Stewart Butterfield

摘要

Daniel Stewart Butterfield（出生名 Dharma Jeremy Butterfield，1973 年 3 月 21 日生于不列颠哥伦比亚省 Lund 一个嬉皮公社的小渔村）是少数被同行公认为"两次靠 pivot 救活公司"的连续创业者——Flickr（来自一款失败的 MMO 游戏 Game Neverending）与 Slack（来自一款失败的 MMO 游戏 Glitch 团队内部 IRC 工具的副产品）。他的轨迹是几乎所有标准创业书都难以塞进同一个模板的：一个 Cambridge 哲学硕士（专攻生物学哲学与认知科学）、一个 越战逃兵之子在无电无水的小木屋里度过前 5 年、一个把 Yahoo 辞职信写成连续段落的"锡匠世家诉苦"的奇人、一个把自己产品在 MIT Technology Review 上公开称为 "a giant piece of shit" 的 CEO、一个在公司 IPO 时选了不需要的 direct listing 把 700 名员工一夜变成百万富翁的董事长——也是一个在 Salesforce 收 Slack 后 18 个月就以 "fantasies about gardening" 为由真的退休回到 Tom Ford 的 20,000 英亩新墨西哥牧场的人。

他的核心信念可以浓缩成几句反复出现的语录。"We Don't Sell Saddles Here. They are in the business of selling the dream of horseback riding."（2013 年 7 月 31 日内部备忘录，定义了 Slack 的 GTM 哲学，被多所商学院列为案例。）"It became an assumption that you should always be trying to remove friction when the challenge is really comprehension."（2025 年 Lenny 播客上的反产品箴言。）"The job of a CEO is often just to come up with a story that enough people believe that you can make something happen in the world."（2017 年 Masters of Scale 上对自己角色的定义。）"The reason I say you have to be coldly rational about it is because it's fucking humiliating."（关于关闭 Glitch 那一夜——他说创业者最难的不是承认输了，而是公开承认输了。）

他也少见地公开谈论"sufficient known valuable work to do"是 CEO 第一职责的反组织学观点、"hyper-realistic work-like activities"（看起来像工作的伪工作）的概念、"three levels of wealth"（不担心债务 / 不在乎餐厅菜单价格 / 不在乎度假费用，再往上"都差不多"）的财富哲学、以及"如果你的工程师不开心，他们大概率没在生产"的领导直觉。他是科技 CEO 中罕见的"哲学家退休派"——离任 18 个月后接受 Lenny 采访时坦言 "I'm mostly just chilling"，没有下一家公司，没有书要写，没有 podcast 要做。

一、生平时间线

第一章：Lund 公社童年与"Dharma"身份的起源（1973–1978）

1973 年 3 月 21 日，Dharma Jeremy Butterfield 出生于不列颠哥伦比亚省（British Columbia）一个名叫 Lund 的小渔村。这个村庄位于温哥华以北、Sunshine Coast 公路的尽头（North America's "End of the Highway"），住户当时不超过几百人。

他的父亲是逃避越南战争征兵令的美国人，1960 年代末期带着家人北迁加拿大，落脚在 BC 海岸的一个公社（commune）。前 5 年 Stewart 与父母住在一座没有自来水、没有电的小木屋里——这一事实后来被 Mat Honan 在 Wired 的封面专访 [12] 写进开篇，也被他自己在 Masters of Scale [10] 上反复讲述。

他在 Masters of Scale 上自己评价这段早年公社经历对自己的塑造：

"I'd like to say that some of that 'no running water, no electricity' rubbed off in me in an Abe Lincoln kind of way. But I don't know if that's actually true."

"我倒是想说，这种'没自来水、没电'多多少少像林肯那样塑造了我。但我也不知道这是不是真的。"

Masters of Scale, 2017

在同一次访谈他把童年对父亲的最深印象之一——一个看似无关紧要、但后来反复成为他对"游戏"和"产品"思维框架的事——讲了出来：

"My dad loved to play bridge, and he didn't like playing bridge against the computer — there was just nothing there. He also wouldn't have invited the same three people over to his house just to hang out and do nothing. But inviting them over to play bridge and there was this magic. It's exercising a part of your brain which is fun to exercise, but there's also camaraderie, and there's trash talking, and there's a good amount of competition."

"我爸爱打桥牌。他不喜欢跟电脑打——电脑里什么都没有。他也不会主动把同样三个人邀来家里只是为了发呆。但邀他们来打桥牌就有一种魔力。它在锻炼你大脑里一个有趣的部分；同时也有同伴感、互相嘲笑、还有相当程度的竞争。"

Masters of Scale, 2017

"It's not games that are so interesting to me, it's play as an excuse to interact with people socially."

"我感兴趣的并不是游戏本身——而是把玩当作社交的借口。"

Masters of Scale, 2017

这两句话后来被他自己回看为四款产品（Game Neverending / Flickr / Glitch / Slack）的共同精神祖先。他在 Invest Like the Best 上明确把这个内核串起来：

"All four of those, the two games, Looker [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... establishment of identity and participation or interaction and the gradual accretion of the residue of those interactions that increases in value over time."

"那四个东西——两个游戏、Flickr、Slack——在我看来本质上是同一件事。都是用计算机技术促成人际互动……身份的建立、参与或互动、以及这些互动随时间沉淀下来的'残渣'不断积累出价值。"

Invest Like the Best, 2021

改名为 Stewart（约 1985）。 他在 12 岁那一年自己决定从 Dharma 改名为 Daniel Stewart Butterfield。Wikipedia [01] 与 Mat Honan 的 Wired 专访 [12] 都记录了这件事，但他本人在公开访谈里很少展开细节——只在被问到时承认确实是 12 岁自己决定的，不是父母的主意。一个出生在公社、被取了印度教/佛教意义的孩子，在大约准备进入正式中学教育的节点把名字换成一个稳重的苏格兰名字——这件事本身就是他后来风格的预演：精心设计自己出现在世界面前的方式。

"I was interviewing to go to this private school in Victoria, British Columbia, where I grew up. They asked me what I want to be when I grow up and I said, President of the World and the World's First Trillionaire... I think it's a very strategic answer [those schools are always fundraising and having a trillionaire alumnus would be of great benefit to them]."

"我当年面试 Victoria 的那所私立学校。他们问我长大想做什么，我说：'世界总统兼世界第一个万亿富翁。'……我觉得这是一个非常有策略的回答——这些学校永远在筹款，要是有个万亿富翁校友对他们将是巨大的好处。"

20VC, 2020

这种"7 岁就知道讨好考官但选了一个无人会信的极端答案"式的混合智识与玩世不恭——后来反复出现在他的辞职信、产品备忘录、IPO 路演里。

第二章：Victoria 与哲学训练（1978–2000）

家庭：被多次创业熏陶的童年

Stewart 在 Stanford GSB View From The Top [223705] 上把童年环境概括为"持续观察父母经营生意"：

"Over the course of my childhood, once I was aware of what was going on, [I saw] maybe five or six different businesses. And that was good practice. I think I started looking at the world that way."

"我的整个童年里，等我懂事之后，我大概看着我父母经营了五六门生意。那是很好的练习。我从那时开始就用那种视角看世界。"

Stanford GSB View From The Top, 2020

他在多次访谈里都强调，这种"反复看到一家从筹款→愿景→计划→执行的小生意周期"是比 MBA 更早的创业教育。

母亲是他后来"反思式乐观"思维方式的根源——他在 Stanford GSB 上讲了一个 16 岁车祸的故事：

"My mom is incredibly supportive to the extent that when I was 16, I got in a car accident, just totaled the car, my dad's car. And my mom's reaction was, well, it's really good that you did that because you learned an important lesson about driving safety. which is not the reaction I was expecting."

"我妈对我支持到这种程度——我 16 岁那年出了车祸，把我爸的车撞报废了。我妈的反应是：'嗯，你做了这件事其实是好事，因为你学到了重要的交通安全教训。'这不是我预期的反应。"

Stanford GSB View From The Top, 2020

这种"把失败重新框定为数据"的母亲反应模式，后来在他对 Glitch 关闭、Yahoo 辞职、Slack 早期挫折的处理中反复显现。

UVic 与哲学的偶然选择

1992 年（19 岁），Stewart 进入 University of Victoria，主修哲学。他在多次访谈里反复声明这个选择毫无浪漫色彩——是用排除法选出来的：

"I really wanted to do a degree in cognitive science, but the school that I went to didn't have cognitive science... Philosophy is a pretty light set of requirements, even to do an honors degree. So I chose philosophy literally like that. It was like of those four [computer science, psychology, linguistics, philosophy], the one that had the fewest requirements. But after I started studying it... the fundamentals of philosophy I found super fascinating."

"我本来想读认知科学，但我的学校没这个专业……哲学的必修课最少，即使是 honors 学位也一样。所以我选了哲学，就是这样——这四个里面（计算机、心理学、语言学、哲学）必修最少的那个。但我开始学之后……发现哲学的基本问题极其迷人。"

Stanford GSB View From The Top, 2020

他在 2185180 (Invest Like the Best) 上详细谈过自己后来对哲学的实质性态度——它既是一个"枯燥的、被剥皮过的"学科（其他学科都从哲学里独立了出去），也是一个"无穷无尽的不可回答问题的来源"：

"At some point, everyone was a philosopher. If you were interested in the world in an areligious way... Things like biology in the 19th century split off into its own discipline and psychology, anthropology, sociology, computer science, linguistics, women's studies. Until all you had left was like an area of inquiry that is not directed at anything except for itself and language. So in one sense, it's really boring... but once you're into it, I still find it really fascinating because there's so many unanswerable questions."

"在某个历史时期，所有人都是哲学家。如果你是用一种'非宗教'的方式对世界感兴趣……生物学在 19 世纪独立出去，然后心理学、人类学、社会学、计算机科学、语言学、女性研究……一个接一个分出去，剩下来的就只是一个不指向任何具体对象、只关心自己和语言的探究领域。所以某种意义上它确实很无聊……但一旦你进入它，我至今仍觉得极其迷人，因为有那么多不可回答的问题。"

Stanford GSB View From The Top, 2020

1992 年第一次上网：Usenet、IRC 与"逃离地理"

他大学一入学就接触到 internet（1992 年）。这是他自己回望时认为最重要的童年/青年事件——比哲学课更重要的"形成事件"：

"For someone who grew up feeling at a remove to the greater world, the idea that you could transcend geography and you could transcend time and you could find these communities of interest was really just magical. And so 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."

