This time, we’re speaking with Erin Bury, CEO of Willful, an online platform that makes it affordable, convenient, and easy for Canadians to create a legal will online.
Erin is a journalism grad who has spent over a decade working in startups. She’s spent time as a startup marketer, tech journalist, and head of a creative agency that worked with startups & consumer tech brands like Lyft and Rover.com.
Can you tell us more a bit more about Willful?
The idea came to my husband and co-founder, Kevin, after the experience of a family member passing away suddenly. Although this person had a will, they had never discussed end-of-life planning with their wife or family. The family found themselves debating over details like what type of funeral he would have—would it be a burial or a cremation?
Through all of this, Kevin began to wonder—how has something that’s so certain, like death, not been touched by technology at all? He started looking into it and found that the majority of Canadians don’t actually have a will.
The product originally started as something called Final Blueprint, an online account that stored everything outside of your will and acted as a tool for your executor or family member to wrap up your life when you passed away. However, after launching it and hearing crickets, we realized that nobody really likes to think about death. We decided to make the Will itself an entry point because it’s something that everyone needs. We reworked the product as Willful and launched in October of 2017. We’ve been on the market for just under two years and in that time we’ve created over 7500 documents for customers across Canada. We’re active in five provinces, and we’re hoping to be live across the rest of Canada by the end of the year.
This role seems to be a step away from your previous experience. How did you make that leap?
When Kevin had the idea for Willful, I was running a marketing agency called Eighty-Eight. Prior to that, my background was in marketing and communications and working as a technology journalist on the founding team at BetaKit. When Kevin told me his idea, I wasn’t ready to dive in yet. I was an investor in the friends and family round and an advisor to the company and Kevin actually worked with my agency on all of the original branding and website design so I was definitely involved from the beginning, but from the sidelines.
It was never my intention to join Willful full-time but after six years at the agency, I was looking for the next challenge and wanted to get back to working on the product side. Around that time, we found out that that Willful been accepted to FounderFuel, a Montreal-based venture accelerator. I also realized that if I went to work for another start-up, Kevin would probably kill me because he needed some help getting Willful to the next level and he really wanted me to join. When the FounderFuel opportunity came through it seemed like the perfect time so I officially joined the team in March and have been going ever since.
Can you talk a bit about how different this is from your past work experience?
My passion has always been, number one—marketing and communications and building a brand, and number two—operations and running a business. Running my agency was really the first time I had a chance to manage my own P&L and get my hands dirty on all things operations while also being a subject matter expert and leveraging my online marketing side.
The biggest difference between the agency and Willful is not necessarily the focus of my role. I’m still working on the operations side while also building the Willful brand, but I would say the nature of the product vs. service business is where I see the main difference.
Selling marketing and graphic design services to companies is so different from selling a Will to an individual consumer. It’s a very different experience working with 10 clients vs. 5000 customers, invoicing clients directly vs. using Stripe for payment processing, and selling in one market vs. selling in multiple provinces with different tax brackets.
I think the biggest difference is the B2B versus B2C focus and how that’s affected what we need in terms of operations. From a marketing standpoint, it completely changes how we position the company, who we’re targeting, and the channels that we’re using. These days, while my job functions are very similar, the way I execute them is completely different.
Did you find it challenging to change your mindset from the service-based agency model to the product-based model?
To be honest, it was really refreshing. Every company is a rollercoaster, but I feel like when you run a product business there are more things in your control. For example, I don’t have to worry about a client firing us or saying that they’re going with a different agency. It’s been a nice change to not have to track my time and worry about billable hours and to not have to worry about clients paying late, which was the bane of my existence and something that we always tried to improve.
Every company is a rollercoaster, but I feel like when you run a product business there are more things in your control.
One of the biggest challenges I faced at the agency was pricing our services—how to price them accurately, but fairly, so that we would be compensated fairly for our work but not be overpriced compared to our competitors. In the product space, it’s pretty simple. We have three pricing tiers and we can look at our competitors to see where we stand. It’s very transparent, whereas, in the world of agency and services, I think it’s very opaque.
