The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 80 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Crusson: Slack was pretty much destroyed by Microsoft Teams
“At that point, Microsoft launched Teams, and I don't know if you remember this moment where Slack put an ad in the, I think it was the New York Times, copying the Apple versus Microsoft thing from ages before, going, you know, welcome to the game, welcome to t…”
Butterfield: Employees instinctively push to hire direct reports to boost status
“The overwhelming majority of people you hire want to hire more people who report to them. And it's not because they're evil and it's not because they're stupid. In fact, they're smart because everyone knows that the number of people who report to you correlate…”
Baxley: Slack and Pinterest Struggled Because They Lacked Long-Term Vision
“Slack and Pinterest, I think are examples of companies products that became companies, but neither one of those places really knew what to do next because they didn't have a bigger vision of the change they were trying to see in the world.”
Yehoshua: Design for tomorrow's larger user base, not today's
“The number of people using your product today is usually, unless you're a Google, far smaller than the number of people are going to be using your product tomorrow. So design it for the people, the bigger number of people who are going to be using it tomorrow.”
Weiss: Microsoft built Teams defensively to protect Office against Slack
“I think, you know, the origin of Teams really was a defensive move for them to protect Office, because Office is an incredible, very profitable kind of monopoly in the productivity space. And so I think when they built Teams, it was more of a kind of covering …”
Silber: Proactivity and external context will transform ChatGPT user interaction
“I think proactivity is a big untapped kind of part of the experience that we're really excited to think about. You know, we're starting to see this with ChatGPD work now where it actually has pretty good suggestions based on, you know, your calendar or your Sl…”
Fung manages engineers via Claude sessions connected to all repos and Slack
“The other shift that I've recently done is I actually have a quad code remote session that I enlist in all of our repos. And so this way I have full visibility into the work that everybody's doing. And this instance, he also has access to all our Slack channel…”
Pincus: Slack succeeded with proven and better features without anything new
“Slack was a great example because I think Slack might've just been proven and better and no new. And that's even better.”
Willison: StrongDM used coding agents to simulate Slack, Jira, and Okta APIs
“So what they did is they built their own simulation of Slack and Jira and Okta and all of this software they were integrating with. And the way they did that is they basically took the API documentation for the public APIs for Slack and the client libraries, t…”
Butterfield: Designers should reduce cognitive burden instead of click count
“And if we, if people could get over the idea of reducing friction as a number of goal or reducing the number of clicks or taps, do something, and instead focus on how can I make this simple? How, how do I prevent people from having to think in order to use my …”
Butterfield: Leaders who fail to see endless product flaws should not run companies
“If you can't see almost limitless opportunities to improve, then you shouldn't be designing the product, or you shouldn't be in charge of the company”
Butterfield: Slack wouldn't have grown without emotional product conveniences
“It wouldn't have grown the way it did without those little conveniences which caused people to form an emotional connection because a lot of our growth came from, you know, startup A uses Slack, and then someone leaves startup A for startup B, and startup B do…”
Butterfield: Highly differentiated products require building the product and market simultaneously
“If your thing is different in any significant way from the alternatives you're not just creating the product, you're creating the market. They're really kind of one and the same.”
Block engineer built an ambient AI setup that autonomously drafts pull requests
“And so he built this system where it's essentially just watching everything he does all the time. And he'll be talking to a colleague on Slack or an email, and they'll be discussing some feature that they think is useful to implement. And then a few hours late…”
Houston: Slack-like collaboration tools fragment time and cause cognitive overload
“Things like slack which are wonderful tools also chop up your day into little fragments and sort of make you like cognitively diabetic. Cause there's like a lot of empty carbs. In our collaboration and our collaboration tools.”
Yehoshua: Stewart Butterfield is Silicon Valley's best product thinker
“I think he is the best product thinker in the valley, or he's not working in product right now. He's taking time off, but he's got this combination of long-term thinking in, in the details.”
Berger: I was fired from Slack three separate times
“I was fired from Slack three different times, which I feel like has to be some kind of startup record.”
To protect deep work, check email once daily and Slack hourly
“Turn off notifications. Quit Slack. When you're doing deep work, check your emails once a day and just like literally go through them in like five minutes. They're off the times. Most of them are useless. Check Slack only at the top of the hour.”
Weiss: Adding user clicks can often improve non-transactional software UX
“There's a saying we also have, which is more clicks can often be okay. You know, you often have in, you know, optimization, you know, experimentation circles, like, oh, every click, remove it. But I actually think in a lot of software when it's not transaction…”
Weiss: Teams evolved into a video conferencing tool competing with Zoom
“I think as Teams has evolved over time, it's become much more of a video conferencing product that competes with like Zoom and Google Meet, the people who use Teams use it completely different than Slack where you live and breathe and channels and work and kin…”
Weiss: Fully automated AI 'chief of staff' for Slack won't arrive soon
“I don't think that's gonna quite be possible anytime soon, but I think like Spotify heading towards that north star, you end up developing, I hope a lot of really compelling projects for instance along the way.”
Shipper: Workplace AI agent interactions will happen mostly in Slack
“I think there's this little thing in people's heads where they really like to keep their personal and work agents separate. And I think there's a whole territory. Our COO Brandon Gell calls this computer errands. There's like this whole territory of using pers…”
Butterfield: Slack was first to scale and standardize magic links
“Someone else invented, I want to be clear that I had seen that idea somewhere else, like someone else, a blog post about it or something like that, but we were the first ones. To my knowledge, that, that really kind of, like, scaled that and made it a standard…”
Butterfield: Glitch was abandoned with $9 million in capital remaining
“We still had like nine million dollars left and everyone still liked the game and we were all happy working on it. But I think by that point I had exhausted every non-ridiculous long shot idea to make it commercially successful. And so Decided to abandon it.”
