S03|04: Making Estate Planning Accessible and Affordable with Erin Bury

Erin  00:01

It's such a reminder that life is short and that you need to live life in the moment. You can't put it off for retirement. Tomorrow is not guaranteed, and I think that really has shaped how I live my life. I take the trips, I spend time with my kids, I take the risks, because you just have no idea what tomorrow brings. And so Willful makes me, and I think a lot of other people at the company reflect on how precious life is and to live in the moment a little bit more.

Leah  00:28

Hello and welcome to Season 3 of The Founder Mindset, brought to you by ATB. I'm your host, Leah Sarich, and I'm delighted to be back for another season of talking to Founders about what it's really like to build a company from that first big idea. If you've listened to previous episodes, you know, I was a journalist for over 20 years, so I'm more curious about why anyone would ever want to become an entrepreneur, not so much about the business model, product, market fit and so on. I want to understand why entrepreneurs keep going, why they think they're the ones to solve a massive problem, why they want to make a real impact in the world. And if you're here, I bet you want to know why, too. Let's find out. Joining me today is Erin Bury, Co-founder and CEO of Willful, an online estate planning company, giving Canadians peace of mind by helping them get their end-of-life plans in place. Erin, thank you so much for being here.

Erin  01:22

Thanks for having me. Leah, excited to be here.

Leah  01:26

We’re gonna have a lot of fun today, because we're both journalists. How much fun? Is that?

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Erin  01:30

So much fun? And when I meet people, they usually ask—are you an estate lawyer? And they're always surprised to hear I went to journalism school.

Leah  01:38

See, this prepares us for all kinds of things. I get the same questions. When I was a health reporter, they were like, so did you go to med school? Are you a doctor? Are you nurse? Like, no, just journalism school. So yeah, it really gives us a nice foundation, including being the founder of a company. How incredible is this?

Erin  01:53

Well, exactly. I mean, I when I was in journalism school, did not think entrepreneurship was in my future. I don't even think I knew what it was back then. So I love reflecting on that and seeing how I became an accidental entrepreneur, and my career looks very different today than I thought it would back at Carleton J School in 2003.

Leah  02:13

No kidding. Well, let's dig into that a little bit. So what was going on in your life? How did you actually end up becoming an entrepreneur?

Erin  02:21

Well, I really firmly believe, I mean, this podcast is all about the Founder mindset. I believe there are two types of entrepreneurs. There are born entrepreneurs of which I am not one of those, and then there are entrepreneurs who just happen into it, you know, accidentally or on purpose. But, my husband Kevin, is really one of those born entrepreneurs. We met when we were teenagers. We started dating in our 20s, and from the moment I met him, he was one of those people that always had businesses on the go. Was constantly thinking of ideas. I mean, he's still that person. He comes to me with business ideas weekly, and I'm like, Kev, we have a business. It's going, well, let's stick to this one. And I was not that person, right? I mean, growing up in the 90s, entrepreneurship wasn't sexy. It wasn't really talked about. You didn't have these role models like Sarah Blakely at Spanx, who had shown that that was a viable career path. I think the gold standard back then was to go work for a Fortune 500 company and maybe you'll get your own office one day. And that's what I saw with my mom. She was a marketing executive at Nortel, and I just aspired to be like her. So she went to journalism school and then went into marketing. And I said, that's what I'm going to do, too, because it looks really fun to work at this big company with an expense account and all of these business trips. And then it was really through a mutual friend that I met my first startup boss, Sarah Prevett, who's a serial entrepreneur from London, Ontario, she hired me to work at her startup as a second employee, and it was just, I'll keep it short, because I know we don't have seven hours for this podcast, but it was really just through osmosis and exposure that I think you know, working as a tech journalist, working at startups and talking to entrepreneurs all day long, it really rubs off on you, and you start believing that you can solve a problem that you encounter, instead of waiting for someone else to solve it.

Leah  04:09

And that's really what it is, isn't it? Because entrepreneurs are so good at identifying, hey, you know, this doesn't make sense, like something's missing here, we can fix this problem. And then you're right, it kind of gives you that little bit of confidence, like, well, if they can do it, I should they can do it, surely I could do it.

