Pre-Slack: Meeting Stewart
A first memorable talk with Stewart Butterfield at Northern Voice, 2009. A connection from a mutual friend. A failed game called Glitch. A newer new thing called Slack.
New to A Slack Story? Check out: Introduction: what if the startup myth comes true.
On a bright spring morning in 2009 I stood outside the Forestry Sciences Centre at Vancouver’s University of British Columbia waiting for Stewart Butterfield to arrive.
Inside the building, the MC of a conference I had helped organize was on stage kicking off the program. Stewart had, through a loose mutual acquaintance, committed to doing the morning’s keynote talk. The keynote talk was set to start in less than 10 minutes. Stewart was yet to arrive.
Did I feel nervous? Yes. Water is wet. I tried to stay calm and replay the steps that had brought me to that point. Perhaps I could find a hole in the process to patch in 10 minutes? Day dreaming didn’t hurt or help.
The conference was called Northern Voice and felt very much of the time, started by a collection of geeks, technologists and idealists who wanted to build an event that met them at the intersection of their interests. It was run by volunteers through a non-profit called the Northern Voice Conference Society.
No one talked about ‘Web 2.0’ but that label probably fit it best. It was earnest and inclusive and community driven. There was a general trust in connecting technologies, transparency and the enablement of more voices to be heard. Our collective default setting was optimism. We had hopes.
When we had brainstormed ideas for keynote speakers, Stewart’s name had come up. He was from Vancouver, mostly. He seemed thoughtful and successful and like he would have something interesting and different to say.
But he’d been a reach. Could we get him? Would he be available? Would he say yes and show up and do a great job? Our honourarium was exactly zero dollars. For out of town speakers, we covered their travel. The commitment from Stewart that we’d received second hand felt tenuous. Maybe we should have planned for an alternate keynote speaker that morning? We had not.
Already a star
At the time, Stewart was already a star in the business-tech-geek niche that mattered to us. He had co-founded Flickr and sold it to Yahoo! for many millions. He’d been on the cover of Newsweek and The Guardian and Business Week. He’d written a widely circulated resignation letter when he left Yahoo! that starts out, “As you know, tin is in my blood.” He’d done it all with an authenticity and style that cut through cynicism and felt real. He’d sold his company but not his soul.
So yes, he could be afforded a broader patience, I told myself as I waited. The loose mutual acquaintance who had secured Stewart as a speaker had proven to be eventually reliable in the past. We had promoted Stewart’s talk through channels that he would have likely seen. But the nagging and obvious question remained: would he show up and would it be vaguely on time?
A silver Audi whipped into the parking lot. I could see it was Stewart and waved to him. He grabbed his shoulder bag and hustled inside. I paid his parking and followed. We stood together backstage while the MC finished the set up of the day’s program.
“I’m not really ready for this,” Stewart said.
“What’s your talk about, Flickr?”
“No, the Internet.”
“Well that’s big enough.” I took a pause. “People will like that. They’re a good audience.”
“Fuck it, here we go.” And he walked on stage.
I don’t remember the talk much because I basically watched the audience, who had no clue of my personal scheduling drama, and were keen to see the star. They responded well and it was an imagined crisis averted in total. Okay, onwards. I got ready for the rest of the program.
That moment of anxiety I’d held in the parking lot before Stewart arrived blurred into that social rush of details and problem solving and “hey, great to see you again” of a conference day.
But one of the advantages of running a conference for tech geeks at that time is that everyone memorialized important events. So it’s easy to find posts describing Stewart’s talk on blogs. And I’m happy to report, people loved it.
The Internet, a love story
The talk was called, The Internet, a love story. It stands up very well to time, and I think provides some foundational insight into how Stewart saw the web and software, and the nature of technological progress for humans.
An excerpt from the live stream of popular tech blog, Miss604:
Stewart’s keynote begins as a photo story, from an image of a shack in the woods to illustrate his home town of Lund, to black and white hippie photos of him and his parents, and a young Stewart in a “Radio Shack Computer Camp” trucker-style hat.
“Back then, in 1992, the internet was a way to keep in touch with people going to university in other places,” mentions Stewart while sharing some of his old usernames and email addresses (that, at the time, were at least 20 characters long). He’s also showing some postings he’s made to groups online (circa 1993) including his first online community rec.music.phish.
…
Stewart moves on to “this is who I am” and shows images of various ways people express themselves and who they are, from bumper stickers to hairstyles and clothing. “People tend to pick up more adhoc bits of culture,” A photo of a crowded auditorium pops up with Apple notebook symbols glowing (and a little red arrow points out the single PC user).
“In the early days, photography was about memory preservation,” notes Stewart as the Flickr logo spins up on to the screen. Trends Stewart highlights include: Ubiquity of capture devices, Spread of the network, Change in perception and attitudes — participating is no longer weird.
…
Stewart address the changing role of computing over the years including, ‘Relationship-based computing’ which replaces document-based computing which replaced application-based computing (from Stewart’s slide).
Update: The presentation ends with “Anyway, this is why I love the internet.”
