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“Talk to someone who has been the executor of someone’s estate” with Erin Bury and Jason Hartman

Talk to someone who has been the executor of someone’s estate. Estate planning falls to the bottom of the list for most millennials who feel like death is decades away — so to highlight the importance of having an estate plan, find someone who had to execute their relative’s will and close their estate — […]

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Talk to someone who has been the executor of someone’s estate. Estate planning falls to the bottom of the list for most millennials who feel like death is decades away — so to highlight the importance of having an estate plan, find someone who had to execute their relative’s will and close their estate — and ideally find someone whose relative passed away without a will. Ask them about the steps they had to take in both cases, and hopefully it will underscore how much easier the process is when you have a will. This is also helpful to pull together information for your executor outside of just the will — for example I have a Google Drive folder called “When I Die” that includes a ton of info for my executor — what I want done with my social media accounts, final posts for my Twitter/Instagram accounts, a list of all of my subscriptions and banking/insurance accounts, and more — some people might think that’s intense, but I want to make it as easy as possible for my executor once I’m gone.

As a part of my series about strong female finance leaders, I had the pleasure of interviewingErin Bury. Erin is an entrepreneur, speaker, startup advisor, and former technology journalist. She is the co-founder and CEO at Willful, an online estate planning platform that makes it easy for Canadians to create a will in less than 20 minutes. At Willful she’s responsible for driving the company’s mission to make it easier for Canadians to prepare for and deal with death in a digital age. Erin is a frequent speaker with Speakers’ Spotlight, and has appeared in publications including The New York Times, Forbes, and CNN. She is a board member at Save the Children Canada, and a member of the #Tech4SickKids advisory council for SickKids. She was named one of Marketing Magazine’s top 30 Under 30 marketers, and her claim to fame is being retweeted by Oprah — twice.


Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Banking/Finance field?

I didn’t set out on a path for a career in fintech. I’m a journalism grad who pursued a career in tech marketing after university. I first spent time running communications at a startup, then spent two years as a tech journalist at Canada’s biggest startup publication. During that time I covered countless fintech companies, and watched as companies like Shopify and Square started to take off. I then ran a communications and branding firm for almost 6 years — we worked with large companies like PayPal and Sonnet, as well as fintechs like Mylo and LowestRates.ca. While I was running the agency my husband came up with the idea for Willful. It was inspired by a personal experience — his uncle passed away suddenly and his family was left with unanswered questions about his funeral and burial wishes, and he looked into it and found that the estate planning process was largely the same as it was 20 years ago, and he saw an opportunity to improve it through technology. My agency helped with the naming, branding, and launch marketing for the company, and I was an investor and advisor from day one. When I moved on from the agency in March 2019, I decided to join Willful full-time as CEO. We see estate planning as one of the key pillars to a financial plan, and a key part of the fintech landscape.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

I think the most interesting thing that happened as we grew Willful was our “pivot” — that’s an overused word in the startup space, and it essentially just means that something didn’t work with your product/service and you need to readjust to find product/market fit. The original idea for Willful was actually to help people store everything outside of a will — messages to loved ones, social media posts or preferences, or a list of accounts for their executor. We were so excited about the idea, and the day we launched we thought we were geniuses — but we heard crickets. Turns out death is an uncomfortable subject, and people don’t want to think about it unless they absolutely have to. Seems obvious now, but it took us launching that original product to learn that we had built a vitamin — a nice to have — instead of a painkiller — a need to have. That’s when we decided to refocus on wills — every time we discussed the original idea with people they would say “oh, it’s like online wills? I need a will!” So we went back to that feedback and used it to switch gears, and this time when we launched we had customers from day one, and we found product/market fit quite quickly.

Are you working on any exciting new projects now? How do you think that will help people?

We’re really working on trying to bring estate planning into the same conversation as investing, saving, and insurance. Having a will in place is so important, and not having one means your family will have to spend so much more time and money to close up your estate — not to mention it means your assets likely won’t be distributed the way you would have wanted. But people are so reluctant to think about or talk about estate planning because it’s uncomfortable to think about death. We’re trying to make it more approachable by reframing it around peace of mind for your family, and leaving a positive legacy. For anyone who has had a family member pass away without a will, they understand how much work it is — but for people who haven’t had to deal with that, there isn’t much of a sense of urgency. If we can show people that having a will is just another component of your financial plan, like life insurance or retirement savings, I think we can help avoid the type of situation that arose with my husband’s family.

