From Clown to CEO: The Outrageous Emails of Stewart Butterfield

Stewart Butterfield, the co-founder of multiple tech giants from Couchsurfing to Slack, has a personality quite as fascinating as his ventures. His candid and often humorous emails shed light on his unique perspective and creativity. Dive into the hilariously candid communication of this tech pioneer and explore the personality behind these innovations.

Resignation Letter: A Glimpse Into Stewart's Mind

From jesting about his “flatulence works” to making bold resignations, Butterfield's email correspondence offers a second layer of depth to who he is as a person. Let's dissect the letter he wrote that resigned him from his role as CEO of Slack, a company he helped build from the ground up.

It all started when his partner in crime, Tyler Hall, who was one of the co-founders of Slack, stepped down from the board of directors. This event prompted Butterfield to reflect on his position and the future of the company. In his resignation letter dated 2019, he clearly stated his reasons for stepping down, outlining his personal and professional motivations.

"I wanted to make sure that your company [Slack] thrives while I am here. Too much focus on my own role and impact here risks my becoming myself, not you. I am stepping down and can focus on initiatives that can support your work in ways that don't directly diminish my oversight,"

With these lines, Butterfield underscores his dedication to the company's growth and the well-being of its employees. Rather than keeping the company running solely on his vision, he wanted to ensure that its success was grounded in the collective efforts of its members. This decision serves as a powerful lesson in the importance of stepping aside and trusting in the team to lead the company to new heights.

The Hilarious Side of Stewart Butterfield

Butterfield's bold and creative personality is not just limited to his visionary business moves. His candid emails often reveal a playful and sometimes absurd sense of humor, showcasing his unique perspective on everyday events. Here are a few notable instances.

Flatulence Approval

In a typical office setting, conversations about bodily functions might be left unwritten. Not so with Butterfield. In one email to his employees, he humorously suggested that flatulence might be a valid reason for an employee to step away from their desk. The email went viral and highlighted his comfort with his human side and the ability to find humor in everyday life.

"We should amend our policy to permit bowel movement. If an individual is farting so loudly or persistently that it interferes with the ability of the office to function, that is a problem. And here I am ignoring the occurrence of flatulence. What if someone is having difficulty going?"

This joke about office flatulence demonstrates Butterfield's humanity and willingness to embrace the quirks and challenges of his employees' daily lives.

Interviewing with Butterfield

Another notable email addresses interview processes. Butterfield reminisces about how his previous job as the CEO of Couchsurfing differed from the current model of interviewing. His unconventional approach is evident through his witty and humorous anecdotes.

"The discussions are mostly for the sake of it. You'll have to listen to something like, 'So what makes you 120% upon being offered a job here? What makes you 120% (that is, ten percent beyond the usual point 100%)? Share a few stories that give us ideas about you, your motivation, your commitment. It's all good. Just keep one or two specific examples and make sure you have them ready. I know you've interviewed at old-fashioned companies where they started talking about your weaknesses. We don't do that. We assume everyone's perfect. So instead, we talk about these things. Stand up and give a speech. Do it with more than an earnestness but not a shtick. I like to interview by asking questions to which I happen to already know the answer. It breaks up the rote interviewing and you and I both want to keep things lively. Mostly, we want you to understand us and the company and whether you are a good fit,"

This email provides insight into Butterfield's unique interviewing style and his belief in finding individuals who align with the company’s values.

Legacy and Influence

Through his candid emails, Stewart Butterfield has established himself as a tech luminary whose guidance extends beyond his business achievements. His emails are a testament to his ability to connect with his team, clients, and even the public at large, with authenticity and humor.

The legacy of Couchsurfing and Slack will forever be intertwined with the quirks and innovative spirit of Stewart Butterfield. While his emails might range from the mundane to the profound, they all share a common thread: the importance of human connection and the value of a good laugh. As we continue to celebrate his achievements, let us also remember his unique contributions to the tech world and the inspiration he offers to aspiring entrepreneurs and tech leaders alike.

So, let's all embrace our inner Stewart Butterfield—whether that be showing some flatulence approval or conducting a mock interview with ourselves, and remember that in the tech world, there's still room for a little creativity, humor, and humanity in the most unexpected places.