Erin  04:24

Well, exactly, I think, you know, after working at that startup with Sarah, I was on the founding team at BetaKit, so I put that journalism degree to good use, and I spent a couple years just writing about and interviewing entrepreneurs from all over the world, from the brand new Founders all the way up to the Mark Cubans. And I think through reporting on so many of those, not only was it contagious, this excitement and this passion for entrepreneurship, but to your point, it also made me realize a lot of these people don't have business degrees or backgrounds in the space. A lot of them, you know, just happened upon this problem or this opportunity that they wanted to solve, and they're just chipping away at it. And it does kind of make you realize it is a mindset thing, right? This idea of encountering a problem and believing you can solve it, and also having these skill sets that I think are so important for entrepreneurs, from resourcefulness to resilience and perseverance.

Leah  05:22

Yeah, those come up all the time in these conversations. I mean, that's why it's called The Founder Mindset, because it is a unique mindset. It is unique to this kind of work. But what I love about it, particularly talking to Founders all the time, is that there's so much for all of us to learn from Founders about those sort of key characteristics that you just mentioned, you know, that resilience, that ability to problem solve, and sonI think there's, I think entrepreneurs are really interesting and inspiring that way. So speaking of which, let's get over to Willful. So how did you get to Willful? And tell me what inspired you to start this company in the first place?

Erin  05:58

Absolutely. Well, full credit goes to my husband, Kevin, as I mentioned, he's the ideas guy. I think I'm more the operator side of it, not the ideas person. And you know, again, he was always coming home with business ideas. He worked in a cement plant. He had always worked in trades, no business background. And his uncle passed away in 2015 and he did have a will, but he hadn't discussed funeral and burial wishes or any of the other components that families need to talk about and deal with when someone passes away, and he'd been married for 35 years at the time he died, and had never talked about any of this stuff with his wife. And that was the first moment where Kev said to me —why is it so hard for people to talk about this stuff? Even a husband and wife that have been buried for decades couldn't answer that simple question—do you want to be cremated or buried? And so we had to argue about it and stress at a time when we should have been grieving. And inevitably, if you've ever been to a celebration of life or a funeral, it causes you to think about your own end of life plans, and when we went to get our own wills and end of life plans in place as a result of that, we were faced with the same barriers that a lot of people listening probably were, you know, quoted four figures to get these documents in place, with hundreds of dollars of fees in future if we wanted to update them, making appointments during work hours, going to an intimidating lawyer's office, and really just a reticence, I think, to address this and think about it. So that was really the impetus where Kev said—hey, I think this could be a business. I've looked into it. There are companies doing this in the UK and in the US, and in Canada, there's not anyone who's taking the ethos behind Wealthsimple, which is democratizing a really complex, opaque topic, and doing it in a beautiful, user-friendly way, online, and maybe we could do that for estate planning. And we looked at each other, and he's not an engineer or software developer, I'm not an estate lawyer, and yet somehow we thought this was a great idea to do. We found great partners, obviously, but we always say Willful is by consumers, for consumers, we filled the gap, we built the product that we wanted to see, and we're super passionate about the mission behind the company. There's a reason we sell to the average Canadian instead of, for example, software that streamlines and saves time for lawyers, because ultimately, I sleep very well at night knowing that we sell something that I believe really helps people.

Leah  08:27

Oh, how wonderful. Okay, but before we get into the specifics of how Willful works and et cetera, I do want to just dig a little bit into that notion of, yeah, I'm not an estate lawyer and he's not a software developer, and we did it anyway. So why? Why did you guys think that you could do this?

Erin  08:43

Well, Kev used to call me the dream killer because at the time, I was the editor in chief at BetaKit, and he would come home from his trades job, and he would tell me his latest business idea. And I would always be like—this guy did that. It's already out there. And I would constantly be like—no, that won't work. There's seven startups doing that already. So he got to calling me the dream killer, and I certainly tried to kill this one as well, right? Hey, you know, you're not an estate lawyer, so how are you going to tackle the legal content? Well, neither of us are engineers. How are we actually going to build this thing? But I feel like the number one most important thing when launching a business is an absolute unbridled passion for the problem that you're solving. And he and we had that in spades, and so the rest of it, we figured out, right? We found a friend from high school who built the first version of the site. He cold-called state lawyers until one of them finally took our call and agreed to draft our legal content as a partner. And I think it was just, I think a lot of it is naivete, right? If you've never founded a business before, you don't actually know what's involved with it, and that's a good thing, because I think if you did know, it's like doing a home renovation, right? Ask anybody who's done it, would you do it again? The answer is probably going to be no because we found asbestos, and all of it ended up costing more and taking longer, but I'm glad we did it, and that's kind of how I think first time business owners are; you don't know all of the storms that you'll face, all of the uncertainties and challenges, and so it's really easy to be optimistic and very sure of… well, yeah, why not us?

