His online gaming ventures failed miserably but a sneaky tech tool fueled a shocking turnaround
While revolutionizing the internal communication of businesses, which created a $27 billion empire
Conscription … a word the military uses when they want people to join one of the branches of the armed services but doing so on a compulsory bases. You and I know it as being drafted into the military.
Here in the U.S., our military has used the draft six different times:
The American Revolution
The American Civil War
World War I
World War II
The Korean War
The Vietnam War
But not everyone who is selected for the draft wants to willingly join the military. For instance during the Vietnam War, a staggering 209,517 men were charged with violating the Military Selective Service Act.
During the war itself, which lasted from 1955 until 1975, there were 503,926 desertions in the United States military.
An estimated 30,000 to 100,000 Americans fled the country to avoid the draft, with many relocating to Canada.
One of those men who fled the country was David Butterfield. He took his wife Norma and their young son Dharma Stewart and traveled to a remote fishing village located near Lund, British Columbia, Canada.
Lund is a small, coastal town on the Sunshine Coast, approximately 120 kilometers (75 miles) northwest of Vancouver. It lies at the northern end of Highway 101, often referred to as the "end of the road," where the pavement gives way to rugged wilderness and the Desolation Sound marine area begins.
There aren’t many people who live in the area, with a current population of just a few hundred. But it was an ideal spot for David and Nora, who wanted to live a nonconventional lifestyle or what we call hippies. In fact they lived in a commune.
It was the perfect way to “be off the grid.” With no formal type of communication, i.e., telephone, or even a mailing address, this made it difficult for the military to track David down.
Besides no communication, there wasn’t much to this commune. For the first five years David, Norma and Dharma Stewart Butterfield lived in a log cabin without running water or electricity. Furnishings were few with perhaps some chairs and two beds.
The Butterfield family resided here until Dharma was about five years old, around 1978, before moving to Victoria, British Columbia. The rustic life they lived was harsh and labor intensive. His parents couldn’t endure it any longer and longed for a more conventional urban life, especially for their young son.
A Computer Way of Life
While in Victoria, Dharma’s dad got a job as a real estate salesman. Norma and David became involved in community-oriented projects. They founded the David and Norma Butterfield Foundation for Sustainable Communities in 2000.
The two also founded South Island Development in the early 1980s, focusing on restoring heritage buildings and later developing sustainable community projects like the Coast Hotel and Harbourside condominium complex, as well as the award-winning Shoal Point at Fisherman’s Wharf.
With money coming in, the family could now afford a house with all the normal conveniences such as a bathroom, electricity and a kitchen. A much different lifestyle than living in the commune.
When he turned 7, his dad bought Dharma a computer, an Apple II that used floppy disks. Dharma loved it. In fact it sparked what would become a life long fascination with technology and computers.
He was so into his computers that Dharma taught himself how to code, even creating basic video games.
At around the age of 12, his family changed his name to Daniel to better fit in with his peers. He also started using his middle name Stewart more often. He was fortunate enough to attended St. Michaels University School, a private institution in Victoria, where he continued to nurture his curiosity of technology.
From there he attended the University of Victoria, and supported himself by designing websites for local businesses. While technology and computers were his first love, oddly enough he earned a B.A. in philosophy in 1996.
One year later, Stewart met his future wife, Caterina Fake at a dinner party. The two were invited along with a few other mutual friends. Caterina had just graduated from Vassar College and expressed an interest in technology. So Stewart and Caterina started hanging out with one another, which then turned into formally dating.
Not only did they decide to date but to also form a technology company called Gradfinder.com. The idea behind Gradfinder was simple … it served as a social networking platform aimed at helping university students and alumni connect online, offering features like profiles and messaging.
The venture gained some traction but mostly among the students attending the University of Victoria. And the business struggled financially. That’s why just one year after launching Gradfinder, Stewart and Caterina decided to sell it, which they did for around $50,000 to $100,000.
While it was a modest amount of money, it provided enough funds for the duo to move to San Francisco but not before getting married.
Gaming to Your Heart’s Delight
The move to San Francisco brought Stewart and Caterina closer to the epicenter of technology start ups.
They were anxious to form a new technology firm but funds were tight. So Stewart took on freelance web design and consulting work, leveraging his self-taught coding skills to help support the couple. Caterina, with her background in art and design, also picked up freelance projects, including web design and user experience work.
As they settled into their new environment and money was flowing in more steadily, they started working on plans for a new company. In 2002, they founded Ludicorp, a company initially focused on building an online multiplayer game called Game Neverending.
The concept of the game was a browser-based, social experience blending creativity, exploration, and community interaction. The game was set in a whimsical, abstract universe where players could chat, share items, and build relationships, with a focus on community dynamics.
Users could also craft objects, design environments, and contribute to the game’s evolving world, similar to later sandbox games. However their game were unlike traditional video games because they completely avoided violence. Instead Stewart and Catarina prioritized exploration and quirky activities like collecting or trading.
They even built a special section into the game where users could upload and share photos to create a real sense of community.
Unfortunately their company operated on a small budget and their dream game never fully took off. What they learned if anything from this experience is that gamers wanted traditional games, violence and all.
