Bruce Croxon made his mark as a digital pioneer by co-founding Lavalife and revolutionizing how people connect. Under his direction, he grew this early tech start-up into the marque brand in online dating with over two million users. Partner, chairman and CEO, Croxon helped lead the company’s growth from four to 600 employees, while achieving revenue of just under $100 million.
Since the sale of Lavalife, Bruce has been active as both an investor and advisor in growth stage companies in the technology sector. As an ex-Dragon on CBC’s Dragons’ Den, he added a broad range of businesses and products to his portfolio that tapped into his passion for digital media, health and marketing. Croxon currently helms Round13, a company dedicated to investment in growth stage Canadian tech companies. He also co-hosts The Disruptors on BNN and CTV, a weekly show spotlighting Canadian business and believes our entrepreneurs can hold their own with anyone in the world.
Bruce Croxon talks about his journey as a founder and an investor and the one question that helps him push through difficult times. He also shares why mental health is important to him and why therapy can be an incredible investment in today’s world.
Thank you for doing this interview. A few months ago, I was reaching out to people asking, “Hey, who would be great allies for mental health?” And the organizers at CIX had mentioned you and your amazing panel on mental health.
Yeah. My pleasure.
The mission with For Founders by Founders is not just to champion mental health, but to showcase the more human side of leaders.
Because we're always on our best behavior.
Always on the best behavior.
Always putting our best foot forward. It's all marketing and you know, we're on the venture capital side. We're looking to attract entrepreneurs. If you're an entrepreneur, you want to put out that you're successful, so that somebody might be interested in investing in you.
Sitting here, you and I, it's easy to look and see how it happens.
Yeah. I am curious to ask. You have been very successful as a founder and an investor. What's your story?
My story going way back then... I'm a lifelong entrepreneur and I have always been attracted to the notion of creating enterprise, starting with something small and getting it to something medium. I've always been inspired by new ideas and I've always believed that ideas have to come from somewhere, so it might as well be me.
I came by it honestly. I'm the son of immigrants that showed up with very little and not much in the way of education either. I was always inspired by people, usually men in those days. I'm in my 50s so when I was growing up, it was usually men that were out... A whole generation of them that started with very little and made something of themselves through hard work and stick-to-it-ness, so I was always inspired by that.
I couldn't start with nothing. My dad provided, so we already had a head start. But you know, I was always attracted to create things. I created a number of things over the years and then hit one that did well. Still, if you add up all the hours I spent trying to do things and then put a number on them, I'd probably start crying… Sort of the entrepreneur's dilemma, right?
Because you put way more time in, then you can usually measure monetarily. It is a clear choice with sacrifice. Anyway, with three other guys, I created a social media platform called Lavalife. We were lucky enough to exit that in 2004. I stayed on as CEO till mid-2006 and then sort of poked my head up after doing some angel investing. I said, “Look, you know, I don't really want to go back into doing the same thing every day.”
Technology in Canada today appeals to my entrepreneurial instincts. Our days are filled with avariety and ups and downs and trials, and there is satisfaction as you land on somebody or a company that you can help get from infancy to something that is impacting other people's lives. It's the opposite of a passive career choice. I find investing to be a great combination of entrepreneurism and operating.
Because instead of operating one company, I'm helping to operate nine at the present time and it keeps things stimulating. That's how I ended up here. You know, we're a couple of years into establishing Round 13 now and are 100% focused on Canadians and Canadian entrepreneurs. Very focused on the technology sector, which is an exciting and interesting place to play.
When you look back at your journey, what’s been the most surprising part?
I'm always surprised by the gap between having an idea and just the incredible amount of work that it takes to realize that idea. I mean, it's so easy in our world to look at an outcome and just say, “I thought of that.” That could have been me or you know, these seemingly overnight success stories.
However, the reality is what we do is such a rare instance where things happen overnight. Under the cover is like an incredible amount of sweat, anguish, fatigue, and determination. Continually being tested as to what your limits are.
Knowing that even in the background, you've got that old saying, “One life to live. What am I doing?” It is a cliché, but at the end of the day, we all end up in a box, right? Different ages, but we're all going there.
We got certain amount of time, so how do you want to spend it? Am I only here after all these years? You know, those kinds of things, so I am always surprised by the gap between perception and reality. In this sort of fast-paced world of trying to scale and create things out of nothing.