Leah  10:20

I love that. I love that. Okay, so let's go into a little bit of a 101, on Willful. So first of all, how does it work?

Erin  10:26

So Willful is like tax software. We guide you through, telling us about your life situation so we can tailor the experience. And then we help you appoint the key roles in your legal documents, like wills and power of attorney documents, and then we also help you create supporting documents like asset and liability lists and funeral plans. And really, the mission behind the company is that every single Canadian adult has a comprehensive end of life plan, so when they pass away, their family has not only the legal documents, but all of the other details and wishes that makes planning celebrations of life and putting their wishes into action extremely easy and low stress. It's all fully guided online. We work with the state lawyers in each province to draft the legal content and to keep it up to date and improve it over time. And we have a team of human experts that help people get through the process,

Leah  11:21

That's amazing. And you are in all the provinces now, aren't you?

Erin  11:25

We are. We launched in Ontario in 2017 so we're just approaching our eight year anniversary, and we've now launched across Canada, which is awesome, including a fully bilingual platform in Quebec, which, if you're not aware, has a completely different legal system, and so that was a lot of work to get to launch there, but really important to us.

Leah  11:43

That's amazing. Congratulations. Tell me a little bit about the pricing and the structure, how that works.

Erin  11:48

Yeah. So, I mean, estate planning really hasn't changed for 100 years. You know, the process is still the same as it was in 1925 which is, you go to a professional, you pay, typically, an hourly rate or a set fee to create your documents. Your lawyer sits across from you and or notary, depending on your province, asks you a bunch of questions. They fill out the answers in their template. And then, if you ever want to go back and make changes, you're paying an hourly rate, which can obviously add up if you're making lots of changes over time. So on Willful we really wanted to reduce the barrier to entry, the main barrier, which is cost and so on Willful you can get a will for $99 that includes free changes in future. So you can come back and make edits as your life changes. And then if you want a will and power of attorney documents, it's $189 so really trying to make it more accessible to the average Canadian, because, you know, over half of Canadians don't have a will and that number is about 90% of people under 35 so it's clear that we need to do some work to empower people. And you know, it's not just selling wills, so we have an interest in people getting wills, but there's a huge cost impact to our courts and our governments and all of the infrastructure. When people pass away without a will, it means that the courts have to step in to appoint an executor to wrap up your estate. If you have young children and a guardian needs to be appointed, then the family courts have to step in. It's just going to cost more and take longer, both for the family that's left behind, as well as for our government systems. So, you know, making it affordable and lowering the barrier to entry is a really important step in increasing those percentages.

Leah  13:33

Yeah, amazing. So how many employees do you have these days?

Erin  13:37

I think we're at about 23 today. We, you know, it's interesting, when I used to have a tech marketing agency, prior to Willful and I think for reporting on technology companies for so long, there's certain proxies that people use to equate to the success of the company. One of those is the amount of funding raised, which now, in retrospect, I realize, Oh, we're celebrating people giving away pieces of their company. Maybe that's not a success metric. Maybe it's the Bootstrappers who are onto something. And the other one is size of team, right? You meet someone at an event, how big is your team? How many employees you have? And obviously, I've really come to learn that, you know, the goal is to do things in a really lean way, and number of employees doesn't equal greater success, it just means more overhead. And so I also am the type of person where team culture is super important to me. I love knowing the names of my team's pets and what they did last weekend, and I've never seen myself as someone that wants to run a 1000-person company. So I love that. Over the last eight years, we've really stayed small and supported with external vendors when needed. We just did our annual team retreat on Prince Edward Island, and it's so awesome as a fully remote team to spend that time in person, and be together.

Leah  14:54

How wonderful. Sounds great. So then maybe the question is how many Canadians do you think you have helped with these huge, life changing decisions?

Erin  15:05

Great question. So over 300,000 people have used Willful and to create hundreds of thousands of documents, from legal documents to the supporting ones, like asset and liability lists. We're a direct to consumer company, so you can go to our website and buy it off the shelf from us. But we also partner with amazing enterprises who help their audiences get a will. So for example, Amazon Canada offers a free will to every single one of their Canadian employees as a part of their perks package. CIBC and Scotiabank are both amazing partners who distribute Willful to their retail banking clients. And so that's been really helpful for us, because obviously one of the big challenges when you're a young startup is not having a ton of money to get the word out there and build the brand. And so those partnerships have have added a lot of trust, but also helped us reach more Canadians.

