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Movers and Starters: Chris Gory
Chris Gory's road to success is a result of old-fashioned patience and perseverance.

Movers and Starters is an exclusive series that profiles the individuals who drive Toronto’s startup community.

Chris Gory is the owner and President of Insurance Portfolio Financial Services–an insurance agency that helps Canadian employers with their employee benefits coverage.

When you first went to university, what did you think your career was going to be? What did you want your career to be?
We all have those things where we wanted to get into one thing but we never did. I wanted to get into communications. So I went down to Brock University. They had this program in Communications, which I thought was going to be the dream program for me…but after about three minutes, I thought, “What am I doing here? I am being asked to critique a 1930s silent film from Russia. I know nothing about this, I have no interest in this, I have to get out. I have to go find myself.”

So I left after one year. And I took two years off and worked at Sporting Life. I did everything from selling tennis rackets and tuning skis and tuning rackets there. And I realized when I was there that what I thought I wanted to get into was urban planning, and I went down to St. Mary’s in Halifax which had this great program. And St. Mary’s was one of those school’s that had partnered with the Technical University of Nova Scotia so that if you did three years of your undergrad, you could transfer for over two years of TUNS and finish with your Master’s in five. And when I was down there, they dropped the program.

 [Laughs] While you were there?

Yeah. After my finish year there. So I just ‘I’m going to finish off,’ and that partnership wasn’t there between St. Mary’s and TUNS so I couldn’t do that anymore, so I just finished off my degree and came home.

What was your first post-University job?
I worked for the Globe and Mail. They had just bought the Financial Times, and I was hired on a contract basis to come in and integrate the two circulation services. It’s not a well-known thing, but while I was there, we discovered that the numbers for the Financial Times were quite, quite inflated. Quite inflated. At that time, I had been there for around 6 or 7 months. And one day the fella who was in charge of circulation and the assistant were both gone. And then the publisher of the paper came up to me and said, ‘I need numbers on our circulation,” and I said, “Fine, I can pull all of the reports off the system.” And I provided her with the numbers–it was a small publication at the time. I calculated our numbers at 56,000. Well, the circulation manager had estimated they were over 80,000, and the publisher was quite livid. So when they came back, they let me go. And within two weeks, the circulation manager and the assistant circulation manager were let go.

Yeah. So that was quite a rude awakening. But when I was doing a lot of work with computers and I realized that’s really what my true love was, so, I thought ‘let’s go incur some more student debt and go to college.’ Because the Globe had said, “If you want to get into computers here and work with us and use your geography background, go and get a computer education.” So I went to Humber College.

What’d you take?
Computer Information Systems. So now that is seven years of post-secondary. And when I was in my final year of doing that, I met my wife. She was a Music major at U of T. And we met at the Brusnwick House. Just under four years later, we were married. My wife’s grandfather had started an insurance brokerage in 1926. Her parents bought it from her grandparents in the 1970s and when we were married, they were running it. So when I finished with Humber, they put me in contact with the software company that actually did insurance software, I worked for there or two years, then I moved over into the insurance side of it And I’ve been there since 1997.

Okay. And when did you start your own shop?

In 1999. So what happened was they have a brokerage that does auto, home, and commercial insurance–and they had been doing that very well–and I started the life and benefits side. I brought certain people in to work the life side of it–I don’t like that stuff, I don’t like dealing with it. And I started working with employee benefits right after that. And I had this revelation about four years ago–I’ve got to marry to the two. Marry the tech side with the insurance side.


I’ll continue to take in new clients, but my whole focus will be on marketing to the tech industry. I know that side of it. My father started selling computers in 1976. He started selling these big Wang Mainframe Computers. And I used to go in there and spend–


How big were there?
Oh, they were huge.  They took up an entire wall of a room. I remember as a child, the only thing you could do was play checkers or chess. Or print off dirty pictures. They were all ask-key characters. If you looked up close, you would just see question marks and asterisks and ampersands and what have you.

