Day 1: Vancouver
Stewart was running late. Either that, or I was at the wrong address. I checked the email: 1140 Homer Street, a glass door between a bar that was closed and the entrance to the courtyard of a high-end restaurant.Inside the glass door, I could see carpeted stairs running up to a second floor. The neighbourhood was called Yaletown and consisted of a few square blocks of renovated warehouses and narrow streets – exposed bricks, thick wooden posts and beams.A hundred years ago it had been a train yard. Now its street level was full of bars, restaurants, hair salons, boutiques and pet boutiques. Its upper floors housed video game programmers, search engine optimization consultancies and local branch plants for Sony and Amazon and Apple. Surrounding the renovated warehouses towered glass-skinned, concrete-cored condos.When people visited Vancouver fashionably, this was the neighbourhood they often started their visits in.Stewart appeared along the sidewalk, in conversation on his phone. He opened the glass door and I followed him up the stairs along a carpeted corridor to the back of the building to a door with a Tiny Speck logo: 250B.The office was about 20’ x 20’, a room with brick walls and large windows facing south. A model of a white galleon hung from the ceiling and turned out to be a kite. A mounted walrus head hung on the wall. A crocheted circle hung in the corner and read in pink stitching, B***h don’t kill my vibe.One other person sat in the office with headphones on, typing at a computer, looking focused. Stewart placed his bag on the desk in the corner and sat on an office chair with a padded cross for a backrest. The other person in the office took off his headphones and introduced himself: “Hey, I’m JR.”Working with StewartJR pointed me to the two empty desks and told me to take my pick. I set myself up and pretended for a few minutes to be getting started.Actually, I was waiting for Stewart to get off his call. When he showed no sign of wrapping up I figured I might as well get started. I’d written a proposal for the work I was going to do. I should assume I had been right with that direction and get started doing it.And that experience — waiting, trying to get on with the work as well as I could, checking in again — was what working with Stewart was like for the most part in those early days. He had very specific guidance to impart on everything, when he became available to impart it.I would like to say it was easy. He was obviously incredibly bright and capable. I would like to say it was fun. We were doing hard work on great problems. But the general theme of my early days I recall as mainly a search to find direction. Stewart was super busy and direction was scarce.Often times, when I was trying to get feedback from him, waiting for feedback from him or looking to book time with him, he’d deflect the requests. “Businessman things,” he once said to me as he shrugged, getting off a call and coming to chat. That became our shorthand for all the other things that occupied him: businessman things.I had to just keep working on my jobs, do my best with my own judgement and wait.First Steps to the EpiphanyWhen I felt stuck on what to do next, I often went back to a book written by Steve Blank called Four Steps to the Epiphany.I had a dog-eared copy full of notes that I found really useful for structure and process at the early stages of a startup where we found ourselves. Four Steps was useful for structure because Blank had founded and built many huge B2B software companies, and the book reflected an idealized view of how he’d done it.I’d used the tactics of the book before with good results, and we were definitely still on the first step of the four: Customer Discovery. Here’s the flow chart of the process of Customer Discovery.The main point of all these boxes is that you need to “get out of the building,” as Blank says. And talk to customers. Test things with them. Listen.Other times when I needed guidance on the next thing to work on I’d just put on my own businessman hat and ask: what is the next best thing for me to be doing? Or, what is the thing that the business needs me to do? I found it an effective way to get out of my own head, and any frustrations I might be having, to focus on keeping moving ahead. I wished I’d done it more when I had run my own startup.As a result of waiting and asking what needed to be done, I ended up doing a lot of different things — researching the market, drafting positioning documents, writing website copy. Basically, trying to keep pushing to answer the key question I felt like we needed to answer – What is Slack?This wasn’t a smooth process. I found many dead ends and I was basically trying to catch up to Stewart. Looking back, I’m sure I have some Stockholm syndrome in my recall, and some survivorship bias in my recollections. (Was it really that bad or just a circuitous way to find the right direction?) But I did learn quickly through taking initiative and either rarely making headway or commonly making mistakes. This didn’t always please my boss, but I think it did show myself and my peers that I was committed and contributing.And to be honest, in those early days, I really had no sense of what was to come with Slack. The whole operation struck me as held together with bailing