Leah  16:00

How wonderful, amazing. Now, you sort of glossed over this, but yeah, maybe the VC dollars raised isn't necessarily the metric, but I'm very curious to know how you think about fundraising and VC dollars and that kind of thing.

Erin  16:13

Having come from running a professional services firm, which most professional services firms are self funded, they're profitable, and they just grow with revenue, reinvest the profits, not all, but certainly mine. And so that was a learning experience I was really looking for from Willful. Could we have bootstrapped it? Probably, you know, we were generating revenue from the moment we launched, but we knew that there was a pretty wide open space in the estate planning space in Canada, and that raising capital would both be an amazing learning opportunity for us as Founders to understand how to navigate that landscape, and then also a way to just accelerate and leapfrog our process and to kind of put a stake in the ground in the market. If you asked me the million dollar question of, would I raise funding in building another company, I think it depends. I mean, again, I think we glorify funding as as an ecosystem, but I would say the investors that we have on board have been extremely supportive, extremely helpful, have opened doors for us. I mean, we have an amazing partnership with Arbor Memorial, the largest Funeral Home chain in Canada, which came from an intro from one of our advisors. So both our investors and advisors have been huge supports and cheerleaders for the company. The only thing that has really that makes me hesitant to do it again is just the amount of time and energy and effort, and also it really depends on the type of business you have, right? The constant feedback that we received from investors was, you know, you're Canada only, no one likes that. They want to see global scope, because they need you to be the next unicorn, and candidate is a smaller market in a global context. We're transactional, right? So  we're a one time purchase. We're not B2B SaaS, which is very sexy to investors, and we're B2C. And so, you know, a lot of VCs and investment firms really love that very specific global B2B, SaaS recurring revenue model. And that's just not us. And so the investors that we do have on our cap table, which is everyone from Michelle Romano, from our Dragons’ Den deal to VC firms like our lead investor, Tactico out of Montreal, to tons of ex-Shopify angels, not tons several. They all really believe in what we're doing and and I think our growth has showed them that it was worth the vote of confidence.

Leah  18:41

Oh, I love that. I love how you're thinking about this. And you know, you talked a little bit about this too, but I want to dig into it a bit more, this notion of the culture and values that you lead with in your company. Can you talk a little bit about that culture and how your values shape it?

Erin  18:56

For sure? I mean, for us, like most other companies, our values used to be posters on a wall when we had an office, and they really included things like accountability, empathy for our customers. Many people are coming to Willful because they've lost a loved one, or they've been diagnosed with an illness, so there's a lot of empathy that goes into thinking about and talking about a difficult subject like this. And so those values guide our interactions with our customers, but they also govern how we operate as a company, and post COVID, we went fully remote, and so that's been really helpful to kind of live and die by our values at Willful so things like accountability, like I don't care when your green slack light is on. I don't really care about your working hours, as long as you coordinate with your team on meetings. We use, the entrepreneur operating system. Everyone knows the company goal, our long term mission, your goals for this quarter, and everyone is accountable to them. And outside of that, be flexible. Pick your kids up from daycare, go for a stroll in the afternoon on a beautiful, sunny day. So I think that's really governs our culture. It's flexibility, autonomy, but in exchange for those things, accountability and empathy for the other folks on our team,

Leah  20:09

I love it. We talk a little bit about, you know, what Willful does, but I just want to take a moment to reflect on that. I mean, this is a company that deals with people in their really darkest, potentially days, you know, days that are really, really challenging and emotional. What's that like for you as an organization? What's it like dealing with people at this time of their lives?

Erin  20:28

Yeah, it's so interesting. Because often creating a will, even though it's about what happens when you pass away, it's motivated and precipitated by a happy event. The number one reason people create a will is the birth of a child. So people are often coming to us for happy reasons. But the opposite is also true, and again, that value of empathy really comes into play. People often ask me at cocktail parties, not that I'm going to many with two kids under four, but let's say at the park, they ask, you know, it's a morbid subject, it must be hard to think about this all day, and I always say—No, it's the exact opposite. Hearing these stories every day about why people are creating wills, about people who have lost loved ones, about family members coming to get details about their loved one who had an account on Willful it's such a reminder that Life is short and that you need to live life in the moment. You can't put it off for retirement. Tomorrow is not guaranteed, and I think that really has shaped how I live my life. I take the trips, I spend time with my kids, I take the risks, because you just have no idea what tomorrow brings. And so Willful makes me and I think a lot of other people at the company reflect on how precious life is and to live in the moment a little bit more. And I've asked many of our employees over the years, like, you're 25 you could go work at some cool e commerce company, you know, Shopify, whatever it is, why Willful, right? And their answer is always the same, which is, I want to do something that actually has an impact. And whether it's, you know, the legacy, gifts to charity that we foster through, through wills, or whether it's just, knowing that every time we sell a product, someone's family is going to have an easier time when they pass away, I think that really resonates with people feeling like there's a purpose that goes beyond just the bottom line.