Perception versus reality. That’s an interesting dilemma.
I've been able to watch it over 35 years. The big difference is the amplification. Now there are no secrets anymore. Right?
With the onslaught of social media, the digitization of everything, and being connected 24/7, you have to work really hard to not be an open book or to not be constantly aware of what everybody else is up to around you.
It's tougher to do your own thing and not be affected than it ever has before. I know for sure, no matter how well you're doing or think you doing, someone is doing better. Even the words like “imposter syndrome,” it's only come up in the last decade.
There can be such a gap between what we portray to other people versus who we actually are. Especially given the pressures of today’s age. What was your turning point in terms of carving your own path?
I was very lucky in that, I've marched to a slightly different path for as long as I can remember. I have a dad who has a favorite saying. He says, "What's the worst that could happen?" It's always something I ask myself all the time.
I remember with Lavalife, we really believe that company culture could create a tremendous amount of value if done right. We put an extraordinary effort into developing that. It didn't resonate when all of the sudden, investors looked at us like, “What are you talking about?” This was before things like “core values” were part of the business language. It just didn't matter because we saw it working for us. We believed it and we're not going to cater to you.
We were emboldened early by people that believed in us. The earliest influences, parents. My dad with his expression, "What's the worst that could happen?" If you ask yourself that, before you portray something or reveal who you are, the answer you usually find isn't that bad.
Here's something I want to ask because when you shared about that story about Lavalife, there were naysayers. I know founders sometimes lose their way as the pressure builds.
During the toughest times, what has allowed you to pull through?
Partners. Yeah, I've never done anything on my own, and that's not to say I don't enjoy it. I love my own company. I'll travel on my own. I've done things on my own, but I've never done a business on my own and I have no desire to.
Surrounding yourself with people that have your back. That you trust and feel safe with, that are not going to exploit your weakness. Are you being authentic? It's really important. It's rare and increasingly rare for people to have all the answers.
When you speak to that, my hope with the releasing of these stories is that more people can feel comfortable being real with each other. Rather than pretending and putting on the armour that we feel so pressured to do.
I can think back to times in the 15-year Lavalife journey, I've been scared. I've been scared as a leader, scared that this decision that we've made is going to sink the company. I'm a worrier by nature. Not a warrior, a worrier. I'm worried by nature. A lot of people that are results-oriented don't really rest while there are still things up in the air.
The curse of small businesses, there's always something up in the air. I've gone through my anxious times and my scared times and it is having people that have the same stress, same goals, and same worries around you that enable you to get through.
I'm scared of that happening, but it's not the end of the world. By keeping your relationships authentic and surrounding yourself with good people, it can help see you through.
Thank you for sharing that. The message to not trying to go at it alone, it's more important than ever. Especially with the kind of problems that founders want to solve. One of the things I've admired about founders is the courage that it takes to go for those things.
It's different kind of courage.
Our grandparents went to war. They were in trenches, where bombs were going off left, right, and center and they're 18, 19 years old. Or they're flying missions where the odds of survival were one and two; that's courage.
Creating a company is a responsibility and responsibility to the people that invest in you and the people that are employed by you. You're right to feel a responsibility, but it isn't life and death.
Perspective. Right. What's the worst that can happen?
What's the worst that could happen?
What's been the hardest part or the scariest part?
I think for me, the scariest part is… Heaven forbid, you wake up when you're 75 and look back and say, “Why did I do that?” The fear of living in regret or the fear of thinking there's something you didn't do, or a life that you should have led that you didn't lead.
I think is the scariest part of any choice because by making a choice, you by default give up other things. Right? Particularly as an entrepreneur or an investor because I believe to succeed, you have to really give it your all.
Often there's not a lot left, right? Heaven forbid you end up in regret. I think the odds on that happening go down the more you know yourself, the more support you've been given to do what you love, not what's expected of you.
It goes back to that gap we talked about. Not because I want to do it, but because I've been raised this way. The larger the gap between those two things, the more troubles coming.
Yeah. I agree.
A big part of me should have been a foreign correspondent, plopping myself down into developing countries and war zones. Staying up there for long periods of time and maybe starting local businesses and wandering the world. Those are the times that I've been the happiest.
