The life and career of Stewart Butterfield, the Flickr cofounder and Slack CEO who just sold his company to Salesforce for $27.7 billion

Megan Hernbroth,Avery HartmansDec 3, 2020, 22:56 IST

Slack CEO Stewart Butterfield.Drew Angerer/Getty Images

Stewart Butterfield founded Slack in 2013 after selling his first startup, Flickr, to Yahoo for more than $20 million.
Slack became one of the fastest-growing companies ever, achieving a $1 billion valuation less than a year after it officially launched.
Butterfield, whose birth name was Dharma before he changed it at age 12, was born in British Columbia and majored in philosophy in college.
He's currently engaged to a fellow tech founder: Jennifer Rubio, the cofounder of luggage startup Away.

Stewart Butterfield is on a roll.

In the early 2000s, Butterfield created Flickr, which sold to Yahoo for over $20 million. Now, his latest venture, Slack, one of the fastest-growing business apps ever, has been acquired by Salesforce for $27.7 billion.

The workplace messaging app, born out of a now-defunct gaming startup Tiny Speck, will help Salesforce compete with its chief rival, Microsoft, during a time when office communication technology is more essential than ever.

Here's how Butterfield, 47, got his start and built a wildly successful, multibillion-dollar startup.

This is an update to a story by Maya Kosoff first published in 2015.

Butterfield was born in 1973 in a small fishing village called Lund in British Columbia. His parents didn't have running water in their log cabin until he was 3 years old. His family moved to Victoria, British Columbia, when he was 5 so he could attend school, according to BBC.

Carpenter Creek in New Denver, British Columbia. Citizen of the Planet/Education Images/Universal Images Group via Getty Images

Source: BBC

Butterfield was born in 1973 in a small fishing village called Lund in British Columbia. His parents didn't have running water in their log cabin until he was 3 years old. His family moved to Victoria, British Columbia, when he was 5 so he could attend school, according to BBC.

Butterfield's father, David, was a sergeant in the US Army who had a moral qualm with the Vietnam war. One night, he decided to desert, driving to Canada to avoid being sent overseas. In Canada, he met Butterfield's mother, Norma, according to Wired.

A driver at the border crossing between the US and Canada. Associated Press/Elaine Thompson

Source: Wired

Butterfield's father, David, was a sergeant in the US Army who had a moral qualm with the Vietnam war. One night, he decided to desert, driving to Canada to avoid being sent overseas. In Canada, he met Butterfield's mother, Norma, according to Wired.

Source: Wired

Butterfield told BBC that his parents "were definitely hippies" who "wanted to live off the land." They originally named him Dharma, but when he turned 12, he changed his name to Stewart, which he now regrets. "There are no good characters named Stewart," Butterfield told Wired.

Mike Blake/Reuters

Source: BBC, Wired

Butterfield told BBC that his parents "were definitely hippies" who "wanted to live off the land." They originally named him Dharma, but when he turned 12, he changed his name to Stewart, which he now regrets. "There are no good characters named Stewart," Butterfield told Wired.

Source: BBC, Wired

At age 7, Butterfield got his first computer, an Apple II. He taught himself to code. and once he was in college, he designed websites for extra money. "I was among the first cohort of kids to grow up with computers," he told Business Insider.

An Apple II computer, which came out in 1977. Jaap Arriens/NurPhoto via Getty Images

Source: Business Insider, BBC

At age 7, Butterfield got his first computer, an Apple II. He taught himself to code. and once he was in college, he designed websites for extra money. "I was among the first cohort of kids to grow up with computers," he told Business Insider.

Source: Business Insider, BBC

Butterfield graduated from the University of Victoria in 1996 with a philosophy degree. He later received his Master of Philosophy from the University of Cambridge.

The Great Court at Trinity College, part of the University of Cambridge. JUSTIN TALLIS/AFP via Getty Images

Source: Wired

In 2000, he joined his friend Jason Classon at Classon's startup, Gradfinder.com. The internet bubble had just burst, but the pair still managed to sell Gradfinder.com for what Butterfield describes as "a healthy profit" to Highwired six months after launching the company. Classon went to work for Highwired and Butterfield went back to web design freelancing.

Charles Platiau/Reuters

Source: Business Insider

In 2000, he joined his friend Jason Classon at Classon's startup, Gradfinder.com. The internet bubble had just burst, but the pair still managed to sell Gradfinder.com for what Butterfield describes as "a healthy profit" to Highwired six months after launching the company. Classon went to work for Highwired and Butterfield went back to web design freelancing.

Source: Business Insider

Butterfield created a contest called the "5K competition," which encouraged people to design websites in under 5 kilobytes. It took off. "It became unexpectedly huge, in every country in the world," Butterfield told Business Insider.

The 5K contest still has a website. 5K contest

Source: Business Insider

Butterfield created a contest called the "5K competition," which encouraged people to design websites in under 5 kilobytes. It took off. "It became unexpectedly huge, in every country in the world," Butterfield told Business Insider.

