“Having an Executive Mindset” with Erin Bury, Co-Founder & CEO of Willful

On this episode of Journey Map, we’re speaking with Erin Bury, Co-Founder and CEO of Willful. We talk with Erin about the important influence of a mentor on her career, aspiring to help other entrepreneurs, and poutine.

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Transcript:

Welcome to Journey Map, the audio experience that deconstructs the career paths taken by some of the world’s most interesting people. Today’s guest graduated from Carleton University with a Bachelor’s in Journalism and a Minor in History. She started out her career as an Account Coordinator for Environics Communications, then moved on to become a technology writer for BlogTO. From there she went on to become Director of Content and Communication for Sprouter, until 2012 when she became Managing Editor at BetaKit — one of Canada’s leading tech publications. Then in 2013 she moved on to be Managing Director of Eighty Eight, a Toronto based communications agency focused on growing startups, technology firms, and large brands looking to reach those audiences. After 5 great years at Eighty Eight, in 2019 she left to become the new CEO of Willful. For those of you that don’t know, Willful is an online platform that makes it affordable, convenient, and easy for Canadians to create a legal will online. She’s also an advisor to startups Pawzy, Pressed News, Quill and a board member for Save the children Canada. She is a force in Canadian tech, and is a trailblazer in lawtech, specifically. Today’s guest is Erin Bury. Erin, welcome and thank you for taking the time to join us on Journey Map!

EB: Well thank you so much for having me. I am very excited to be here and thank you for that kind intro.

DH: I had a different version that was much less kind and I felt you know will save her from that embarrassment today. I’m kidding (laughter).

EB: Okay perfect.

DH: So here’s what I want to start off with. In 2012I think the first time we met each other we both won Marketing Magazines Thirty Under Thirty in the same year and when I went back and looked at the write up they did on you. I still have of course because I’m super egotistical,I still have a copy of that issue. I went back and read the bio that’s there on you and Sarah Prevette who some people know, or who lots of people know as the founder of Sprouter and BetaKit both places that you worked. She said that you are indispensable and that losing you would be like having a limb missing and then she goes on to say in the article that she would be disappointed if Erin didn’t go out and start her own company at some point. so I’m assuming she’s quite proud of you, do you still stay in touch with Sarah?

WB: Well Dave that is a great question because she is really who I consider to be not only my mentor in my career but also the person who put me on an entrepreneurial path. I certainly never aspired to be an entrepreneur. I went to journalism school with the full intention of getting a corner office job at a big company. My mom is the marketing director so I really aspired to follow in her footsteps, and going to work for Sarah really introduced me to the completely different path or journey of entrepreneurship and small business. So to answer your question yes we still keep in touch, I text with her often, she has been a mentor to me while I was working for her and beyond. At the time that I moved on to run the agency I think she was a little disappointed that I didn’t start my own company instead, but I think it’s all in good time. To me you know it’s like when people ask “Oh you’re a journalism grad are you write a book?”I say like writing a book or starting a company you don’t just do it because you can, you do it because you have a plot or an idea that you could literally can’t sleep because you’re thinking about it so much. Now that I launched my own company of wine tours in Prince Edward County and joined my husband at Willful I can proudly say that I have gone on to become an entrepreneur and that is all due to her. I hope she’s proud but you probably have to ask her yourself she may actually say absolutely not. (laughter)

DH: I should have actually reached out to her in advance to get an updated quote but C’est la vie. So while you’re at Sprouter and when I said in the intro that it was kind of the first time I heard of you I think myself at the time as well as lots of people in our community kind of thought that you were running the show at Sprouter. Obviously not not to try to take anything away from Sarah, but you did become basically the public face of the brand so what was that like? Was that intentional or did it just happen? Did you feel that way at the time? How did that all come together?

