Lessons From The Hard Times: A Conversation With Bruce Croxon

Lessons From The Hard Times: A Conversation With Bruce Croxon

Leadership | Posted by YouInc.com - April 6, 2020 at 12:30 am

Entrepreneurship isn’t an easy journey. Bruce Croxon learned that lesson early on during his first job delivering Globe and Mail newspapers. The former Dragon, co-founder of Lavalife, and managing partner at Round13 Capital grew up in Scarborough alongside an entrepreneurial father. But, despite his father’s business nearly disappearing while Croxon was in his youth, he wasn’t deterred by the ups and downs. 

“I’m not an ideas guy,” Croxon tells me when we talk at 8 a.m. on a recent Thursday morning, humbly dismissing himself from the success of Lavalife, the dating website he co-founded more than 30 years ago and sold for $150-million USD. “My strength is recognizing someone else’s idea and helping them realize the dream.” 

One look at Croxon’s Instagram reveals the love he has for his family and the outdoors, and despite his career success and hobbies, he isn’t shy about how hard balance can still be. In our conversation, we dig into what he’s learned from his father, how he builds himself up during the hard times, and why we need a more realistic approach to achieving balance: 

YouInc: Tell us about your first job. 

Bruce Croxon: The Globe and Mail paper route. I was 12-years-old and I made $5 to $7 a week. I walked to get the papers at the plaza by about 5:30 a.m. and my route was done by 7 a.m. Then I’d go home and get ready for school. I’d also have to go out and collect from people who received the paper. Most mornings I didn’t feel like getting up, but people needed their paper. I learned perseverance from a young age. 

YI: What did you learn from your family about work? 

BC: My dad showed up in Canada in the late 1950s with $60 and a grade-eight education. He was good at math and calculating figures, so he got a job keeping the books at a car dealership, among other places. During this time, General Motors would finance you to start a franchise—they saw him as someone with potential and supported him; he scraped together what little money he had saved and invested the money into a car dealership and then into a good chunk of land in Toronto. He made an entrepreneurial career of himself through risk-taking. My dad and other men of that generation - because that’s the way it was then - became my heroes in how entrepreneurship could be pursued with different backgrounds and education. 

You have to get used to living with constant change.

I had early exposure to what it took to be an entrepreneur: to be dedicated, work hard, and still do stuff you don’t feel like doing. I also experienced the inevitable rollercoaster of being an entrepreneur through my dad’s career. He had partnered on a large chunk of land to build the country’s first automobile shopping centre. The industry shot up to 24 per cent, so the whole business almost came down. Our house went. Our cottage went. Everything went in the pursuit of ensuring the business didn’t disappear. 

The Question We Need To Ask Ourselves 

One of my dad’s favourite sayings to this day: “what’s the worst thing that could happen?” We have to ask ourselves this question as entrepreneurs. The worst that could happen in my dad’s case was that he’d have to go back to keep someone’s books. He wasn’t going to starve. 

I learned that when things are going well, don’t hang onto that feeling too tight--it’s probably not going to last. Conversely, when you hit a trough and it seems like you’re not going to get out of it, hang in with the right people, do the right thing and stay true; you’ll come out of that, too. It’s called a cycle--entrepreneurs live it every day, week, month, quarter, year. You either get used to the feeling or you don’t, and if you can’t, then it’s probably not the career choice for you. You have to get used to living with constant change. 

YI: What were you doing in the days leading up to Lavalife?

BC: I was trying anything I could to fulfill a personal dream of building a company. In the years before that, I had a number of ideas, which had varying success. I was making a living as an entrepreneur, but hadn’t figured out how to scale anything. My goal was to do more than make a living, my goal was to build a company around an idea. And I would say up until Lavalife, I had a series of projects, most of which made me a living or contributed something, but they were far short of building an organization and something I could scale. 

You have to ask yourself: what problem am I trying to solve and how big is this problem? How much are people willing to pay to have it taken care of?

YI: You’ve talked about finding “the need” for a product or service. What led to finding the need that became Lavalife? 

BC: I’m not an original ideas kind of guy. My strengths are identifying someone else’s idea and helping them grow and realize the dream.

Two of the people who became my partners - David Chamandy, and Ed Lum - were mucking around with this technology that connected people over the phone. It was called interactive voice response and it was before voicemail officially launched in the product. That turned out to be the killer app for the technology, but it was also useful for sending messages back and forth. 