twine, dedication and gumption. The team was obviously talented and committed to each other and believed in the promise of their new product.But I wondered: what had I gotten myself into? I had conversations in the evening with my wife about just that question and the natural follow up: where could this possibly be going? It was not clear at all Slack was headed to any success.In my job search before agreeing to join Slack I had been close to joining other companies: a well-funded and growing software suite for lawyers called Clio, a social media monitoring company called Hootsuite. They were each prospectively offering me more money and a more mature company, further along in its product development. What, my wife rightly wondered, was the reason to join this failed game company and bet on their new, unproven, weird product called Slack?I didn’t really have a good, coherent, well reasoned answer. But the main two things that made Slack compelling at the time were the team and the culture.Team and cultureThe reason the team was compelling is easy to unpack. They were simply way better than any team I had worked with before. They were more accomplished. They worked harder. They were smarter. They were faster. They were deeply online people who had been using the Internet and working on the web through the late 1990s and early 2000s and had extensive expertise in how it worked both technically as well as socially. They also really seemed to like each other and had terrific chemistry.And to unpack the chemistry is really to unpack the culture. Here were people who shared the same values: fun, work, ambition, a collision of high and low brow references, an appreciation for going to the nth degree to get something just right.They were each mildly weird and unbalanced in their own ways and happy being weird and unbalanced together. An element of fun and humour underpinned everything they did. The tone was serious and light, demanding and humane, focused and wandering, all at once. We posted a sign above the door of our modest office that became a call to ambition: More Holey Moley.Standards for work were set really high and I responded well to that. Here were people who produced great work and could also recognize great work across domains. Here too was as close as I had come to a meritocratic culture for everyone. I realized I could make copy editing suggestions to Stewart on a piece of writing he’d sweated over, but only if my suggestions were all really well considered, packaged up in an accessible format and actually improved the end product. Praise, when it rarely came, was well earned. There were no workplace equivalents of participation medals.(Many years later I found myself telling a group of executives I was leading on a tour of Slack’s 10-storey headquarters in San Francisco that the company had always been a liberal arts software company. When puzzled about something not working, no one felt embarrassed quoting Wittgenstein (“It is not how things are in the world that is mystical, but that it exists.”) right beside Homer Simpson ("The lesson is: never try.”). No one had to be convinced that people made decisions based on some concoction of emotion and reason, that artistry mattered as much as technical acumen. No one talked about “soft skills” as if they were on the Nice to Haves list for employees.)And the culture of Slack came alive in its strongest way for me in those early days in written words, and how written words were evolving. The team really used their own product all day and every day, and beyond into the evenings. Everything was in Slack, organized into channels that acted as streams of communications and events and emotions and jokes.As JR himself, my first Vancouver teammate beyond Stewart, wrote in The death of Glitch and Birth of Slack:When I joined the company, I’d been given a crash course in how we worked together on my first day. No email. Everything happened in IRC: a chat protocol from the late 80s. We had a server set up with channels based on topics of discussion: #general for company-wide chat, #deploys for new code releases, #support-hose for inbound customer support requests, and so on.Alongside this we added a few other things we needed. A simple FTP server which posted uploads into the #files channel. A system that wrote our chat logs to a database so we could search them and read old archives.A set of integrations that posted updates from other systems into IRC: whenever a new user signed up for Glitch, or bought credits, or wrote in for support, it showed up in a channel. Whenever we deployed code, or got a new review on the App Store, or tweeted from our Twitter account, it showed up in a channel.Taken together, this allowed us to communicate in real-time, share files, find anything we’d ever talked about at the company, and keep track of everything happening with the business – all while avoiding the unique 21st-century hell of email reply chains and fragmented organizational knowledge.This was the experience I had too, and so many other early Slack employees had. They were both new to the company and the way it worked.At first if felt disorienting and overwhelming. Then quickly the work streams became indispensable and I started dreaming in channels. I couldn’t imagine using anything else.Channels were themed based on