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" I remember working with a guy named Andrew Braccia at Yahoo, and Yahoo was the company that bought Flickr. Everyone on his team was hard working and reliable, did what they said they were going to do, on top of everything, and seemed to be operating at this level of productivity and effectiveness that I found difficult to manage to. "

Stewart Butterfield

Difficult

Company

Remember

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" It's very difficult to design something for someone if you have no empathy. "

" People sometimes forget how early Flickr came. Facebook didn't add photo sharing till a year after Flickr was acquired by Yahoo. "

" Email is the lowest common denominator. It's the way you get communications from one person to another. There isn't really an alternative. Sometimes people will have Facebook messenger turned on, but 99 percent of the time, if you're sending a message to a human you don't know well, you're using email. "

" It's easy to hire too fast and have chaos and disorganization and insufficient management. "

" Inside a company, you can mandate that everyone use the same technology, which means you can go a little bit, I don't know, higher fidelity than the lowest common denominator technology. "

" I think of myself more as a designer than a serial entrepreneur. As a designer, the easiest way to see that something happens is to start a company and then be the boss, and then people have to do what you say. "

" At my first job in the mid-to-late '90s, almost every product was from Microsoft. Everything was designed to work together - Windows for workgroups, shared M drives, etc., etc. "

" There's a lot of automation that can happen that isn't a replacement of humans but of mind-numbing behavior. "

" I almost never go to news sites - it's overwhelming how much content is out there. But I will pay attention to what my friends are picking up and sharing. "

" If you work at a 10,000-person company, and you're using e-mail as the primary means of communication, then you probably have access to a couple hundredths of 1 percent of all the communications happening across the company. But if you use Slack, you might have access to 10 or 20 percent. "

" You may be trying to drive in a particular direction that people don't necessarily understand at first. In our case, we knew the users we had in mind for this product. So in the early days, we looked at our customers, really just testers at that point, and we paid extra attention to the teams we knew should be using Slack successfully. "

" The most productive employees, from my experience, are those who go home at 5:30 P.M. but are hyperfocused at work. People can only think really hard for six to eight hours a day. "

" Sometimes you will get feedback that is contrary to your vision. You may be trying to drive in a particular direction that people don't necessarily understand at first. "

" For the first five years of my life, I grew up in a log cabin in coastal British Columbia in a very small town, like 300 people, mostly hippies. No running water, no electricity. When I was 12, I changed my name from Dharma to Stewart. At that age, you just want to be normal. "

" One advantage that I think Slack has for most people who use it is, you pull out your phone, you look at the home screen, there's the Slack icon. You know when you tap this one, it's all the people you work with, and it's only the people you work with. And that's a big advantage. "

" There was a lot of dialogue between the people who were developing Flickr and their users to get feedback on how they wanted Flickr to develop. That interaction made the initial community very strong, and then that seed was there for new people who joined to make the community experience strong for them, too. "

" The social use of Slack does drive awareness - it's a good thing for us. "

Stewart Butterfield

Use

Social

" I don't think it ever occurred to me that I wouldn't be an entrepreneur. My dad became a real estate developer, and that work is usually project-based. You attract investors for a project with a certain life cycle, and then you move on to the next thing. It's almost like being a serial entrepreneur, so I had that as an example. "

" One of the advantages of something like Slack is that I tap on the app icon, and it's just the people at my company and just the people I work with. There's a strong boundary there which aids in comprehension. It's one less molecule of glucose in my brain to manage it all. "

" I think tech lives inside of a society that still has a lot of systemic racism and doesn't stop at the boundaries of the tech industry. But neither is it especially exacerbated by being around technology. But it is maybe exacerbated by the irrational decision making of people who are trying to make money. "

" I think we are reluctant to move people out of an organization when there is not a good fit. It is typically not because someone is stupid or lazy or incompetent; it is a lot more subtle than that. "

" I had hippie parents, and I found it difficult to figure out how to rebel against them. "

" I tend to be a lot more honest and transparent with employees than most bosses are. But I've had people tell me - even those who love working with me - that I'm terrifying, which is hard for me to imagine. "

" I think email's going to be around for, like, another 10,000 years. It's a great way to cross organizational boundaries. "

" Silicon Valley is the engine for wealth creation. They've displaced energy, they've displaced financial services, and if we don't start including a broader array of people in that, the same group of people is going to rise to the top. "

" We'd never make Slack an email client, but it's good to support sending emails into it. There's quite a bit of formatting you can do. When I get an email from the outside world that I want to share with team, I cut and paste it into Slack. But really, I should be able to import that email as an object. "

" It's hard to overestimate how much the perception of the quality of the V.C. firm you're with matters - the signal it sends to other V.C.s, to potential employees, to customers, to the tech press. It's like where you went to college. "

" Email will probably be around for many decades to come. It's hard to say what will happen 20 years from now, but email has been around for decades, and it will likely be around for decades more. "

" I rarely in a working day go more than 10 minutes without looking at Slack. "

Stewart Butterfield

Without

Working

" I have a couple of things I do to clear my head when I need it. The first is exercise, the kind of exercise that makes me lie on the floor afterward gasping for breath and wonder if I'm actually going to be able to breathe enough to not die. The other one is playing music. "