Erin Bury on planning your digital afterlife

Look, no one particularly enjoys thinking about their mortality. But given that 56% of Canadians don’t have a will, it’s a conversation that Willful and their founders Erin Bury and Kevin Ouds think more people should be having with their loved ones. Founded in 2017, the Toronto-based company wants to help Canadians take the pain out of making end-of-life arrangements through their online platform.

In July, Willful teamed up with CIBC to help more Canadians create wills online. Here, we chat with CEO and co-founder Erin about the partnership, insights from her career and what’s next for Willful.

This interview has been edited for length and clarity.

Could you tell us a little bit about yourself?

I wasn't one of those kids who had 17 businesses in high school. After graduating from Carleton with a degree in journalism, I decided to go into public relations. In 2007 I got a job at an agency called Proof where I worked with tech companies as clients. My goal was to climb the corporate ladder and eventually have a corner office at a Fortune 500 company. But my path was totally thrown off course when my mom introduced me to someone named Sarah Prevette. She was going out on her own to launch a company called Sprouter, and she approached me to be the first marketing communications hire. At the time, I didn't know what entrepreneurship or startups were, but I took the leap anyway to join her at Sprouter in 2008. That was kind of my introduction to the startup space and what set me on the path to becoming an entrepreneur and passionate startup advocate today. I also spent about two years on the founding team at BetaKit as the publication's first managing editor. And that I think is what solidified the fact that I wanted to be an entrepreneur because, by interviewing founders and writing stories about them daily, I constantly got to hear about these people doing incredible things.

How did the idea for WIllful come about?

My husband's uncle unexpectedly passed away in 2015, and he hadn't spoken to his wife (Kevin's aunt) about his end-of-life wishes. The family had no clue whether he wanted to be cremated or buried, what type of service he would want or where all of his important documents and information were stored. And about a year later, Kevin was hospitalized with septic arthritis in his ankle for about a week. And he was lying in bed, the hospital bed one night after I went home from visiting hours, and he thought, "If I were to pass away in here, I would be putting Erin and my family through the same thing that my uncle just did because I don't have anything prepared."

He looked into what's out there in terms of planning resources and found that options were to go to a lawyer and pay thousands of dollars or use a website that looked like it was designed for our parents.

So, that was the impetus: these brushes with death in his own life made him realize how little we plan and think about our passing. The goal behind Willful was to create a user-friendly, affordable, digital platform that helps Canadians build their end-of-life plans and share them with family members. We launched with wills in 2017 and have since branched out to focus on other end-of-life planning aspects.

Can you give us some insight into your business model?

Right now, we're a transactional business. Essentially you pay once, and then you can create your legal documents, like your will and power of attorney documents and make changes to those over time as your life changes. We also have tools that help you record your burial and funeral wishes and record a list of your assets. The idea is that, over time, we'll add additional products and services to help you create a more comprehensive estate plan and make sure your family has access to it.

What's next for Willful? You recently teamed up with CIBC–can you talk a little bit about how that partnership came about?

One of the biggest challenges for any small company is distribution. You can have the greatest product in the world, but as a startup, you don't have Super Bowl commercial money. One of the ways we found the ability to get in front of Canadians is through partnerships. We've partnered with brands like Allstate, Canada, and Arbor Memorial funeral homes. Now, CIBC is our first big financial institution partner, and we share the similar goal of giving Canadians financial peace of mind. We spend so much of our lives trying to accumulate wealth, working with financial planners, and opening savings accounts and RRSPs. And yet, most people don't consider estate planning as part of their financial plan. We're excited that CIBC is not only that shining a spotlight on estate planning because they have such a vast network, but also that they've chosen Willful as the kind of vehicle for their customers to do that easily.

As for what's next, we're focused on other products and services that help people build a comprehensive estate plan. This will include building out more funeral and burial planning options and partnering with folks like Arbor Memorial to help people pre-plan their funerals or services.

What’s your advice to someone just starting out in their career?

Work at a startup. No matter what you want to do in life, go work at a startup even just for a year, because the pace at which you'll move will be so much faster. You get exposed to so many other things beyond your kind of core competency. I think at big companies, there are a lot of "I cant's" and a lot of limiting mindsets, but startups tend to focus on being a lot more resourceful and in general, there are lots of ideas floating around for how to get things done.

Learn to invest. When you get that first paycheque, set up that RRSP and compound interest will be your best friend. When I was 16 and working at a grocery store, I definitely didn't prioritize retirement savings, but I wish I could go back in time and start saving earlier.

Build a strong personal network and brand: I've been laid off before and I was at another startup that eventually ran out of money and shut down. During all of those low points, I leaned on my network to help me find my next opportunity. Now, as an entrepreneur, having that strong network leads to opportunities like the CIBC partnership and other things. So as a new grad, my biggest piece of advice would be to get out and go to events, schedule coffee meetings and join community groups to build your network—that will be the single biggest secret to unlocking a really great career.

Now for the fun part: What are some of your favourite books, podcasts and TV shows?

Podcast: We Regret to Inform You, a Canadian podcast all about stories about failure. It's a reminder that everyone faces setbacks and that when you do, you have to just keep going.

Books: I have a million book recommendations, but one of my favourite business books is The Power of Habit. It's all about habit formation and how to make things automatic in your life. On the fiction side, I love The Midnight Library, which is about all the different paths you can take in your life and the impact your actions have.

TV shows: My favourite lately is Yellow Jackets. During my four months of maternity leave, I made my way through Downtown Abbey so that's another recent favourite.

What are some of your work-from-home essentials?

I keep it simple. I need my MacBook, AirPods, a second screen, and a stocked kitchen because I feel like I'm one of those who snacks every two hours.

How do you start your mornings to ensure a productive day ahead?

One word: Peloton. I'm a big believer in exercise as therapy for startup founders. I usually start my mornings— obviously with my daughter first— by taking a Peloton class.