Source: Business Insider

Butterfield met Caterina Fake, who was then a blogger, in 2000. They got married two years later and in 2007, they had a daughter together. They got divorced six months after her birth, according to Wired.

Andrew Toth/Getty Images for Vanity Fair

Source: Wired

Butterfield met Caterina Fake, who was then a blogger, in 2000. They got married two years later and in 2007, they had a daughter together. They got divorced six months after her birth, according to Wired.

Source: Wired

Shortly after their honeymoon, Butterfield and Fake founded Ludicorp, an online multiplayer gaming startup, with Classon. This time, timing did not work in the team's favor: After 9/11 and another tech bubble burst, the company couldn't raise money.

Drew Angerer, Getty images

Source: Business Insider

Shortly after their honeymoon, Butterfield and Fake founded Ludicorp, an online multiplayer gaming startup, with Classon. This time, timing did not work in the team's favor: After 9/11 and another tech bubble burst, the company couldn't raise money.

Source: Business Insider

Butterfield got the idea for his next venture, Flickr, as he was throwing up from food poisoning in a New York hotel. Butterfield's team had created a photo-sharing platform but realized it wouldn't be successful if it required both parties to be online at the same time. They made some changes, and Flickr began to take off.

From left: Cal Henderson, Stewart Butterfield, Eric Costello Courtesy of Stewart Butterfield

Source: Business Insider

Butterfield got the idea for his next venture, Flickr, as he was throwing up from food poisoning in a New York hotel. Butterfield's team had created a photo-sharing platform but realized it wouldn't be successful if it required both parties to be online at the same time. They made some changes, and Flickr began to take off.

Source: Business Insider

Flickr was revolutionary at the time for a few reasons: For one, photo-sharing in the cloud was a new concept on its own. But Flickr also pioneered features like tagging, user authentication, and adding permissions for which contacts can view your photos. Yahoo snapped up the company in 2005 for between $22 million and $25 million.

Former Yahoo CEO Marissa Mayer. Mario Tama, Getty Images

Source: Wired

Flickr was revolutionary at the time for a few reasons: For one, photo-sharing in the cloud was a new concept on its own. But Flickr also pioneered features like tagging, user authentication, and adding permissions for which contacts can view your photos. Yahoo snapped up the company in 2005 for between $22 million and $25 million.

Source: Wired

Butterfield and Fake relocated to the Bay Area and joined Yahoo as part of the acquisition. But three years later, Butterfield was fed up and tried to quit. The company asked him to stay on for a few more months to keep up appearances (Fake had just quit too) so Butterfield spent several months doing nothing, not even showing up to the office, according to Wired.

Kimberly White / Stringer / Getty Images

Source: Wired

Butterfield and Fake relocated to the Bay Area and joined Yahoo as part of the acquisition. But three years later, Butterfield was fed up and tried to quit. The company asked him to stay on for a few more months to keep up appearances (Fake had just quit too) so Butterfield spent several months doing nothing, not even showing up to the office, according to Wired.

Source: Wired

Finally, in June 2008, Butterfield was able to resign. He sent a 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."

Brendan McDermid/Reuters

Source: Wired

Finally, in June 2008, Butterfield was able to resign. He sent a 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."

Source: Wired

When he left Yahoo and Flickr, Butterfield wanted to make the multiplayer game he started working on with Ludicorp. He rounded up 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."

Cal Henderson speaks at Business Insider's IGNITION conference in December 2018. Jin S. Lee

Source: Business Insider

When he left Yahoo and Flickr, Butterfield wanted to make the multiplayer game he started working on with Ludicorp. He rounded up 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."

Source: Business Insider

But while "Glitch" had a "hardcore cult following," it was hard to justify the $17 million in venture capital that had been poured into it, Butterfield told Business Insider. "The game was too weird for most people," he said.

A screenshot from "Glitch." Glitch

Source: Business Insider

But while "Glitch" had a "hardcore cult following," it was hard to justify the $17 million in venture capital that had been poured into it, Butterfield told Business Insider. "The game was too weird for most people," he said.

Source: Business Insider

Tiny Speck found the perfect pivot: the communication tool Butterfield and his team had built to chat in real-time in the game. It became known as an instant-messaging platform called Slack, which formally launched in 2013.

Beck Diefenbach/Reuters

Source: Business Insider

Tiny Speck found the perfect pivot: the communication tool Butterfield and his team had built to chat in real-time in the game. It became known as an instant-messaging platform called Slack, which formally launched in 2013.

Source: Business Insider

Slack's growth impressed some of Silicon Valley's most prominent venture capital firms, like Andreessen Horowitz and Kleiner Perkins. It became one of the fastest-growing companies ever, achieving a $1 billion valuation less than a year after it officially launched.

Marc Andreessen, left, and Ben Horowitz. Brendan McDermid/Reuters

Source: Fortune, TechCrunch

Slack's growth impressed some of Silicon Valley's most prominent venture capital firms, like Andreessen Horowitz and Kleiner Perkins. It became one of the fastest-growing companies ever, achieving a $1 billion valuation less than a year after it officially launched.