Are you finding the pace different?
When I was a journalist, I was always waiting for news to happen and my life and schedule were dictated by that. In the agency business, you’re always on the client’s time. If a client calls you and says, “I have an emergency, can you help?”, nine times out of 10, you’re going to say yes. It felt like you could never truly relax because you’re always waiting for a client emergency or for more work to fall into your lap or for something to go wrong.
When I moved to the product side, what I really wanted was flexibility. That doesn’t mean working less, it just means the ability to work on my own time. For example, today, I felt tired from travelling to Toronto (from Montreal) and slept in until 9 am. And that’s not something you would ever be able to do if you’re working in an office with a team who expects you to be there at 8:30 am every day. There are definitely fears that keep me awake at night, like what if we have a bug that I don’t know about? But I think the worries are different, they’re less external and more internal.
What are the main pressures you feel now in comparison to working in an agency?
The unique thing about service businesses is that they often scale based on the need and demand of clients. Most agencies follow the same pattern, where an individual subject matter expert starts consulting and then finds that they have more work than they can deal with. They hire 2-3 more people and all of a sudden, they find that they have this boutique agency that they’re running and they have to learn how to manage that.
Most agencies don’t take venture funding or external funding, they just grow slowly as client demand comes in. That can result in disaster because there have been lots of agencies who have one client that makes up 80% of their revenue, and then that client leaves and they’re screwed. But in most cases, there’s not as much pressure to raise funding or to grow and scale as quickly as there is on the product side.
On the services side, all you need to care about is whether your clients are happy because if you have happy clients, they’re going to tell other people and you’re likely going to be able to grow based on word-of-mouth. On the product side, you’re always building a narrative about your company and the trajectory it’s on so that you can sell that story to investors. That includes things like sales, your team, and public perception. I feel like the biggest challenge is always making sure you are building a narrative of upward trajectory, while also ensuring you’re actually meeting that narrative from a numbers perspective, because honestly, a great story can get you in the door, but it’s not going to get you through due diligence.
Your business partner is also your husband. Can you tell us a bit about the dynamics of that relationship?
I think we understood the dynamic of how it would run going into it. When I joined as the CEO, Kevin moved into running business development and partnerships and all of our legal partnerships. What was helpful was that we understood each of our strengths and values. He’s got this amazing legal subject matter expertise that I don’t have and works very closely with all of the lawyers. He also understands and respects my experience with finance and operations and all of the things that he struggled with when he was running the company on his own. We’ve found a good balance.
When you tell people you’ve started a company with your husband, they react by saying either “Oh, my God, I could never do that, we’d probably kill each other,” or “Wow, that sounds so cool! I could definitely work with my spouse,”. There’s no middle ground! More often than not, it’s “I would kill them.” We only got married last October so we’re newlyweds who are also working together.
It’s always challenging working and living with your partner because there’s no divide between work and personal life. One of the good things is that I never have to explain why I’m working late but the flipside is you don’t have anyone who’ll stop you from working late.
The advice we heard time and again when we started working together was to make sure you set aside time for yourselves. I think that’s probably been the hardest thing for us, especially because we’re living in Montreal and participating in FounderFuel. We’ve been on 24/7 for the past four months. That’s why we’ve booked a trip to Scotland at the end of summer, just having a bit of time where we’re not co-founders, we’re just husband and wife.
What are some of the lessons you’ve learned as an entrepreneur?
One of the lessons I’ve learned from Kevin is that resourcefulness is more important than experience. Kevin’s background is in trades and project management, he was not a business guy and didn’t have any background in legal or tech. When he told me he wanted to start this business, I said, “I believe in this idea, I think it’s a great opportunity, but are you sure that you are the right person to do this?” And he said, “Yeah, I know, it’s going to be hard but I have this vision, and I want to do it.” I really respect that he has successfully gotten to a place where the business is doing well. It definitely was hard for him along the way but I think it forced him to be really resourceful. When he had $5,000 to get a prototype built it forced him to find someone who could build it for that price. When he didn’t have a co-founder, it forced him to learn the skills he needed to be an owner-operator.