Leah  22:24

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The one question I do ask every entrepreneur that sits in this chair with me is, there had to have been a moment, though, when you were building, when it was really like a do or die moment, or a really pivotal moment, that go or no go conversation, can you think of one of those when it came to building Willful that you'd like to share?

Erin  23:06

Yeah, there's one that sticks out very prominently, which is, you know, it's always this dance in the early days of I wish I had like a wealthy aunt who could have just written us a large check, but we didn't have our own money to invest at the time in Willful, and we didn't have any rich relatives or cushion and so we raised a small friends and family round of literally $5,000 each check for many people, including my mom, who I think is very happy that Christmas dinners aren't awkward, because Willful is doing well. But you know, we needed to get to the next level. So we got to the phase of launching, but then we needed to invest in actually building out full time team members instead of just this contract developer who had been supporting us. And so we simultaneously to looking for this person and trying to hire, essentially, a CTO. We were also looking for angel investment going out. We were not big enough to look at VC, but we were too big to look at friends and family, and we had already run that well dry. So we started talking to some folks, you know, obviously I had a good network from being a tech journalist for many years, and we started chatting with some folks, and found an ex-Shopify friend who was looking to invest. But it was this delicate dance of trying to woo this first employee, this first technical employee, and putting together a comp package for him, while not actually knowing if we'd be able to pay his salary, because we're over here trying to, woo the investor to write the check. And I remember we got married in October of 2018 and we were on our honeymoon in New Zealand, and I remember Kevin sitting on a FaceTime with this person, who became the first employee of the company, negotiating his comp package, and they kind of shook hands on the deal, and Kevin hung up the phone, and I'm like—we don't even know if we're able to pay his salary, and he's like, Well, I have to, I have to trust it. I can't let him go, and I need to trust and, you know, we got back from our trip, and we did get that check, and no payroll bounced, and everyone was happy, and he ended up being at the company for many, many years. But it was one of those moments where you're like, Okay, this, we're putting the cart before the horse here.

Leah  25:21

Yeah. I mean, how did you guys have the confidence to do that, though/

Erin  25:26

I think that it was me on the FaceTime, i'd be like, let's talk in a month. Actually, our COO Julia, who's amazing. She's on parental leave right now, and she's really my right hand person at Willful. We met in early 2020 and it was or even 2019 and it was one of those things where we immediately had a connection. It was love at first sight, Colleagues Edition, and I was like, I need you to come work with me. She felt the same, but I just didn't have the money, and we were at a point in the business where I wasn't raising funding, and so I couldn't just make that bet. And so we just kept in touch for probably a year. She took another job, and ultimately, when COVID hit, we were,, fortunately or unfortunately, it made everybody contemplate their mortality and rush to get a will in place, because all of a sudden there was a sense of urgency to it. And so we did end up hiring Julia in April. I remember she started on our highest revenue date ever because we had an article in Canadian Press that was syndicated across all of these media outlets. It was really amazing milestone, but it was just one of those… sometimes you pull the trigger and you hire the person before you know if you'll be able to pay them. Sometimes you're more prudent and you wait until the time is right.

Leah  26:39

That is incredible. Well, congratulations on both those hires. They sound amazing. Thank you. The one thing that we also talk about on this podcast is that we all know that being an entrepreneur, it's not your traditional sort of nine to five job. It can be very all consuming at times, and I'm very curious about how that affects your personal life, whether it's your family, your friends and that kind of thing. And of course, I'm not just asking the female entrepreneurs. I'm asking everybody this question, by design, absolutely. But what is it like to build this company alongside, say, building your family?

