When Erin Bury and her husband, Kevin Oulds, experienced an unexpected death in their family four years ago, it spurred them to create a business that would help others in the same situation. They realized there needed to be an easier way for people to have a plan in place so that their wishes are known. Today, Willful, their digital will creation company has a growing team and the entrepreneurial couple has lots to look forward to—including a new family member and an upcoming appearance on a beloved Canadian TV show. Here, Bury, Willful’s co-founder and CEO shares the highs, lows and happy surprises of starting a new company.

Founded: 2017

The elevator pitch: “Willful is the easiest way to create a will online in Canada in as little as 20 minutes for as little as $99.”

The a-ha moment: “Kevin’s uncle passed away unexpectedly and the family was scrambling to find documents while debating what he would have wanted. Kevin and I looked at each other and said, ‘you know, we’re using apps to save money, order rides and book travel. But there’s nothing that exists to help organize end-of-life wishes.’ So, we thought we could build something.”

How I got started: “I was running a tech marketing agency at the time and was looking for something new to do. Kevin kept encouraging me to join him at Willful and I didn’t know anything about wills—but every time I talked to someone about it, they’d say, ‘oh, I need a will. It’s on my list, I just haven’t done it yet.’ I started to realize that cost and convenience were a huge factor, and I became really passionate about the problem. I joined Willful as CEO about 18 months after it launched.”

Biggest challenge to date: “Funding the company in the early days. We raised a little bit of money from friends and family, but we had to finance the company on our own credit cards. I’ve compiled a big document of all the grants, loans and capital from the government or other sources that I’ve been able to find. I constantly share that list with other entrepreneurs because it’s complicated to navigate this system.”

How COVID-19 changed business: “We had our busiest six weeks ever at the outset of COVID-19. People were coming to us out of fear and anxiety, and we’ve always tried to market around this idea of peace of mind and legacy. We had to pause all of our marketing and take a step back to ask ourselves how we could add value. So, we ended up doing free wills for more than 5,000 healthcare workers over the past year.”

What advice did you wish you had starting out? “In startups, everything takes twice as long and costs twice as much as you think it’s going to. As a founder, you want to move at the speed of light and you’re constantly asking, ‘why aren’t we doing more?’ Patience is a virtue. And focus is important—there’s going to be a million different directions you can get pulled in. You have to be strategic about how you spend your day and what you focus on.”

What advice are you glad you ignored? “Many people told us we should make Willful a business-to-business program, where we would sell our software to estate lawyers so that they could load their clients’ content in. I didn’t disagree that it was a great business idea—it just wasn’t for us. We knew from the beginning that our ultimate mission is to make sure every Canadian adult has a will.

Growth to date: “We’ve raised about $2 million in funding, which has really helped to power our growth. We’re now a team of 15 people and we’ve expanded to eight provinces. We’ve also partnered with brands—our biggest partnership to date was with Allstate Insurance. And we filmed Dragon's Den in June, which is airing on this upcoming season!”

Favourite thing about starting a business in Toronto: “I started working in startups in Toronto in 2008 and have spent over a decade going out to networking events, meeting people night after night. I have a really close circle of fellow female founders, all of whom are building companies in Toronto. And the best thing about the group is that not all of us are having the worst day on the same day, so you can kind of cheerlead and lift people up. You have to surround yourself with people who are going through the same thing.”

What it’s like to talk about death with clients: “Most people are uncomfortable talking about death. A lot of the people are coming to our site because they’ve just lost a loved one and it’s motivated them to get their own end-of-life planning in order. We broach death by being empathetic and empowering people with information about why they might want to plan for this, to help ease the burden on their families.”

On writing her own will: “I’m embarrassed to admit that I was 33 when I wrote my will! When Kevin started the company, he joked, ‘You must write your will, because it’s so embarrassing if the wife of the founder of an online will company dies and doesn’t have a will.’ It was a good reminder that half of what we do is just education about wills.”

What’s next: “I’m eight months pregnant, so starting a family. Our biggest customer base is new parents, so I think that gives us a lot of empathy for the decisions that they’re making and what they’re going through. Next year is about going beyond the will: things like life insurance and recording other end-of-life wishes related to social media and digital footprints—all of these other things you can do to prepare your family. That’s really where Willful wants to be: Not just the best online will provider in Canada, but the best provider of end-of-life planning tools.”