Should I have been doing that all my life, versus being in Toronto, Canada? Growing technology businesses, becoming relatively wealthy, and then investing in the next generation of tech? That's always been my biggest fear. Am I being my authentic self?
I appreciated that you set the trend for authenticity at CIX. It allowed me to speak at the same panel [mental health] as yours the next year. I'm curious to ask: what's your passion for mental health?
I divide into two sections. Pre-having kids and having kids. I'm a dad, I've got it 13 and a 16-year old now. A lot of the people that I'm investing in now, or that I'm mentoring or that I'm associated with, they are quite a bit younger than me.
I think when you become a parent, you think about it a lot differently. Like you put it in a different perspective. I want nothing more for my kids than to be 100% comfortable with what they choose to do.
I don't want them to do it for me. I don't want them to do it for any other reason other than what makes them happy. They have to put food on the table, you have to look after yourself, but beyond that, what I want them to ask is, “Why am I doing what I'm doing? Is it because I want it or because somebody is expecting me to be? How close is this to my true self?”
It's an incredible and growing challenge.
I wonder in terms of mental health, right? Just this idea of having the space or the opportunity to get perspective. To discover yourself or to explore these things. What have you explored that's been helpful for you?
Aside from mind-altering drugs, you mean? She laughs. Actually, it has been quite helpful in my younger formative years. Then I traveled a lot. I traveled the world a lot and met a lot of people that were very interesting and smart people.
I've learned from a relatively young age to be very open-minded about people and their choices. When you become judgmental about things, the world can be a pretty harsh place because there's always something to judge. If you're walking around judging all the time, I don't think that's a happy existence. Right?
Accepting people for who they are, trying to learn from them. I deliberately went out into the world at a very young age. Pop myself down to pretty remote places and tried to figure them out. I was lucky enough to get influenced by some people and experiences that gave me the courage to say: “There is not just one right way to do things.”
That takes a lot of pressure off where you don't have to sort of feel you have to fit into a specific mold.
I love to ask, there's founders, investors, all kinds of people who are going to read the stories. What can people do to take care of their mental health?
You have to find a place that you feel comfortable in sharing. There's a whole industry of therapists. Especially if you're leading a company, it's not anyone else's interest in the company to just to ask about you. They're looking to you a lot of the times for direction.
The luxury of being able to have an hour or two hours a week, to sit with people who spend their entire life studying how the brain works. Everyone thinks that their situation is unique, but for people that spend their life talking to people that are struggling with things, you're not all that unique.
You look around, everybody's got something that they are dealing with.
Everybody has something and it’s a luxury to spend an hour talking to somebody about you. You don't have to ask about them; they're there to listen to you.
Therapists are there to help you and I've found that extremely helpful in my career because the smart ones really are smart. You realize that your situation isn't all that unique. You get an outlet to work through some stuff and you might go two, three, four times, not feeling you're moving, but they are.
I think it's an incredibly smart investment. It's funny like all entrepreneurs rely on high energy and good sleep, so they'll invest in being in top physical condition. Getting their workouts, eating right, sleeping right. You're willing to invest in those kinds of things, but the most important thing is your brain. So why wouldn't we make the same investment there?
Take a risk and share your weakness, share what's causing you to lie awake at night because what's the worst that can happen? By sharing that, is someone going to call the bank and tell them to call your loan? I don't think so.
One last question for you. What can the tech community do to support mental health?
I think having the conversation is an excellent start. Part of the cause of what we're seeing is also the opportunity. The sharing of information has never been easier. Cutting through the noise and the clutter can be a challenge, but having the conversation and putting it out there.
Having these events, forums, and outlets where empathy can be created, ideas can be exchanged, and conversations can be had. I think is a really good start. I think we've got the same challenge any business does in terms of marketing.
It is, “How do you make people aware that this is available? How do you make people aware that it's okay to have the conversation?” The only way to do that is that it's not an overnight thing. The only way to do that is to start with the conversation.
Start with the stories, get people together to share them. By doing that, the stigma comes down. As you get words on a page, it becomes action. Changes in behavior and fundamental changes in how we go about our life; they take time.
Thank you for being part of this movement. For helping moving this forward.
Yeah, I'm curious to see how it all turns out. Reach out if you need anything else, right?
Yeah, most definitely.