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Interviewing Toronto Entrepreneur: Darrell Keezer

Updated: Oct 12, 2018

Welcome to our Friday Feature: Toronto Entrepreneurs segment, where we bring you insights, experiences, inspiration, and advice from prominent entrepreneurs in the Greater Toronto Area!

We’ve interviewed business leaders who have been kind enough to take the time to share their experiences with us on what it’s like starting their very own business (and nurturing it as well)!

We believe that these stories would be valuable to other aspiring or established business leaders. On behalf of, we hope that you enjoy reading this as much as we enjoyed creating it! Feel free to share this story with your networks.

Introducing Toronto Entrepreneur: Darrell Keezer, Founder of Candybox Marketing Inc.

Company Profile

Company name: Candybox Marketing Inc.

What does your company do? Digital Marketing Agency

Year launched: 2008

Number of employees: 20+


The Interview

1. How did you get the idea to start your business?

I was working for a small company and a lot of my customers kept asking me if I knew anyone in Digital Marketing. I looked into solutions and it was hard to find good providers that could actually do everything that my customers needed. I customized Candybox’s offerings based on what I heard what real customers wanted and found the right team members to execute.

2. What's the best/worst thing to happen since you started your business?

The best thing has been winning a number of awards over the past few years. It’s been awesome to see an entire industry recognizing our team for our work. Recently we’ve won awards from the Governer General of Canada, CAMP and Growth 500 by Macleans.

3. What are some of the challenges you’ve faced as an entrepreneur?

I started Candybox when I was 23, but I probably looked 18. It was hard to convince customers to trust me with their annual marketing budget when I looked like one of their kids. I know that I didn’t get certain deals because of my appearance so I had to mitigate this with more online or phone meetings to gain trust and credibility.

4. What are some lessons you’ve learned as an entrepreneur?

Listen to your customer, they may not know what they want, but they know what they need. If you are able to listen to all of your customer’s problems, you will be able to innovate better solutions each day. Companies that lose touch with their customers may have a viable business, but not for long.

It’s all about your team. It doesn’t matter how talented you are as an entrepreneur, your business success is based on the team that you build. Entrepreneurship is a team sport. 5. What are the best parts about entrepreneurship?

I don’t have a fear of being laid off. Coming from the corporate world, I realized early that you can get laid off any day of the week, no matter how well you are performing. If you don’t fit the organizational structure, or if the company is not doing well, you could be next on the chopping block.

I love that I can spend all of my time focused on growth and not worried about my job.

6. What has been your most effective form of advertising?

We practice what we preach in regard to advertising. We have a healthy mix of search engine marketing, social media marketing that sends qualified traffic to a handful of landing pages. Although we get most of our business through referrals and repeat business, we are adding new customers each week through targeted campaigns through digital marketing.

7. Who are the entrepreneurs you look up to?

Richard Branson is one person that I follow closely. He is a ruthless marketer, risk taker and lover of people. He has a great work-life balance and loves what he does. It’s always been a dream to meet him in person. 8. What goals have you achieved for your business so far?

We’ve experienced 50%+ growth every year for the past five years while maintaining a great company culture. Growth is hard, but we’ve been able to improve the quality of our products and services through rapid growth.

9. What are your goals for your business in 2018?

We are on track to growing our company by 50% as we have in previous years, and every year it gets harder to maintain this growth trajectory.

We are also looking to increase our team from 20 people to 30 people by 2019 so that we have a lot of redundancy across different departments.

10. Where do you see yourself and your business in 5 years?

In our industry, the game changes every single year. We have to constantly reinvent ourselves to stay relevant and competitive. Although it’s hard to know what business will look like, we are hoping to more than double our own team within the next 5 years giving us a company of 50 digital marketing experts.

11. What upcoming projects are you working on?

If I told you, I’d have to kill you.

Joking aside, we are looking at making our websites stupid-fast with new technologies. We are reducing page-load times from seconds to milliseconds, and building more interactive lead-generation strategies for our clients. That’s all I can say right now.

12. What trends are you seeing in your industry?

Digital media has drastically changed our lives. Without a doubt, it has revolutionized the way businesses communicate and connect with consumers on a daily basis. Some of the trends we're seeing is an increased utilization of technology in business landscapes. At Candybox Marketing Inc., we explore how to assist businesses in disrupting the status quo to generate leads and build relationships. 13. What business advice would you give yourself if you were to start all over?

Hire faster. Even though we’ve grown over the past five years, the first five years I was hesitant to hire new people which I believe stiffled our growth. I spent too much time balancing resources and schedules instead of just hiring more people and spending more time selling.

14. Last but not least, let’s end off with a fun fact! What might we be surprised to know about you?

I only work 9-5 with some exceptions. From the first day, I’ve tried to maintain a work-life balance because I didn’t want to start a business to be consumed by it. My wife Tammy & I have had 4 kids in five years and we’ve never wanted to sacrifice our relationship with them for the business. After 5pm I turn my phone off and become dad for the rest of the day.

Social Media

Let's get social. Follow Candybox Marketing Inc. on social media! LinkedIn - Facebook - Instagram -

Twitter -

Many thanks to Darrell for sharing his story with us! Stay tuned for our next featured Toronto Entrepreneur!

Do you have someone in mind who should be on our Friday Feature – Toronto Entrepreneurs segment? If so, email

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