In short, Stewart was a local boy from Lund (literally, the end of the road just 128 kms north of us in Vancouver, population 287). He’d gone out and made good in the wide world, and done it with style and without losing his credibility. I don’t think it’s too far reaching to say that he was a small hero to us in that Northern Voice crowd.
Did it matter that his talk was a redo of other materials he’d already delivered? Did it matter he improvised? Nope. People rooted for him. He was a legitimate headliner to kick off the conference. So what if he wasn’t as polished as others? He was a star.
A newer new thing
I’d like to say at this point that Stewart and I lost track of each other for a few years, but that wouldn’t be true, because we never really had much track of each other to begin with.
Sure, we recognized each other. We shared a few other brief conversations in passing at events like the launch of his next initiative, Glitch. But we were not close or even casual friends. I didn’t have his email address. Time passed.
Then a few years later a mutual friend introduced me formally to Stewart. I was looking for a new job. Stewart was looking for help for his newer new thing, which he did not name.
It was May, 2013 and my son had been born in February. The software company where I had worked wanted to offer me parental leave. Actually, they had to by law. But in reality I was the oldest person at the company (at 37 years old) and no one else had children. It was one of the many startups around where the employees were not much more than salaried children themselves.
Going back to work after 5 weeks at home, I soon found that my now much-less-flexible home life clearly clashed with my work life. Expectations became irreconcilable with reality. There was only so much time each day and I had to prioritize.
So I had left the company in April and started reaching out to trusted folks I knew, looking for a better option.
One of those folks I trusted was Rebecca Reeve. I’d worked with Rebecca on a number of projects and we’d found good success. She introduced me to Stewart, by email, copying Stewart, just like this:
James, just told Stew you've recently become available and he wanted me to send a quick intro. Tiny Speck is working on a new workplace comms tool. I'll let you two take it from here.
And Stewart wrote back one minute later:
Thanks Rebecca :)
James — I know you.
This was the start, and it started to give me a glimpse into the story of the guy I was going to work closely with for the next few months and years.
Stewart was Stew to friends (at the time). He worked with people he liked and trusted. He used text as a playground for expression (check that em dash!). He used both emoticons and formality in business communication. He valued and knew the value of his own voice and seeing people. What else? There was so much that I would have to find out. We were off to the races.
Stewart and I met for coffee at the JJ Bean on the corner of Davie and Homer in downtown Vancouver. We talked briefly for context (here’s what I’ve been up to, what have you been up to?) and he demoed a new product for me.
As he demoed, I had what seemed to be such an embarrassing lot of questions about the basics – why did the text scroll from bottom to top? Did people really use emoji in their work communication? Could anyone really join each of the #channels and see the full archive of what everyone was saying? Were people really going to pay for this when they didn’t pay for other chat tools?
Somehow those total noob questions didn’t sour things. Stewart asked me for a proposal to do some marketing work for Tiny Speck’s new product on a 3-month contract. I typed up a proposal and sent it to him. A few reference calls later and I had a start date to kick off my work in their office: June 5, 2013.
Okay, great. Now, what was I actually going to be doing?
Call it marketing
From my conversation with Stewart and some press coverage I found, I had a rough idea of what was going on, but I really knew so little.
After leaving Yahoo! to get back to his first love of tin smithing, Stewart had gotten many key members of his Flickr team together again. They’d raised $16-million of funding from A-list venture capitalists to build an online game. They’d launched Glitch.
Glitch had been cool and lightly fun, “a virtual world that looked and behaved like a Dr. Seuss book as re-imagined by Cheech and Chong, in which players helped the eleven sleeping giants in whose dream this world existed by carrying out acts of creativity and cooperation.” But it had been a commercial failure and closed down 6 months earlier, in December, 2012.
When the Tiny Speck team (the company behind Glitch) closed down the game and broke the news to their investors, they had offered them two options: they could give back the money they had left ($2 to $3-million) or they could pivot to work on something they had cooked up internally – a team communication system called Slack. The investors didn’t want their money back and urged the team to push on with Slack.
Why not cut their losses? The larger picture, which I would guess was in the mind of all the investors and employees and drove the decision, was the hope that Glitch could repeat a pattern of pivoting from failure to victory.
Glitch’s predecessor, Flickr, had been born from another failed game called Game Neverending. The photo sharing feature of Game Neverending took off because it launched just as smartphones with embedded cameras hit the market and as digital cameras rose to prominence. Stewart and the team saw that uptake and refocused the company to build solely for photo sharing. They had pivot precedence.
So Flickr had been a huge hit born from a failed game. Could Slack follow the same course and become a hit from a failed game? That was the question.
And that was the situation I started with at Slack: big expectations, a small team, a prior hit, some money still in the bank and a looming, palpable, practically haunting fear of another failure.
Up next:
After Slack, a new project. A sculpture inspired by an article about a translation of an ancient story. Finding home.
Wow. Such a flashback. I remember Stu’s NV talk.
I remember that Northern Voice! At one point our friend Darren Barefoot and I debated the meaning of a new-ish term: social media.