Dennis Bennie On Being An Entrepreneur

The Luminari founders sat down with renowned entrepreneur Dennis Bennie, who moved to Toronto from South Africa in the late 1970s. Bennie’s past roles have included co-founder of software and tech companies Mission Electronics and Delrina. More recently, he’s invested in popular local brewery and beer company, Mill Street,  and decided to back the University of Toronto’s Creative Destruction Lab. During the Luminari speaker series, Bennie discussed what it was like the first time he saw a spreadsheet on a computer and how he marvelled at the Internet. He also explained his switch from accounting to technology—and how his background in accounting gave him an edge. Here are our takeaways from the conversation with Bennie.

Don’t be afraid to risk everything.

“When I made the decision (to leave accounting), I clearly had to have a large appetite for risk because I was at the point where I used to do mental counts just to make the rent check every month. If you wanted to go out for a big dinner, it had to be budgeted. That’s where I was in my life.”

If I weighed everything up, I could say, “Look, I can always go back and become an accountant again.” But maybe I enjoyed it so much it was the best incentive to go out and try to succeed.”

I have a vivid memory of walking out of the office. I finally decided I was done.

I had this briefcase, I looked right at it, and I threw it in the garbage.”

Failure is part of learning.

“That is what entrepreneurial direction is all about. It’s about going from one failure to the next failure with an equal amount of enthusiasm for all of them.”

You look at any company. For example read about Uber. Wow! Imagine what was going in there on and we’re only just getting part of it.

“Looking back on Delrina: there were a few times I thought we’re never going to get this done. Sometimes, it’s just difficult. There’s people issues. There’s product issues. Marketing issues. Look at every startup that I’m involved with. It takes a long time to get over those first years and gel and there are so many things that could go wrong.”

“At the time, there just weren’t enough people doing this, so you had to find a kinsmanship of just a few individuals who were doing this with you. The software companies in Toronto at the time that I connected with, we’re all still buddies. There were six of us, maybe 10 of us. Kevin O’Leary was one. Kevin and I are still old friends because he had a software company. There were just very few people doing this.”

“The way careers are going to be crafted in the future for success is going to force you to be more entrepreneurial.”

“You will have to become more comfortable with how putting yourself first. It’s going to be an ongoing learning process. An ongoing process of making yourself that much more desirable. That’s going to become a natural thing.”

Timing is everything.

“I think if you looked at the various factors for success: it’s people, it’s product, it’s marketing. But, If I had to pick one thing, it’s timing. When we got into the market it was probably 6 months, 12 months, 18 months ahead. Everyone wanted to become a craft beer producer.”

Be honest and kind.

“I have a very straightforward approach. I’m comfortable being confrontational. I like to call a spade a spade. It’s often not as easy to be direct and honest with people as it should be. I think that the whole story that my teeth (are the softest part of my body)…I used to say that to make sure people would respect me.”

“The essence of good management is to be honest. There are two attributes that I think make you a good person: honesty and kindness.”

“If you want to be honest, the first person you have to be honest with is yourself.”

“This took me a long time, but luckily I’ve matured over time and have realized that we’re all just little specks.”

“You’re very fortunate to have good people around you. And there’s the essence of being a good manager. Good management begins with those forms of honesty. The kindness factor, I don’t know if I really have it, but it’s an ability to listen to others so carefully that you can actually go into their world and make their decisions a lot easier.”

“Most smaller companies, it’s very difficult to find a style of managing and a way of motivating people and doing things. Almost inevitably, if someone doesn’t fit in, by the time they decide they should tell them that hey should find another job or move along, everyone in the company is wondering why it took so long.”

As you become more confident or comfortable with what you can do and what you can’t do, it becomes easier to be honest with everyone around you.”

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