Proust Goes Tech With Erin Bury, CEO of Willful

Between speaking at events, writing for publications, and even running a bike wine tour company as a side gig, Erin Bury didn’t even know she was tired until a mentor pulled her into her office and told her to slow down. Bury now looks at that moment as one of the biggest gifts in her career: being told to buy out of what is derisively called “hustle porn.”

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To her that means having a set of canned responses on how to say “no” on standby, drinking wine on Tuesdays, and sometimes snoozing the alarm even if a productive morning was in the books.

Choosing to slow down has helped “bring clarity” to her current job as the CEO of Willful, a Toronto based startup that helps people make wills online, without seeing a lawyer. Beyond that, Bury is a board member for Save The Children Canada, and was once retweeted by Oprah.

In this Proust Goes Tech we chat with Erin to learn about how her grocery store job helped her be a better leader, her issue with The Office, and why her husband calls her Mary Poppins.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I would probably be a tech journalist. I’m a journalism graduate and spent a couple years on the founding team at BetaKit, which is one of Canada’s top startup publications. I saw that the skills journalism taught you, like writing, specifically and learning to interview people, was really helpful regardless of what career path you went on.

I think being a journalist is basically [taking] a masterclass in becoming a great entrepreneur because you just literally talk to, hundreds of entrepreneurs who are doing cool things.

I found it inspiring daily to hear about those ‘Aha’ moments that led people to start their companies, because it really taught me that inspiration can come from the most unlikely of places. And that, everyone’s origin story is different and everyone’s path to success is different.

Also, as a founder, the strongest thing you have going for you is your story.

Your main fault?

I think the biggest thing that I struggle with, and the thing that I know I need to improve, is having difficult conversations. I’ve always been the kind of person who shied away from confrontation, or from having difficult conversations. And when I was a teenager I had to call in sick to my high school job at the grocery store as a cashier. I would make my mom do it for me. Yeah. And when I had to resign from a job once, I was physically ill for days leading up to telling them, because I was so scared about having that conversation.

Now, it’s not as much as an employee having to have tough conversations with a boss or with HR, it’s more about having tough conversations with team members.

And inevitably, you have to have tough conversations when you’re running a team. And that could be everything from letting someone go, to having a conversation about performance and giving them constructive feedback, to putting someone on an improvement plan.

So I definitely know that those conversations still give me competition and give me a lot of anxiety, but they’re necessary.

The quality you most desire in a tweet?

So easy, it’s humor. There’s nothing better than a hilarious tweet thread and meme I love. I think especially when there’s so much heaviness today. There’s a lot of heavy content on Twitter and there’s so many great political discussions and conversations around gun control; you see them happening daily. But I use Twitter for its humor.

Your idea of misery?

My light version is a world without pizza, because I love pizza more than anything in the world. But to me, misery is professional boredom. When I watch movies or shows like The Office, I think that living that would be my ultimate doom. I hate being bored, I thrive off of being challenged, which is why I’m attracted to working a career like journalism which literally every day is different by nature.

The Office is fun to watch, not fun to live.

What do you appreciate the most in your friends?

Some of my friends have a similar careers, like one of them works with me at a wine tour business I run as a side gig. So those are the friends I appreciate that identify with my day to day.

Then I have friends that have absolutely nothing to do with that world. And they’re my escape. They have completely different jobs. They can’t identify with my job and I always leave get togethers with them feeling refreshed. You kind of live in this bubble as a founder, being on 24/7. Again, I think it’s the hustle porn trend and there’s a sense of guilt that you’re not working on your business. When I have dinner with them, I feel like we’re completely refreshed and I’ve taken a vacation.

Your chief characteristic?

Positivity. My husband, who is also the co-founder of Willful, always calls me Mary Poppins because he says he has never met someone who is so unfailingly positive all the time. It’s definitely something I got from my mom.

If I see my friend go through a break up or a job loss, I say let’s cry today but tomorrow I’m going to call you about next steps and why this was a good thing.

What skill do you wish you possessed?

The first entrepreneur [who] I worked for, she told me that I was a bad judge of character. I always like to see the best in people, I have a really hard time seeing people for what they really are. I assume the best in people, and usually that’s great quality but I think I get taken advantage of sometimes. I wish I had the ability to see people for what they truly are and was a better judge.

Your most impactful book?

The most impactful book I read in a business context is The Power of Habit by Charles Duhigg, a New York Times reporter. It’s all about habit formation in people and how habits can be incorporated into your business to be more successful. It’s really fascinating in understanding human nature.

What defines success?

It would be constantly being challenged and learning new things. You know, I think, after five years running of my marketing agency, I went on my honeymoon. We went on our honeymoon for three weeks to Australia, New Zealand, and Fiji. And before I left, I said to the team that I’m going to try and take time off, but if there’s anything urgent, you know, send me a note. And for three weeks, no one reached out to me. And I kind of realized that I had made myself needed, but not necessary in the organization. And that there was nothing left for me to do, there was my job was done. I realized I’m not challenged anymore. I’m not faced with a ton of obstacles. This is a well oiled machine. And that means it’s time to move on. Other people might consider success to be, you know, staying in that job for 20 years and running it smoothly.

So the first indicator of success is definitely, to me, at least constantly learning and feeling like you are challenged constantly and always feeling a little bit stressed out that you don’t know everything.

When is confidence lost?

I think to me confidence is lost when you don’t feel like an expert at something that you usually feel like an expert at.

Which buzzword is exhausted?

Oh my god, I have to say this all the time, and it drives me crazy: CAC. Customer acquisition cost. It sounds odd and like I’m cursing. When I say it, my mom is like “Pardon?” It’s not exhausted as a concept because it’s just a basic fundamental of running a strong business. But the acronym? Especially when said verbally? I think it’s definitely exhausted.

What virtues do others have that you don’t?

Patience. I feel like having a smartphone has actually made me a less patient person. And I’m sure a lot of people can identify with this, because anyone under the age of 40 probably can. I can’t stand in line idle for more than 30 seconds without looking at my phone. I like I just have to have constant stimulation. And I think it’s a weakness of our generation that we can’t just simply be.

What impact do you want to leave behind?

Being known as someone who helped other entrepreneurs find their footing. My legacy that I want to have is that I’m someone [who] people would say took time out of their day to help those that were just coming up in the industry behind them. And that I was a helpful person that helped advance the careers of other entrepreneurs.

What’s the biggest problem tech is failing to solve?

Tech addiction. I think it’s a problem that was created by technology. And it’s a problem that there is an onus on tech firms to contribute to solving, but it’s inherently at odds with their business models. When you look at companies like Facebook, their business model relies on us using their technology as often as possible. While I believe that they’re doing a good job of saying that they want to help us use their tools, less, I think it’s a PR play. I don’t think it’s actually fundamentally one of their core values, their core values are to make us use their product as much as possible to increase their bottom line.

Illustration Credit: Li Anne Dias