"对于一个从小就感觉与广阔世界存在距离感的人来说，'你可以超越地理、超越时间、可以找到属于兴趣的社群'这个想法简直就是魔法。从那一刻起，'用计算机技术促成人际互动'就是世界上最有意思的实用想法。"

Invest Like the Best, 2021

他第一次接触的协议包括 Usenet、email、IRC、Unix Talk——IRC，这个 1989 年的古老协议，22 年后会变成 Slack 的起点。

他对早期互联网的描述带有刻意的去英雄化色彩：

"It was a nerve-wracking and very irritating thing to use. You can see people backstaging to fix their typos."

"用起来真是又紧张又烦人。你能看见人在后台修自己的错字。"

Invest Like the Best, 2021

这种对"现实里的、不完美的、技术体验"的关注，后来在他对 Slack 通知设计、注册流程设计、@channel 滥用治理上反复出现。

Cambridge：从"想留下"到"被劝退"

1996 年从 UVic 拿到哲学 BA 之后，Stewart 申请到剑桥大学（Clare College）攻读哲学硕士（MPhil），论文方向是 19 世纪科学思想史、生物学哲学与认知科学。

1998 年 MPhil 毕业之际，他在 Mat Honan 的 Wired 专访里坦言对未来的迷茫：

"By the time I finished my master's degree I really had no idea of what I was going to do except for be an academic because, you know, the big five philosophy firms aren't always hiring."

"硕士读完时，我真的不知道自己除了'当学者'之外能干什么——你也知道，'五大哲学公司'并不总是在招人。"

Mat Honan, Wired

但他随后被两位本科时期的教授劝退了学术路径。他在多次访谈里把这次反复出现的"老师对我说，别走学术这条路"作为人生关键介入：

"I had advice from a couple professors over the course of my career who essentially were, this is a terrible life, please don't become an academic... So I took that advice."

"我整个学术早期收到过几位教授的建议，本质上都是同一句话：这是一份糟糕的生活，请不要走学术。……我听了他们的建议。"

Stanford GSB View From The Top, 2020

具体在 Invest Like the Best 上，他更详细地描述了一位本科教授的话：

"you don't want to do this. If you love it, you can subscribe to the journals, you can go to the conferences and you're good at it. But I wish that I wasn't a professor and I started in the 60s and have graduated hundreds or even thousands of PhDs and they're all looking for jobs."

"你不会想做这个的。如果你爱它，你可以订阅期刊、可以去会议，你也擅长这个。但我希望我自己不是教授——我从 60 年代开始干，已经培养了几百甚至几千个 PhD，他们都在找工作。"

Invest Like the Best, 2021（转述教授原话）

"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. And I think if he [my professor] hadn't done that, I very likely just would have ended up an academic."

"98 年我做出了放弃 PhD 项目、去互联网工作的选择——那时候互联网很新、很令人兴奋、工资是任何哲学相关工作的两倍。如果他（我那位教授）没有那么劝我，我很可能就成了一个学者。"

Invest Like the Best, 2021

Gradfinder 与"5K 大赛"（2000–2001）

1998–2000 年间，Stewart 在 dot-com 圈做自由 web 设计师，并创立了一项叫做 "The 5K Awards" 的小竞赛——参赛网页必须把全部资源（HTML/CSS/JS/图片）压缩在 5KB 以内。这是当时设计师圈著名的 craftsmanship 比赛之一，吸引了大量极客参与。这个比赛预示了他后来对"约束催生创造力"和"细节克制"的偏好。

2000 年 2 月，他离开自己第一份 dot-com 工作（就在 dot-com 崩盘前夕），跟 Jason Classon 一起把 Classon 的一个想法分拆为 Gradfinder.com——一个让校友们重新联系彼此的网站。Gradfinder 在 dot-com 危机期间居然以盈利方式被收购。

Stewart 在 20VC 上把 1998–2000 这段总结为：第一次完整经历了"上行—崩盘—小公司被收购"的循环，也是他 Caterina Fake 的相识时期（两人后来 2001 年结婚）。

第三章：Ludicorp、Game Neverending、Flickr（2001–2005）

Ludicorp 的成立：要做一个"看不见输赢"的 MMO

2002 年夏天，Stewart 与 Caterina Fake（妻子）、Jason Classon（Gradfinder 联合创始人）在温哥华成立 Ludicorp。第一个项目是 Game Neverending：一款受 Neopets 启发的大型多人在线游戏，没有"输/赢"判定，玩家可以收集物品、聊天、参与角色扮演与小群体行为。

Stewart 在 Invest Like the Best 上对它的简介带着 hindsight 的清醒：

"The first game was called Game Neverending and came from the realization that you could make dynamic webpages... It probably would have failed anyway, because the idea is not especially commercially viable. It was, you know, 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 it was the dot com 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."

"第一个游戏叫 Game Neverending，源自我们意识到可以做动态网页这件事……它大概反正也会失败，因为这个点子并不特别有商业可行性。没有战斗、荒诞、超现实、Monty Python 加 Dr. Seuss 的世界——受众非常窄。但它失败也是因为我们 2002 年才开始：dot-com 崩盘、WorldCom 和 Enron 会计丑闻、9-11。这就是史上最糟的市场环境。"

Invest Like the Best, 2021

"We couldn't raise any money for that... so it was a really black and bleak-looking point in the history of financial markets generally, but anything as frivolous as a game was just not going to get funded."

"我们根本融不到钱……那是金融市场普遍最阴暗的时期之一，但任何'看起来像游戏'这么轻浮的东西就更不可能被资助了。"

Masters of Scale, 2017

他在 Masters of Scale 上还讲了一个关键的财务事实——团队走到了一个状态：

"We got to the point where the only person on the team who got paid was the one person on the team who had kids. And we needed some kind of 'Hail Mary."

"我们走到一个地步：团队里唯一拿薪水的是那个有孩子的人。我们需要某种'最后一搏'。"

Masters of Scale, 2017

食物中毒的 Flickr 灵感（2003 年末–2004 年初）

2003 年底，Stewart 飞往纽约谈一笔（最终未成的）合作时，在飞机上得了食物中毒。他在 Masters of Scale 上对这一夜有完整的描述：

"And this sounds almost made up, but on the way, I got food poisoning on the plane, puking on the Van Wyck on the way into New York, arriving at the hotel. Just being sick all night — it's like 3:00 or 4:00 in the morning — trying to keep anything down, like ginger ale or water. And the whole idea for Flickr came to me."

"这事听起来几乎是编的，但当时——我在飞机上得了食物中毒、在 Van Wyck 高速上一路呕吐进纽约、到了酒店。整夜病着——大约凌晨 3 点或 4 点，努力让自己吃下任何东西，姜汁汽水或水之类的。然后 Flickr 的整个想法就来了。"

Masters of Scale, 2017

但他特意强调，这个"灵感"不是关于摄影的宏大愿景，而是一个求生反应：

"It wasn't coming from a grand vision of what photos could be — all that stuff came later. There was no insight, it was just like, 'Can we not go out of business?"

"它不是来自'照片可以做成什么'的宏大愿景——那些都是后来才有的。当时根本没什么洞见，就是一句：'我们能不能不要倒闭？"

Masters of Scale, 2017

第一版 Flickr：Game Neverending 的内置工具

Stewart 在 Masters of Scale 上详细描述了第一版 Flickr 的样貌——它是直接搬用了 Game Neverending 的游戏 UI：

"We had this game interface. In the game, you had an inventory, you could pick up objects. We made that inventory a shoebox full of photos. And you could do interesting things, like drag photos around on to group conversations and they would pop up on the other person's screen. You could annotate them in real time. And there was chatting in the game, so you could talk to the fellow players — that became a cornerstone of Flickr."

"我们有一套游戏界面。游戏里你有一个'物品栏'，可以捡起物品。我们把那个物品栏变成一个装满照片的鞋盒。你可以把照片拖到群聊上、它会在对方屏幕上弹出。你可以实时给它加标注。游戏里有聊天，所以你可以跟其他玩家说话——这后来成了 Flickr 的一个基石。"

Masters of Scale, 2017

"Here's the twist, though, that was the first idea for Flickr, which was actually, really, a terrible idea that had a lot of technological innovation, and so it wowed a lot of people, but it wasn't a very useful product."

"但转折点在这——这个 Flickr 的第一个版本其实是个糟糕的点子。它有很多技术创新、很多人被惊艳，但它不是一个特别有用的产品。"

Masters of Scale, 2017

Flickr 在 2004 年 2 月 10 日以 FlickrLive 的名义首次发布——一个带照片交换的聊天室。三个月内，团队开始意识到照片才是用户真正想用的核心功能。

"Maybe three months in, it was pretty obvious that Flickr had legs."

"大概三个月后，Flickr 有戏这件事就很明显了。"

Masters of Scale, 2017

他在 Masters of Scale 上自己讲过这一段：

"It was rough. And there was definitely differing opinions. There was a lot of arguments about what we should be doing. And for a time, we were working both on a game and on Flickr. The team was still really split, so we had a vote."

"气氛很糟。意见绝对是有分歧的。关于我们应该做什么有很多争论。一段时间里我们同时在做游戏和 Flickr。团队还是分裂的，所以我们投了一票。"

Masters of Scale, 2017

"And I remember this really distinctly, because I had to do some backroom politicking. After the first vote ended, it was a tie game. So I called up one of my co-founders, who was in New York, and had to do some horse trading. I felt like I was a senator."

"我记得特别清楚，因为我得做一些幕后政治。第一次投票打平了。我打电话给一位在纽约的联合创始人，做了一些利益交换。当时我感觉自己像个参议员。"

Masters of Scale, 2017

他直接对那个有孩子、还在拿薪水的联合创始人说：

"If you'd like to continue to get paid, there's only one way we're going to do this."

"如果你还想继续拿薪水，我们只有一条路可走。"

Masters of Scale, 2017（转述自己当时对联合创始人的话）

"We had another vote the next day and this time the Flickr side won. At that point, I think we had less to lose and there was less invested. It wasn't as traumatic as the next big pivot, which was Glitch to Slack — that was seven years later."

"我们第二天又投了一次票，这次 Flickr 那边赢了。当时我们已经没什么可输的、投入也少。它没有后面那次 pivot（Glitch 到 Slack，七年后）那么有创伤。"

Masters of Scale, 2017

Flickr vs Snapfish/Shutterfly/Ofoto：把照片当作"社交媒介"

Stewart 在 Masters of Scale 上对当时照片市场的判断后来被反复引用：

"Almost all the photo sharing at that time was entirely centered around printing, and that was the idea of what people wanted to do with their general photographs. So that, in one sense, made it very easy."

"当时几乎所有的照片分享都围绕'打印'这件事——人们以为这就是一般照片想做的事情。这某种意义上让我们容易很多。"

Masters of Scale, 2017

"There was a lot of competition at the time — there was Snapfish, Shutterfly, there was Ofoto, which Kodak had bought, and Kodak had put a lot of muscle behind it. And none of them thought of the internet, as far as I could tell, as a social medium in itself, and a worthwhile place to put photos."

