Stewart Butterfield

Co-founder & Former CEO, Slack · 3 appearances on the record.

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Stewart Butterfield is the co-founder and former CEO of Slack. He also co-founded the photo-sharing platform Flickr.

47statements → 25claims → 11claims resolved → 64%fully supported → 3.87/5average certainty → 1.38/5average debate potential → ≈4.5/5argument clarity, estimated → 18said about them ↓

7 supported 2 partly supported 2 contradicted 14 not checkable as stated how the 25 claims stand · each chip opens the sources

1 prediction · 24 assertions · 3 opinions · 12 insights · 5 disclosures · 2 what ifs · every statement was checked. The prediction and assertions are the 25 claims: statements the public record can support or contradict. 11 are resolved, and 14 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Stewart argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Butterfield: Slack saw massive surges across every metric during COVID onset
“In the early stages of this, yes, we saw a huge increase in the number of new teams being created, which is kind of people signing up for Slack in the first place, converting to paid status, the customers who are already paid, adding more users the people who …”
Stewart Butterfield May 9, 2020 ▶ 4:38 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes

Their most notable contradicted claim

Assertion Contradicted
Slack sold $1M in software within three weeks of its official launch
“Within maybe two weeks or three weeks of launching that officially, we had sold a million bucks worth of slack.”
Stewart Butterfield Jul 30, 2018 ▶ 46:20 Slack & Flickr: Stewart Butterfield

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Stewart Butterfield on measured tape to publish a rate. This says nothing about how they speak.