So, my dad started selling computers. When we were growing up, we had a Commodore 64 and Vic-20s in the house. We always took computer course in high school. And then with the computer background from Humber, I knew that I knew that side of the business. I had done programming over the years. So, I thought, ‘I’m really going to start marketing to the tech side.’

What was the hardest part about trying to marry the two, from the tech side? What were the concerns of the clients?
I don’t really think the clients really had any concern. I find that this industry is a “Who you know,” industry. You have trouble finding those initial clients that really give you the credibility. You know I can go and tell somebody until I’m blue in the face ‘I know computers, I know the industry’ but when you can actually say “yes, I work company A, B, C, D, E and F,” or whatever, people in this industry give you a lot of credibility instantaneously.

I can go in and say ‘I work with this company and that company’ but we can also help you in this way. We need to have benchmarking data. We know the norms in the industry, so we’re not going to sell you something that you don’t want or need.

What was the biggest thing you hadn’t thought about that you learned in your first year of owning your business?
That’s a good question. [long silence] As a business owner, even when you’re starting up a business, you’ve got to get your eyes set on that big prize–what you want your product to be, what you want your goal to be, what you want your business to be–but I find that you still get bogged down with HR. It’s such an important part of your business, but it is such a time-consuming part of your business.

In what sense?
I remember at one point, I brought in five salespeople and I had them all sign agreements with me that they were going to put all the business through my agency, and then to find out that they’re not. They’ve actually gone out on their own and they were selling business independently, violating our agreement.

How did you find that out?
I was at an insurance event and I went up to an insurance company that I didn’t deal with and they said “Oh, we know you.” And I was like, “How’s that?” And they’re like, “Oh, we do deal with so and so from your office.” And I said, “Really. I own the business. I sign all the contracts, I sign all of the cheques, how come I don’t know you?” They said, “Oh, we’ve been dealing with him for three years.”


So I pulled the fella aside when I get back to the office and I said ,“You’re in violation of contract.” And he basically said, “Well, I’m doing you a favor by coming in her.” And then I said, “Well, stop doing us favours and get the hell out of here. You have 30 minutes.”


So, I’ve found that you want to keep your eyes on that goal–we all have to have goals–but HR can drag you down. And you HAVE to find the right people to surround yourself with. You’ve got to get those right experts in because you don’t want to handle that, you want to offload as much as you can because HR will be the death of you.


I remember around right after the recession hit n ’07,’08, I was at a golf trip down by Myrtle Beach, and I met a guy who had an electrical company with 96 staff members. And I asked him “What’s your biggest problem? Is it markets? Is it customers? ” And without missing a beat, he said, “HR.” I was like, “That’s interesting.”


I’m a smaller company, he’s got close to 100. And yet we have the same problems.

What do you think the secret is to ensuring you have the right people? Or even in an interview when you know someone is like, “This guy’s right.” Or “This girl’s right.”
I think the key for me, really, is you really have to get a lot of third-party providers–people that you trust and know the industry. You still have to focus on the HR, but you don’t want to spend all of your time on the HR. If you don’t focus on your HR, your staff is going to walk away. They’re going to find somebody who is going offer them more, give them bigger promises. I find that if you surround yourself with people who know your history–you know from an insurance standpoint, we want to have accountants and lawyers and other professionals who know our side of the industry and who will give us the right advice. So that when they tell us something, we know it’s the gospel. It’s correct. And that’s how it has to be done.

That takes a lot of time off of us. We can offload other parts, we can offload payroll and other things. Getting those key providers in there is true. But that’s also how we market to the tech industry.

Speaking of the tech industry, even with your extensive knowledge growing up and around the tech industry, what’s something that you’ve learned in dealing with it recently that you almost didn’t anticipate?
It’s a small industry. It’s the personal relations. I also find that it’s trust. You know, I can go in and say “I work companies A, B, C, D,” and I can use their names because I have their approval–my clients include 500Pixels, ShopLocket (who came ExtremeStartups), SiteScout, Massive Damage, EndLoop–when I can go in and say, “These are my clients,” you get instant credibility.

