prided myself on being straightforward. I think my Partners, my CEOs, my friends, my family, will say, "Matthew is always himself. He's always straightforward with people.” I think I am pretty direct.

With me, you know where you stand, you know what I'm thinking. I don't need to play poker. I'm not one of these guys that always needs to be Mr. Poker Face. And I think I have been successful being a VC, investing in dozens of companies and building a successful VC practice doing just that.

My mantra goes something like this, “Let's save ourselves a lot of time and headaches by eliminating the BS. Let's deal with what needs to be dealt with.  We all have several matters that require our attention and proverbial fires to put out and I have other companies that I need to deal with. So let's just communicate.”


I know many people in our community are struggling with mental health. What's a message for people out there, especially for founders? What is something you want them to know?

If you're a CEO of startup for example, your company is important and you feel as though it's your baby and therefore your whole life. Making your whole life about how well your company does or how much money you raise can be very unfulfilling. What's important is how you treat other people and build strong relationships with your team, board, investors and customers will hopefully lead to a successful business.

My message towards those who struggle with mental health would be to reach out and talk to someone. That is always a good first step. Struggling alone can be very isolating and make matters much worse.



And if you could take that first one or two steps, hopefully, the rest of the journey will come a little bit easier.

For those struggling in business specifically, I want to remind people that as a VC and board member, I'm not your enemy. I'm exclusively your partner. That's my approach with all of my CEOs. I want my teams to be healthy and successful because I want them to have the latitude to build a great business and then ultimately exit. I love watching them succeed and will do anything to help them do so.

If you're a CEO and you feel you need to pull an all-nighter to keep your business going, you don't!  Work smart. Take a step back. Get a good night's sleep. Go play hockey. Go for a walk with your friend. Put your phone away. You'll be alright.


Thank you for your time. Thank you for being part of this movement, the first wave.

Sure, my pleasure. I think it's a really important topic. Because without a healthy ecosystem, there is no ecosystem.



I look at mental health as no different than if I broke my leg or if I had heart disease. There’s no difference in my opinion. If you break your leg and you get rushed to the hospital, no one questions that. It's like, "Okay, that guy broke his leg. Put him in a cast and he'll be alright." And there's a methodology there. There's a process there.

But if someone says, "Oh, I'm not feeling well today. I'm a little down,” or whatever the terminology you want to use is, people will say that person is ‘off’. That person has issues. Right? That's BS.

And so, why should we treat someone breaking their leg with more dignity and provide more treatment than someone who is experiencing mental health issues? If this interview is a little way that I can contribute to that, then I'm very proud to be participating.


Yeah, thank you for being one of those voices.

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