Money is wrapped up in all kinds of unpleasant emotions. Shame, embarrassment, fear, regret. We all experience these feelings about our money at one time or another, but we’ll be damned if we actually talk about it. To help eliminate the stigma around making mistakes with our money, or feeling scared about our financial security, we’re introducing Financially Naked — a series where people have the space to bare all about their most vulnerable financial experiences, mistakes, and regrets. Because let's face it: we all have them.
My husband has always been an ideas guy. Most people go through their day and see problems that need to be solved, but Kevin has always viewed those problems as opportunities to fill a need (and, ideally, to become a millionaire in the process). Since we started dating more than 10 years ago, he’s had countless ideas for products and companies — so many, in fact, that he started calling me the “dream killer” because I would routinely shut down his half-baked plans.
Early on in our relationship, Kevin was the main breadwinner. I was making peanuts in an entry-level PR job, whereas he was a unionized employee with a pension at a cement plant. There was just one problem: he hated his job. It was physically and mentally demanding, and even though the money was good, he couldn’t picture himself hauling bags of cement day in and day out for 30 years. He saw entrepreneurship as his ticket out.
His big idea came in 2016, about a year after his uncle passed away unexpectedly. Watching his family have to guess at what his uncle’s end-of-life wishes were — combined with two personal near-death experiences — convinced him that the universe was trying to tell him something. He set out to launch a company that would help people organize their end-of-life plans online.
When he approached me with the concept, I think my verbatim reaction was “Could you pick a less sexy business idea?!” But I knew there was little competition in Canada, that estate planning was a process not yet touched by technology, and that it was something every Canadian would have to deal with at some point. So, despite him having only about $5,000 in startup money and no technical background, I gave him my blessing to quit his job and start the company. By doing so, I also appointed myself the main breadwinner for an undetermined amount of time — a gift I was happy to give if it meant creating opportunity within the business, but one I didn’t anticipate would invite resentment into our relationship along the way.
Some days, I felt alone in caring about or stressing about our finances. Other days, I felt plain resentful... because I couldn’t say no to any paid engagements
At first, I found it easy to assume the financial burden because it seemed like a short time before we would again go back to two incomes. But when Kevin launched the first version of the website, we heard crickets. By this time, the financial balance of power in our relationship had already begun to shift. I’d gone from my low-paying PR job to a full-time position running a marketing agency, and was building a speaking career that helped bring in extra money. Pretty soon, a year had gone by, I was still paying the bills, and he was no closer to bringing in any money.
Realizing he had to pivot, Kevin changed the company’s focus, raised money from friends and family, and set out on phase two. By then, it was the spring of 2017, and he’d gone without a salary for more than a year. Meanwhile, we’d just purchased a home in Prince Edward County, and the renovation costs were piling up. I was also hoping we could get married sometime this century. In order to supplement our income, Kevin got a part-time job at a tool store. It wasn’t anywhere close to equal in terms of income, but at least it was something. Fortunately, phase two was a big success, and the new version of the site, now known as Willful, launched in October 2017.
The company was growing, but it still wasn’t enough to draw a salary. Any revenue brought in in 2018 went to paying contractors and investing in marketing. Tension started to emerge between us. Not only was I acting as the primary breadwinner, I was also paying all of our bills and managing all of our money. Some days, I felt alone in caring about or stressing about our finances. Other days, I felt plain resentful that on top of my full-time job, I had to fly out to Yellowknife, Edmonton, or Halifax to speak at an event because I couldn’t say no to any paid engagements. On the flip side, Kevin resented the fact that he had to work a part-time job that distracted him from the business he was trying to build (though he understood the necessity), and that he didn’t have his own disposable income. He felt like he couldn’t even buy a shirt without asking me first.
To combat these feelings, we committed to focusing on the long-term vision to build and one day sell Willful, knowing that our short-term sacrifices were in service of a much bigger goal. Kevin took on painting and project management jobs on weekends to help fill the income gap, which helped to alleviate the burden and reassure me that we were both in this together. We persevered, and even managed to get married right in the thick of startup mode. Tying the knot at a financially tumultuous time actually helped me reframe how I thought about being the breadwinner. It went from being “my money” to “our money.”
Three years ago I would have been tapping my toe impatiently waiting until Kevin could take money out of the business. But now that I’m part of the business, I want to re-invest every cent
Last spring, a few months after our wedding, I decided to move on from my agency. I was ready for a new challenge, and it just so happened that Willful was accepted to a startup accelerator program, which gave me the opportunity to join as CEO. So in April 2019, we went from one growing business and one secure salary to being coworkers without one. Both of us have yet to draw a salary from the business. We pay the bills with the income from my speaking business, which continues to thrive, and through other sources like renting our Prince Edward County house on Airbnb.
Three years ago I would have been tapping my toe impatiently waiting until Kevin could take money out of the business. But now that I’m part of the business, I want to re-invest every cent. It’s become our business, and together we see the bigger picture: hold off on paying ourselves now, make it work however we can, and hopefully have a bigger payout in the future.
I’ve learned that the financial balance of power is always going to shift in a relationship. It’s flip-flopped for us over the past decade, and I’m sure it will continue to over the next 10, 20, 30 years. Regardless of the tough moments, I have no regrets about helping Kevin on his startup journey. I always tell him that regardless of whether or not the company succeeds, the sheer fact that he took the leap to start it is what I care about most. I’d much rather be the primary breadwinner every now and again if it means I have an ambitious partner who chooses risk and entrepreneurship over complacency. That, to me, is priceless.
Illustration by Jeannie Phan.