Erin  27:09

Yeah. I mean, I joke sometimes to Kev that, I wish today, I just wish I worked for the government, right? This idea of like, clock in at this time, clock out. Don't bring your work home with you. Tons of paid leave a pension. But I wouldn't trade entrepreneurship for anything, because I think what you give up in some of the in the ability to disconnect, you make up for in spades in a commitment and a passion to what you're doing. I never have the Sunday scaries. I never wake up dreading going to work. I genuinely love what I do. I love working with the team, and I have autonomy and flexibility, right? I don't have a boss, other than our board. I don't have a boss that's saying—Do this or don't do this. I have flexibility in that everyone knows. I have two kids under four, so, yeah, I am going to pop out at 4:30 for daycare pickup most days, and I'm going to have to log off for, you know, my my daughter starts kindergarten in the fall, and school starts at 9:15. No one's going to care if I log on a bit late. So I think there are trade offs like I only took four months of mat leave with both of our daughters. Would I have taken a year if I worked for the government, maybe. But I'm okay with those trade offs, because, again, it's building this vision that feels really meaningful. It feels like a family business, because my husband and I own it together and and to me, it is also about legacy, right? Life is short? How do I want to spend my weeks? I want to spend my time on doing something meaningful that actually helps people, and I know as an entrepreneur, that means that, yeah, you're going to think about it 24/7 there's going to be sacrifices, but I'm also Leah, listen, I think we came out of the 20 of the early aughts, and this toxic culture of entrepreneurship equals working 24/7, burning yourself out, cutting out friends, fitness, sleep, family in service of this goal. And I just think that's total BS. I spend time with my kids every day. I do not stay up till midnight working. I get eight hours of sleep every single night. I work out every morning, because that is my mental health. It helps me be better and on at work. Are there days where that's not the case Absolutely, or even phases of the business? But I think overall, we've been fed a lot of untruths about the right way to grow a business, and what you have to give up of yourself to do that.

Leah  29:34

Thank you for sharing that, because I think that is really, really important, particularly for younger entrepreneurs who might be even just thinking, is this something I can do? What does this actually look like? You know? And I think it's really important to outline that this romantic idea of this person you know, working away forever, and then all sudden, it's a unicorn. That's not really true either, right? And so, I mean, we have to dispel some of those myths. And that's something I really like to do on this podcast. So thank you for sharing that.

Erin  30:00

Yeah, you hit the nail on the head. This is not a sprint. This is a journey. Kevin first got the inkling for Willful in 2015 the site launched in 201, we're eight years in, and we still are very low on the mountain. And so, you know, you also have to think about lifestyle design, sure, you maybe in the first year when you have no kids, or you're single, or you don't have a lot of family commitments, you can absolutely work that more intense schedule. We certainly did when we were in Founder Fuel the accelerator program in Montreal, or at other phases of the business when we were raising money. But think about 10 years in the future, it's not sustainable for yourself, and your life changes, and you get different priorities. And so yeah, I'm a big proponent and very vocal about a, you can build a family while building a business. And B, if you are working 16 hour days, you are the problem. There's diminishing returns after a certain amount, and if anything, you're probably working on things that are not high impact, and you're not doing a good job of delegating or elevating things to your team.

Leah  31:03

Yeah, or prioritizing, absolutely, I agree with you. But out of curiosity, what do you do to make sure that you stay well and grounded and able to lead in the way you like to?

Erin  31:14

I am a very type-A A organized person. My husband will definitely tell you this. He is a much more of a creative and so I'm pretty anal and regimented about it. I get up every day at five-thirty or six to work out before my children wake up, which I don't want to do, but that's the reality of my life right now. I make sure I get enough sleep. Reading is my favorite hobby, so I need to set aside amazing time for it. And I'm a really social person. I'm an extrovert, so for me, it comes very naturally to me to carve out time for social events and for family. One thing that we've done at Willful that I found game-changing, especially with two young kids, is we do half-day Fridays, so our workday ends at 1pm on Friday, if you message someone at 2pm people might be online finishing things, but it's like messaging someone at six on a Friday evening. People have started their weekend, and I found that to be game-changing. It's only four hours, but that's me time, right? That's when I read my book, I go to the spa, I run errands for the weekend if we're having guests. I really find that to be a game changer, because especially with kids on weekends, there's not a lot of downtime, and I'm definitely one of those—thank God it's Monday—they're back in daycare people right now. But I look to a lot of other Founders, like the Three Ships Founders. I find they're also very inspirational on Instagram about prioritizing and balancing self care with building a business. Because, you know, I read something about Bill Gates going to a cabin in the woods once a year for a week with no internet access, just to think, and that sounds like, as an extrovert, that sounds terrible to me. I don't want to do that. But what I took away from it is, especially as your business grows and you're getting out of the weeds and you're working on your business instead of in your business. There should be space. There should be space for reflection, for thinking and showing up as a frazzled, you know, tired person that's not at your best is not helping the business. It's not helping you, it's not helping your family. So what feels like self indulgence, sleeping well, working out, eating healthy, or maybe having that glass of wine and pizza on Friday. These are the things that actually keep me at my best when I'm working.  

