In '98, I made the choice to give up on the PhD program and go work on the internet, which was like new and exciting and paid twice as much as any philosophy related job you could get. I think if he hadn't done that, I very likely would have ended up an academic, which is not a horrible life, but I'm very grateful for the life that I ended up with.

For someone who grew up feeling utterly removed to the greater world, the idea that you could transcend geography and you could transcend time and you could find these communities with interests. It was really just magical.

From that moment, the idea of the use of computing technology to facilitate human interaction was just the most interesting practical idea in the world.

Here's the thing, all four of those, the two games, Flickr and Slack are to me, kind of at their essence, the same. It's all the use of computing technology to facilitate human interaction.

In 1999, I started a competition called the 5K contest and it was the best website or page that you could create in five kilobytes or less. That's, from today's perspective, an absurd, really small data, but in the world of 1999, where, I don't even know, maybe 35% and 40% of US households had internet access of any kind and it was 95% plus dial-up, you really had to respect the constraint of bandwidth consumption. I think because of the excesses of the era and the fact that the competition actually began in early 2000 when the dotcom crash started, there was a real much greater degree of enthusiasm for this thing than I would expected.

Because I thought like my community of internet people, some bloggers and stuff like that would enjoy it, but instead, it was like, I was interviewed for Playboy and in Brazilian newspapers, and Pravda, like the Russian news service. It just became a worldwide phenomenon.

Actually, it probably would have failed anyway, because the idea is not especially commercially viable. It was a no combat absurd, surreal, Monty Python meets Dr. Seuss world, has a pretty narrow appeal.

But it also failed because it was 2002 when we started it. So, there was the dotcom crash and then there was WorldCom and Enron accounting scandals, and then there was 9/11. It was just the all time worst market conditions, and certainly the worst time to try to raise money for something that was online.

No one wanted to invest in internet facing stuff, so it was very hard to tell whether this was a good idea or not, because there's no signal from the market that said, "This is an investible idea," because nothing was investible at that time.

We raised a little bit of friends and family money, we spent about a year or so building a prototype. The prototype was well received, but it was going to take us another year and a half to finish it and we literally couldn't raise any money at all.

We got to the point where the one person on the team who had kids was the only person who was getting paid and then we decided to try to find something else we could do that would make use of the technology that we'd already developed, but that would be quicker to get to market. And that thing was Flickr, but it was also a bad idea at first.

Because we had developed this game client and we had a messaging server on the backend, we just repurposed the game client as a photo-sharing client.

But I will say that in the early days of Flickr, one of the things that made us successful was we had APIs for everything.

You could just do anything you wanted and that excited people and they experimented. A handful of apps that people created out of the APIs, I think had genuine popularity and were useful, but mostly, it just created a community of enthusiasts.

In the case of Slack, it created 2,000 apps in the app directory and something like 900,000 custom integrations that are actively used by a customer. These are integrations that customers created themselves. That's like a mind boggling number. Had we not done that, had we kept it in a black box, I think there would've been a lot less utility.

The approximate cause of that is pretty prosaic. I told my then boss that I'm quitting, and he said, "Okay, that's fine. Can you please send it to me in an email so I can forward it to HR."

People have parsed it for all of this meaning because Yahoo was in a really weird state at that point in 2008. When I started there, we had significantly more revenue than Google. By the time I left, Google was, I don't know, probably 5X or 8X Yahoo's revenue.

But I was just ripping off the style of Thomas Zweibel, the fictional publisher of The Onion, in the paper versions of The Onion. Maybe they do it online too, but he had a column that was written from this crotchety 19th century titan of business perspective, and so that's how that came to be.

There's an order or maybe two orders of magnitude, more people online, and they had faster connections, and they had better computers, and hardware was cheaper, and we were more experienced. It's just all of these 10X factors that led us to believe that, well, we'll never possibly fail this time.

We did again, and this is the long story, and maybe the idea wasn't commercially viable, but I think that the real reason was we went all in on flash as a client technology and kind of a content pipeline management technology at a time when flash was about to die and people's discretionary computing time shifted from PCs to mobile.