Everything Stewart Butterfield said on How I Built This that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
Recurring fundamental doubts about a business or employee are almost certainly correct
“There's a saying, if you're thinking about firing someone, a lot You should just fire them. Meaning that, like, that intuition, if that keeps coming up, it's almost certainly correct, and you wouldn't be thinking that all the time if there was a real shot at m…”
Stewart Butterfield Jul 30, 2018 ▶ 30:49 Slack & Flickr: Stewart Butterfield
Prediction Not checkable as stated
Butterfield: Slack and Many Companies Will Retain Significant Remote Workforces
“One of the big topics is, do you expect to have a significant portion of your workforce remote when this resumes? And universal, yes. So I definitely expect that for us. I expect that for many companies.”
Stewart Butterfield May 9, 2020 ▶ 8:42 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes
Opinion
Butterfield: Non-violent social MMO games are commercially horrible ideas
“It's a horrible idea commercially. Like, it's just, there's not enough people who are interested in it.”
Stewart Butterfield Jul 30, 2018 ▶ 10:44 Slack & Flickr: Stewart Butterfield
What-if
Butterfield realized Glitch could never justify its $17.5M venture investment
“It was never going to become the kind of business that would justify 17 and a half million dollars of venture capital investment.”
Stewart Butterfield Jul 30, 2018 ▶ 30:33 Slack & Flickr: Stewart Butterfield
Insight
Email fundamentally cuts new employees off from historical company knowledge
“In email, if you join a company that has been around for 30 years and has been using email since its inception, You get an empty inbox. You're completely cut off from the whole history of what's happened before you got there. And almost all of the email, like,…”
Stewart Butterfield Jul 30, 2018 ▶ 35:52 Slack & Flickr: Stewart Butterfield
Assertion Not checkable as stated
Butterfield: Slack's first two remote weeks were its most productive ever.
“The first and second week after work from home order were probably the two most productive weeks in the history of the company.”
Stewart Butterfield May 9, 2020 ▶ 7:33 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes
Insight
Butterfield: Teams Shifting from In-Person Meetings Should Over-Invest in Written Communication
“I think if you didn't have to rely on it before, if you were really reliant on in-person meetings to kind of get work done or get decisions made yeah, over invest in, in written communication and experiment with video tools to find the ones that work.”
Stewart Butterfield May 9, 2020 ▶ 7:50 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes
Insight
Butterfield: Internet's Significance Will Match the Invention of Written Language
“And I think when we look back tens of thousands of years to this time, it will seem as significant as the development of written language, because it just allows this accretive knowledge allows the accessibility, it allows this instant communication and coordi…”
Stewart Butterfield Jan 30, 2020 ▶ 4:28 Live From The HIBT Summit: Stewart Butterfield
What-if
Glitch might have survived if it had not bet on Flash
“And we had made a bet On Flash as a technology for delivering the game, which wasn't going to work on mobiles, and I think in the end that, that really was the nail in the coffin. If it hadn't been for that, I think it would have been worth trying a little bit…”
Stewart Butterfield Jan 30, 2020 ▶ 6:52 Live From The HIBT Summit: Stewart Butterfield
Insight
Butterfield: Shutting an online community is like ending a small civilization
“Any of you who have participated in online communities, especially in the early days, where, like, the online community was the nexus of all of these friendships and all these relationships, when they disappeared, that's it. Like, people can say, we're gonna m…”
Stewart Butterfield Jan 30, 2020 ▶ 9:38 Live From The HIBT Summit: Stewart Butterfield
Assertion Not checkable as stated
Only 8 of 45 Glitch employees stayed to build Slack
“So there's 45 people at the company, and eight of them were going to stay on to work on Slack. So for the other 37 people, we did kind of career coaching. We wrote reference letters. We set up interviews for them. We ended up getting everyone a job”
Stewart Butterfield Jan 30, 2020 ▶ 10:28 Live From The HIBT Summit: Stewart Butterfield
Opinion
Slack's biggest challenge is creating a brand-new software category
“I think we still face that as a major challenge for Slack, because it's like a brand new category of software that doesn't really replace anything specific that you were using before.”
Stewart Butterfield Jan 30, 2020 ▶ 12:10 Live From The HIBT Summit: Stewart Butterfield
Disclosure
Flickr was initially built to be sold for $1M to fund gaming
“And that thing ended up being Flickr, and I think when we started it, the intention was, we'll build this, and someone will buy it for, like, a million dollars, and then we can use that million dollars to finish the game.”
Stewart Butterfield Jul 30, 2018 ▶ 12:06 Slack & Flickr: Stewart Butterfield
Opinion
Modern venture investors would unanimously advise against Flickr's early $20M acquisition
“I mean, like, a hundred percent of the time, they would give the opposite advice today.”
Stewart Butterfield Jul 30, 2018 ▶ 21:48 Slack & Flickr: Stewart Butterfield
Insight
Butterfield: Working with a spouse during an early startup is uniquely stressful
“It's pretty challenging to work with your spouse, especially in the early days of a startup, so this is going back many years now, when we first started working on Flickr, like, out of money, and it's not just the business is out of money, it's like, we're out…”
Stewart Butterfield Jul 30, 2018 ▶ 25:48 Slack & Flickr: Stewart Butterfield
Assertion Not checkable as stated
Investors treated the Slack pivot like buying another lottery ticket
“None of them wanted their money back, and not for altruistic reasons, but we had already spent two-thirds of it, so their options were, like, we can get back a third of what we gave you, or they can buy one more lottery ticket and say, keep the money we'll kee…”
Stewart Butterfield Jul 30, 2018 ▶ 39:42 Slack & Flickr: Stewart Butterfield
Insight
Unlike most enterprise software, Slack requires unanimous team buy-in to work
“Unlike most software, you can't unilaterally decide to use Slack with your colleagues. Everyone has to buy in.”
Stewart Butterfield Jul 30, 2018 ▶ 42:32 Slack & Flickr: Stewart Butterfield
Assertion Contradicted
Slack sold $1M in software within three weeks of its official launch
“Within maybe two weeks or three weeks of launching that officially, we had sold a million bucks worth of slack.”
Stewart Butterfield Jul 30, 2018 ▶ 46:20 Slack & Flickr: Stewart Butterfield
Insight
Organizational alignment dictates success more than an individual leader's strategic decisions
“What I found is what matters is performance at the level of the organization. Cause to the degree that everyone's pushing in the same direction, you're able to achieve something. If people are pushing in opposite directions, then, you know, you can put as much…”
Stewart Butterfield Jul 30, 2018 ▶ 51:22 Slack & Flickr: Stewart Butterfield
Insight
Butterfield's three tiers of wealth: debt-free, ignoring menus, ignoring vacation costs
“I really feel like there's kind of, there's three levels of wealth in the world. The first level is, I'm not stressed out about debt. Like, people who no longer worry about their credit card bills or their student loans, that's like level one of wealth. Yeah. …”
Stewart Butterfield Jul 30, 2018 ▶ 53:21 Slack & Flickr: Stewart Butterfield
Assertion Supported
Butterfield: Slack saw massive surges across every metric during COVID onset
“In the early stages of this, yes, we saw a huge increase in the number of new teams being created, which is kind of people signing up for Slack in the first place, converting to paid status, the customers who are already paid, adding more users the people who …”
Stewart Butterfield May 9, 2020 ▶ 4:38 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes
Insight
Butterfield: Channeling energy to help in a crisis calms personal anxiety
“In times of crisis like this, I think people have a really strong instinct to help. And if there's a place for you to put that energy it's not just productive and effective. It's also kind of spiritually calming. You're less anxious if you're, if you feel like…”
Stewart Butterfield May 9, 2020 ▶ 5:16 How I Built Resilience: Live with Stewart Butterfield and Steve Holmes
Disclosure
Butterfield: Glitch had capital left over when the company shut it down
“In fact, we had money left over when we decided to shut it down, but it was apparent that it wouldn't work”
Stewart Butterfield Jan 30, 2020 ▶ 5:21 Live From The HIBT Summit: Stewart Butterfield
Disclosure
Butterfield left $10M in equity for a $35K buyout before dot-com crash
“And so around the end of February of the year, 2000, I quit. I walked away. I thought I was walking away from like ten million dollars in equity. And I got bought out for 35,000 dollars on my way out.”
Stewart Butterfield Jul 30, 2018 ▶ 6:49 Slack & Flickr: Stewart Butterfield

Show 23statements(23 left)

The other half of the tape: Stewart Butterfield's own voice is left out of every number here. Other people bring the name up 18 times in 13 episodes on How I Built This. every mention, with the transcript →

Who brings them up most Guy Raz 18

Every mention by year

tap a year for its mentions
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035201820192020202120222023episodes it came up in
0022.545201820192020202120222023episodesmentions per episode
2023 4 mentions in 1 episode
2021 1 mention in 1 episode
2020 6 mentions in 5 episodes 1 per episode
2019 5 mentions in 5 episodes 1 per episode
2018 2 mentions in 1 episode

Appearances (3)

EpisodeDateSpeaking time
How I Built Resilience: Live with Stewart Butterfield and Steve Holmes May 9, 2020 7m
Live From The HIBT Summit: Stewart Butterfield Jan 30, 2020 11m
Slack & Flickr: Stewart Butterfield Jul 30, 2018 39m
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