"当时有很多竞争对手——Snapfish、Shutterfly、Kodak 收购并大量投入的 Ofoto。但据我观察，他们没有一个把互联网本身视为一个值得放照片的社交媒介。"

Masters of Scale, 2017

Caterina Fake 的"逐人欢迎"文化。 Stewart 在 Masters of Scale 里特意把 Flickr 文化的根归功于 Caterina：

"I think one of the strengths of Flickr was a really unique culture, and a huge amount of effort went into setting that. So Caterina Fake, one of the founders of Flickr, and my ex, she greeted every single user individually. There's another designer on our team, a woman named George Oates, same thing. And so I think a lot of what made Flickr great in the end came from that germ of a really strong and positive community."

"Flickr 的一个长处是它真的有一种独特的文化，而这种文化是耗费了巨大的努力去建立的。Caterina Fake，Flickr 的联合创始人之一、我的前妻——她亲自对每一个用户表示欢迎。我们团队还有一个设计师叫 George Oates，也是这样做。最终 Flickr 的伟大之处很多都源于这种真的强烈而积极的社区萌芽。"

Masters of Scale, 2017

第四章：Yahoo 三年与"锡匠"辞职信（2005–2008）

Yahoo 收购：一年内完成

Flickr 在 2004 年 2 月公开发布。仅仅一年多之后，2005 年 3 月 20 日，Yahoo 以约 $22–25M 美元（部分来源报为 $35M）收购了 Ludicorp。

Stewart 在 Masters of Scale 上对节奏的回忆是带有惊愕的：

"It all happened so fast. We launched in February 2004, and by March 2005, the acquisition by Yahoo! had closed. Basically a year in market, and maybe 10-and-a-half months before we were in the middle of negotiations."

"一切发生得太快。我们 2004 年 2 月上线，2005 年 3 月 Yahoo 的收购就关闭了。基本上才在市场上一年，10 个半月就已经在谈判中了。"

Masters of Scale, 2017

收购后 Caterina Fake 与 Jason Classon 很快离开了 Yahoo；Stewart 留下来担任 Flickr 的总经理（General Manager），直到 2008 年 7 月。

Yahoo 三年的萧条：从他与 Caterina 离婚到他对 Yahoo 文化的失望

这三年是 Stewart 个人和职业两条线同时低谷的时期：

• 2007 年前后，他与 Caterina Fake 的婚姻结束（两人有一个女儿，2007 年出生）。
• Yahoo 在这段时间从市值远超 Google 的公司滑落到收入只有 Google 1/5–1/8 的状态。

Stewart 在 Invest Like the Best 上对这段的评价是冷静的、带有自己一贯的不指责风格：

"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?"

"我跟我当时的老板说我要辞职，他说，好吧没问题，能不能麻烦你给我发一封邮件，我好转给 HR？"

Invest Like the Best, 2021

开篇的那一段后来被 John Gruber 在 Daring Fireball 上打了五星好评：

"As you know, tin is in my blood. For generations my family has worked with this most useful of metals. When I joined Yahoo! back in '21, it was a sheet-tin concern of great momentum, growth and innovation."

"如你所知，锡流淌在我血液里。我们家族世世代代都在和这种最有用的金属打交道。我 21 年加入 Yahoo! 时，它是一家充满势头、增长与创新的薄锡板公司。"

致 Brad Garlinghouse 的辞职信, 2008 年 6 月 18 日

整封信延伸了"Yahoo 是锡匠铺、却跑去做了 dies、punches、铜、钢、各种与锡无关的奇怪业务"这个隐喻——把企业漂移用一个 19 世纪手工业者的视角讽刺到底。

Stewart 自己在 Invest Like the Best 上揭露了灵感来源：

"I was just ripping off the style of Thomas Zwiebel, the fictional publisher of The Onion."

"我就是在抄 The Onion 那个虚构出版人 Thomas Zwiebel 的文风。"

Invest Like the Best, 2021

Thomas Zwiebel 是 The Onion 长期使用的虚构 19 世纪雪茄业巨头风格人物——这种"过时的、用词夸张的、自命不凡的 19 世纪资本家"语调，是 Butterfield 后来反复使用的文学装置（"We Don't Sell Saddles Here" 也带有类似的"虚构 19 世纪马具公司"框架）。

辞职信几天后被泄露给 Valleywag（科技八卦网站）。Reid Hoffman 在 Masters of Scale 上称之为 "an epic — and rather confusing — resignation letter to his boss at the time, Brad Garlinghouse. It's odd and wonderful."

一个被反复弄错的细节：是"tin"不是"tofu"

后来很多回忆把这封信误记成"我要去做豆腐"或类似的隐喻。它实际上是"tin"（锡）——一种 19 世纪工业革命中真实的、被现代工业取代的手工业金属。Stewart 自己在公开访谈里从未自我纠正这个误传，可能因为对他而言两种说法都同样不要紧。

第五章：Tiny Speck 与 Glitch：第二次失败（2009–2012）

"这一次不可能失败"——所有 10x 因素叠加

2009 年，离开 Yahoo 一年后，Stewart 与 Cal Henderson（Flickr 的 CTO）等人共同成立 Tiny Speck。第一个项目本质上是 Game Neverending 的精神续作——一款叫做 Glitch 的浏览器 MMO，世界观被 Stewart 描述为 "Dr. Seuss meets Monty Python meets Borges"。

他在 Masters of Scale 上的归因带着 Cambridge 哲学家的克制：

"The idea was pretty much the same as Game Neverending, except that the technology was much better, so people could be much more creative and you'd be higher fidelity."

"想法基本和 Game Neverending 一样，只是技术好太多了——人们可以做更有创造力的事，画面也能更高清。"

Masters of Scale, 2017

"A game world with no combat, very absurdist — probably too high-brow, and too intellectual — Dr. Seuss meets Monty Python meets Borges. Already you can tell that in an era where Farmville was just beginning to take off, this was not an easy sell to America's casual gamers."

"一个没有战斗、极度荒诞的游戏世界——大概太高雅、太知识分子化了——Dr. Seuss × Monty Python × Borges。你已经能看出，在 Farmville 刚开始流行的时代，这对美国休闲玩家并不容易卖。"

Masters of Scale, 2017

他与 Reid Hoffman 在 Masters of Scale 上对这次决策有最坦诚的复盘——完美的"10x 因素叠加"反而成了陷阱：

"From our perspective, now we have some money, so that makes it easier; now we have better connections. But also, computer hardware got 100-fold better in those seven or eight years. We were more experienced and capable as engineers and designers. So the thought was, 'Oh, we can't fail this time.' There's just no way that with all of these 10Xs that combine to make it 1,000 or 10,000 times easier for us — it would be impossible to fail."

"从我们的角度看：我们有些钱了，所以更容易；我们有更好的人脉。而且这七八年里计算机硬件好了 100 倍。我们作为工程师和设计师都更有经验。所以当时的想法是：'哦，这次绝对不会失败。' 这些 10 倍因素叠在一起把难度降低了 1000 到 10000 倍——失败是不可能的。"

Masters of Scale, 2017

他在 Invest Like the Best 上更精炼地总结了"为什么 2009→2012 的有利条件并没有救他"：

"The second failure was very different. So we created Flickr. It was acquired by Yahoo. We worked at Yahoo for several years. And then we thought, okay, now it's 2009 versus 2002. And there's all of this amazing open source software that didn't exist before... it's just all of these 10x factors that led us to believe that we'll never possibly fail this time. And we did again."

"第二次失败完全不一样。我们做了 Flickr，被 Yahoo 收购了，在 Yahoo 工作了几年。然后我们想，2009 年比 2002 年好太多了。有那么多以前不存在的、惊人的开源软件……就是这些 10 倍因素让我们相信'这次绝对不可能失败'。然后我们又失败了。"

Invest Like the Best, 2021

Flash 押注：技术债的累积错误

Glitch 押注在 Adobe Flash 作为客户端技术上。Stewart 在 Invest Like the Best 上对这个决策的复盘很尖锐：

"We went all in on Flash as a client technology... at a time when Flash was about to die and people's discretionary computing time shifted from PCs to mobile."

"我们全押 Flash 作为客户端技术……正好是 Flash 即将死掉、人们的可支配计算时间从 PC 转向移动设备的时候。"

Invest Like the Best, 2021

Glitch 没有移动版本（Flash 在 iOS 上从未被支持，Android 上的支持在 2012 年也被 Adobe 自己停止）。这本身就把它从大众游戏路径切断了。

Glitch 的轨迹与 "unlaunch"

• 2011 年 2 月：Glitch 从 closed alpha 转为 beta。
• 2011 年 9 月 27 日：正式公开发布。
• 2011 年 11 月 30 日：Glitch "unlaunched"——上线两个月后被退回 beta 状态。这是一个非常罕见的决策，反映了 Butterfield 后来反复展示的"早点面对现实"的特征。
• 2012 年某时：Andreessen Horowitz 领投 Series B，团队累计融资约 $17.5M，员工 45 人左右。

那一夜：失去信仰

Stewart 在 Masters of Scale 上对 Glitch 死亡那一刻的描述是他最经常被引用的句子之一：

"At this point, I've learned that this is not going to be a commercially viable creation. It was incredibly powerful for the small minority of people for whom it worked. So they spent 20 hours a week playing, and they were very committed, it was a super-tight community. But most people — like 97% percent who signed up — would be out of there within five minutes."

"此时我已经知道，这不会是一个有商业可行性的作品。对那一小撮真的爱它的人来说，它的影响力非常强：他们一周玩 20 小时，特别投入，社区也极其紧密。但大多数人——大概 97%——注册后五分钟内就走了。"

Masters of Scale, 2017

"The last 18 months were just a series of experiments in like, 'What if we did this, what if we tried that? Maybe it's just missing this feature.' We were pretty good at getting people's attention, because we had more of a reputation, we were more connected, so we could get lots of articles written about us. It did always seem like the next thing was going to be what saved it. Something that just didn't work."

"最后 18 个月就是一连串实验：'我们这样试试？那样试试？也许就缺一个 feature？' 我们抓人注意力的能力其实不错，因为我们有声誉、人脉好，能让媒体写很多关于我们的文章。每次都觉得下一件事会救它。从来没有奏效。"

Masters of Scale, 2017

然后是那一刻——他自己用"失去信仰"这个宗教语汇来描述：

"There was this night where I just lost faith. I just realized, ok, I have tried the 15 stack-ranked best ideas we could possibly come up with to turn this around, and I don't think the 16th was going to work if the first 15 didn't."