the work happening in the company. Anyone could jump into any channel and any conversation in any channel. This was incredibly powerful because you could read and join in any work stream. It was also an incredible responsibility because you could disrupt or derail any work stream.For us, the channel was the canonical work stream. If something wasn’t in a channel it might as well not exist. Messages from humans and computers mingled together in channels because both were essential to the work. We quoted these messages. We quoted each other. We learned to do Slack as we were doing it. As a result, a style of writing emerged combining the best aspects of each of our individual writings. As I watched and participated, an aesthetic spread.That’s a bit abstract, so here are some examples.The parenthetical voice became common because we relied on writing so much that we had to accommodate and show different perspectives at once. Not including the parenthetical in an important message felt like you were making an argument but not showing your work (and I may be totally wrong here but I think it made the whole reliance-on-writing culture possible because it counterpointed and disarmed arguments and objections as well as me vs you arguments). Including the parenthetical made explicit that you had done more work than shown, and were open to other perspectives.Searching became an expected default behaviour so that people would try to self serve their own questions. Having access to the entire history of communication of the company meant you had a responsibility to use that history. When you had a question, you learned that it was pretty unlikely to be the first time that question had ever come up. So the rule was: seek to solve first through search. Only ask for help, and tax a teammate to answer, if you couldn’t answer for yourself, or had searched and found a partial answer and wanted to confirm it or clarify.Emojis were simply a more efficient way of acknowledging someone and providing an emotive response than writing. Plus, they were like a game too. Could you come up with a clever emoji that acted as a commentary such as 💸 when you were busy buying ads? Could you complete a 👉 👈 with a teammate in consecutive messages, like a texted high five?Often times, we quoted things to make sure our messages were clear. (Did you mean when you said .)We worked at mastering the simple markup syntax in Slack that let us decorate our text for meaning and to show off. We learned keyboard shortcuts to emphasize words, arrange text and build lists. To be any good at Slack the company you had to be good at Slack the product.Playing the Slack gameWhen people on the team were going for lunch or getting up to do an errand they would type ‘afk 30 mins’ — meaning, away from keyboard for 30 minutes — to let teammates know they would be out or reach for half an hour. To some folks this small gesture might seem trivial or even nagging. But I found it rather charming.Here was a team very tightly connected who consistently offered up small signals of belonging and courtesy to each other. ‘afk’ meant more than just ‘I’ll be away from my keyboard for a period of time.’ I read it was meaning ‘You may need me in the next 30 minutes and I won’t be available but I will be thereafter’ and ‘Here are some expectations I can share with you as a small sign of caring’ and even ‘I trust you to tell you what I’m doing and to provide transparency to you.’No one mandated that we had to type ‘afk’ if we were going to be offline or unreachable. Like all great group rituals, one person started it, another saw it and imitated it, and then it became normalized as a small courtesy. It started before I arrived and I’d guess carried over into Slack from IRC.Other chat acronyms also populated our communication — OTOH (On The Other Hand), IMHO (In My Humble Opinion) or just IMO (In My Opinion) and YMMV (Your Mileage May Vary) — as ways to humanize and soften messages. But it was afk that struck me as most representative of the type of place Slack could be.Years later, as the company added new employees at a blistering pace, an official Slack style guide was written and included in training. New employees otherwise tended to be a bit mystified at first and hesitant to jump in to such a fast mode of working. Open felt exposing to them. Transparency felt threatening. What if they made a mistake?But that was still many years away, and we had to sink or swim for ourselves in the meantime. We were still very much in Customer Discovery and hadn’t even considered Step 2: Customer Validation.In short, right from Day 1, I found these Slack folks were people who read and wrote and created things in the world and loved to do so. I felt like I wanted to be one of those people rather than someone selling lawyers on revision management. I wanted to belong. These felt like what I hoped could be my people.Up next week:Missionary vs mercenaryHow to answer the key question — What is Slack? Finding a role. The missionary vs mercenary continuum. Meatball restaurants don’t last.NotesFour Steps to the Epiphany is also available as a PDF from Stanford. It’s still a terrific resources for anyone considering or running a startup. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com
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