Pivot in the Right Direction
By late 2003, Stewart and Catarina decided to put aside the Game Neverending and instead focus their attention on the photo sharing aspect because that’s what the games used the most.
In essence they restructured the game’s infrastructure, including its database. And they did so with the help of a few colleagues … Cal Henderson, Eric Costello, and Serguei Mourachov.
With everything in place, in 2004 they launched Flickr, the first of its kind photo sharing platform. Key features of Flickr included tagging, marking photos as favorites, and group photo pools. The decision to pivot to photo sharing turned out to be the right decision because the platform gained in popularity and rather quickly too.
When I say it gained in popularity quickly, I mean it happened really fast. It had 250,000 registered users in its first year. Within a year that number surged to over 2 million users.
The growth was so fast that it caught the attention of Yahoo!. Just one year after it launched, Yahoo stepped in bought Flickr for $25 million.
As part of the deal, Stewart was brought on as Flickr’s General Manager. In this role, he oversaw the platform’s development, growth, and integration into Yahoo!’s ecosystem, managing product direction and collaborating with various Yahoo! departments.
Yet Stewart wasn’t a corporate kind of guy and he longed for his days of being an entrepreneur. On July 12, 2008 he quit his job at Yahoo!.
In 2009, he and his wife Catarina moved back to British Columbia to restart their lives as entrepreneurs.
But they needed to stay in touch with their partners Cal, Eric, and Serguei who remained in San Francisco. So Stewart and his buddies built an internal communication app, which allowed them to chat with one another whenever they needed. Not only could they share messages but also files, and get updates in real time.
Now that they had the ability to stay in touch with one another, they could concentrate on forming this next business venture, Tiny Speck.
Gaming on Your Mind But Not in Your Wallet
Their goal was to go back to their gaming origins and create a new online game. They were going to leverage the skills and knowledge they gained building Flickr to develop a community-driven game called Glitch … but again without combat, violence or conflict.
However to create the game from scratch, they needed extra funds to hire more developers and engineers. So they turned to investors for help.
Tiny Speck managed to raise $1.5 million in seed funding from investors like Accel Partners and Ron Conway to kickstart development. In 2010, the company secured an additional $10.7 million in a Series A round, led by Accel and Bessemer Venture Partners, to expand the development team and refine the game.
With money in hand, the small tight-knit team worked closely together. Henderson led engineering, Costello focused on design, and Mourachov contributed to backend systems, while Stewart drove the creative and strategic direction of the company.
With their new game operational, they officially launched Glitch on September 27, 2011. Players engaged in crafting, gathering, and social activities, with quirky elements like growing eggs underground or harvesting dairy from butterflies. It also included puzzles, skill-building, and an API for external developers to create add-ons.
Despite a cult following, Glitch struggled to attract a large audience, partly due to its unconventional design and Flash’s limitations (the platform it was built on), especially as mobile gaming rose.
Unfortunately by December 9, 2012, the game was shut down due to insufficient player numbers and high operational costs.
The Tiny App That Became A Big Breakthrough
Although Stewart was determined to create a highly successful online game, it just wasn’t going to happen for him. But don’t despair Dear Reader because the little app they built to stay in touch with each other would become a technology breakthrough.
With the blessing of his backers, Stewart went to work further refining the communications app the group had built. This would be the center piece of their business. All communications without gaming.
Knowing they would focus their time, attention and resources on the chatting app, Stewart renamed the company Slack Technologies, which stands for “Searchable Log of All Conversation and Knowledge.”
Sometime in March 2013, Slack was functional enough to be tested. So Stewart reached out to friends at other tech startups, including Rdio and Cozy, to beta-test it. Feedback was critical—testers highlighted pain points, like channel overload for large teams, prompting features like channel descriptions and member counts.
This feedback helped Stewart and his team fix the glitches pointed out in the beta-testing phase. It took them about five months to integrate all the suggested changes.
Once those changes were complete, Slack was now ready for its public debut. It was officially launched in August of 2013. Its growth was explosive, hitting 15,000 users within two weeks and 500,000 daily active users by mid-2014. The platform’s appeal lay in its ability to streamline workplace communication, reduce email clutter, and integrate with a growing number of new apps coming online.
By 2019, Slack had over 12 million daily active users and went public via a direct listing, valuing the company at around $19 billion. Stewart finally achieved his big tech breakthrough.
But there was more to come. In 2020, Salesforce acquired Slack for $27.7 billion, integrating it into their suite of tools for their business customers.
Butterfield retired as Slack’s CEO in 2022 but remained with the company as its chairman. He has an estimated net worth of $1.6 billion.
Today Slack has 65 million monthly users and 38.8 million daily users. The platform is used by over 750,000 organizations, including 200,000 paid customers. White Slack might have been first, it ranks number three in business communications, outpaced by Microsoft Teams, which holds the largest market share.
The history of Slack is a classic tale of serendipity and adaptability, turning a side project into a global standard for workplace communication.
Amazing Quotes by Amazing People
“The measure of intelligence is the ability to change." - Albert Einstein