"那一夜我就突然失去了信仰。我意识到，好吧，我已经把我们能想到的 15 个排名最高的 idea 都试过了，如果前 15 个不行，第 16 个也不会行。"

Masters of Scale, 2017

他在 Lenny 2025 上把这个时刻进一步阐发为一种"冷血理性"是必要的反人性能力：

"The reason I say you have to be coldly rational about it is because it's fucking humiliating. You have to convince so many people to get a company. You have to go to investors. You have to go to early employees and say, you should leave your other job and come work for this because here's the incredible future we're imagining... and so, I think for a lot of people, it feels better to just keep doing it until it dies of suffocation due to lack of capital or something like that than to admit like, okay, I was wrong. This didn't work. And it's humiliating. It's painful. It's wrenching."

"我之所以说你必须冷血理性，是因为这事 fucking 羞辱人。你为了创办一家公司说服过太多人。你去找投资人；你去找早期员工，跟他们说'你应该辞掉现在的工作来跟我做这件事，因为这是我们想象的不可思议的未来'……所以我觉得对很多人来说，干到资金耗尽自然窒息死掉，反而比承认'好的，我错了，这事没成'更容易。承认本身是羞辱的。痛苦的。撕心裂肺的。"

Lenny's Podcast, 2025

CEO 的核心工作是讲故事

在 Masters of Scale 同一段访谈里，他第一次明确表达自己后来反复使用的 CEO 哲学：

"Man, it is so hard, because the job of a CEO is often just to come up with a story that enough people believe that you can make something happen in the world. You have to convince investors, and you have to convince the press, and you have to convince potential employees, and you have to convince customers. And I had done a lot of convincing of people, a lot of convincing of people to come work on this project, to leave whatever thing they were working on before, quit their job, get paid poorly in exchange for equity in something that just didn't work."

"兄弟，这件事真难，因为 CEO 的工作很多时候就是想出一个故事——让足够多的人相信你能让某件事在世界上发生。你得说服投资人，说服媒体，说服潜在员工，说服客户。我说服过很多人来做这个项目、放弃他们之前的工作、拿低工资换股权——而这件事最后没成。"

Masters of Scale, 2017

他在 Stanford GSB View From The Top 上把"决定关闭"那天的所有人会议描述得几乎像电影场景：

"The day that I made the announcement internally [shutting down Glitch], I called this all hands and people were already a little bit apprehensive... I locked eyes with someone as soon as I started talking who about two or three months before I had convinced to move to a new city with his wife and two-year-old daughter away from where his in-laws lived... I was gonna tell him that he didn't have a job anymore. That was really, really hard."

"我向内部宣布关闭 Glitch 那天，开了一次全员大会。大家进门时就已经有点紧张……我刚开始说话就和一个人对上了眼——大约两三个月前，我说服他带着妻子和两岁的女儿搬到一个新城市、远离他岳父母（岳父母原本在帮他们带孩子）。我即将告诉他：他没有工作了。那真的、真的非常难。"

Stanford GSB View From The Top, 2020

这位员工的名字叫 Tim Lefler。Tim 自己后来回忆当天的开场：

"Stewart came in and had a very somber look on his face. He had puffy eyes; he looked tired... And he came in, and the very first thing he said to us was, 'It's over,' and that we were shutting the game down."

"Stewart 走进来，脸色非常凝重，眼睛浮肿、看起来很累……他走进来对我们说的第一句话是：'It's over.'——我们要关掉这个游戏。"

Tim Lefler, 转述自 Masters of Scale

Stewart 自己回忆那一刻的不可控泣不成声：

"And that was a tough conversation with our board and our investors, because they actually wanted us to keep going. It was a tough conversation with the other co-founders, who also wanted to keep going. We had those conversations, and then we called an all-hands. And I walk into the room — and it was an unusual all-hands; we hadn't announced it before, so there was already some nervousness in the room. And I stand up and start, and I didn't even get to the first sentence and I was starting to cry."

"那是一场跟董事会和投资人都很艰难的对话，因为他们其实想让我们继续做下去。跟其他联合创始人也很艰难——他们也想继续。我们谈完那些之后召开了全员会。我走进会议室——这是一次反常的全员会，事先没有宣布，所以房间里已经有点紧张气氛。我站起来，刚开始讲话，第一句话还没说完我就开始哭了。"

Masters of Scale, 2017

"Hire a Genius"：花掉最后 $5.5M 把每个人安顿好

Stewart 把剩下的 $5.5M 现金用于一种他后来命名为 "salvaging the good" 的关闭操作：

"We made a website called 'Hire A Genius', and we put everyone's LinkedIn up there, and everyone's portfolio, and everyone's photo. And we worked on writing reference letters and doing resume coaching. And we ended up getting every single person a job. We were able to give customers a choice of their money back, or they could let us keep it, or we could donate it to a set number of charities. So we were able to do that in a way that was really kind of elegant, and built a lot of good will that would be useful for us later."

"我们做了一个叫 'Hire A Genius' 的网站，把每个人的 LinkedIn、作品集、照片都放上去。我们花时间帮大家写推荐信、做简历指导。最后我们给每一个人都找到了工作。客户那边我们提供选择：退款、保留余额、或捐给我们列出的几家慈善机构。所以我们用一种相当优雅的方式做了这件事——这后来为我们积累了大量善意。"

Masters of Scale, 2017

他在 Stanford GSB View From The Top 上补充了一个最后会让所有看过这个故事的人记住的转折：

"Because we had $5.5 million left of that money, we were able to shut down in a relatively elegant way. So we made a portfolio site which had everyone's resumes and did a bunch of reference letter writing and career coaching and helped get everyone a job. In most cases, a better job than they had when they were working for us... that one person, Tim Leffler, ended up joining Slack a year later, so that part all worked out too. But it doesn't mitigate at all what it felt like in that moment. It was pretty terrible."

"因为我们还剩 $550 万，我们能用一种比较优雅的方式关闭。我们做了一个 portfolio 站点，包含每个人的简历，写了大量推荐信、做了职业辅导，帮所有人都找到了工作。大多数情况下比他们在我们这儿工作时更好的工作……那个人，Tim Leffler，一年后加入了 Slack——这部分也算圆满收场。但它一点也不能减轻当时那种感觉。那真的非常糟糕。"

Stanford GSB View From The Top, 2020

决定早关而不是耗到最后一美元

这个决定本身后来被 Stewart 总结为他"早面对现实"的核心实践：

"We definitely knew that we wanted to keep working together, and we still had money left. Investors didn't want their money back, because — I don't need to tell you, but why would you rather take a two-thirds loss when something might come out of it? We still had $5 and a half million dollars, or something like that left in the bank. So we didn't have to shut down, and I think that there's a real temptation to go to the last dollar and hope that there's some kind of 'Hail Mary' that will save it. The good thing about shutting it down early was that we had the ability to just not do anything for a couple of months."

"我们当然知道自己想继续一起工作，而且还有钱。投资人也不想退回钱——你不用我说就明白：当事情还可能出结果时，谁会愿意接受三分之二的亏损？我们大概还剩 $550 万。我们其实不需要关闭。我觉得'坚持到最后一美元、希望出现一个 Hail Mary 拯救它'的诱惑是真实存在的。早关闭的好处是我们有几个月可以什么都不做。"

Masters of Scale, 2017

第六章：Slack 的诞生（2012–2014）

Slack 的"史前史"：3.5 年的内部 IRC 工具

Slack 不是 Glitch 死后从零开始的。它是 Tiny Speck 团队过去 3.5 年间为自己内部沟通搭建的工具——以 1989 年的 IRC 协议为基础，渐进加上了：

• store-and-forward 消息日志（解决 IRC 离线就丢消息的问题）
• 可搜索的数据库
• 文件服务器集成
• 部署提醒、客户支持工单等系统通知集中到 channel
• 这些 channel 上的所有历史

Stewart 在 Masters of Scale 上详细描述了这个工具的起源——它不是被设计出来的，是被需求逼出来的：

"When we first got started, and there were only four of us, the natural thing for us to use was a very old internet protocol called IRC, an Internet relay chat. It pre-dates the Web by a couple years. And because it's so old, it misses a bunch of features that are now considered just standard."

"我们刚起步、只有四个人时，最自然的选择是一个非常古老的协议——IRC（Internet Relay Chat）。它比 Web 早几年。因为太古老，它缺少很多现在被视为标准的功能。"

Masters of Scale, 2017

"So one of the things it misses is store and forward of messages. So if I want to send you a message, and you're not connected at the moment I want to send it, I just can't. There's just no way for me to do it. And so we built a bot that would log all messages that were sent when you were offline, so you could read them when you got back online. And once we had that, we were like, 'Oh, wow. It would be super convenient to be able to search these messages.' And since we already had them in a database, it was easy to search them."

"比如它缺少消息的'存储转发'。我想给你发消息但你不在线时，我根本发不出去。所以我们做了一个 bot，把你离线时发给你的消息全部记下来，等你上线再读。一旦有了这个，我们就想：'哦哇，要是能搜这些消息就太方便了。'——而它们已经在数据库里了，搜起来很容易。"

Masters of Scale, 2017

"We Couldn't Stop Using It"

Stewart 和 Cal Henderson 在 2012 年底关闭 Glitch 后做的第一件事，是花几个星期"什么都不做"。然后他们意识到——这个团队对一件东西真正离不开：

"It wasn't something that we thought about, or talked about. It didn't have a name. It was just in the background. But as we started hiring people, they would join and they would have this archive of everything that happened before they got there, as opposed to most companies, where you hire someone and they start with an empty inbox. They're completely cut off from that history."

"我们从来没认真想过它、谈论过它——它甚至没名字。它就在背景里。但每次我们招新人，他们一加入就能看到一份在他们到来之前的所有事情的归档——而其他大部分公司你招个新人，他从一个空 inbox 开始，完全被切断在历史之外。"

Masters of Scale, 2017

"We realized, wow, this is hugely a productive way of working and I think all of us agreed we wouldn't work without a system like this again..."

"我们意识到——哇，这是一种生产力极高的工作方式，我们所有人都同意，再也不会在没有这种系统的情况下工作了……"

Tiny Speck 团队复述, BuildingSlack.com

Stewart 在 Lenny 2025 上把这种"产品的隐形史前史"表达得最清楚：

"We were working on Glitch, this game, where we used IRC for internal communication, and we added a bunch of IRC, which became the proto Slack. I think Slack had an enormous advantage in the fact that we were working on this for several years, without actually explicitly working on it and only doing the minimum number of features that were absolutely guaranteed to be successful."

"我们当时在做 Glitch 这个游戏，内部沟通用 IRC，我们在 IRC 之上加了一堆功能——那就成了原始版 Slack。我觉得 Slack 有一个巨大的优势：我们已经为它工作了好几年，但又不是显式地在做它，而且只加那些'绝对会成功'的最小必要功能。"

Lenny's Podcast, 2025

"Hugely a productive way of working"——3 周内的 pivot 决策与 72 小时的 pitch deck

Stewart 在 Masters of Scale 上记录了 2013 年初这次决策的速度：

"Within a couple weeks, I think three weeks, we decided — and there was a lot of stupid ideas first — but we decided that this internal communication system we had developed while we were working on the game, that could be a product, and we started building that. And we had a great practice, but it was a vision that might have well been passed down on to the mountaintop."

