Where there’s a will, there’s a way

Written by Jacqueline Leung



City MOGULS: Founder Profiles Series


Tell stories of strength, growth, and resilience. Inspire readers by asking founders the hard questions and creating “a-ha” moments and conversations within the CM community.



Willful - https://willful.co/ - create a legal will online.

Erin Bury, CEO and Co-Founder


It’s difficult to determine exactly how COVID-19 has impacted the Canadian economy. With Canada’s unemployment rate reaching a record 13.7% in May, and with one in seven small businesses at risk of going under, it’s hard to imagine any business owner trying to set any milestone other than ‘survive’.


Online estate planning startup Willful entered the pandemic like most businesses, prepared for the worst but hopeful for the best.


But unlike most businesses entering the pandemic, Willful experienced a 500% spike in demand for its product, and shortly after COVID-19 shut down the economy this Spring, the Toronto-based company raised $1 million to grow its business.


Erin Bury, CEO and Co-Founder of Willful, admits that fundraising in the middle of a global pandemic was “a bit of a roller coaster.” The company signed a term sheet (a document outlining the terms of an investment between an investor and a startup) at the end of February, but by the time COVID-19 hit hard in March, several investors had pulled out of the deal.


Although it took some time to convince investors that “death-tech” is recession proof, Bury said the moment she knew the business would be OK was a few days after the pandemic hit, when she saw sales and traffic go through the roof.


“Unfortunately, it [the pandemic] caused a lot of fear and anxiety and caused people to think ‘oh my God, I need to get my will in order,’” Bury explained. Willful officially closed their seed financing in June.


So, what exactly is “death-tech”?


Willful’s story starts like most startups, from a personal need that can’t be fulfilled by anything out in the market.


In 2012, Willful’s Co-Founder and Bury’s husband, Kevin Oulds, experienced a family death that changed his life forever. In the months that followed Oulds’ uncle’s death, Bury recalls how difficult it was for the family to make decisions during a really tough time. The inevitability and unpredictability of death led to the birth of Willful in 2017.


Willful is an estate planning platform that aims to make it easier to plan for the end of life and aims to destigmatize that conversation with Canadian families.


“Estate planning hasn’t changed in decades,” said Bury. “We’re disrupting the status quo by moving the process online and making it more accessible to people regardless of their location, income, and ability.”


Since joining the company in 2019, Bury has led Willful’s expansion into multiple provinces across Canada, and recently helped launch a petition to allow for digital signing and storing of wills (yes, that’s all still paper-based).


But Bury didn’t grow up wanting to become an entrepreneur. In fact, she wanted to climb the corporate ladder and dreamed of becoming a marketing executive at a fortune 500 company.


The “Sliding Doors” moment


After graduating with a journalism degree and working briefly as an entry level employee at a PR agency, Bury was recruited by a woman entrepreneur and left with a tough choice; she could continue to work hard and get promoted in her current role, or she could take a risk and leave a comfortable job to work at a startup.


We were at the height of a recession and it was actually a really tough decision.” Bury remembers thinking, “you aren’t good enough, you can’t do this; what are you doing leaving a stable job?”


Bury credits her Mom for pushing her to take the role at Sprouter, a Toronto-based startup that was eventually acquired by Postmedia. Bury worked as the company’s Director of Content and Communications.


The experience led her to an executive role at a communications agency called Eighty Eight, where she worked for six years. Today, Bury is an entrepreneur, speaker, and startup investor and advisor.



No regrets


Another “Sliding Doors” moment happened when Bury left her role at Eighty Eight in 2019. At the time, her husband, Oulds, was in the early stages of building Willful and was largely managing the company on his own. When he asked Bury to join him, she told him she’d only join as the CEO.


Today, as the CEO, Bury says she has no regrets. She loves her job and says Oulds, along with the rest of the Willful team, keep her balanced and positive. When the pandemic hit, Bury says the company’s executive team gave them the foundation to keep building.


“When I was working at a PR agency, they used to say, ‘it’s PR, not ER’,” Bury explained. “I take that with me now. It’s a marathon, not a sprint.”


That resilience is what helped the Willful team stay focused even after months of pitching to investors, hundreds of “nos”, and a signed term sheet that ultimately fell through because of the global pandemic.



Bury remembers VCs (Venture Capitalists) saying that Willful isn’t sexy enough, not global enough, too ‘direct-to-consumer’. But the team kept chipping away. They started with an angel round of about $100K, then raised another round with Shopify executives in their network, before meeting investors at startup accelerator FounderFuel who ultimately led their most recent $1 million round.


Bury recognizes that she is privileged to even have Shopify executives in her network, but when it came down to it, it was Willful’s bump in sales that convinced investors to hand over their money in the middle of a global pandemic.


Don’t follow the lead


Although raising money was the right path for Willful, Bury says the biggest myth in the startup community is that everyone should go through the same round of funding. “There are so many great companies that just bootstrap. Business success is as much about what you don’t do as it is what you do,” Bury said.


“Part of the reason we wanted to raise money was for the experience of it,” Bury explained.


In Canada, female founders only receive 4% of venture capital. In the U.S., that number drops to just 2.2%.


At home, Bury was able to garner support from Tactico, a Montreal-based VC firm that makes investments through targeted special purpose vehicles. Willful’s latest seed round was also supported by York Angels and Real Ventures.


For startups that do decide to raise money, Bury says the most important thing to understand is your cap table. “Know how much you own and how much you will give away,” Bury advises. “The average founder only owns 7% of their company once they sell. Map this out from the beginning.”


Also, Bury says, “read the book ‘Venture Deals’ by Brad Feld. It’s the bible for startup raising.”


Planning ahead


These days, Bury and the Willful team are planning ahead by “looking at ourselves as consumers and asking, ‘what do we need?’”


At a time when it’s hard to predict whether it’s even safe to go into an office, building resilience is key to maintaining a positive attitude, especially at work.


Whenever someone on her team is having a bad day, Bury reminds them that “the only way through is through. Exercise is the best reminder of that - when I go for a run away from my house, I know I have to turn around to get back. Just put one foot in front of the other and things will work themselves out.



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