Caitlin MacGregor, CEO and co-founder of Plum, was telling a story. She was describing how, in the first year of her company’s existence, she moved from New Hampshire with her husband and seven-month-old baby back into her mother’s house in Petrolia, Ont., to save money.
She was in her early 30s. She and her husband, Neil, and their baby, would sleep on two mattresses in her brother’s childhood room. She thought it would be for three or four months. It turned out to be a year and a quarter.
Listening to MacGregor describe her company’s early days to a lunchtime audience at Communitech Tuesday (the event was called Pizza with the Prez, an ongoing series of talks delivered by local founders about their companies’ stories), it was impossible not to marvel at the doggedness and grit, and incomprehensible commitment, it takes to build a company.
Today, Plum, whose software-as-a-service platform helps companies identify and hire employees, is on track and thriving, and has grown to 18 employees. Getting to that stage, however, was something else.
MacGregor described how she and her husband would drive the 2 ½ hours each week to Waterloo, or 3 ¼ hours to Toronto, to get help from Communitech and MaRS, respectively. When she gained entry into a Communitech program called Hyperdrive, the forerunner of what is now known as Rev, she was able to move to Waterloo and out of her childhood home. But the challenges, and the mistakes, were just getting started.
“It took five years,” she said Tuesday, when asked how long it took before the day-to-day fate of the company wasn’t in constant play. It was in February of 2017 that she closed a nearly $2-million seed round, finally gaining a little peace of mind.
“Finally,” she said, “I could breathe.
“I had the right executive team in place and I had enough money to keep the lights on to get us to the next milestone. At that point I also brought on a manager of finance, so I literally had somebody who was able to say, ‘You’re fine.’”
You’re fine. How many of us go to work every day wanting those words to ring as true in the morning as they do in the evening? For most of us, the need for certainty, to know ‘you’re fine,’ leads us to the relative security of a paid position rather than the white-knuckle life of a startup.
“In six years, I’ve never missed payroll once, but it’s gotten close a couple of times,” MacGregor said. “When I stopped worrying about making payroll, that’s when I was able to breathe.”
MacGregor acknowledges that not all personality types are able to absorb the risk and the stress of entrepreneurship. She is often asked to speak to Fierce Founders Bootcamp cohorts – Fierce Founders is a Communitech program that helps female entrepreneurs – and talks to would-be entrepreneurs about personality, and stress, and whether the emotional ride inherent in starting a company is right for them.
“We go over their personalities,” MacGregor says. “There are certain things that are harder emotionally on certain people. That constant being beaten down is not healthy. It’s something that hurts them to constantly be in a situation where they’re having failure after failure.”
In her case, MacGregor says she mostly thrives in the role, and the uncertainty. But she also acknowledges that she has help on call, and that’s a luxury not all company founders have.
“I don’t do it alone. I have so much support from my co-founder, who is my husband. I had support early on when we moved in with my mom. I had support with the kids.
“The only way I’m able to do this is I have an equal partner, and no matter what flexibility we need in our lives, we can always make it happen. If I have to be away, there’s somebody else to cover for me with no resentment.”
Still, she admits there have been days where she and her husband have wondered if it makes sense for them to have, as she says, “all their eggs in one basket.
“Those lows, while you have support, sometimes there’s no escaping it. There’s no backup plan. There’s no one person’s career you can lean on instead of the other. There have been times where we’ve said, ‘Do we really have to make our lives this difficult?’”
MacGregor said that when she started Plum she thought that “in three years, we’d be super successful, exit the company, and be multi-millionaires.” It didn’t quite work out that way.
She told the lunchtime crowd that once she realized that success, if it was to come, was a long-haul project, she also realized she had to make the time to live her life while she was building her company. Life couldn’t stay on hold forever. So she got married. She had kids.
Today, MacGregor can look back and know she has weathered storms that have defeated many others. The takeaway? The rewards can be great, but so too are the risks. It’s a gamble not everyone will take. All other things being equal, it’s the committed, the brave, the ones with grit – like MacGregor – who survive and thrive.