"几个星期之内——我想是三个星期——我们做出了决定，之前先有不少蠢点子。我们决定：我们做游戏期间开发的这套内部沟通系统可以做成产品。然后就开始做了。我们有非常扎实的实战经验，但那个愿景听起来几乎像是从山顶上传下来的。"

Masters of Scale, 2017

最让他自己事后惊讶的是 pitch deck 的稳定性：

"There's this deck that I put together that was like, 'I think we should make Slack.' So we hadn't actually started making it yet, and I showed this to new employees when they start at Slack, and it's in our archive. Because the amazing thing is, it had the pricing that we went live with, it's exactly the product vision, it's exactly the way we marketed it. Everything was preset, and we didn't have to change it, because, I think, we had three-and-a-half years of practice, and finding product-market fit for our market-of-one team."

"我有一份 deck，标题大致是'我觉得我们应该做 Slack'。当时我们还没开始做，但我后来在 Slack 入职时给新员工看，这份 deck 还在我们的归档里。令人震惊的是——它的定价正是我们上线时用的定价；产品愿景一模一样；营销方式一模一样。所有东西都已经预设好，根本不需要改，因为我们已经为这个'一个团队的市场'做了 3 年半的 PMF 寻找。"

Masters of Scale, 2017

"I think all that stuff actually took place in 72 hours, and within a week, we were definitely on this plan."

"我觉得这些（决策、deck、定位）实际是在 72 小时里完成的，一周之内我们就完全在执行这个计划了。"

Masters of Scale, 2017

"Dogfood Without Ego"——Stewart 自己的方法论命名

Stewart 在 Masters of Scale 上对这种"不刻意设计、只为自己用、自己感到痛了就改"的工作方式给出了他自己的命名：

"But again, it was — and this, by the way, I think is the greatest software development methodology that's impossible to replicate, which is, don't think about what you're doing, have no ego. There's no speculation, there's no, 'I can imagine a user would want to.' To spend a minimum number of minutes addressing the most aggravating problems that you have, and just use it, and then see."

"顺便说一下，我觉得这是最伟大、却不可复制的软件开发方法论——别去想你在做什么、放下自我。没有推测、没有'我能想象一个用户会想要什么'。花最少的时间去解决你自己最受不了的问题，然后用它，然后看会怎样。"

Masters of Scale, 2017

"Pfft, Good Luck"——A16z 合伙人对 Slack 的反应

2012 年底 / 2013 年初，Stewart 去 Andreessen Horowitz 提案要把 Tiny Speck 的剩余资金转向 Slack。他在 Masters of Scale 上把 a16z 合伙人会的反应保留得颇为真实：

"Part of the pitch was, 'We think that one day, in the fullness of time, if we're incredibly successful, we will get to $100 million dollars in revenue on this business, and that it could thereby be a billion-dollar business.' And there was a lot of 'Pfft, good luck', not a huge degree of enthusiasm. But that was our whole ambition, and we exceeded that last year, and we doubled it again this year. We really underestimated how big of a deal it could be."

"提案的一部分是：'我们认为在足够长的时间里，如果我们极其成功的话，这个生意能做到 $1 亿美元的年收入——也因此可能是一个十亿美元的公司。' 当时听到的是很多'呵呵，祝你好运'，没有太大热情。但那就是我们当时的全部野心，我们去年超过了它、今年又翻了一倍。我们真的严重低估了这事能有多大。"

Masters of Scale, 2017

开篇定下了全文的隐喻：

"We don't sell saddles here. The slogan of the saddle-makers was 'We Sell Saddles,' and they did. They were the best saddle-makers in the world. … But they did not understand what they were selling."

"我们在这里不卖马具。马具匠的标语是'我们卖马具'，他们也确实卖。他们是世界上最好的马具匠。……但他们不理解自己卖的是什么。"

Internal memo, 2013-07-31

他把"Acme Saddle Company"放进了一个虚构世界——一个绝大多数人甚至不知道有"骑马"这回事的世界。战略性的结论是：他们不应该把自己看作马具公司，而是"卖骑马这个梦想"的公司。

最核心的几句被广泛引用：

"What we are selling is not the software product. … We are selling Organizational Transformation. We are selling a reduction in information overload, relief from stress, and a new ability to extract the signal from the noise."

"我们卖的不是软件产品。……我们卖的是组织转型。我们卖的是信息过载的减少、压力的缓解、以及从噪声中提取信号的新能力。"

Internal memo, 2013-07-31

"The best — maybe the only? — real, direct measure of 'innovation' is change in human behavior."

"对'创新'唯一真实而直接的度量——也许吧——就是人类行为的变化。"

Internal memo, 2013-07-31

"When you want something really bad, you will put up with a lot of flaws. But if you do not yet know you want something, your tolerance will be much lower."

"当你非常想要某个东西时，你能容忍很多缺陷。但如果你还不知道自己想要这个东西，你的容忍度会低得多。"

Internal memo, 2013-07-31

"Ensuring that the pieces all come together is not someone else's job. It is your job, no matter what your title is and no matter what role you play."

"把所有部件拼在一起不是别人的工作。是你的工作——无论你的头衔是什么，无论你扮演什么角色。"

Internal memo, 2013-07-31

"Why the fuck else would you even want to be alive but to do things as well as you can?"

"他妈的活着是为了什么？不就是为了把事情做到自己能做的最好吗？"

Internal memo, 2013-07-31

Stewart 后来在 Lenny 2025 上揭示了这份备忘录的意图：

"The point of it was to start to instill those ideas as early as possible and really create this alignment inside of that small team so that it could persist and survive as we grew and scaled."

"它的目的是尽早把这些想法植入团队，在那个小团队里建立这种 alignment，让它能在我们成长和规模化的过程中保留下来。"

Lenny's Podcast, 2025

最值得注意的是——Stewart 后来把这份 2013 年内部备忘录在 Medium 上公开发表时一个字都没改。这本身是一种公开承诺。

Slack 上线：第一周 8,000 客户

• 2013 年 8 月：Slack Preview Release 公布。
• 2013 年底：早期客户已经包括 Rdio、Cozy、Wantful 等小型公司——Stewart 和他认识的创始人花了"dozens of office visits"才把每家公司转成 Slack。

Stewart 在 Masters of Scale 上对早期销售难度的总结：

"We also underestimated how hard it would be to get people to switch, because no one thought that they needed anything."

"我们也严重低估了让人们切换的难度，因为没有人觉得自己需要任何东西。"

Masters of Scale, 2017

"We weren't competing with anything else that was out there, other than the use of email, which is pretty much impossible to compete with, and whatever it was that people did, whether that was using a bug tracker, or a wiki, or Google Hangouts, or Skype. No one thought that they needed Slack."

"我们没有真正的竞争对手——除了 email（基本无法竞争），以及人们之前用的各种东西——bug tracker、wiki、Google Hangouts、Skype。没有人觉得他们需要 Slack。"

Masters of Scale, 2017

"We went out and started trying to convince other people to use it, which was way harder than we thought it was going to be. Social proof was a thing that we needed."

"我们开始挨家挨户去说服别人用它——这比我们预想的难太多了。我们需要社会证明。"

Masters of Scale, 2017

2014 年 2 月正式公开发布。24 小时内 8,000 个客户注册。

"What actually made it hard was, you have to get a whole group of people to change all at once; it wasn't just one person. The benefit of that, though, once you're able to break through, is once the group starts doing it, what was difficult about it becomes its benefit. It's very hard to get the group to change to anything else once they switch. So Slack was a really interesting product to scale in the early days, because it had very, very little network effect between companies, but a huge binary, 100% or just nothing, inside of companies."

"真正难的是——你必须让一整个团队同时改变，不是一个人。但一旦突破之后，那种困难本身反过来成了它的护城河：一旦一个团队切换过来，要他们再切换到别的产品就非常难。Slack 在早期是一个非常有意思的产品——公司之间几乎没有网络效应，但公司内部是一个巨大的二元的全或无切换。"

Masters of Scale, 2017

第七章：超级独角兽到 IPO（2014–2019）

增长：从 5–10% 周增长到 12M DAU

• 2014 年 8 月：Mat Honan 在 Wired 写出他后来定义 Butterfield 公众形象的封面专访——把 Stewart 写成 "the most fascinating profile you'll ever read about a guy and his boring startup"。当时 Slack 已经超过 12 万日活注册用户。
• 2015 年 4 月：估值 $2.8B，付费订阅 20 万，DAU 75 万。
• 2015 年 12 月：$340M 融资，DAU 200 万，付费 57 万。Inc. Magazine "Company of the Year"。
• Stewart 在 2014 年 11 月的 Offscreen Magazine 发表了他唯一的另一篇主要散文 "Rules of Business"（2015 年 3 月转发到 Medium）。

"Rules of Business"——他的五条"规则"

[16] 这份散文是除"We Don't Sell Saddles Here"之外 Butterfield 唯一的另一篇公开主要文章。五条规则如下：

1. Pretend like you're a human being.

"Practice being not-designers: stop what you're doing, close your eyes, take a few deep breaths and then look again like you're just a regular person encountering this product/service/user interface/object/page/poster for the first time."

"练习'当一个非设计师'：停下你在做的事，闭上眼睛，做几次深呼吸，然后重新看——就像你是一个普通人、第一次遇到这个产品/服务/界面/物件/页面/海报。"

Rules of Business, Offscreen Magazine, 2014

"With the possible exception of artists and architects, no one is more full of shit than designers. We can find a way to justify anything."

"可能只有艺术家和建筑师比得上——设计师是最满嘴胡话的群体。我们能为任何东西找到一个理由。"

Rules of Business, Offscreen Magazine, 2014

2. Make it inevitable. 建立对所欲结果的信心，并让每一个行动都对齐那个不可避免性。

3. Every job you do has your signature on it.

这一条来自他童年的一段父亲故事——父亲请人来劈柴堆码，结果柴堆码得不齐整，父亲拒绝付款，问那个工人：

"do you really want to sign that?"

"你真的要在那上面签名吗？"

Rules of Business, Offscreen Magazine, 2014（转述父亲）

寓意：你做的每件事上都有你的签名。"signature"对他是一个反复出现的隐喻——后来也用在他对 Slack 团队的内部要求上。

4. Everyone should always be trying to make it easier for everyone. 来自他做乐队的经验——"实时和别人深度配合，时刻调整自己以辅助队友"。

5. Know why you're doing it. 直接呼应 "We Don't Sell Saddles Here" 的最后一句——"Why the fuck else would you even want to be alive but to do things as well as you can?"