Because we still had money, because we had a relatively big user base who were very engaged but we had a really a leaky bucket, it was very difficult to add new users to the game we were working on, which was called Glitch.

I felt very stuck in this position because on the one hand you have a narrative of, "Good entrepreneurs are resilient," "When everyone else thinks it's a bad idea, it's probably a really good idea," "You have to dig in, prove people wrong," "Keep going even when times are dark."

On the other hand, there was a morning when I woke up and I was just like, "I can't do this anymore. I'm the CEO, I'm the chairman of the board. I'm sure that this is not going to work." And it's actually hard to convince everyone else.

So we would have an idea, we try it, didn't work. Have another idea and then like ... At first, you can fill up posted notes, those giant boards, you can fill up whiteboards with ideas and you argue about which ones are the highest value and then one by one you kind of eliminate them.

Months go by, a year goes by, another six months goes by and it's like, "Shit. These were all of the ideas that we thought were the worst ones to begin with and we only have three left. So this is probably not going to work.”

We had been using, going all the way back to 1992, internet relay chatter, IRC, as the backbone of our communications. But because IRC is a 1989 era protocol, it didn't have really basic things that people associate with messaging services, so it didn't have the ability to store and forward messages.

If you and I, Patrick, were online at the same time, I just couldn't send you a message. It just wouldn't reach you. So, we built a bot to log all the messages that people sent so you could catch up again when you came back up online.

Just incrementally, over the course of many years, we made these improvements that were based on something being so exasperating that we couldn't stand it anymore or something being such an obvious opportunity that we couldn't help but take advantage of it.

When I say we, I mean it's 90% Cal Henderson co-founder and CTO. Once we had the messages logged in database, you want to be able to search them. And once we realized that everyone's attention was focused or aggregated here, we started doing things like database alerts would flow into the channels, or when you uploaded a file to the file server, that would be announced with the URL, so you didn't have to tell people, and the daily stats around where you posted into channels. All the stuff that became precursors to Slack.

Then, when we decided to shut down the game, we realized that we would never work without a system like this again, and so probably other people would like it too.

That’s why what we’re selling is organizational transformation. The software just happens to be the part we’re able to build & ship (and the means for us to get our cut).

We’re selling a reduction in information overload, relief from stress, and a new ability to extract the enormous value of hitherto useless corporate archives.

We’re selling better organizations, better teams. That’s a good thing for people to buy and it is a much better thing for us to sell in the long run.

We will be successful to the extent that we create better teams.

That was tough, the first three or four external teams to use Slack it took dozens of tries, like, going to their office and showing them and we learned a lot there about, marketing probably isn’t the right term, and I think we actually had this problem a little bit with Flickr because Facebook came out and just stole the social photo sharing market while Flicker was trying to decide whether it wanted to be social photo sharing or a community for people who are interested in photography.

But if you can’t explain what you’re doing well enough that someone to whom you explain it can go on to explain it to someone else, then it’s a real problem because otherwise, you’re going to have to do all the explaining.

So we struggled to figure out the way to talk about it, what advantages it had, what it was for. But when it’s net new and it’s not replacing something else, it’s very difficult.

Slack is the kind of thing that you don't know you want, but once you have it, you can't live without it. That's great except that people don't know that they want it.

Trying to explain to someone why they might want something that they have no idea that they want is tough. Not just because you have to create that understanding that's a prerequisite for desire, but also because people have a really finite amount of time and they have a set of concerns that are already occupying their mind, more or less all the time.

I feel like I, and the team more broadly, have tried hundreds of things. It's rarely the case that something just works. It's more that each action kind of chips away at the problem.

The things that we did that were most successful were those things which made life more convenient for people.

And one of those was for example, typing your password on your phone is a pain, so we’ll send you a magic link that logs you in.

Or because, for complex reasons, most people wanted to have notifications for every message in Slack when they first signed up, so they felt comfortable and knew how it worked. But we didn’t think that was a good way for them to set their preferences long-term. After a few notifications, we would interject and say, “Would you like to switch to our preferred settings?”