EB: Yeah I think that’s a great question because to your point I think a lot of people thought that because I was the public face of Sprouter they just assumed that I was like the founder or that I was the chief executive, which was a very nice assumption for them to make. I think it was very intentional on Sarah’s part, Sarah is more of an introvert and she was really all about sitting in the office working long hours and doing things behind the scenes. She really didn’t love going out to events and putting on a show and you know being that outgoing person for the brand. The reason she hired me she always said was so that I could do that job, she didn’t want to be the one that was out in the community all the time. Obviously she would go to events and build her network when it was relevant, but she wanted to hire me with the knowledge that I would be the person out there, that I would be the face of the brand. I think she was really happy that I stepped into that role and embraced it, and it worked really well for the both of us, for me it was an excellent way to meet people, to grow my network very early on in my career, to get experience with things like media interviews, and writing for publications, and speaking at events. For her it was the way where she knew she had someone out there building her brand day in and day out, but she could really sit behind the scenes and focus on the things that really matter to the growth of the business. I think it worked out for both of us. Now that I am thirty four and I’m running this business I absolutely see where she was coming from. Not just as you get older but also as your priorities change when you’re CEO of a company you don’t always have time to be going out to events and to be the public face of the brand the brand, nor do you have the energy to at the end of a really long week of investor meetings and things like that. So I completely now understand where she’s coming from in respect to that decision that she made and now I’m the one at Willful to say Hey who on the marketing team or who on this team wants to attend this event because I do not want to.

DH: There’s far too much Netflix and pizza to be consumed in this world today to waste our time going to events.

EB: I completely agree.

DH: For those who don’t follow Erin online I just gave you a snapshot into one third of her content which I totally appreciate so that’s awesome. One thing I didn’t touch on actually in your intro or in your bio is that you’re also an accomplished speaker as well, with speakers.ca representing you. So my next question is really if you were to dive back into childhood, adolescence, or early adulthood. Were you doing things that would later set you up for that success to being the public face of the brand, or being a professional speaker? Were you a drama kid? What was the background there that led you into feeling comfortable in that arena?

EB: That’s a great question. I mean I look at all of the exceptionally talented young folks who are graduating from university today and they have so many extracurriculars and volunteer activity and I was not that person. I got excellent marks in high school but by the time I got to university I knew I didn’t want to do a Masters or PhD, and I spent a lot of time watching DVDs of CSI, eating poutine, and going out to very fun bars in Ottawa while maintaining good grades. s I was not the person that was in drama club or doing those things outside of school that set me up for a career in speaking. I would say that you know Jerry Seinfeld has a famous joke that people’s number one fear in life is public speaking, and our number two fear is death so if you’re at a funeral you’d rather be in the casket than giving the eulogy. I think I am firmly in the camp that is not terrified to get up in front of a crowd and my natural outgoing personality I think is the thing that helps me the most with feeling confident, being a public speaker, and being on stage in front of hundreds of people. That being said I still get super nervous when I’m doing it, not that I’m an infallible person who never gets the nerves but I think what I learned from working with Speaker Labs this amazing speaker training company in Toronto is that your nerves come from lack of preparation. So I’ve been intentional in recent years with my speaking to really focus on delivering the same three presentations tweaked for different audiences but really getting confident in that content and in delivering that content. To me speaking has always been a really nice way to supplement my income and a way to build up the brand for myself and for the company, but it’s not my core revenue driver it’s not my passion. I think it’s also helpful for me to know that no speaking engagement is live or die for me and it just kind of nice to have, and I certainly did not spend my teenage years in theater production in preparing myself for that moment.

DH: You recently publicly announced in January of last year, so a year now January 2019 that you would be joining the startup founded by your husband and that you’d also be joining it as CEO. What does the behind the scenes on that decision look like? you can take that question wherever you want to go. I guess where I am trying to lead is I’m assuming it’s a super strong relationship but also some super difficult and intense conversations lend to it or maybe not. What did that whole decision process look like?

EB: Yeah it’s a great question. Just to give them some context my husband had started Willful in late 2017 and I had always been involved with it from the beginning, obviously when you live with someone you essentially become a part of their start up even if you don’t want to. But I was invested in the company, I was actually an adviser from the start and my agency did all of the initial branding, naming, and launch marketing for it, so it felt like I was a part of the team from the beginning. In late 2018 we had just gotten married and I was looking to do something new, the agency had gotten to a place where you know I was looking for a new challenge. It had never actually occurred to me to join Willful just because I thought this wasn’t the direction I wanted to take my career in. I figured I’d either start my own thing or take a bit of time off and really figure out what I wanted. I had that typical millennial existential crisis trying to figure out what I was actually passionate about, and what I wanted to do next. That was the mindset I was in when I moved on from the agency early last year. But then we end up getting into Founder Fuel, a startup accelerator in Montreal and they really like for people to have co-founders as part of the program. When I started actually looking through the criteria of what I was looking to do next I realized at the end of checking those things off like autonomy, the ability to make my own decisions, the ability to grow a brand that I cared about, a strong mission all of those things Willful checked those boxes. So it was kind of a conversation where I said look I’d love to join, now that I’ve had time to breath and take a little bit of time off now that we have a really great opportunity in front of us to go and scale the business. I’d love to join but because I have a really strong history of operational experience I think I would only be comfortable joining as CEO because that’s where my talents would best be used and I think it would be the best thing for the company. My husband said “You know I completely agree with you I’ve gotten into it as far as I can go I’m not the best person to be in that operational role” and so he very kindly said absolutely come and run the company, I’ll move into this other role focusing on f,y,and z. It really wasn’t that tough of a conversation in terms of logistics it was more getting me to the place where I knew that was the right choice for me. Now looking back a year later it seemed so obvious because I’ve never been happier and it’s just such an exciting journey. I’m sure we’ve all been through the existential moments in our life when we’re like what the hell are we gonna do with our lives, mine just took a little bit longer to get there.