自我贬低作为产品燃料：MIT Technology Review 的那句话

2014 年的 MIT Technology Review 采访里，Stewart 对自己刚发布的产品说出了一句惊人的话：

"I feel like what we have right now is just a giant piece of shit. It's just terrible and we should be humiliated that we offer this to the public."

"我觉得我们现在做出来的就是一坨巨型大便。糟糕透顶。我们应该为把这玩意儿放给公众感到羞愧。"

MIT Technology Review, 2014

后来他的员工自己打印了 40 份贴在墙上当作激励物。Stewart 在 Lenny 2025 上回顾这件事时说：

"To me, that was like, you should be embarrassed. If you can't see almost limitless opportunities to improve, then you shouldn't be designing."

"对我来说，那就是——你应该感到羞愧。如果你看不到几乎无穷无尽的改进机会，那你就不应该做设计。"

Lenny's Podcast, 2025

Slack 的反 IPO 直觉：Direct Listing

2019 年 6 月 20 日，Slack 在 NYSE 通过 direct listing（不是传统 IPO）上市，代码 $WORK。Stewart 在 Andrew Ross Sorkin 的 CNBC 采访中给出的核心解释非常坦白——Slack 不需要 IPO 资本（balance sheet 上当时有 ~$800M 现金）：

"The big one for us was not to have to raise more capital."

"我们最重要的一个原因是不需要再融更多资本。"

CNBC, 2019-06-20

"In a direct listing, potentially 100% of the shares are tradeable. And there's many sellers and there's many buyers."

"在 direct listing 中，潜在 100% 的股份都是可交易的。卖家很多，买家也很多。"

CNBC, 2019-06-20

"Starting three years ago, we started trying to run Slack as a public company."

"三年前我们就开始按上市公司的方式运营 Slack。"

CNBC, 2019-06-20

他在 20VC 上又把这件事的本质拆解为一个几乎纯粹的资金需求问题（去除了所有"宣言"色彩）：

"The real decision, I think, came down to do you want to raise more money. And if you don't, then a direct listing is better than an IPO... we started three years or so before, maybe four years before we went public for what we call Public company readiness. In fact, PCR was an acronym inside the company to refer to that and the kind of discipline and the governance mechanisms and the controls you put in place are incredibly valuable. The actual mechanism by which you come to be listed I think is much less important."

"真正的决策其实就归结为一个问题：你想不想再融钱？如果不想，那 direct listing 比 IPO 更好……我们在上市前三年、可能四年就开始做'上市准备'，内部我们用 PCR 这个缩写来指代——其中你建立的那套纪律、治理机制和内部控制是极其有价值的。至于上市的具体机制，我觉得没那么重要。"

20VC, 2020

direct listing 的两个直接结果：

• ~700 名员工当日变成百万富翁（没有 6 个月 lockup）
• Stewart 本人成为亿万富翁
• 到 2021 年 vesting 完成时，超过 1,000 名员工是百万富翁

Slack vs Microsoft Teams：5 年的存在性威胁

Stewart 在多次访谈里把 Microsoft Teams 描述为 Slack 的存在性挑战：

"If Slack's successful to the maximum extent, that's an existential threat to Microsoft... because if people stop paying attention to email, if email declines in relative importance compared to the other software you use, that's a really difficult position for them."

"如果 Slack 取得最大程度的成功，那对 Microsoft 就是存在性威胁……因为如果人们不再关注 email，如果 email 相对于其他你用的软件的重要性下降，那对他们就是非常困难的位置。"

20VC, 2020

但他立即自我修正：

"I don't think that's actually true because so many other things would change in the world on the path to that. But I think that is a thought process."

"我其实不认为它真的会发生——因为要走到那一步，世界上太多其他事情也得变。但这是一个值得想的思路。"

20VC, 2020

他对 Teams 实际上"为什么赢"的判断很冷酷：不是因为 Teams 更好，是因为它免费、绑死在 Office 365 里：

"It got a lot better as Microsoft. I think there's a bunch of things that make it much more of a challenge for us today than it was then. And it's not just that it's better, because it's actually not better enough compared to how it was that any of our large customers could switch to it."

"Microsoft 的 Teams 变好了很多。今天它对我们的挑战比当年大得多。但不只是因为它好了——它好的程度其实并没有让任何我们的大客户能切换过来。"

Odd Lots, 2023

"If you hear that there's two alternatives, one's Slack and one's Teams, and because you're an Office 365 customer, Teams is already free and integrated with all of your Microsoft tools, then why would you even evaluate Slack?"

"如果你听到有两个选项——Slack 和 Teams，而你是 Office 365 客户，Teams 已经免费、已经和你所有的 Microsoft 工具集成了——那你为什么还要评估 Slack？"

20VC, 2020

第八章：Salesforce 收购、退场、园艺（2019–2023）

Stewart 在 TechCrunch 采访里直接讲了这个起点：

"I actually talked to Bret in the early days of the pandemic to see if they wanted to sell us Quip because I thought it would be good for us, and I didn't really know what their plans were [for it]."

"我其实是在疫情早期跟 Bret 谈，看看他们是否愿意把 Quip 卖给我们——因为我觉得对我们有好处，而且我不知道他们对它的计划是什么。"

TechCrunch, 2020-12-04

"He said he'd get back to me, and then got back to me six months later or so."

"他说他会回复我，然后大概六个月后才回过来。"

TechCrunch, 2020-12-04

Stewart 公开否认 Microsoft Teams 是收购的主要驱动因素：

"I don't think that was really an important part of the rationale, at least for me."

"我不认为 Microsoft 是这个决策中一个重要的因素——至少对我来说不是。"

TechCrunch, 2020-12-04

他更愿意强调的是品牌独立性：

"They paid a lot of money for us, so they want us to do more of what we were already doing."

"他们为我们付了很多钱，所以他们希望我们继续做我们一直在做的事情。"

TechCrunch, 2020-12-04

这件事在 Butterfield 的整个职业生涯中是一个反复出现的模式：他从来不预设好结果——食物中毒夜里想出 Flickr、想买 Quip 结果卖了 Slack。Reid Hoffman 在 Masters of Scale 上把这种特质总结为 "From our path, what do we see?"（从我们走过的路上看，我们看到了什么？）——而不是 from-scratch ideation。

最常被引用的几句来自他给员工的告别信：

"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."

"这是一段漫长而疯狂的旅程。我不会去做下一件创业的事。听起来可能老套，但我真的要花更多时间陪家人。我们一月份有个新生儿。"

Slack departure memo, 2022-12-05

最被疯传的一句是他写自己的"幻想"：

"As I said in my announcement to Slack team, these days my fantasies are about gardening...I really am going to spend more time with my family (as well as work on some personal projects, focus on health and generally put time into those things which [are] harder to do when one is leading a large organization)."

"正如我在给 Slack 团队的公告里说的——这些日子我幻想的是园艺……我真的会花更多时间陪家人（同时做一些个人项目，关注健康，把时间投入到那些一个人领导大型组织时很难做到的事情上）。"

Slack departure memo, 2022-12-05

"I'm going to work on some personal projects, focus on health, and try to learn as many new things as I can."

"我会做一些个人项目，关注健康，并尽可能多地学习新东西。"

Slack departure memo, 2022-12-05

关于时机和 Bret Taylor 同周辞职这件事：

"Planning has been in the works for several months. Just weird timing."

"这件事其实计划了好几个月。只是时机很怪。"

Slack departure memo, 2022-12-05

第九章：牧场生活（2023–现今）

不是公关式的退休：他真的在做园艺

[15] 显示 Stewart 离开 Salesforce 之后的实际行动与他的告别信高度一致——这是他的告别信中最值得关注的事实之一，因为绝大多数科技 CEO 在写完类似告别信后会在 6–12 个月内宣布下一家公司或基金。

地理分布。 他和 Jen Rubio（Away Luggage 联合创始人，2020 年结婚）现在分居在三个地方：

• 科罗拉多 Aspen
• 纽约
• 新墨西哥的牧场——他们买下了设计师 Tom Ford 的 20,000 英亩 Cerro Pelon 牧场

两人在房地产上累计花费约 $140M（据 ARTnews 等公开报道）。

天使投资。 30+ 早期投资组合。Stewart 的天使投资风格非常"老 Slack"——他偏好已经做出深度内部工具的团队（Vectara、Linear、Panobi、Tandem、Assembled、All Turtles）以及金融基础设施类（Neo Financial Series D, 2024 年 11 月）。

艺术收藏与哲学性的合作。 他和 Jen 进入了 ARTnews Top 200 Collectors 名单。他们在新墨西哥成立了一个艺术基金会，正在与艺术家 Alicja Kwade 合作一个项目——Kwade 的作品大量涉及时间、可能世界、本体论——这是 Cambridge 哲学硕士背景的延续。

儿女。 Stewart 总共有三个孩子：与 Caterina Fake 生的女儿（2007 年生）、与 Jen Rubio 的儿子、以及 2023 年 1 月出生的女儿——也就是他在 2022 年告别信里提到的那个"即将到来的新生儿"。Stewart 在 Lenny 2025 上提到这个女儿"是在我最后一天上班的三天后出生"。

Lenny 2025："我大部分时间就是在 chilling"

离开 Salesforce 两年半之后，Stewart 终于接受了 Lenny Rachitsky 的访谈（2025 年 11 月发布）。这是他第一次系统讲述自己离任后的状态：

"I'm mostly just chilling. I left Salesforce two and a half years ago and I have a two and a half year old. She was actually born three days after my last day, so a lot of time with family... No new company to announce. The big challenge has been I think these things [phones] are kind of destroying the world. What we're good at is making software, so if you can find some way to make software that helped people use their phones less often, then that would be a big winner, but I haven't come up with anything good."

"我大部分时间就是在 chilling。我两年半前离开了 Salesforce，我有一个两岁半的女儿——她其实是在我最后一天上班三天后出生的，所以我花了很多时间陪家人……没有新公司要宣布。最大的挑战是——我觉得这些东西（手机）正在毁掉这个世界。我们擅长做软件，所以如果你能想办法做一种让人们少用手机的软件，那将是大赢家——但我还没想到任何好点子。"

Lenny's Podcast, 2025

他对自己当下的工作描述：

"[A lot of] philanthropic work. Nothing to announce there yet, but there's like some cool projects I'm working on and a lot of personal creative art projects and supporting other artists."

"[很多] 慈善工作。还没什么可宣布的，但有一些不错的项目在做、很多个人创作艺术项目、以及支持其他艺术家。"

Lenny's Podcast, 2025

二、深度洞察

关于产品：Comprehension > Friction（这是他最重要的反产品箴言）

Stewart 在 Lenny 2025 上把"减少摩擦"这种当代产品教条直接反过来：

"It became an assumption that you should always be trying to remove friction when the challenge is really comprehension. If your software kind of stops me and asks me to make a decision and I don't really understand it, you make me feel stupid."