I’ve talked to prospects who’ve spoken to somebody else about insurance and I’ll look at what their quote and be able to see and say, “This is completely off-base. They’re upselling.” When you can go in with that knowledge of the industry and gain that trust by being straightforward, that’s a huge advantage.


Also, it’s a small industry. When you’re a business owner you throw the Monday-Friday, 9-5 schedule out of the picture.


I’ve gotten clients I know because I was responding to emails at 11:30 at night on a Friday. One I’m still working on right now. Not too long ago, we were emailing back and forth on a Friday night at 11:45. The prospect hasn’t come to fruition yet, I hope it will. But I think there’s something about always being there. It’s the trust. It’s the credibility.

That’s very interesting. A lot of what you said is stuff that–especially hanging out in the startup sector–that’s completely the start-up ethos, you’re never done working until you achieve your goal. What’s your goal? Do you have a greater goal for your company or are you just trying to scale?
Just keep going. I think part of it is that I grew up with a mother who was a business owner. She was a charted accountant and had her own firm. I saw the challenges she had with her firm–it was never big, 8 or 9 employeees–but I saw the challenges she faced And my father was in computer sales. He was going in on weekends. Neither job was 9-5.


I had that start-up mentality because I saw my mother build up her own firm. And I remember going in heling her move boxes on a Saturday when she left the firm she was working for to start up her own. I learned then that you can’t go Monday-Friday if you relaly want your business to succeed.

What drives you? Is it wanting to grow your company? Is it something about your passion for insurance and technology?

It’s all of it. I love it. I love it. I don’t have the ability to code. If somebody said, “You’ve got to code, Ruby on Rails, “ I couldn’t do it at all, but I love this industry. And I think that’s one of the things that I’ve got going for me. I’ve focused on the one industry and I love it. I want to help these people. I want to focus on all these companies and help them. I love reading TechVibes. I love reading TechCrunch. I love Marc Evans’s newsletter, which comes out on Saturdays. I’ve been sponsoring for almost a year now. I love reading all of the news on there. It’s exciting to me. I still read news about other businesses, but this is far more exhilarating to me. If you’re going to get involved, you really gotta just dive in. You can’t dabble.


I find that there’s so many disciplines in insurance–group benefits, life, critical illness–if you dabble in all of those, you’re a generalist. You’ve really gotta focus on one. And I’ve found on the employee benefits side, if you focus one industry you really know it well. You look at the guys downstairs at ExtremeStartupss, they want to surround themselves about lawyers who know the industry, with accountants who know the industry. They’re not going to call the guys you see on TV, running ads as personal injury lawyers. They’re not going to do it. They want to go with the guy who knows the industry.


I’ve taken on a few clients–ShopLocket was one of them–they spoke with people about insurance and I looked at their quote, and I was like, “Are you kidding me?” We scaled it back to what the industry wants, based on what I see in my client base and also based on the benchmarking data.

I think you have to have passion for the industry. Whether you’re building the start up or you’re a provider to the start up industry. I think you have to have a passion. And when you’ve got that passion, it shines through. You don’t want to come across as cheesy, you want to come across as genuine, and if you have that passion, it shines through.

What’s some advice you’d like to impart on young people in the start-up sector, or your own personal/professional ethos?
I guess my belief is that you need to find something you love. I stumbled across the insurance industry not when I was 21 or 22. I didn’t take insurance courses when I was in university or college. Find something you like and really…be patient. Don’t rush into something you don’t care for. Really think things through. You’ll find what you like. And when you find that thing…it’ll make building it up so much easier.

I’m 47. I got into insurance when I was 29. If I had rushed into things, I would have joined my mother in accounting and been miserable. I worked at Globe. I learned I like the computer side. I went back to school. I didn’t rush into it.


But I stuck with it. When you lose that big account, when you don’t get that customer you think you’re going to get, when you have those days–they’re terrible. But in the long run it’s all worth it when you can sit back and look at this incredible asset or thing that you’ve built. There’s nothing like it.

For more information on Chris, you can follow him on Twitter @CDN_Benefits


Jordan Sowunmi is a writer and editor at the Toronto Standard. He is on Twitter: @jordanisjoso


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