Round 2: How Red Apron’s Jennifer Heagle left a $20M tech enterprise to follow the ‘slow road to success’

Jennifer Heagle
Jennifer Heagle

In his book, Shop Class as Soulcraft, author Matthew Crawford describes how his high school guidance counsellor once used the image of a mechanic in dirty overalls as a warning of something to avoid becoming. He goes on to explain that this was the beginning of an era where young people were pushed away from manual competence toward university and professional careers, with the follow-on being a decline in overall job satisfaction and feelings of fulfillment.

Round 2 is a series of stories that explore what came next for people who may have followed that advice, but have since chosen ways to live more tangibly in an increasingly abstract world.

Jennifer Heagle is one of the original founders of Red Apron, an Ottawa specialty food store that sells prepared meals and emphasizes locally grown ingredients.

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Her story is an arc that follows a Hobson’s choice between making a business viable or being on the street looking for work. Of achieving exceptional success only to question whether how she was applying her talents was truly fulfilling a deeper need for meaning. 

Heagle’s first chapter started in the early ’90s when she became president of Proterm, an Ottawa-based tech services company, after her parents, who had started the business, decided to move Stateside. It all began with the proposition, “Run the business and make it a success, or close it down and find another job.”

The business started when the world of tech was changing.

“Things were taking off in a way we were attached to. We just started growing. I can’t even remember how; all I remember is the stress,” she recalls. 

To meet Heagle is to immediately sense her deep intelligence, so when she describes growing the business to more than 100 employees and $20 million in revenue, it’s not surprising. But through it all she remained a reluctant entrepreneur.

“I absolutely felt trapped. The commitment is huge, but the idea of quitting never crossed my mind,” she says, explaining that simply walking away wasn’t an option because of the impact on so many other people’s livelihood.

“I was honestly in survival mode for 10 years, I just thought, ‘I’ve got to get through this somehow.’”

When she finally sold the business, despite having outwardly achieved and proven so much, she describes being relieved.

“There was light at the end of the tunnel,” she says. “I could move on.” And for the next seven years Heagle applied her finely tuned business skills in a consultancy, a period she extraordinarily describes as “healing and recovery time” from her previous experience. 

Her journey to becoming a chef and running a successful food business was serendipitous. It started with a Christmas gift of a couple of courses from the prestigious Le Cordon Bleu Ottawa Culinary Arts Institute, which led to full-time study that allowed her to focus on food and thinking about her life.

“I went into that experience with no expectation. I just wanted to be happy,” she says. “It then dawned on me, I’ve got a toolkit of skills, so let’s start a business.”

But this time she knew she’d never do something again unless she was passionate about it.

A new definition of ‘success’

After a brief stint starting and running a restaurant, she knew that the hours and lifestyle weren’t for her. She met someone who wanted to partner, a person coming from a similar place to her own – both were mothers with young kids – and that the beginning of Red Apron wasn’t about “dreaming big.”

Instead, for her and her partner, Jo-Ann Laverty, it was about putting boundaries around what she was willing to do.

“Saying you’ll do anything is a recipe for craziness,” she says. “Working within your personal boundaries means you have to work harder.” 

Heagle believes that being a mother also gives her a different view on what success needs to encompass. With young kids, “at any cost” was no longer an option. More success doesn’t mean more happiness, she says.

“I don’t want to work 80 hours a week if the trade-off of more money is giving more life to work.”

“I don’t want to work 80 hours a week if the trade-off of more money is giving more life to work. I’m not interested in that.”

Red Apron was started without its partners putting a lot of money into the business, which forced them to be modest.

“We could only grow when we had the money. We could have started bigger (and) lost money for five years, but we didn’t,” Heagle says. “We’ve had a slow road to success. It’s been 15 years now, but it’s safer, less stressful.” 

Ultimately, Heagle’s lesson is about knowing what integrity you’re defending and being open to more than one idea of what it takes to be successful.

When I asked if, given the chance, she’d do it again, she explained, “150 per cent yes, I don’t know who I’d be without Red Apron. It’s one of the things I’m most proud of.”

Because the business is such a reflection of the personal values of the founders, cutting corners and finding hacks that would lead to more profit is not at the forefront of their mission. 

What I love most about Heagle’s story is that what’s meaningful for her encompasses the whole potential of business.

“We make a difference in more than just the food we make, but in the jobs we create, in the small farms we support – in how we help others thrive,” she says. “It’s about giving a shit because not everyone does. We could make more money, but our values don’t allow us to do that.”

Having heard Heagle’s story, it’s easy to understand why her customers would be loyal. But something even greater is in understanding how the pursuit of happiness comes by not focusing on success at any cost, but instead in creating a business with values and a commitment to something bigger than the bottom line.

Robert Hocking is a marketing strategist and teacher who’s endlessly inspired by the creativity of commerce.

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