"它（'减少摩擦'）已经变成一种假设——但真正的挑战是 comprehension。如果你的软件在某个时刻让我停下来做一个决定、而我又不真的理解，你就让我觉得自己很蠢。"

Lenny's Podcast, 2025

"I think the secret is most, 70%, 80% or whatever of a product design is in that comprehension step because people, if they do ever open the preferences tab and look at all the options, rarely have an idea."

"我觉得秘诀在于——产品设计的 70%、80% 都在 comprehension 这一步。人们如果真的打开 preferences 看那一大堆选项，他们大多没主意（不知道应该怎么选）。"

Lenny's Podcast, 2025

而代替 "remove friction" 的口号应该是：

"If there is one mantra that I would use to replace that [reducing friction], it's don't make me think... One is it's expensive to make a decision. You literally burn glucose. There's a metabolic action. There's ATP created in the mitochondria in your neurons... Also, there's an emotional aspect, which is if your software kind of stops me and asks me to make a decision and I don't really understand it, you make me feel stupid."

"如果我要用一句话替代'减少摩擦'，那就是'不要让我思考'……一是做决定是昂贵的——你字面意义上在燃烧葡萄糖。神经元里有线粒体在产生 ATP。这是代谢消耗。二是有情感层面——如果你的软件让我停下来做一个我不真的理解的决定，你就让我觉得自己很蠢。"

Lenny's Podcast, 2025

他用 B2B SaaS 销售作为反例：

"I'll always try to get more people through the early stages of the process to understanding what Slack is. If I fill in the blank with like a dozen new-ish SaaS tools and I asked you, hey, why don't you use fill in the blank? The answer is almost never going to be it's too expensive or is lacking some feature I want. The answer is almost always going to be I have no idea what that does. The problem is almost always comprehension, but we treat it as if the problem is friction inherited from e-commerce."

"我总是会试着把更多人从早期阶段带到'理解 Slack 是什么'的状态。如果我列出十来个相对新的 SaaS 工具问你'你为什么不用 [X]？'，答案几乎永远不是'太贵了'或'缺一个我要的 feature'。答案几乎永远是'我不知道它是干嘛的'。问题几乎总是 comprehension，但我们把它当成是从电商继承来的 friction 问题。"

20VC, 2020

关于产品：S 曲线的"功能效用"心智模型

"This is pretty easy because it's a very familiar S-curve... the first bit of effort you put into something doesn't result in a huge amount of value and then there's some magic threshold where it produces an enormous amount of value and then continued investment doesn't really pay off."

"这其实很简单——是一条非常熟悉的 S 曲线。你最初投入的一点努力不会产生大量价值；然后到达某个魔法阈值后会产生巨大价值；再继续投入收益就不再增长了。"

Lenny's Podcast, 2025

他要求 PM 和设计师把每一个功能放到这条 S 曲线上的具体位置——下面的"平地"（投入了但还没产生价值）、中段的"陡坡"（每一点投入都产生巨大价值）、还是上面的"平地"（再投也没用了）。很多失败的产品在第一个平地放弃；很多浪费资源的产品已经过了上面的平地却还在继续投。

关于产品：The Owner's Delusion / 看起来像工作的伪工作

这是他对组织内部低效的一个原创概念：

"Hyper-realistic work-like activities goes along with this other concept called known valuable work to do. And when I say known, I mean both you know what it is and you know that it's valuable."

"高仿真度的类工作活动'和我另一个概念紧密相连——'known valuable work to do'（已知的有价值的工作）。我说的 known 是双重的：你既知道它是什么，也知道它有价值。"

Lenny's Podcast, 2025

伪工作（hyper-realistic work-like activities）是那些看起来跟工作长得一模一样的东西：开会、做一份关于做下一份 deck 的 deck、预演一下下次预演的会议。它们的物理和社会行为模式都跟真正的工作没有任何区别——这就是为什么它们这么难根除。

他直接把这个判断的责任放在领导者头上：

"Ultimately, it's the leader of the organization that has the responsibility to make sure that there is sufficient, known, valuable work to do. That's actually harder than it might appear."

"归根结底，组织的领导者有责任确保有足够的、已知的、有价值的工作可做。这比看上去难得多。"

Lenny's Podcast, 2025

而当人们陷入伪工作时——他绝不让员工背锅：

"It's actually your responsibility to make sure that there's sufficient clarity around what the priorities are and explicitly saying no to things upfront and stuff like that rather than... 'hey, you guys are a bunch of idiots wasting your time on this thing that doesn't matter."

"你的责任其实是确保对优先级有足够的清晰度、明确地说不、提前划清边界——而不是事后责备'嘿你们这帮傻瓜在浪费时间做这件无关紧要的事'。"

Lenny's Podcast, 2025

关于组织：CEO 的核心工作是讲故事

这是他在 Masters of Scale 上对 CEO 角色最完整的定义：

"The job of a CEO is often just to come up with a story that enough people believe that you can make something happen in the world."

"CEO 的工作很多时候就是想出一个故事——让足够多的人相信你能让某件事在世界上发生。"

Masters of Scale, 2017

"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 gonna have to do all the explaining."

"如果你不能把你在做的事讲得足够好——让你讲过的人能继续讲给下一个人——那就是个真问题。否则你得一辈子自己讲。"

Stanford GSB View From The Top, 2020

关于决策：寻找一个根本性的理由

"There's almost always to me one reason that's fundamental and can still be wrong... in the absence of some fundamental reason for something, the challenges that inevitably arise just generate their own problems of pros and cons and indecision and hesitation."

"对我来说几乎总是有一个'根本性的理由'存在——它可能仍然是错的。但如果没有某个根本性的理由，过程中必然出现的挑战就会自己生出更多的利弊清单、犹豫和拖延。"

20VC, 2020

他把"靠 A/B 测试做决定"称为"数据驱动决策的腐败"：

"There's a thing that I think has infected Silicon Valley, the corruption of data-driven decision-making. People just haven't really looked at the history and philosophy of science to see how rigorous you have to be to have the scientific certainty about something, and they believe that a little bit of A-B testing will give them the result."

"硅谷被一种东西感染了——数据驱动决策的腐败。人们没有真正了解过科学史和科学哲学，没看过要有多严谨才能对某件事有'科学确定性'，他们以为做一点 A/B 测试就能拿到结论。"

20VC, 2020

A/B 测试只能找到局部最优。如果你距离全局最优很远，它会让你陷在错误的山头不下来。

关于组织：创始人 CEO 拥有难以复制的"道德权威"

"The qualities of leadership that I think are important are entirely independent of the quality of decision-making in different domains of the business and founders like me who remain the CEO, I think have a huge advantage. We don't have to be as good as leaders as like a professional CEO would be because we're the founder because there's like something of the soul of the company that's tied up with us. We have this moral authority, which would otherwise be very difficult to cultivate."

"我认为重要的领导力品质，跟你在不同业务领域做决策的质量是完全独立的。而像我这样的'仍然在任的创始人 CEO'，有巨大的优势。我们不需要像专业 CEO 那样擅长领导力，因为我们是创始人——公司的灵魂里有一部分是绑在我们身上的。我们拥有一种道德权威——这是其他方式很难培养出来的。"

20VC, 2020

关于组织：先听坏消息

"At Berkshire Hathaway, they had a sign over one of the conference rooms or maybe Warren Buffett's office or something like that that said, tell us the bad news first. It is only the good news that can wait. Part of that is creating a culture where people are open about the problems of not falling prey to what Charlie [Munger] calls the Persian messenger syndrome."

"Berkshire Hathaway 有一个会议室或者 Warren Buffett 办公室上面挂的牌子——'先告诉我们坏消息，只有好消息可以等'。这是在创造一种文化：让人们对问题保持开放，不要陷入 Munger 所说的'波斯信使综合症'。"

20VC, 2020

"For me, listing all the challenges or the problems or things that aren't going well is an expression of optimism because I believe that we can do something about them. For certain personality types, I think it feels like the opposite. It feels like doom and gloom or pessimism or dwelling on the things that aren't going well."

"对我来说，把所有挑战、问题、不顺的事情列出来是一种乐观的表达——因为我相信我们可以为这些做点什么。但对某些性格类型，那感觉像是末日感、悲观、对负面事物的沉湎。"

20VC, 2020

关于组织：尽早做多样化招聘

20–30 人节点是 Slack 多样化招聘的真正分水岭。Stewart 在 Stanford GSB 详细描述过这个"链式效应"：

"Start early. I think that's the biggest thing. When we were 20 employees, I would say, between 20 and 30 maybe, we're like, wow, this is a lot of white dudes. In that case, it wasn't too late, but it was close to too late. It was more of a slog to get started, because what happened was we have one black woman engineer, and then another one comes to interview, and she sees the first one, and suddenly it's like a completely different assessment of what's going on here, and then there's two, and then the third one comes for an interview, and it feels like there's community, and people talk and have a network."

"早开始。我觉得这是最大的一件事。我们 20 人左右时——我会说 20 到 30 之间——开始意识到，哇，全是白人男性。当时还不算太晚，但已经接近太晚了。启动会更艰难——因为接下来发生的事是：我们有一个黑人女工程师，下一个来面试的黑人女性进来看到她，整个评估就完全不一样了；然后变成两个；第三个来面试时，就感觉这里有个社区，人和人之间能交流、有人脉。"

Stanford GSB View From The Top, 2020

他对"降低标准"的所谓担忧给了直接反驳：

"There's a really pervasive and incorrect belief that you would have to lower the bar to hire someone who isn't like the canonical candidate, like the archetypal candidate for this role. I think that's usually not the truth for two reasons. One is if you just have to look harder, you're gonna see more people and in fact that can raise the bar... for two people with like equivalent credentials, the person who's probably going to be more talented, more capable, and had to overcome more obstacles to get to where they are is going to be the one who doesn't have the traditional archetypal presentation."

"有一种非常普遍但错误的看法——你必须降低标准才能招到一个不像'经典候选人'的人。我觉得通常不是这样，有两个原因。一是你只是需要找得更努力——你会看到更多人，事实上这能提高标准。二是——对于两个简历相当的人，那个为了走到这里克服了更多障碍、更有才华、更有能力的人，往往是那个不符合传统'原型'的人。"

Stanford GSB View From The Top, 2020

关于商业：Tilting Your Umbrella

Stewart 在 Lenny 2025 上把"Slack 内部的口号"用一个温哥华下雨的小故事讲了出来：

"Most people don't have good taste and don't invest. You're probably familiar with the Jeff Bezos line, 'your margin is my opportunity.' It's pretty obvious what he meant by that."