Leah  33:32

I love that. I love it. So we've talked about some of the things that can be challenging when it comes to being an entrepreneur, but I would also love to know, what do you absolutely love about being an entrepreneur and working in this space?

Erin  33:45

Well, when I moved on from my agency, Kev had started the foundations of Willful while I was still working running that agency, and when I moved on, I remember saying to him, I don't know what I want to do next, but I wrote down all of the things that I love most. You know that I've really loved from past roles, whether that was building BetaKid or working with that entrepreneur, Sarah at her company, or running an agency. And that list included building consumer brands, brands that actually touch people instead of B2B, culture, team culture and kind of building and mentoring teams and setting the vibe for how they operate, building a brand from the ground up, taking nothing and turning it into something where now I go to the park and people say, oh, yeah, Willful, of courseI know Willful. That, you know was really, I was really passionate about, and I remember him looking at me and being like, you know that you just described joining Willful as CEO, right? And I'm like, no, no, no, I don't want to work with my husband. Are you nuts? We just got married six months… a few months ago, I'm not coming to work with you, but that's exactly what happened, right? It was this idea of, whenever I meet someone who's struggling with that next move in their career, my advice is never write down the company you want to work for. It's make two lists. What do you not like? So we can process of elimination, the things that you shouldn't do, and what do you absolutely love, not the role, but the things in the role, the things that bring you joy and light you up. And then how can you find something that is the closest fit to that list? For me, that was joining Willful and strangely enough, it has, you know, as much as I think working with your spouse can divide you, I think, if anything, it's just brought us so much closer together, to have this shared purpose, this vision, and now with two kids, it feels like we're building this legacy, right? We're not just building a business. We're building a legacy.

Leah  35:39

That’s amazing. But what is it like to work with your husband? Like, let's just not gloss over that.

Erin  35:44

Oh, my goodness. Leah, I'm sure there's a podcast where I could be a version of this, where I could be like, it's amazing. We love it. In reality, as I mentioned earlier, we are two very different people who work very differently. So I'm extremely Type A very anal, organized to do list, methodical, just like Julia, our COO, we work together. Total dream, absolutely, very similar styles. Kev is so important, the role he plays in the business, but he's so different. He's the up in the clouds, the dreamer, the what if we did this, and he is not the Type A to do list like, I'm gonna be super methodical, and so I think at first we butted heads because our styles were so different. I would give him a list of things to do and then be annoyed when he hadn't methodically checked them off. He would be annoyed that he would come to me and say—What if we've sold urns on our website? I'm like, stop. Like we're no, we're doing this thing right here. And I think over time, we've come to appreciate that for us, working together means not working directly with each other on projects, and we don't have to, right? I can be over here doing these things, you can be over here working on those projects. We really love being involved at a strategic planning level together and doing the heavy thinking around the business. But Julia and I are much better colleagues than Kevin and I, and it now works great because we know that.

Leah  37:05

Oh, that's amazing. I love it. You also like working with startups as an advisor. You do a lot of this work, don't you?

Erin  37:11

Yeah, which is funny, because you always feel a bit of imposter syndrome when someone says, like, hey, you know stuff. Can you come advise us? I'm like, What are you talking about? I don't know what I'm doing, but specifically the one that I've really loved advising over the last year has been Ownright, which was previously called Doormat, and they're essentially Willful for real estate closing. So taking that experience of working with a real estate lawyer, going in, in person, signing paperwork, and actually streamlining that into a beautiful online process, which we used when we when we bought a house recently. So it's a beautiful experience, and it's been so… I think again, especially women, there's a lot of imposter syndrome. Why me? Why am I the person running this company? Someone else could do this better. And actually, it's been so wonderful, because you realize how much you've learned in eight years, because all of the things that Ownright is going through in year two or year three are all of the same things that we went through at that time and I now have the hindsight to say—oh yeah, that happens all the time. Here's what we would do, or here's our policy around that, or some resources I can share. And so it's helping them, but it's also helping me just to reflect on like, we have come a long way, even though we still have a long way to go.

Leah  38:27

Oh that's incredible. I love that, that sharing of knowledge is really special. It really does remind you… oh, I have created significant value here, and I actually have, as you said, so much to share. I love this.

Erin  38:40

They're starting a company years later than we did, and so I also love seeing what tools they're using, and I definitely, absolutely get reciprocal value in learning from them as well, which I think is a beautiful symbiotic relationship.