What do you think makes your company stand out? Can you share a story?

I think what makes Willful stand out is our user experience. There’s a lot of opacity around complex processes like investing, filing your taxes, and creating legal documents, and they intimidate people. We wanted to bring the same simplicity to estate planning that Wealthsimple brought to investing, or TurboTax brought to filing your taxes — and we wanted to focus on beautiful design, since we’re millennial consumers who not only want function, but also an elegant, simple interface. We’re not reinventing the wheel with online wills — but I think we stand apart from the other solutions available in Canada because of our focus on brand. One story that illustrates this is about Wealthsimple — we were Wealthsimple customers when we came up with the idea for Willful, and we really wanted to emulate their focus on brand and user experience — so much so that we called the project “Willsimple” in the early days until we settled on a name. Fast forward to about a year after launch, and we were able to partner with their team — the first estate planning platform to partner with Wealthsimple. That was a proud moment for us — we felt like we came full circle to be inspired by this platform and then to have them want to partner with us.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. Wall Street and Finance used to be an “all white boys club”. This has changed a lot recently. In your opinion, what caused this change?

I likely have a unique take on this, because my background is in marketing and journalism — not in banking. I’m more likely to be at a coworking space than on Wall Street. But the startup world is very similar to the finance world in that there’s a dearth of women at the top, and a lack of females controlling the money. It’s common for female startup CEOs to pitch to only male investors, to see an all-male lineup at a conference, and to generally see a lack of diversity in companies. I think the shift towards increased diversity in finance and tech is partly due to the high-profile cases of discrimination and sexual harassment at companies like Uber — it has become a business imperative to have inclusive workplaces, and to deal with bad apples swiftly. The days of The Wolf of Wall Street are gone, and we demand more of companies and their cultures. It’s also partly due to the research that shows that female-led companies and female executives help companies become more successful. More voices at the table just generally leads to making better decisions that include all consumers, and I think it’s becoming increasingly unacceptable to have all-male executive teams and boards.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to this report in CNBC, less than 17 percent of senior positions in investment banks are held by women. In your opinion or experience, what 3 things can be done by a)individuals b)companies and/or c) society to support this movement going forward?

Since I’m an entrepreneur, I think one way to ensure there’s more representation is to start more companies in the space. We often wait until we’re invited to the table, and entrepreneurs like Alexa von Tobel from LearnVest or Sallie Krawcheck from Ellevest have shown that sometimes, it’s better to just take matters into your own hands and build your own version of the ideal company in the banking/finance world.

On the company side, they can publicly commit to diversity and inclusion initiatives — and this goes for banking and tech. Saying you want to hire more female engineers is one thing — but making efforts to find those candidates and market to them is another. Companies have to not just talk the talk, but walk the walk by doing the work to get in front of marginalized groups.

And as a society, we have to support with our wallets. Just like we are more likely to purchase from companies who support causes we care about, we should refuse to purchase products from companies who have homogenous executive teams and boards. We have power as consumers to demand change from industry leaders.

Let’s now turn to a slightly new topic. According to this report in Fortune, nearly two-thirds of Americans can’t pass a basic test of financial literacy. In your opinion or experience what is the cause of these unfortunate numbers? If you had the power to make a change, what 3 things would you recommend to improve these numbers?

There are two clear reasons the numbers are so low: number one, we don’t learn the basics of financial literacy in school. And number two, it’s still taboo to talk about finances in most houses and peer groups. People don’t sit around comparing credit scores or retirement savings, and they certainly don’t learn the basics in school, so the onus is on us as individuals to seek out information. Unfortunately most of us don’t learn good habits early, and we never have a solid base understanding of financial literacy, so that snowballs into a society that’s generally not great at managing their money or living within their means.