Mike Krieger says Claude has 'no chill' in group Slack channels
“I like to say internally, like Claude has no chill. Like if you put Claude in a Slack channel, it will chime in either way too much or too little.”
Truell: Future IDEs will integrate external surfaces like Slack
“So I think that, you know, what the IDE is will totally change over time. And kind of our approach to, you know, having our own editor with premise non, it's gonna have to evolve over time. And I think that that will both include, you can spin off things from …”
Kao: The organizational blast radius of poorly written memos is heavily underestimated
“I think the blast radius of a poorly written memo is way bigger than most people think. So if you're just shooting off a message in a Slack channel with 15 other people, and it's confusing, and you didn't include information you should have included, there's g…”
Bolt is developing an agentic Slack bot to act as team developer
“We're actually creating a you know, like a bolt, like Slack bot that's whose job is to Basically act like a developer on your team. And so you can be like, in a thread, you can be like, Hey, I think we should add a homepage. It's like, yeah, okay. Like at bolt…”
Rachitsky: Reader Survey Ranks ChatGPT Ahead of Gmail and Slack
“I did a survey of my readers and asked them what tools to use every day in your work and most use. And ChatGPT was Number one above Gmail, above Slack, above anything else. 90% of people said they use ChatGPT regularly.”
Houston: SaaS productivity companies commonly suffer from a 'sophomore slump'
“Many in SAS SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next platinum album. Right. So, you know, Dropbox has fallen into that category. Yo…”
Shopify moved all large group announcements off Slack to Meta Workplace
“What we did was we moved all announcement information. So like anytime you're sending a status update or large group announcement, we moved all of that to like Facebook meta workplace, like Facebook for work, basically which is now being deprecated. So we'll h…”
Stewart Butterfield's 2014 Slack master plan already included AI
“So in 2014, he wrote a master plan for Slack, which was build a product people love. Build a network that Slack connect, build a platform that makes all of your other SaaS products more valuable, the Slack platform, and then do some magic AI stuff.”
Raviv has avoided opening Slack before noon for eight years
“I block off my morning from meetings. You know, a lot of people give that tip. I go even further and I don't open Slack before noon. I've been doing this for eight years. I don't open Slack at all”
Crusson: Atlassian targeted tech teams while Slack targeted business teams bottom-up
“Atlassian was going after the users in tech teams. Slack was going after the users in business teams. And in both cases, what happened was a bottom up adoption.”
Crusson: Competitor feature launches reflect research from a year earlier
“Your competitor, like if you think of what they do as an iceberg, like the top side, what comes out of the water is what they've shipped in terms of features, but it's based on all this stuff that they've built in terms of research. An understanding of their c…”
GitLab bans internal email in favor of public issues and Slack
“GitLab is very anti-email in a lot of ways. Obviously we use it for external communication, but internally it's on an issue. It's in Slack or it goes into the handbook, right?”
Character VC uses Notion over Slack and email to reduce urgency
“At Character, at our VC fund, we Had a conversation and decided we're going to try to have our main communication happen in notion so that if we're talking about something, it's in a form, it becomes a document, and the expectation of how you react and respond…”
Scott: I fired a coaching client for giving feedback over Slack
“I once coached someone who kept giving feedback over Slack and I finally just quit coaching him. I was like, I, if you keep making this mistake, I'm not, I can't be your coach.”
Weiss: Incubating product teams must be exempt from quarterly reviews
“And I think when we have those teams, I think it's important to just give them space to run, to give them kind of a gel free card for maybe the normal process of, you know, okay, our planning quarterly reviews and make it feel something that is like the pace o…”
Weiss: Most PMs, designers, and engineers joining Slack lacked enterprise software backgrounds
“Certainly the majority of PMs, designers, and engineers who joined Slack had never worked at an enterprise software company before. It's not like most people had worked at Oracle or SAP. It's most people had worked at consumer companies or game companies, and …”
Weiss: Living in your own software blinds teams to beginner user friction
“If you work on Figma or you work on Slack, you also live in Slack and you live in Figma all day. So you can become more of a power user than anyone else on earth. And what we were realizing, especially for people trying to build Slack for the next million cust…”
Noah Weiss: Prototyping real software beats static design mocks
“By far the biggest thing, which is more of a cultural shift is that we stopped spending so many cycles on design explorations of like static mocks or walkthroughs and said, how quickly can we get into prototyping the path in real software? Even if it's messy a…”
Weiss: Software creators' 'owner's delusion' prevents building simple products
“Often, actually, that kind of owner's delusion that someone else will care as much about the software that you built as you do prevents you from actually making something that's simple, comprehensible, understandable”
Weiss: Five Active Users Made Slack Teams 400% More Likely to Upgrade
“What we found was that if you could get five people using Slack the majority of the work week to just communicate at all, that would be a successful team. They're going to be 400% more likely to upgrade over the next six months.”
Weiss: Slack is testing internal prototypes of conversational AI bots
“I can safely say we have a lot of prototypes internally where we are playing with this.”
Weiss: Product-Market Fit Is a Stack of S-Curves Across Audiences
“Product market fit is almost like you keep stacking these S curves where you get product market fit in a small group, and then you suddenly reach like exponential growth because you can crack that whole group, that type of audience. But then you start declinin…”
Mixpanel gives engineers direct, unfiltered access to all customer feedback feeds
“What this created was this culture where all engineers and designers could consume that raw feed of direct points of customer with no gatekeeper, no process to access it, no pre-aggregation.”
Walter: Interviewing skills are critical for PM career growth via top companies
“The other skill that I'll also call out, which nobody talks about for some reason is interview skills, you know, because so much Of what gives you a chance to become better as a PM is working at a great company. And how do you get that job beyond networking is…”