Leah  38:54

Absolutely, do I have this correct that you also have done nonprofit work, quite a bit of it?

Erin  39:00

Yes, I am very passionate about impact, both with the company…, we've committed 1% of Willful to through the Upside Foundation to Sick Kids Hospital, and obviously we're very big proponents of legacy giving to charity and wills. On the personal side, again, speaking of imposter syndrome, I remember the former CEO of CBC, or an executive there Bill chambers. He was the CEO of Save the Children Canada at the time, and he asked me out for coffee. And I thought it was just going to be to pick my brain on digital marketing, because I was running a marketing agency at that time, and when he asked me to join their board, I looked around in the coffee shop like, what me, why would you want me on your board? That time, I was like 35 I had never been on a board before. I didn't even know what that meant. And I'm so glad I said yes, because obviously I'm very passionate about anything to do, especially now as a parent with children's welfare around the world and Save does amazing work on children's rights globally. But also because I think it did again, this idea of—Just say yes and you can learn. And the board has been so wonderful in educating me, and now six years later, I am the one who's bringing on new board members and mentoring them, but it's been really fulfilling. And then I also live in Prince Edward County, Ontario, and I'm a huge reader. We already talked about that. It's my number one favorite hobby. I love reading, and I love reading to our kids, whether chat, GPT drafted stories or actual books. And so I work with a local literacy charity here called County Kids Read that's all about getting books in homes, because that's one of the top signals for literacy rates and a love of reading.

Leah  40:36

Well, clearly I love that. I have a tendency to do volunteer with an organization here called Calgary Reads… same kind of idea, yeah, and Word Fest as well. So I have a feeling we could talk about that for a very long time.

Erin  40:49

We'll start a book podcast next year. We don't have enough on our plate, right? Leah,

Leah  40:53

Okay, I'm serious, let's do it. But this does tie in nicely to this notion of impact, whether it's your nonprofit work, whether it's the work you're doing at Willful or other things that sort of fill up your own tank. How do you think about impact? You can answer this personally or even with Willful or both.

Erin  41:11

I have a really simple definition of it, which is leaving the world a better place than you found it, and that can be as simple as paying for someone's Tim Hortons order behind you and brightening their day. And as meaningful as hopefully having some sort of event at Willful that means that, personally and through the company, we can influence causes we care about by writing big checks, I think it covers the gamut. For me, impact is also the example I set for our daughters. You know, I grew up in a house where there was a really strong working mom who taught me a lot about ambition and hard work and dedication, and I want to model that for our girls to hopefully pass that down the line in our family. So to me, impact is not just money. It's how you make people feel. It's how you spend your time. It's the qualities like I try to be a very kind person and generous and helpful, whether that's to a new Founder that asks for advice or whether that's to a stranger at the park. I'm sure I'm not always perfect at it, but yeah, that's it's definitely one of my core values is just, how do I have impact on my community, on my loved ones and on the wider ecosystem.

Leah  42:22

Love it. Love it. All right? Well, as we move towards the end of this conversation, I ask the same two questions every time you are the Co-founder of this company, you're writing the story for Willful. How do you hope that story goes? I

Erin  42:35

I mean, from day one, our mission has always been every Canadian has a will and a solid estate plan. And so if I could write the story, and we're not talking about feasibility here, the story would go that the government starts mandating that every Canadian has to create a will when they turn 18, and that Willful is the provider that they choose to fulfill that.

Leah 42:58

Oh, I love this. I love this.

Erin  43:00

Why not when you get your driver's license? Why not sign you up for a will as well?

Leah  43:04

Why not, right? Just another check the box situation. I love. As the Co-founder, how do you hope your own personal story goes? I mean, we're called The Founder Mindset, so how do you hope your own story as a Founder goes,

Erin  43:16

Yeah, it's such a great question. I mean, pre-COVID, if you had told me that I'd be living in a town of 1600 people versus downtown Toronto raising two kids and happy as a clam, I don't think I would have believed you, but having kids has really shifted my priorities. I want to be at home more. I want to be out at tech events less. And so for me, true success in the future means my girls are happy, our family is happy, I have a lot of flexibility, autonomy and choice, right? I love the book The Psychology of Money, and in that book, they define true wealth as waking up in the morning and being able to do what you want to do with the people with whom you choose. And that's my goal. My goal is not have a yacht. My goal is wake up in the morning and define my day on my terms.

Leah 44:06

I love it. Erin, thank you for this conversation.

Erin 44:08

Thank you so much, Leah for having me.

Leah  44:19

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Leah  44:45

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