If I could wave a magic wand and change 3 things, it would be first to add a basic financial literacy course to every high school in North America to learn things like budgeting, investing, saving, estate planning, and insurance. The second thing would be to make certain personal finance books required reading in that course — primarily The Wealthy Barber and The Automatic Millionaire. Third, I would mandate that everyone over the age of majority has to get a Power of Attorney document, since most people don’t get a will until they have kids, a spouse, or assets, but a POA should be mandatory for everyone who isn’t a minor.

You are a “finance insider”. If you had to advise your adult child about 5 non intuitive things one should do to become more financially literate, what would you say? Can you please give a story or example for each.

1. Follow personal finance bloggers on social media. Having these people in my Instagram/Twitter feed and reading their posts helped me so much in my early twenties to learn about budgeting, saving, and the basic principles of financial literacy. They’re also a great daily reminder to live within your means. Some of my favourites include MapleMoney, RateHub, and Jessica Moorhouse.

2. Take advantage of apps so you have no excuse to not have your finances in order. Today you can do everything finance-related on your phone — whether it’s buying life insurance, investing, or banking. Find apps that fit your situation, and commit to signing up. I use Wealthsimple for my savings and investing, Mylo for savings, Drop Loyalty for loyalty points, Borrowell to track my credit score, and an everyday banking app — when they’re on your phone, there’s no excuse for not being diligent.

3. Talk to someone who has been the executor of someone’s estate. Estate planning falls to the bottom of the list for most millennials who feel like death is decades away — so to highlight the importance of having an estate plan, find someone who had to execute their relative’s will and close their estate — and ideally find someone whose relative passed away without a will. Ask them about the steps they had to take in both cases, and hopefully it will underscore how much easier the process is when you have a will. This is also helpful to pull together information for your executor outside of just the will — for example I have a Google Drive folder called “When I Die” that includes a ton of info for my executor — what I want done with my social media accounts, final posts for my Twitter/Instagram accounts, a list of all of my subscriptions and banking/insurance accounts, and more — some people might think that’s intense, but I want to make it as easy as possible for my executor once I’m gone.

4. Listen to How I Built This — NPR has an amazing podcast series called How I Built This, and each episode follows the story of a successful entrepreneur and how they grew their business. It’s a great way to hear the stories behind fintech success stories like Betterment, and it inspires you to want to work at a startup, or launch one — which I think is the best experience for new grads, and a great way to become financially literate in business.

5. Stay on top of your credit score. Learn early on what affects it, which agencies are influencing it, and which credit vehicles/accounts are being tracked. Having a good credit score makes such a difference when applying for loans, mortgages, or credit vehicles for a business, and too many people don’t learn early on about how the scores actually work, and what they can do to take ownership over what’s being tracked/updated.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve always been very grateful to Sarah Prevette, the first entrepreneur I worked for in 2008. Prior to joining her company as the 2nd employee, I had never aspired to be an entrepreneur or to work in startups — both my parents worked for big companies, and entrepreneurship wasn’t “cool” when I was growing up in the 90s. I was introduced to Sarah by my mom, who worked with her at the time, and she sold me on leaving my job to join her company — and I’ve never looked back. That job made me fall in love with startups, and it put me on a path to becoming a lifelong entrepreneur. Sarah is now the founder of Future Design School and she’s doing amazing things to help school boards embrace technology and innovation.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favourite quote comes directly from my mom — “positivity is a choice.” I’ve always been a very positive and happy person, and my mom has always been that way as well. She once said to me that she decides to be positive and to have an optimistic outlook — you can wake up in the morning and look at the world as a glass half empty, or you can decide to look at things through a lens of optimism. I’ve always remembered that when I have a low point in our business, or I’m just having a bad day, and it helps me reframe my thinking.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Unsurprisingly, my movement would be a movement to ensure every adult has a will and Power of Attorney documents. We’re about to experience the largest wealth transfer in history between the boomers and the next generation, and over half of adults don’t have a will in place — that’s a recipe for disaster, and it’s going to mean so much effort for the families dealing with it. Another thing we’re trying to inspire is for every person to leave a legacy gift in their will to a charity — it’s sometimes tough to give money to charity when you’re building your wealth, so a legacy gift is a great way to ensure you have a positive impact after you’re gone.

Thank you for all of these great insights!

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