In Conversation: Distinguished Alumnus Stewart Butterfield ’91

Stewart Butterfield

This article originally appeared in the Winter 2018 issue of School Ties.

Canadian entrepreneur and businessman Stewart Butterfield ’91 is best known for his work as co-founder of the photo sharing website Flickr and the team-messaging application Slack. Last May, the recipient of the SMUS Distinguished Alumni Award in Entrepreneurship and Information Technology spoke with Head Girl Aysha Emmerson ’18 before a school audience about success, growing up and his journey as a tech entrepreneur.

The following interview is edited for length and clarity.

AE ► How do you define success?

SB ► I would say happiness. Not simple, pleasure-based happiness, but the satisfaction that comes from paying attention to all the good things that life has to offer and to relationships with other people.

AE ► Do you believe there are qualities that define a successful person?

SB ► The list of qualities on the wall here look pretty good – courage, honesty, service and respect. But if I had to pick just one, among the people I have had the pleasure to get to know who are far more successful than me, an outward-facing mindset and being of service to others is a near constant.

AE ► How have you changed since you were at the school?

SB ► I was pretty obnoxious then, I would say. I was probably never as well behaved as one might hope students are. It’s hard to say if that’s changed.

I was just young, to the extent that any of you, as teenagers, sometimes are insecure, obnoxious, attention-seeking, obstinate, or any those things that are forgivable in the grand scheme of life. It took me some time to learn how to really be me.

Whenever I welcome new employees at Slack, I ask them to put up their hands if they’ve ever treated somebody they loved in a way that they later regretted. Think about that for a second. Have you ever treated somebody you love in a way that you later regretted? If you don’t put up your hand, you may be a psychopath and probably should get some help.

It took me some time and some growing up to find the best ways for creating and maintaining relationships with other people.

AE ► What would you say was the most valuable thing you learned during your time at SMUS?

SB ► That’s difficult because you learn a lot from your relationships with other people. I had excellent teachers and I feel I actually learned quite a bit academically, as one would hope. And the out trips I went on were incredibly valuable and really helped me bond with the people I went on the trips with.

AE ► When you left SMUS, did you have a career plan?

SB ► I had no idea what I wanted to do, and I think all of you should feel safe and comfortable feeling the same.

I wanted to study cognitive science but there was no cognitive science program at the University of Victoria. Cognitive science is typically a combination of philosophy, psychology, linguistics and computer science. At UVic, if you studied philosophy, you could take courses in those other departments, but if you studied the other fields and wanted to get an honours degree, you couldn’t, so it was kind of philosophy by default. Then I became really interested in it.

I studied philosophy at UVic and got my Master’s at Cambridge. But being a bioethicist or becoming an academic are pretty much the only opportunities for philosophers, so my plan was to become an academic.

AE ► Did you find that studying philosophy helped inform your later career?

SB ► These days, as part of philosophy, you study word games and how to be very precise about language. And being very precise about language turned out to be a huge advantage. Clarity of writing is a fundamental skill for any professional.

AE ► Would you say that the soft skills are more valuable than the hard skills?

SB ► Given some baseline level of competence and intelligence, most of the things you might want to do in your career can be learned. You can go to school and figure out how to operate accounting software and the basic principles of accounting and then become an accountant. However, you will be successful in a career in finance only to the extent that you are able to relate to other people, understand organizations and communicate clearly.
I think storytelling, more than anything else, is an underrated skill for any career. To be an entrepreneur, the most important thing you can do is tell stories that captivate people’s imaginations and get them to buy into what you’re selling. In the absence of that, none of the hard skills will make a difference.

AE ► What was your hook into a career in technology?

SB ► I was in the right place at the right time. When I started at UVic in 1992, one of the first things you did was get an account for the school’s UNIX mainframe. That was my first exposure to the Internet – this was maybe a year or so before the LAN took off, so the Internet was known to only about 50,000 people or so. My summer job and job throughout university was making websites for people.

AE ► Tell us about the journey that led to Flickr.

SB ► When I was first exposed to the LAN in 1992, it blew my mind. It’s hard for me to remember what life was like before the Internet, and it’s probably close to impossible for you to imagine what it was like. It was enormously transformative.

I just liked the idea of producing a new technology to facilitate human interaction in a really broad sense. Flickr was borne out of a failed attempt to build a web-based massively multi-player game. I wasn’t particularly interested in games but I was interested in a play pretext for social interaction – then, and throughout my career.

Flickr is just massively multi-player photo sharing. Slack is massively multi-player workplace software. Those key themes – presence, identity, relationships, groups and social mechanics – mediated the software at the core.

AE ► Other than using the app itself, what lessons or takeaways from Slack’s boss can we apply to group projects here at SMUS?

SB ► More than anything else, communication and alignment. All of you have had the experience of working on projects with people with whom you are not aligned. People end up working to cross purposes and, no matter how much effort you put in, you don’t really get anywhere because people are pushing in different directions. When people are aligned, when the roles are clear and there’s some kind of shared consciousness about what’s important, you progress much more quickly.

AE ► What is the typical day look like for you at Slack?

SB ► This is going to be true of any manager at any company, more or less at any level and definitely for any executive at any company – I spend my whole day communicating with other people. It’s one-on-one meetings, it’s larger meetings, it’s reading and writing messages, it’s composing documents, it’s sitting in on other people’s presentations and doing stand-up meetings.

I said that writing skills are important, but being able to speak clearly is also incredibly important. If you’re going to spend 100 per cent of your working effort on communicating with other people, it is a fundamental skill.

AE ► If you could give one piece of uncommon advice to the students here, what would it be?

SB ► I’m going to be contrarian. Sometimes at least be willing to give up on your dreams. I don’t mean be passive. One of the things that allowed Slack to happen was we recognized before we completely ran out of money and energy that the project just wasn’t going to be the kind of business that would justify $8.5 million in venture capital.

You are often told to never give up, to believe in your dreams, that if you can dream it, you can do it… we can go down the whole list of exhortations. I think those statements are essentially correct – perseverance can be very important – but be judicious.

Learning when it is worth it to actively let go and admit you had unreasonable expectations is a highly underrated ability.

Distinguished Alumni Award

The Distinguished Alumni Award recognizes SMUS alumni who have excelled in their chosen fields and who exemplify the core values of St. Michaels University School. Each year, we select a different field and welcome nominations from across the school community.

Nominations are now open for 2019 in the field of engineering. Nominees should demonstrate vision and innovation, dedication, achievement and accomplishment, as well as community involvement.

To nominate an alumnus for the 2019 award, complete the form at


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