Resourcefulness is more important than experience.
I think resourcefulness is one of the things I look for most in team members—the ability to not know the answer to everything but to be able to figure things out. I think resourcefulness is an essential skill for an entrepreneur because you’re innately never going to have all of the skills that you need—no one’s an expert at marketing, engineering, operations, finance etc. You have to be able to outsource and offload the rest.
The other big lesson I’ve learned is the value of a personal brand—the idea of faking it until you’ve made it. I’ve always been really adamant with Willful that it doesn’t matter what happens behind the scenes, it doesn’t matter if you have a mental breakdown one day, and the next day you have zero dollars in sales, and then the next day, a lawyer says “No, I don’t want to work with you,” you have to paint a different story publicly. I see this every day. When I’m out at events, people always say, “Oh, my God, you guys are killing it,” when in reality, they have no idea if we’re successful or not, they’re just reacting to the story we have put forth. The importance of personal and company brands and the story you tell is something I’ve seen work in practice over and over again.
What are some of the pressing challenges your business is facing at the moment?
Finance is always a huge pain point for a start-up because you’re trying to not only manage the day to day tasks like bookkeeping, expense reporting, and all the baseline stuff, you’re also trying to take care of the larger picture like tax planning, grants, forecasting, and budgeting. We outsource to an accounting firm for our day-to-day bookkeeping and expensing and things like that and we leverage a fractional CFO for things like forecasting and modelling. But those two people don’t necessarily talk to each other. Right now, we probably have all the individual pieces, but I’m not sure that we’re doing a great job of actually connecting those dots so that we have the full picture of not only what today looks like but what that’s going to look like a year from now.
At the agency, it was really easy to say, “This is exactly what we’re going to spend this year. And unless we get a massive client, this probably isn’t going to change very much.” In a start-up, it can change on a dime based on a new partnership or deciding to go in a different direction with the product. So I found that’s kind of the biggest challenge on the financial side. Outsourcing to third parties has been really helpful, but I think we need to do a better job of actually connecting those dots.
The other big pain point for us is HR because, like most early-stage start-ups, we don’t have an HR person. At the agency, we outsourced to a fractional HR person who worked with us for a certain number of hours a month—she helped us with things like hiring and performance improvement plans and things like that. We’ll probably go down that route with Willful at some point. Right now we use tools like Collage to manage things like onboarding and offloading and time off.
Another big pain point for us would be putting more of a structure around things like the experience of joining the team, understanding our mission/vision/values and how we communicate those to potential applicants. Investing the time to make sure that we have a baseline HR strategy and process and to document what we need to do to make that process work as we scale is something I think about a lot.
If you could choose to remove one task or responsibility from your day-to-day, what would it be?
At Eighty-Eight, it was definitely Accounts Receivable but now, I don’t know. To be honest, there’s nothing that I absolutely hate about my day-to-day. I could say the mundane things like answering live chats from customers but those are the times that I get to speak with our customers directly and it gives me the most value in terms of understanding the gaps in our current product. I could say something like managing our budget, but I think you should learn more about areas that you suck at as a founder because that’s the only way you’re ever going to get a handle on it. So the only thing I would remove from my day-to-day would be anything related to letting someone go or having performance improvement conversations. I’m really bad at having difficult conversations and it always gives me such anxiety to have those types of conversations with people. Thankfully, I haven’t had to have many of those at Willful.
What’s the best part about being an entrepreneur?
I think the best part of being an entrepreneur is owning your own destiny. There are so many things that aren’t great about being an entrepreneur—there’s a lot of stress, a lot of rollercoaster emotions, and a lot of uncertainty and many people shy away from those things. But the great thing about being an entrepreneur is that you never have to answer to anyone but yourself. You really own your own schedule and autonomous in that respect.