DH: So, I’ll touch on my own journey a little bit which semi mirrors yours to a degree and then I’ll ask you the question I want to ask. So for me there was a definitive moment where I stopped thinking of myself as a marketer and started thinking of myself as an executive. Not even as an entrepreneur or something, like an entrepreneur I often talk with there’s like ‘big E’ and ‘little e’ entrepreneurship and not to be confused with entrepreneurs versus intrapreneurship. The idea of there’s some people who are like ‘big E’ entrepreneurs where the idea of being an entrepreneur is the most important part and the actual realizing that all that that means is that you know how independently run an organization, and so I’ve since started referring to myself as a ‘small e’ entrepreneur and a ‘big E’ executive. It’s because our company isn’t a startup anymore and I think it’s more important for my own headspace to be an executive not an entrepreneur. I know when the moment was that I stopped thinking of myself as this when I went to school for what I was super passionate about and what I wanted my career to be into embracing what I had become I suppose. So for you I see this very clearly, let’s start in journalism, let’s join tech but not on the technology side, then let’s migrate into a services company that focuses on working with tech companies. So it’s like the next layer in and then now jumping into the running of a technology company. Can you pinpoint the moment, the year, the scenario where you realized that Erin Bury is no longer the Journalist and Erin Bury is very much a Technology Executive.

EB: Yeah thank you for sharing your story because I think it mirrors mine so much. I think to me it was a really intentional choice, I think I very much would have built a career on just being a tech journalist or being a marketer.I still think people think of me as someone who is great at PR and marketing, those are still absolutely some of my passions. I think it was after running the operations at BetaKit and then going on to that agency where for six years I was doing you know the finance, the operations, the HR, and people & culture, and all of those things that are outside of marketing that I realized that I’ve gone from a marketer to an executive, someone who’s running the operations of the business. I knew if I had moved on and kept a role as head of communication or marketer of ‘x’ growing start up I really would have continued to pigeonhole myself into that label marketer or PR person. Joining Willful was the moment where I really made an intentional choice for me to say I don’t want to build my brand as the comms person, I want to build my brand as an executive, as an operational entrepreneur who can come in and run a business. I think my choice of joining Willful was a reflection of that and it was a very intentional move away from a career path that includes being the head of comms for you know League or any other of these really cool startups not that it’s not a great job it’s just not the story that I want to build my career.

DH: Right, I think there’s a lot of people who I’m becoming more interested in defining like was there this moment because I think there’s only two types of people there’s people are like “no there was no defining moment” or there’s people who are like “yes the lightning bolt hit me and this is what happened and what changed” and whatever so I appreciate you giving some insight.

EB: It was definitely not a lightning bolt I don’t know if you had the lightning bolt I feel like it was more of a gradual realization that hey I’m actually learning all the stuff around like legal, and finance, and operations, and I’m not just spending all my time on marketing and I don’t actually want to go back to spending all my time on that.

DH: Yeah for me it was a little bit more of a lightning bolt moment for the sake of time I won’t get into it today. I think my experience was like okay well with that lightning strike comes a lot of fear, uncertainty, anxiety, pain and all this other stuff that you can correlate with also being struck by lightning. But listen, here’s the next question it’s more fun, I want you to imagine it’s 2004 you’re sitting in your basement watching Horatio Caine solve crimes, you’re poutine that’s a real sign that you’re from Ottawa id thats your meal of choice, while watching CSI your mom comes downstairs and she’s freaked out because all of a sudden Erin now from 2020 is also there. Once she gets over herself she’s like “what are you doing here?” and you say I just want to tell you what happens to this person sitting here, this is what happens: she founded a county wine tours company, she is going to be business partners with her husband, she is going to do all these amazing things and be a top rated speaker. What do you think your mom says in response?