And that kind of thoughtfulness or consideration, that kind of thinking of yourself as a host and the customers as your guests, is the secret, as it were, to good design.

When we push a same-day fix in response to a customer’s tweet, agonize over the best way to slip some humor into release notes, run design sprints with other software vendors to ensure our products work together seamlessly, or achieve a 100-minute average turnaround time for a thoughtful, human response to each support inquiry, that’s not “going above and beyond.” It’s not “us being clever.” That’s how we do. That’s who we are.

It's important to understand why I think Slack works or why it's been successful. It's not because it's a better way to enter text into a box and hit enter to send it, or to read other people's texts, although we know, obviously, we focus on the design, but channel-based messaging is just very different than individual messaging.

Slack is a communication platform that puts the team or the organization first, as opposed to putting the individual first. An email, I have a unique inbox that is different from everyone else's, as does everyone else.

The difficulty of that, I mentioned, the first day on the job you have a completely emptied inbox, despite the fact that there's all these messages that already existed.

But the other problem is I just don't see things the same way you do. Unless I manually select emails to forward them to you, you'll just forever miss this context, whereas you can join a channel six months after it started, and it didn't matter that you weren't there.

The history was being created and indexed, and you can catch up on it. If you end up in a situation where there's a channel for everything that the organization is paying attention to, so for us, that means every customer, every team, every office location, every function within the company, every incident, every event that we're planning, everything, then everyone knows where to go, at least theoretically, to ask their question or to give their update or to get caught up in something, which is very, very different than email.

I think, this is post facto analysis so it's hard to know if this really true or not, but I think that the reason that Slack has been so successful is because we had a three and a half year long design process where we weren't conscious that we were designing it.

In early January, I’ll be stepping down as CEO of Slack. Also, both Tamar and Jonathan Prince are leaving. Slack will have a new CEO: Lidiane Jones. This is good: Lidiane is amazing. More on this below.

(FWIW, this has nothing to do with Bret’s departure. Planning has been in the works for several months. Just: weird timing!)

Tamar and Jonathan arrived within a month of each other at a critical point in Slack’s development as a company. They were both more experienced than me and taught me a lot (probably more than I know, even now). They helped us grow up. Their individual contributions as leaders were indispensable but they were also team players and helped make us an all-star executive team. Their impact will be felt for as long as Slack is around.

Cal remains the CTO which is good because he’s plainly, no exaggeration, the best CTO in the world. And, Slack’s own Noah Weiss is the new Chief Product Officer. In his seven years (!) as part of Slack he’s led product development in nearly every area at one point or another, and the ambition of our product strategy owes a lot to his leadership. He’s going to keep the bar high, and then keep pushing it higher. Congrats, Noah.

So: why?? Well, we started this company 13.5 years ago (though it’s “only” been 10 years since we started development of Slack itself). It’s been a long and wild run. I am not going off to do something entrepreneurial. Though it may sound hackneyed, I actually am going to spend more time with my family. We have a new baby coming in January. Can I tell you something? I fantasize about gardening. So, I’m going to work on some personal projects, focus on health, and try to learn as many new things as I can.

So, about this Lidiane. You’re going to love her. She’s pragmatic and practical, insightful, passionate, creative, kind, and curious. She’s right at that little diamond-shaped heart in the four-circle Venn diagram of Smart, Humble, Hardworking, and Collaborative. Before Salesforce she spent four years leading product at Sonos where she fell in love with Slack. She has a deep respect for our approach to product, our customer obsession, and our unique culture. She’s one of us.

She also has enormous credibility inside of Salesforce and will be an effective advocate for Slack’s business, customers, and people. She earned that credibility as an EVP & GM, leading Marketing Cloud, Commerce Cloud, and Flow through major technology and business transformations. This will be extremely helpful for us over the next few years.