"多数人没什么品味、也不投入。你大概熟悉 Bezos 那句话——'你的 margin 就是我的机会'。他什么意思一清二楚。"

Lenny's Podcast, 2025

"We would say at Slack, 'Tilting your umbrella is our opportunity.' That's not a great rephrase of 'your margin is my opportunity,' but your failure to really be considerate and exercise this courtesy and really be empathic about other people's experience is an advantage. You can create a critical advantage."

"我们在 Slack 会说——'倾斜你的伞是我们的机会。' 这不是把'你的 margin 是我的机会'重新表达得很好，但意思是：你没有真正体贴、没有发挥这种基本的礼貌、没有真正同理别人的体验——这是一种机会。你可以借此建立关键的优势。"

Lenny's Podcast, 2025

故事的核心是：在温哥华窄人行道上，下雨天的人撑伞过路时只有大概 1/3 的人会主动倾斜自己的伞，避免碰到对面的人——剩下 2/3 的人不在意。在 Stewart 看来，这种"没有人会因此扣你工资但你本可以做"的小礼节，就是产品级别的同理心实践。

关于创业：Parkour 而不是路线规划

"Being an entrepreneur can be a lot like doing parkour... you have to keep moving. You have to keep the momentum and any kind of stalling or hesitating can cause a lot of damage. I like the metaphor of parkour though because it's very opportunistic, continually looking around the environment for what can give you the most advantage or the most leverage and then pursuing that at top speed."

"创业很像在做 parkour……你必须保持移动。你必须保持势头，任何停顿或犹豫都可能造成大伤害。但我喜欢 parkour 这个比喻是因为它非常机会主义——不断扫描环境、寻找最能给你优势或杠杆的东西，然后全速追上去。"

20VC, 2020

关于个人：3 个财富层级（之后都差不多）

"There's kind of three levels of wealth. And one is I don't have to worry about my debts. And the second one is I don't care what anything costs in a restaurant because I very clearly remember choosing between two dishes and one was two dollars more than the other, and I decided I couldn't splurge on the more expensive thing. The third one is you don't care what vacations cost. After that, I think it's probably all about the same."

"财富大概有三个层次。第一个是——我不用为债务担心。第二个是——我不在乎餐厅里任何东西的价格，因为我非常清楚地记得自己在两道菜之间选择、其中一道贵了 $2、我决定不能为那个贵的破费的那个时刻。第三个是——你不在乎度假要花多少钱。再往上，我觉得就基本都差不多了。"

20VC, 2020

"Money as score-keeping... they're very driven by the money, not because they're especially greedy or rapacious, but because it's the way they keep score."

"钱作为计分系统……他们（销售）非常被钱驱动，不是因为他们特别贪婪，而是因为那是他们记分的方式。"

20VC, 2020（转述 Ben Horowitz 的话）

关于自我认识：能看到自己的缺陷但改不了

这是 Stewart 在 Stanford 上最自我嘲讽的一句：

"I think I'm relatively self aware even of those things that don't work and it doesn't matter that I know that they don't work, I still can't change them."

"我觉得我对自己那些'不奏效'的东西也算自知——但即使我知道它们不奏效，我还是改不了。"

Stanford GSB View From The Top, 2020

"I'm constantly worried about the things outside of the company when I'm focused on the company and constantly worried about the company when I'm focused on anything outside."

"我在专注公司的时候会一直担心公司外的事；专注公司外的事时又一直担心公司。"

20VC, 2020

"It's hard not to take it personally when things aren't going well. And unfortunately, on the flip side, when things are going well... it hardly feels like it's something intrinsic to me. So there's a lot of luck and there's a lot of timing."

"事情不顺利时很难不个人化。不幸的是反过来——事情顺利时，又很难觉得这是来自我自身的某种内在。所以有大量运气、大量时机的因素。"

20VC, 2020

关于 AI：Augmentation, Not Substitution

Stewart 在 Odd Lots（2023 年 5 月）上对 AI 的态度是 1960 年保险公司视角下的"Excel 隐喻"：

"Jack Lemmon works at an insurance company... He's literally a cell in a spreadsheet. That is exactly what he's doing. It's like, take input, execute formula, produce output... The same number of people who work in insurance companies today, no one does that anymore."

"Jack Lemmon 在保险公司工作（《公寓春光》）……他字面上就是一个电子表格的单元格。他做的就是这个——输入、执行公式、输出……今天保险公司还是同样数量的人，但没有人在做那种事了。"

Odd Lots, 2023

"In my life, I might have done as much financial modeling as all of humanity did until 1965 or something like that. Because you can just make a spreadsheet and then be like, oh, change this, change this... It allows you to think at a much higher level. So I think about AI, again, in that augmentation capacity and what it will enable us to do."

"我这一生做的财务建模，可能跟 1965 年之前所有人类做的总和差不多。因为你可以做一个 spreadsheet 然后说'改这里、改这里'……它让你能在更高的层次上思考。我对 AI 的看法又回到那种增强的能力——它将让我们能做什么。"

Odd Lots, 2023

但他也加了一个不容忽视的警告——"挖土机隐喻"：

"If your job is to dig ditches, you can only dig so many ditches a day. And if you are given a backhoe, you can dig a hundred times more, 500 times more, whatever the multiple is. But those technologies come with additional risks. You can accidentally knock down a building with a backhoe and you can't accidentally knock down a building with a shovel."

"如果你的工作是挖沟，你一天能挖的沟是有限的。如果给你一台挖土机，你能挖 100 倍、500 倍。但这种技术带来额外的风险——你可能用挖土机不小心撞倒一栋楼，但你用铁锹绝不会不小心撞倒一栋楼。"

Odd Lots, 2023

关于哲学：根本性的问题与"questioning the assumed answers"

"All advancement, all travel down the upward arc, comes from questioning things that we have assumed answers to and don't question enough. You can't go through life questioning everything unless you are a professional philosopher, because it's just exhausting and paralyzing. And yet, the effort that humans have put into digging deep into fundamental assumptions has created most of the progress."

"所有进步、所有向上的弧线，都来自质疑那些我们已经假定了答案、却不去再追问的事情。你不能一生中质疑所有事，除非你是个职业哲学家——那会让人极度疲惫和瘫痪。但人类深入挖掘根本假设所付出的努力，造就了大多数进步。"

Invest Like the Best, 2021

"I believe the most profound question is, why is there something instead of nothing?"

"我相信最深刻的问题是：为什么存在某种东西、而不是什么都没有？"

Invest Like the Best, 2021

他坦承这可能"最深刻"是因为它"最不可回答"。

关于创业：1 公司里的"empire-building"是所有 excess 的根源

Odd Lots 上 Stewart 对硅谷与大科技 excess 的批评是少见的——一个亲身参与超级独角兽周期、并自己在 IPO 时承认 $2.8B 估值已经过分的 CEO 出来说话：

"Slack raised money at a $2.8 billion valuation and people were like, well, that's crazy. And even back then it was apparent and we would say in interviews, this is just zero interest rate. Like this is what happens."

"Slack 以 $28 亿估值融资，大家说'这疯了'。即使当时我们在采访里也会说——这就是零利率现象。这就是会发生的事。"

Odd Lots, 2023

"Even if it's like a two-person empire, it's something. If you become a manager, you want to become a senior manager. If you're a senior manager, you want to become a director. It's a very powerful incentive. If you hire 1,000 people, you have 996 people or roughly 100% who are like, I need to hire. So every budgeting process is I really want to hire. And that to me is the root of all the excess."

"哪怕只是个两人帝国，那也是个帝国。变成经理后你想成高级经理；成了高级经理你想当总监。这是非常强大的激励。如果你雇了 1000 个人，你有 996 个人——大约 100%——都在想'我需要招人'。所以每次预算流程都是'我真的想招人'。这就是所有 excess 的根源。"

Odd Lots, 2023

"If you have infinite money, either from being a monopoly on search engines or having VCs give you lots of money, you can get rid of that constraint altogether."

"如果你有无限多的钱——要么因为你是搜索引擎的垄断者，要么因为 VC 给你大量的钱——你可以完全摆脱预算约束。"

Odd Lots, 2023

三、数据来源

网络研究（16 篇）

1. Stewart Butterfield — Wikipedia — 2026-05-11 — 基础时间线
2. Flickr — Wikipedia — 2026-05-11 — Flickr 起源与 Yahoo 收购
3. Slack — Wikipedia) — 2026-05-11 — Slack 公司历史
4. Butterfield's "Tin-smith" resignation letter to Yahoo — 2026-05-11 — 经典原创文献
5. We Don't Sell Saddles Here — Medium — 2026-05-11 — 经典内部备忘录
6. The Death of Glitch and the Birth of Slack — BuildingSlack — 2026-05-11 — 第二次 pivot 的全过程
7. Why Slack and Salesforce execs think they're better together — TechCrunch — 2026-05-11 — Salesforce 收购的真实起源（Quip）
8. Butterfield's farewell memo (Dec 2022) — 2026-05-11 — 园艺告别信
9. Ludicorp — Wikipedia — 2026-05-11 — 早期公司历史
10. Masters of Scale Ep. 13: The Big Pivot, with Stewart Butterfield — 2017 — 最完整一手叙事；Reid Hoffman 访谈
11. Slack's Direct Listing IPO — CNBC — 2019-06-21 — direct listing 上市当日 CNBC 采访
12. Mat Honan's Wired profile — 2014-08 — 定义其公众形象的封面专访
13. Lessons from Stewart Butterfield — Antoine Buteau — 2026-05-11 — 跨访谈综述
14. Glitch (video game) — Wikipedia) — 2026-05-11 — Glitch 时间线
15. Post-Slack 2023-2025（ARTnews / Wikipedia / Neo Financial 等多源汇编）— 2026-05-11 — 离任后的实际生活轨迹
16. Rules of Business — Medium / Offscreen Magazine Issue 10 — 2014-11 / 2015-03 — Butterfield 唯一的另一篇主要散文

播客访谈（6 期）

未使用但已扫描的（质量过滤掉的）

• "Utility Curves, Friction as a Feature & Craft" (AI Podcast Summaries from Transcripted.ai) — VIDEO 自动剪辑聚合频道，被排除
• "Stewart Butterfield, Cofounder and CEO of Slack" (Money is Not Evil Podcast, 2022-06-03) — 低层级节目，未提供深度新内容
• "Stewart Butterfield on creating Slack..." (The Gray Area with Sean Illing, 2016-09-06) — 已提交 Podwise 处理，未完成索引，标记为 failed_processing
• "Stanford Seminar - Entrepreneurial Thought Leaders: Stewart Butterfield" (Stanford Online, 2015-10-15) — 未提交处理；内容与 Stanford GSB 2020 重叠较多