The best part of being an entrepreneur is owning your own destiny.
A lot of entrepreneurs might argue there’s less flexibility because you’re on 24/7, instead of going into an office at 9 and leaving at 5 and being off the clock. But I would argue that as an entrepreneur, you have a ton of flexibility to take the team to see a movie at noon or give people a Friday off to work from the cottage or to work remotely. Maybe things change when your company grows and you get to 100 people, but in the early days, there’s a lot of flexibility to structure the company the way that you want.
Also, when you’re an entrepreneur, you’re passionate about the vision that you’re building so there’s a lot of fulfilment and satisfaction in building a product that people use. I was listening to Tobias Lütke from Shopify, on the How I Built This podcast yesterday and he was talking about when he started his own snowboarding store, which was the precursor to Shopify. When he got his first sale from someone he didn’t know it was the best moment of his life. Your first sale is an amazing moment and it’s something you can’t replicate. Now he’s devoted his life to helping other people have that moment and that, to me, is so much more powerful than saying, “I help people sell stuff on the internet”.
The vision and the reason why we’re doing it is something I always go back to with Willful. The stress that Kevin’s family went through at the most difficult time in their life, we know that we’re helping people avoid that kind of stress every day. To us it’s not about selling wills on the internet, it’s about giving Canadians peace of mind. The best part about being an entrepreneur is that you’re so connected to that vision and you can see it changing people’s lives every day.
Are there any books or tools that have been helpful to you on your journey?
One of my favourite business books is The Power of Habit by Charles Duhigg. It teaches you the importance of habit formation both in business and personal life. It gets into the psychology of why we sometimes shy away from building good habits.
A recent book that really impacted how I view Willful’s longterm growth is Lost and Founder by Rand Fishkin, founder of the SEO tool Moz. It’s a really honest memoir about his journey raising capital, how that negatively affected the trajectory of his company and led him to turn down a $35 million acquisition offer by HubSpot. It talks about the motivations of VCs vs. entrepreneurs and what building a VC-backed company looks like. When I joined Willful, it really helped to frame an answer to the question that we get all the time, which is whether we’re going to raise VC funding. It made me think a lot about the lifestyle that we want to have, the type of trajectory that we want to put ourselves on and how that will be different if we take venture capital funding. I definitely recommend any entrepreneur read it.
The third book I’d recommend is Built to Sell by John Warrillow. This one was especially helpful in the context of a service business. It’s all about building a business with an exit in mind because most entrepreneurs are gunning for an exit or an IPO. Not all, but most. It goes into detail on how to create all of the things we’ve been talking about today—process and infrastructure and repeatable things that make it easy to showcase the value of your business to potential buyers and to make it easy to hand over.
In terms of tools, I’m a very type-A, organized person so I use Todoist which is a to-do list app. It’s the most effective to-do list app I’ve found and I use it for both personal and professional use. We use Slack for team communication and we use Trello for project management. I also use Pocket a lot because getting distracted by content is one of my biggest challenges and it allows me to save articles for later on. I’m kind of known as the “death girl” now and everyone sends me a million articles about planning death. I save all of those on Pocket and read them at later so I don’t get distracted.
*****
Learn more about Willful on their website — www.willful.co
Follow Erin on Twitter @erinbury and LinkedIn: https://www.linkedin.com/in/erinbury/
Her personal website is erinbury.com/
Connect with BeachHead
At BeachHead, we are passionate about helping businesses scale up from a strong Operations foundation. The BeachHead Organization Audit (BOA) helps founders evaluate their business through an objective lens. Our BOA scorecard allows us to evaluate all aspects of a growing business so we can recommend changes based on what the organization wants to accomplish in the next phase of growth.
If you’re ready to take your company to the next level, reach out and let’s start a conversation.
Email: rdrynan@beachheadstrategic.com
Phone: 416.888-4004
For more posts and insights, follow us on Twitter and Medium and connect with us on LinkedIn