Source: Fortune, TechCrunch

By the summer of 2018, Slack had grown to over 8 million daily active users, even as rumors swirled that Amazon was looking into an acquisition. All told, Slack raised over $1.2 billion in funding, and hit a $7.1 billion valuation in its last round of funding.

Butterfield and actor Jared Leto. (Photo by Dimitrios Kambouris/Getty Images for WSJ. Magazine 2015 Innovator Awards)

Source: Business Insider

By the summer of 2018, Slack had grown to over 8 million daily active users, even as rumors swirled that Amazon was looking into an acquisition. All told, Slack raised over $1.2 billion in funding, and hit a $7.1 billion valuation in its last round of funding.

In April 2019, Slack filed to go public. It made its stock market debut two months later, for a direct listing over a traditional initial public offering. On its first day of trading, Slack shares surged nearly 50%.

Butterfield outside the New York Stock Exchange the day his company went public. Richard / Drew Associated Press

Source: Markets Insider

In April 2019, Slack filed to go public. It made its stock market debut two months later, for a direct listing over a traditional initial public offering. On its first day of trading, Slack shares surged nearly 50%.

Source: Markets Insider

Around the same time his company was going public, Butterfield experienced another milestone: He got engaged to Jennifer Rubio, the cofounder of the popular luggage brand Away, in Tofino, a town near Vancouver. The couple had planned to get married in Peru but decided to cancel it due to the pandemic, according to Rubio's Instagram.

Away cofounder Jen Rubio. Michael Kovac/Getty Images

Source: Jennifer Rubio/Instagram

Around the same time his company was going public, Butterfield experienced another milestone: He got engaged to Jennifer Rubio, the cofounder of the popular luggage brand Away, in Tofino, a town near Vancouver. The couple had planned to get married in Peru but decided to cancel it due to the pandemic, according to Rubio's Instagram.

In December, cloud giant Salesforce announced it was buying Slack for $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."

Drew Angerer/Getty Images

Source: Business Insider

In December, cloud giant Salesforce announced it was buying Slack for $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."

13 successful tech leaders who struggled as immigrants before making it in America

Cookies on the Business Insider India website

The life and career of Stewart Butterfield, the Flickr cofounder and Slack CEO who just sold his company to Salesforce for $27.7 billion

Butterfield was born in 1973 in a small fishing village called Lund in British Columbia. His parents didn't have running water in their log cabin until he was 3 years old. His family moved to Victoria, British Columbia, when he was 5 so he could attend school, according to BBC.

Butterfield's father, David, was a sergeant in the US Army who had a moral qualm with the Vietnam war. One night, he decided to desert, driving to Canada to avoid being sent overseas. In Canada, he met Butterfield's mother, Norma, according to Wired.

Butterfield told BBC that his parents "were definitely hippies" who "wanted to live off the land." They originally named him Dharma, but when he turned 12, he changed his name to Stewart, which he now regrets. "There are no good characters named Stewart," Butterfield told Wired.

At age 7, Butterfield got his first computer, an Apple II. He taught himself to code. and once he was in college, he designed websites for extra money. "I was among the first cohort of kids to grow up with computers," he told Business Insider.

Butterfield graduated from the University of Victoria in 1996 with a philosophy degree. He later received his Master of Philosophy from the University of Cambridge.

Butterfield created a contest called the "5K competition," which encouraged people to design websites in under 5 kilobytes. It took off. "It became unexpectedly huge, in every country in the world," Butterfield told Business Insider.

Butterfield met Caterina Fake, who was then a blogger, in 2000. They got married two years later and in 2007, they had a daughter together. They got divorced six months after her birth, according to Wired.

Shortly after their honeymoon, Butterfield and Fake founded Ludicorp, an online multiplayer gaming startup, with Classon. This time, timing did not work in the team's favor: After 9/11 and another tech bubble burst, the company couldn't raise money.

Finally, in June 2008, Butterfield was able to resign. He sent a 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."

When he left Yahoo and Flickr, Butterfield wanted to make the multiplayer game he started working on with Ludicorp. He rounded up 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."

But while "Glitch" had a "hardcore cult following," it was hard to justify the $17 million in venture capital that had been poured into it, Butterfield told Business Insider. "The game was too weird for most people," he said.

Tiny Speck found the perfect pivot: the communication tool Butterfield and his team had built to chat in real-time in the game. It became known as an instant-messaging platform called Slack, which formally launched in 2013.

Slack's growth impressed some of Silicon Valley's most prominent venture capital firms, like Andreessen Horowitz and Kleiner Perkins. It became one of the fastest-growing companies ever, 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, even as rumors swirled that Amazon was looking into an acquisition. All told, Slack raised over $1.2 billion in funding, and hit a $7.1 billion valuation in its last round of funding.

In April 2019, Slack filed to go public. It made its stock market debut two months later, for a direct listing over a traditional initial public offering. On its first day of trading, Slack shares surged nearly 50%.

In December, cloud giant Salesforce announced it was buying Slack for $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."