Darrell Keezer

Unemployed to Unstoppable

In Articles, Life Issues, Stories, Success, Work by Rob Horsley

Millennial Entrepreneur Silences Skeptics

Darrell Keezer is a fan of hustle. It’s something he looks for in his employees, and something he’s been no stranger to throughout the course of his eventful, yet still-young career. And at just 34 years of age, his business is showing no signs of slowing down.

Keezer is the CEO of Candybox Marketing and Launch48, two companies based in Mississauga, Ontario that serve clients looking to beef up their online engagement with customers and patrons. Candybox is a marketing agency that uses a variety of tools and expertise to maximize exposure between their customer and patron base, such as better advertising placements, social media strategies, and building better experiences for visitors to their websites.

It’s the latter that spawned the initiative Launch48, a separate company that shares the same office space as Candybox but is comprised of a separate staff. Launch48 specializes in designing websites for small businesses and organizations in just two workdays. Keezer’s staff plans content strategies for clients, builds the website, and then trains clients how to use it themselves going forward. Past clients include several Ontario-based churches and summer camps, for-profit companies focusing on investments, wealth management, and real estate.


Keezer released his first book, Pick Up Your Freaking Phone: The New Rules for Entrepreneurs in [2018]. The book details the story of what led Keezer to step out on his own as an entrepreneur after getting his start as a project manager at a software-as-service company.

“My educational background is in marketing, but I got hired on for more of an IT role—I don’t know why,” he says. “But I actually helped this small business grow quite substantially.”

Even early on, Keezer showed a knack for delivering big results from small starts, growing his team to the point where bigger companies began to take notice.

“I started off with managing one person and after about two years I think the team was up to about nine people, who I personally had to hire on and manage,” he says. “And that was me being straight out of school.”

Despite that early success, Keezer’s penchant for growing talent ultimately led to major setback.

“Because we grow too much… we were fit for acquisition” he says. “We got acquired by a company and shortly thereafter that company, going to the recession, laid everybody off.”

The layoff left Keezer with only $8,000 in severance in his bank account, facing the reality of a slow job market and providing for a growing family.

“I was literally canned in 2008, right at the beginning of the recession—and nobody was hiring. At that time I had a kid that was a year old, and another one due in two months.”

Keezer admits he’d always wanted to start his own company, but notes that the timing was definitely accelerated given his family’s needs around the time of his layoff.

“When you’re faced with the pressure…and you’ve got eight weeks to get a paycheque… I made it happen quickly,” he says. “Literally the next morning after I was laid off I started Candybox Marketing and got on the phone and started making calls.”


Keezer’s marketing background, his prior entrepreneurial inklings, combined with the need to provide for his family is what led him to launch Candybox, something he also saw as being important in an emerging business landscape with an increased focus on reaching new online markets.

“I started Candybox because I knew there was a need out there for companies to execute digital campaigns really well, and I didn’t see any companies meeting that need.”

Candybox was ranked 188th in Canadian Business’ 2018 “Growth 500” issue, profiling the top 500 fastest-growing businesses in Canada. Among marketing agencies, the company ranked 16th. With business moving at such a rapid pace, it’s required Keezer to pay close attention to the details of his own job as CEO.

“I would say that my day-to-day changes completely every single year,” Keezer says. “Every year I kind of have to reinvent my job and make sure I’m doing the right things and not the wrong things.”

So far it seems to have paid off, with Candybox expanding by half each of the last five years.

“We grow about 50 per cent every year,” he says, though he notes that he keeps a strict schedule so as not to let work affect his commitment to home life, calling himself a “stickler” for keeping the eight-to-five workday, something he says he’s passed on to his employees.

“My guys work nine to five, and that’s it,” says Keezer, noting that this is not typical for the industry, where it would be far more common to start work at 8:00 A.M. and clock out at 6:30 P.M. while at the same time only being paid for eight hours. “That’s because it’s my value.”

“As soon as 5 o’clock hits, I shut my laptop lid and I go and be dad because I just don’t want to work 80, 90-hour work weeks,” he says. “I could, and I could definitely make the hours count. But I stick to my hours to make sure that my family gets the best of me.”

Being a husband and father of four young children has meant establishing a strict divide between professional and personal commitments.

“I just wanted to make sure that right from the beginning I set up proper barriers, so that I don’t take advantage of it later on.”

Although he isn’t involved in the creative work for individual accounts to the same extent anymore, Keezer does still spend a good deal of time trying to bring new business to the company. Such a routine sometimes forces him to be creative with how his workday is structured and the location at which business takes place.

“I’ve got seven to eight meetings every single day…I also speak at around 50 events per year as a keynote speaker, and so I take a lot of meetings on the go. I’m an advocate of remote working and so you never really know where I am.”

While reinventing his own job has meant more of a focus on big picture company plans for Candybox and Launch48, Keezer expresses confidence in his staff to provide good work for the more than 1,000 clients both companies seek to serve.

“I really have an amazing team of creative people, and it’s their job to really deliver on that strategy and it’s got to be theirs.”