EB: That question, you literally just brought tears to my eyes because honestly this sounds so cliche and silly but like I could not even have imagined the place that I’d be in today. I always say to Kev when I wake up in the morning like yeah there are stressful days and whatever but I’m just so happy because I don’t think I ever dreamed that this path was even possible. I think my mom would probably reply “yeah?”, you know she always believed in me, she always knew that I was my person and that I was always super ambitious. She’s the one who inspired that in me by having a really strong career in showing me that you can really achieve anything as long as you work hard. I don’t think that she would be surprised but she would probably say “Wow that’s a different more unique path than I saw you going on” because I think she very much knew that I was inspired to follow in her footsteps. But it’s a really cool question because people complain about getting older and I always say I would never trade going back to being in university or being in my early twenties because I’m just so grateful for all the highs and lows in my career and where I’ve gotten to. I’m really proud of everything that Kevin and I have achieved together, and I’m just generally a really happy person and happy with where I am in my life. So hopefully my mom would be happy with it, but that was a really amazing question.

DH: Thank you for that and you know maybe tonight you’ll be inspired to find Torontos which is probably still like number twenty by Ottawa standards, and dig up some old CSI episodes. Listen, last question what do you think is the Erin Bury superpower?

EB: Well that’s a great question. I mean my superpower for eating all the poutine and pizza that I want without gaining a pound unfortunately went away in my twenties, so now I spend more time at Barry’s bootcamp eating salad than I do eating poutine. I would say that my superpower is getting people to think about, know about, and care about a brand. While obviously I want to be known as a business operator I still think that my superpower is finding ways to build buzz around a brand. That’s what I did in my first role working for Sarah and that’s something you have to do when you are someone who is building a direct to consumer business. So whether that’s through events, social, PR or whatever else. I think that’s really been my superpower and something that I try to help other entrepreneurs with who maybe don’t come from the same background and have technical expertise but really struggle with how to actually get their product or service out to their potential customers.

DH: I know I said that last question but I’m going to ask one more. If you were to extend your career timeline out another ten years from where it is today. What do you hope is something that you will ten years from now be able to answer as one of your highlights of the last ten years?

EB: I think a lot about this because I learned a long time ago from Sarah, that entrepreneurs don’t aspire to retire. Entrepreneurs are people who have tons of ideas and aspire to keep building companies that they’re passionate about, and to find ways to give back to the other entrepreneurs following in their footsteps. I very much adjusted my life plan from retire at sixty five and travel the world, to keep building companies and keep doing the things that I love with no end date in sight. So in ten years the thing that would make me the most proud is if I’d been able to have some sort of success with my own businesses and to be able to start a small angel fund or family office where Kevin and I invest in non-traditional entrepreneurs. Kevin has a trade background and I obviously am not a technical founder and I’m also a woman, and people that are first time entrepreneurs especially from nontraditional backgrounds. Women tend to have a really tough time receiving funding. So I will consider ourselves extremely successful if we’ve been able to invest in ten, twenty, thirty nontraditional entrepreneurs to help give them the boost of confidence that our angel investors have given us to start Willful.

DH: Well that sounds like an inspiring future. There are many ways one of which I was thinking of that you can start living out that goal now. You can become a shEO activator. We had Vicky Saunders who is a good friend of mine on the Journey Map podcast before in Season One. She has such amazing stats about non traditional if you wanna put that label on it entrepreneurs. There’s some amazing stats that like I’m gonna butcher on the spot but basically investing in female entrepreneurs is like ten times out of ten a better investment than investing in a male entrepreneur. So anyway there are opportunities to start that passion for you just as an idea.

EB: That’s a great idea, great point.

DH: Thank you so much for joining us. I learned a lot more about you than I’ve known in the past and that’s why I like to do this. I really thank you for sharing so openly in some of those questions and it was a pleasure catching up and we’re gonna include links in our show notes to where people can learn more about you. Definitely check out Willful and see all the amazing things that you guys are doing there. I’m assuming that there’s some open positions if not now coming shortly which people will probably be interested in joining because I really think that every once in awhile a startup happens that you ask yourself the question like how did this not exist? like truly how does not exist before? and I think Willful is a prime example of that. Congratulations to you and Kevin on everything you’ve accomplished and looking forward to doing this again sometime I hope.

EB: Thanks Dave, and thanks for shining a light on these journeys. I think it’s always great for me to listen to other people’s stories and hopefully might help someone else who is just getting started in the world of entrepreneurship. Thanks again for having me!