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Stewart Butterfield's Bold Choices Before $27.7B Salesforce Deal

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Chapter 1: Stewart Butterfield's Journey

Stewart Butterfield, the mastermind behind Slack, initially pursued degrees in philosophy at both the undergraduate and graduate levels. After completing these studies, he contemplated a PhD. However, a chance encounter with a friend who had recently completed his own PhD altered Stewart's path. This friend, despite his academic achievements, was struggling in his career, which led Stewart to reconsider his own aspirations.

Twenty-two years later, Stewart sold Slack to Salesforce for an astonishing $27.7 billion, marking the largest acquisition in Salesforce's history. Let’s delve into three bold decisions he made that paved the way for this monumental success.

Section 1.1: A Shift from Philosophy to Web Design

While working toward his PhD in Philosophy, Stewart initially planned his career around academia. However, witnessing his friend's dissatisfaction with a temporary university position made him rethink his trajectory. Stewart realized that if such a well-regarded thesis could lead to instability, his own future might be equally uncertain.

Reflecting on his past experiences, he recalled assisting with website setups during his undergraduate and master's studies, gaining proficiency in HTML and web technologies. This skill set became instrumental as he transitioned from philosophy to web design.

Section 1.2: The Launch of His Second Gaming Venture

In 2002, Stewart launched his first game, Game Neverending. Unfortunately, within a year, he had to shut it down due to the dot-com crash, which left him without funding. Many would have felt disheartened by this setback, questioning their place in the gaming industry. However, Stewart took a different approach; he recognized that the market simply wasn't ready for his game.

Instead of dwelling on the failure, he utilized the technology behind Game Neverending to create Flickr, which was sold to Yahoo for $20 million. This success provided him with the capital to establish Tiny Speck in 2009. Despite the uncertainty surrounding his next gaming venture, Stewart bravely proceeded with the launch of Glitch, which would ultimately prove pivotal in his career.

Chapter 2: Prioritizing Employee Support

In an industry often marred by layoffs, Stewart's approach stood out. In recent years, many tech giants like Google and Amazon have laid off thousands, often leaving employees without support. Stewart faced a similar situation when he decided to close Glitch in 2009, but he chose a different path.

With 45 employees at Tiny Speck, he recognized the challenges many faced in finding new jobs, particularly those with specialized skills. Rather than simply letting his employees go, Stewart and his team created a portfolio site showcasing each employee's resume and provided reference letters and career counseling. With $5.5 million remaining from investor funding, they ensured a smooth transition for those affected.

Most of the employees who were laid off found new opportunities, and the team returned the remaining funds to investors once everyone was successfully placed in new roles. This compassionate and strategic approach exemplified Stewart's leadership and commitment to his team.

Summary:

Stewart Butterfield's journey is marked by pivotal decisions: transitioning his career late, launching a second gaming venture, and supporting employees during tough times.

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