Obviously, there are more details here, but I’m going to let each leader talk about it in their own words. I know this is pretty big news but, if you’ve known me for a while, you’ll know that I just don’t say things I don’t believe. I can’t. So you can trust me when I say that everything is going to be okay. Lidiane, Cal, and Noah already have a great chemistry and are committed to our collective and individual success. Bob is still our Chief Sales & Success Officer, Michael Peachey our SVP of Marketing, Stephen Lee our SVP of Legal, David Ard our SVP of Employee Success, and Robby Kwok is going to keep on Chiefing the Staff for Lidiane.

Thank you for everything. I cannot begin to express my gratitude and it wasn’t till I got to this line that I started crying, so I can tell that’s the heart of it for me. Thank you ❤️

Everyone knows about this six-page Amazon memo and how many of those things can you count? How many times have people actually taken their frustration with the ineffectiveness of certain communications and said, okay, here's what we're going to try? We're going to write a six-page memo, we're not going to have any presentations. Everyone's going to sit in silence and read it all together from the beginning of the meeting, so they really understand we're in the same place, and then we're going to discuss this. That format forces people to come up with a lot more clarity in how they're communicating and all the rationale that goes along with it.

The conversation is that how many days per week do people come into the office. I think that the term hybrid, while it may be useful right now, in 10 or 20 years, it's going to feel like paperless office does now.

It's kind of a quaint and in some sense, bizarre way to think about it. Because the amount of paper in an office is no kind of indication of how effective it is, or even the methods that it employs to operate, because paper is useful in many ways and people getting together physically is useful, but we obviously have the technology today to do what was so exciting for me and others in the nineties, which is transcend geography and transcend, to a large degree, time. The degree to which we take advantage of that, I think will have real productivity impact.

Leaders blame people all the time. Sometimes people are in the wrong role, but if they're in the wrong role, who put them there?

There's a lot of thinking or falling back on the idea that these people are too stupid or they have some other defacto problem that prevents them from doing the thing that your genius mind has envisioned them doing.

That's never the case though. It's on you to figure it out.

People like exercising their talent and improving and learning. I try to take a lot of inspiration on the software product development side, from the way video games work, because if you think about first, you can move and then you can move and jump, and then you can move and jump and shoot. Each level kind of unfolds, introducing a new dynamic for you to master until basically the game ends because the game is essentially one very long tutorial, and once you figure it out, how to play the game, it's over.

I think that's a good approach to making any kind of software, but the satisfaction that people get from that learning is something that feels universal and it cuts across different forms of creativity and different hobbies and different everything. There's nothing more frustrating than having that thwarted. People end up very unhappy at organizations where nothing can get done.

In the work context, it's writing. I don't think I take enough time to leverage that, because if I really work hard in thinking about something carefully and get to that degree of clarity, the impact of something I've written has been certainly disproportionate to the impact of the time I spend in meetings by hour basis.

There's this story I tell in our internal onboarding process of me and our head of project design going for a walk in Vancouver. And our office in Vancouver is in neighborhood that's really narrow, so I'd walk, sidewalks have sandwich boards from vendors out so it's very crowded, you kind of wind around, and so it starts raining while we're on this walk and maybe two-thirds of people had umbrellas with them and we didn't and people are walking towards us on the sidewalk and almost no one would move their umbrella out of the way so that the pocky things wouldn't get us in the eye.

Like I said, the sidewalks were very narrow so we had to keep on ducking. I can come up with many explanations for why this would be, but don't explain with malice that which can be explained by ignorance, so probably it wasn't just that these people have few avenues for exercising power in their lives and they were choosing but this moment to exercise some power, but then there's really only two explanations.

One is that they just walk through the world and they don't see that we're going like this to get away from an umbrella, even though inevitably they had that experience themselves, or they see that this is happening and they're like, "I just can't think of anything I can do to ameliorate the situation."

Despite the fact that it's this, it is tiny, like a hundredth of a calorie worth of effort and a tiny amount of consideration and the point of telling that story is that that's the way, this is a sad way of looking at the world, but that's the way that most people go through the world, they're oblivious to the problems that other people have and if they notice the problems, they're unable to come up with any kind of solution.

Two-thirds of the people just didn't tilt their umbrellas, which means that if you're the kind of person who's willing to tilt your umbrella, there's a whole world of opportunity out there.