Telepersonals was our first brand. We had an interactive dining and entertainment experience. We had a dineline that was sponsored by Toronto Life. You could call and enter a two-digit code for every restaurant and hear about the menu of the day. The restaurant could also change the menu. Another feature was an entertainment line that was sponsored by CHUM FM entertainment hotline. You could call in and learn, “here’s who’s playing at the Horseshoe tonight.” 

Our Big Realization

We realized for the first time that we could measure digitally what people’s responses were to options. When we introduced the option, “press three to meet someone,” the daily statistics of all actions on the site, showed dating was the most popular over who was playing at the Horseshoe or what was being served at Scaramouche Restaurant. The statistics told us there was an incredible demand for the need to connect with people.

The act of sharing what you’re going through is helpful to realize you’re not alone and your feelings aren’t unusual.

We didn’t need to convince anyone; we were trying to solve a problem that didn’t exist. Sure enough, by throwing up an experiment, the public told us we were onto something. That was our moment and then we got to work as quickly as we could to build a $100-million company.

You have to ask yourself: what problem am I trying to solve and how big is this problem? How much are people willing to pay to have it taken care of? 

YI: You’ve said to not hang onto the highs or the lows. How do you build yourself up in moments of self-doubt? 

BC: I’m not a lone wolf. I’ve never done anything in my business life without business partners. I’m clear on the things that I’m good at and I’m clear on the areas that I need perspectives. I’ve always had the luxury of when things are not going well, to be able to draw on the experience of people who are going through the same thing, but experiencing it differently. 

I’ve always found it helpful to talk. If you don’t have partners who you’re talking to, you need to talk to people who are in the business of helping others. The act of sharing what you’re going through is helpful to realize you’re not alone and your feelings aren’t unusual. The odds are you’re not going to surprise other people with how you’re feeling. A lot of fear is not based in rational thought. Fear is a feeling. It’s not supposed to make sense. Continue to ask yourself, “what’s the worst that could happen?” 

YI: Do you believe you can achieve balance as an entrepreneur: time for your business, family, and hobbies? 

BC: I’m conflicted in my answer, because in my experience it’s been difficult to achieve the balance that some people describe as balance: a 9 a.m. to 5 p.m. work schedule, five days a week that allows you to not have to think about your business on the weekend.

I’ve had to make a lot of sacrifices with my personal time and things I’d rather not be doing. When I think about balance for an entrepreneur, I think: give yourself to something for a period of time, make it successful, sell it, and then take time to do something else. That’s my definition of work and life balance for a lot of entrepreneurs. There are different strategies and tactics to ensure you maintain your mental health during these periods of time. But I find it increasingly difficult to create balance because of how easy it is to get information to spawn competition and how quickly the industry is moving. 

Continue to ask yourself, “what’s the worst that could happen?”

I’m not suggesting that it’s a problem, and I’m not suggesting what I said is healthy. The most successful entrepreneurs I’ve seen think about their business all the time. I don’t think that trend or the link between that and being successful is diminishing with what we have coming down the pipe: choices, information, competition, and constant learning. You have to work hard to carve out space to be present. The example of family: you need to carve out that time and be present. Balance can be difficult; it’s one of the biggest challenges we’re facing. 

YI: What do you want entrepreneurs to learn from your journey? 

BC: You have to ask yourself: what core values are going to be most suited to you being successful? Then make sure you stick religiously to what those qualities are when you’re bringing people around you. 

I’ve seen good ideas not work because of teams that weren’t aligned. I’ve seen mediocre ideas do well because the team was killer. The whole process of deciding who you hang with is important. Then, pick something you enjoy when you embark on building a company or starting an idea, because you put in more work than you anticipate. Maybe if you love what you’re doing, when you grind away on a Sunday, after you spend time with your children, it won’t feel like work. 

Tags: business advice, cbc, dragons den, entrepreneur, inspiration, leadership, motivation, success story, lavalife, online dating

Kristen Marano

Kristen Marano covers women and their work for publications around the world. She has interviewed some of the most influential business leaders in Canada and the most passionate change makers in towns and cities as isolated as Perth, Western Australia. Most recently she interviewed Canadian businesswoman Zita Cobb about reinvigorating the economy in Newfoundland through the arts. Kristen's work encourages women to share honest and open perspectives about the emotional challenges of their journeys.

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