The bottom line for the staff at Candybox is getting results for customers and clients, and helping them be better sellers of their own products and/or services. But driving engagement isn’t just a one-step process, Keezer says. It’s more like conducting an orchestra.

“There are companies out there that do web design, there are companies that do Google advertising, and there are companies out there that do social media marketing. But really you need all these things…playing like independent instruments to make one song. And that song has to attract new customers,” says Keezer. “We help [our] customers figure out their song.”

Keezer points to an example of one Christian camp who was looking to increase camper registration, a goal that was greatly exceeded thanks to the work of his creative staff.

Candybox was “able to increase the registrations of camp members substantially, year-over-year, without changing their advertising,” Keezer says, “by adjusting how they say stuff on their website…”

“I think there were like 55,000 campers, and we helped them gain so many new campers that they actually had to purchase another facility to handle the overflow. That’s really cool for us.”

Another example involved an air-conditioning company looking to make a change with how their advertising dollars were spent.

“We spent 12 per cent of their previous year [advertising] budget…and we got them six times the results they had the previous year just by converting everything to digital marketing,” Keezer says. “We’re dealing with some pretty big numbers in regards to what our expectations are.”

Such results have helped cement a strong loyalty among satisfied customers.

“All of our customers stay with us. Our retention is 12 times that of our competition. So we’re not really looking for new business all the time. We get so many referrals of people that want to work with us that, to be honest, we do turn down business.”

A big part of what makes Candybox so successful, Keezer says, is the focus on a unified direction, and a refusal to outsource any of individual components of a customer’s overall online marketing strategy.

“[With] a lot of companies it’s like your website’s being built by three developers in the Philippines, your campaigns are being managed by guys in Bangladesh, your account manager is in Toronto, and your designer’s in Utah. Do all of these people really understand what we need to accomplish here? Are they acting as a team?” asks Keezer. “When we go into organizations, we’re not about selling products, we’re about helping them grow their company or their organization with a cohesive plan.”


At the age of 34, Keezer sits well within the “millennial” demographic, the age bracket (sometimes referred to as Generation Y) born roughly between 1983 to 1996, often characterized as the group who came of age at the turn of the millennium. Keezer says that it shouldn’t strike anyone as noteworthy to see his level of success coming from someone relatively young such as himself. Millennials, he says, have been and are continuing to do great things.

“Ten years ago [being young] was a bit of a barrier to entry — it was actually hard to sometimes get larger clients because they just thought that I was too young to be able to do it. I had to kind of pay my dues over the years [by] proving it,” he says. “Right now, being 34, I don’t feel like any of that stuff holds me back. I feel like ‘the millennial entrepreneur’ is kind of a very-accepted thing. There are 30-year-olds running billion-dollar companies. I think it’s more [accepted] now than it ever has been.”

Some estimates claim about 37 per cent of Canadian workers are from Generation Y, and those numbers are expected to rise to 50 per cent by 2020, though Keezer says that might already be true. By 2025, about 75 per cent of Canada’s workforce will be comprised of millennials. Whatever the actual number is, Keezer says the sun might already be setting on businesses that haven’t figured out how to engage those who now make up the largest segment of Canada’s employed population.

“My concern is for any business that didn’t actually build a good millennial workforce to help with the succession plan, they’re already a little late to the game,” he says.

“Those companies that haven’t been marketing to millennials for customers or haven’t been embracing millennials within their organizations, they just fizzle out and [won’t] be the same as they used to be.

“Things like golf courses, from both the membership and leadership…they’re dying. And they’re dying a very painful death where they just can’t find engagement—but they never tried.”

Keezer doesn’t exactly lament this reality, but doesn’t celebrate the death of legacy businesses either. He is, however, encouraged by the opportunities that exist for businesses who have chosen to look ahead to its next generation of workers and customers and have built their company roadmap with shifting demographics in mind.

“I think there’s a pretty dark future ahead for companies that didn’t start thinking about this five or ten years ago when the warning signs were there…but a pretty bright future for any company that had actually adapted.”

“I think it’s very exciting for new companies.”


Two of the main things millennials want are finding a purpose, and flexibility within their professional lives, Keezer says. Finding those things in outdated business models and workplaces hesitant to adapt can be challenging. As an entrepreneur, he’s given his employees more freedom than has typically been the case for young workers until recent years.

“I started a company because I didn’t just want to work for a corporation,” he says, adding that being ‘the boss’ has allowed him to provide those things for his staff, something he says he loves to do.

“One of my passions is to build good lives,” he says. “I’ve just been privileged enough to be able to lead a company where I set the values.”

Ultimately, Keezer hopes that his employees love their jobs as much as he loves his.

“It’s an absolute privilege to be able to allow people within my company the same rights to an amazing job that I built for myself.”

Rob Horsley
Rob Horsley is a freelance writer. He who lives in Saskatoon with his wife, daughter, and twin sons.
Rob Horsley
Rob Horsley is a freelance writer. He who lives in Saskatoon with his wife, daughter, and twin sons.