Stewart Butterfield is the Co-Founder and CEO of Slack. For more than 20 years, he has been a designer, entrepreneur and technology leader, usually all at once. Butterfield has been regularly recognized for the foresight and innovation that has helped him build two companies that have reimagined how we use technology to collaborate, communicate, share and store information. He has been included on Vanity Fair’s New Establishment List, the Recode 100, he was named one of the 100 Most Influential People in the World by Time Magazine and one of the Top 50 Leaders by BusinessWeek; Advertising Age’s Creativity 50, and the Technology Innovator of the Year by the Wall Street Journal.
Stewart Butterfield was born in a small fishing village in 1973 called Lund in British Columbia. His family resided in a log cabin that did not have any running water in his younger years. He explains, “My parents were definitely hippies who wanted to live off the land. They originally named me Dharma, but when I turned 12, I changed my name to Stewart, which I now regret. There are no good characters named Stewart.”
Butterfield recalled, “We moved to the city when I was five, so I could go to school. That was Victoria, British Columbia, and I was in second grade.” Talking about his education in Victoria, he says, “We were the first class to have computers in the classroom. I was super fascinated by computers in general.” The young boy was amazed by the device and soon taught himself how to code while constantly playing on the computer. Butterfield recalled “that he was among the pioneer cohort of children to grow up with computers.”
However, when Butterfield decided to go to college, he chose to major in a Philosophy Degree and not in technology. But his fascination with computers only increased during that period. He says, “When I got to university ‑‑ this was ’92 ‑‑ I got a Unix account on the school’s mainframe and discovered the Internet. I was just like, [explosion sound ]. I realized at that time how powerful it was. Whatever you were into, if you were a breast cancer survivor, you’re a model train enthusiast, or whatever your deal was, you could find other people online.” He graduated in 1996 from the University of Victoria and later received his Master of Philosophy from Cambridge.
In 2000, he decided to join his friend, Classon, at his tech startup, Gradfinder.com. However, during that time, the internet bubble had just burst, and the pair had to sell their startup at a healthy profit, after which Butterfield went back to freelancing as a web designer.
Butterfield then met Caterina Fake(his now ex), who was then a blogger, in 2000. They got married two years later, and shortly after their honeymoon, the duo founded an online multiplayer gaming startup, Ludicorp, with Classon. Butterfield explains, “We were all fascinated by online communities in the broadest sense, just the human connection that can come out of this transmission of electronic bits back and forth. We were also fascinated by the role that play played in social interaction. When you’re playing a game, it’s competitive, it’s trash‑talking, it gives you like this kind of framework for interacting with people.” He continued, “We wanted to create that on a massive scale. It was primarily text based. We pioneered a lot of really interesting technologies that became Flickr afterwards.” Unfortunately, the team did not succeed in their endeavour; after 9/11 and another tech bubble burst, the company did not manage to raise any funds.
However, Butterfield soon had his eureka moment while throwing up from food poisoning in a New York hotel room. His team had previously created a photo-sharing platform but realized it wouldn’t gain popularity if it required both parties to be online simultaneously. The team made some changes, and Flickr was officially launched.
Flickr was a breath of fresh air at the time for multiple reasons: For one, photo-sharing in the cloud was a new concept on its own. But Flickr was also the first to come out with features like user authentication, tagging and adding permissions for which contacts can view your photos. Yahoo bought the company in 2005 for between $22 million and $25 million.
The couple decided to relocate to the Bay Area and joined Yahoo as part of the company’s acquisition. However, three years later, Butterfield soon hit a dead end and wanted to quit. Yahoo asked him to stay on for a few more months to keep up appearances since Fake had also left Yahoo. So Butterfield spent several months doing nothing, not even showing up to the office. In June 2008, Butterfield resigned and sent his now-famous resignation letter where he described Yahoo as a tin-smithing operation and said he was retiring to tend to his “small but growing alpaca herd.”
After leaving the organization, Butterfield decided to utilize his energy in working on the multiplayer game he previously designed with Ludicorp. He approached some of his former coworkers from Flickr and Ludicorp, including Cal Henderson, to found a startup called Tiny Speck. They started building the game ‘Glitch.’ However, Butterfield says, “While ‘Glitch’ already had a ‘hardcore cult following,’ it was difficult to justify the $17 million in venture capital that had been poured into it. The game was too weird for most people,”
On the lookout for opportunities, Tiny Speck pivoted to a different product. They instead decided to work on the communication tool Butterfield and his team had created to chat in real-time in Glitch. They named the instant-messaging platform Slack, which formally launched in 2013.
Slack’s tremendous growth impressed some of Silicon Valley’s most prominent venture capital firms, like Kleiner Perkins and Andreessen Horowitz. It soon became one of the fastest-growing companies, achieving a $1 billion valuation less than a year after it officially launched. By the summer of 2018, Slack had grown to over 8 million daily active users. The company raised over $1.2 billion in funding and hit a $7.1 billion valuation in its last round of funding.
Talking about the success of the platform, Butterfield says, “I should say, one of the ancillary reasons that I think we’re successful is of the four co founders, at 41, I’m the third youngest. We probably have more engineers over 40 than any other company.”
In December 2020, cloud giant Salesforce announced it was buying Slack for a whopping $27.7 billion, making it Salesforce’s largest acquisition to date. Salesforce CEO Marc Benioff said in a press release: “This is a match made in heaven.”
In conclusion, he says, “One of the biggest lessons I’ve learned is that there has got to be a reason for what you’re doing. You actually have to care about what you’re doing. The business has to be about something. Whatever the point of it is does not have to be inconsistent with making money, but usually if that’s the sole reason, it is not very successful.”
