Kevin Oulds, Founder and CEO of Willful, on Why When There’s a Will, There’s a Way

Kevin Oulds, Founder and CEO of Willful, Entrepreneur of the week, Bay Street Bull

In this weekly series, we profile entrepreneurs approaching the top of their game, and ask them how they got there. From his inspiration to his unique challenges, we asked Kevin Oulds, Founder and CEO of Willful a few quick questions.

Kevin Oulds has always been an entrepreneurial person, but prior to starting his own tech startup he worked in very different fields—at a cement plant and in trades for home/office renovations. At the company, he managed projects for large offices and commercial spaces. The industry taught him a lot about how teams can work together effectively, with the experience unknowingly laying the groundwork for building his first startup and team.

It wasn’t until the sudden death of a close relative, who didn’t have a will in place, that left Oulds wondering if there was a better way. “I saw the difficulties firsthand that our family faced by not having certain conversations beforehand, and the confusion that resulted from not having a plan in place,” Oulds says.

Born out of the experience is Toronto-based company, Willful. Oulds quit his job and launched the online will-hosting platform in 2017 as a way to make estate planning easy. Currently the company serves Ontario, Alberta, and BC, but is working towards expanding across Canada.

“I learned that most people avoid thinking about, talking about, and planning for death and after looking into it, I realized just how big the problem really was,” Oulds says.

A will problem

According to a study conducted by LawPro, over 56% of adult Canadians don’t have a will in place. While additional research conducted by Willful determined that over 80% of millennials in BC alone did not have an estate plan in place. Although there were a number of reasons why, high on that list were reasons like cost and convenience.

Compared to traditional estate planning, Willful is making it much more affordable and accessible for people to get a plan in place. Ultimately, the company is creating an open dialogue around the topic of wills and helping people protect their future, assets, and loved ones.

Oulds made the experience user-friendly through an online platform that guides people through the process without visiting a lawyer. With Willful, people can sit down in their home on their own time to create an estate plan in under 20 minutes—a convenient option for the average person who doesn’t need to spend $1,000 with an estate lawyer when they have a fairly simple estate. Willful helps minimize the costs to help people get over the typically large price tag of making a will.

But the journey hasn’t been without challenges.

Death isn’t sexy

“Death isn’t sexy, but it is something everybody faces…”, Oulds says, also admitting it was tough early on to get potential investors excited about a legal software company dealing with the topic of death.

Finding lawyers to work with Willful was also difficult since they saw technology as a threat to their business, but with time that changed.

Oulds continued to be confident in his product. “When we first launched I think I was like every entrepreneur, I thought we would flip a switch and there was a good chance our site would crash from too much traffic.”, he says.

Willful did have some traffic and sales from day one, but Oulds realized that it takes time to build a brand and to refine your product and service.

His efforts seem to be paying off. In the short time it has been around, Willful has already helped thousands of customers create their wills easily and conveniently online.

Here are three quick questions with, Founder and CEO of Willful, Kevin Oulds.

What does a regular day look like for you?

I would like to say I start by going to the gym, but that’s a work in progress. While no two days are the same, an average day for me is what I imagine would be similar for founders at other early-stage companies. I’m doing a bit of everything from handling customer inquiries, to outreach to potential corporate partners, to working on strategic plans and also making sure others are on track and we are keeping focus on our main goals, which are to expand Willful across Canada, partner with great companies who want to offer Willful as a value-add to their customers or clients, and to expand our platform into a suite of digital products that help people prepare for and deal with death.

What is one thing, non-work related, that helps you stay balanced each day?

That’s an easy one – spending some time with my wife (who is also an investor in and advisor to Willful) watching a movie or Netflix show and just relaxing. It’s important to have a good work/life balance but I’m also trying to get to the gym more and continue to use apps like Calm that also help with the stress of running a business.

What’s the best piece of advice you’ve ever received as an entrepreneur?

There is no shortage of advice getting tossed around and you need to try and take bits and pieces from each source and see what is best for your situation—if it’s even relevant at all. For me I think the best piece of advice was that very early on, entrepreneurs have a lot of self-doubt and I was told that if you don’t take the leap and launch you will always wonder what might have been. I knew I couldn’t live with that question.