Stewart Butterfield: Serendipity in Design and Entrepreneurship [Entire Talk] | Summary and Q&A

October 6, 2015
Stanford eCorner
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Stewart Butterfield: Serendipity in Design and Entrepreneurship [Entire Talk]

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In this video, Stewart Butterfield, the co-founder of Slack and Flickr, shares his background and journey as an entrepreneur. He discusses the power of the internet to connect people and why communication is the fundamental application of computing technology in today's world. He also talks about his experiences with building gaming companies that ultimately led to the creation of successful products like Flickr and Slack. Butterfield emphasizes the importance of resilience in the face of failure and the lessons he learned from his past ventures. He explains how Flickr's technical innovations and early adoption of open APIs helped drive its success. He also discusses the external conditions that contributed to Slack's rapid growth and popularity. Butterfield concludes by highlighting the significance of company culture, including values like empathy, curiosity, and diligence, in building a successful organization.

Questions & Answers

Q: Can you share a little bit about your background and journey as an entrepreneur?

Sure. I was born in a log cabin and didn't have running water or electricity. I started college in 1992 and was blown away by the power of the internet to connect people. I worked on making web pages during college and planned to be a philosophy professor. However, the dot-com era presented exciting opportunities in internet technology, and I decided to pursue a career in that field instead.

Q: Why have you focused so much on social networking and communication in your career?

Communication is the fundamental application of computing technology in human beings' lives. The internet's power to connect people has always fascinated me. From my early experiences on IRC and Usenet to building web pages and creating online communities, I've seen the value in using technology to facilitate communication. Whether it's through gaming or software like Slack, my focus has always been on improving how people connect and interact with each other.

Q: Can you talk about the challenges and failures you faced while building gaming companies?

My experiences with gaming companies like GradFinder and The Game Neverending were not successful in terms of creating popular games. However, these failures led to the birth of Flickr and eventually Slack. The key lessons I learned were the importance of resilience and adapting to changing circumstances. We had to pivot our ideas and technologies, and it took multiple iterations before we found success. These failures taught me to keep pushing forward despite setbacks and to continually iterate and improve.

Q: How did Flickr's technical innovations and open APIs contribute to its success?

Flickr was innovative in terms of its technical infrastructure and its integration of open APIs. We prioritized building a platform that allowed users to communicate, share, and tag photos in a community-oriented environment. The concept of tagging photos was relatively new at the time, and Flickr became known as a place for photos to thrive. By embracing openness and allowing developers to build on top of our platform, we fostered a vibrant ecosystem that contributed to the growth and success of Flickr.

Q: What external conditions have contributed to the rapid growth of Slack?

There are several external factors that have contributed to Slack's success. The increasing number of people coming online and the rise of messaging apps have created a favorable environment for a communication tool like Slack. The proliferation of smartphones and improved internet connectivity have made it easier for people to communicate and collaborate through technology. Additionally, the goodwill created by our handling of the shutdown of Glitch and our commitment to supporting employees and customers has built trust and support for Slack.

Q: What role does culture play at Slack?

Culture is crucial at Slack, and it has been shaped by our experiences and the values we hold. We emphasize empathy, curiosity, and diligence as core traits in our employees. Empathy is particularly important for designers, as it helps us understand and meet the needs of users. We prioritize creating an inclusive and supportive work environment that fosters collaboration and innovation. Our culture has been a driving force in our success and has allowed us to attract top talent and build strong relationships with customers and stakeholders.

Q: How do you envision Slack's potential as a platform?

Slack is more than just a standalone application; it has the potential to be a powerful platform. We are focused on building integrations and expanding our ecosystem to provide users with a seamless experience and connect with other tools they use. Our goal is to make Slack the central hub for work communication, where users can access all their tools and workflows in one place. By continuing to innovate and collaborate with developers, we aim to unlock the full potential of Slack as a platform.

Q: How do you handle setbacks and challenges in your entrepreneurial journey?

Resilience is key when facing setbacks and challenges as an entrepreneur. It's important to acknowledge and learn from failures but not let them define you. I try to maintain a positive mindset and use setbacks as opportunities for growth and improvement. Surrounding myself with a supportive team and maintaining a clear vision for the future also helps in navigating challenges. It's essential to stay focused, adaptable, and committed to your goals even in the face of adversity.

Q: What advice do you have for aspiring entrepreneurs?

Building a successful company requires a combination of factors, some of which are beyond your control. While hard work, innovation, and strategic decision-making are important, luck also plays a role. It's important to surround yourself with a team you trust and to foster a culture that aligns with your values. Being resilient and adaptable is crucial, as setbacks and challenges are inevitable. Stay focused on your vision and be prepared for highs and lows along the journey.

Q: How do you balance high expectations and pressure as Slack's success grows?

Balancing high expectations and pressure is a challenge that entrepreneurs face as their companies grow. Recognizing that success is not a linear path and that there will be ups and downs is important. It's essential to stay grounded and not let external pressures define your self-worth. Maintaining a strong support system, both personally and professionally, can be instrumental in managing this pressure. It's essential to maintain perspective and focus on long-term goals rather than getting caught up in short-term fluctuations or criticism.

Q: What role does communication play in your work and in the success of Slack?

Communication is at the core of my work and the success of Slack. The power of technology to connect people and facilitate communication has always fascinated me. At Slack, we aim to improve how people communicate and collaborate at work. By creating a platform that allows for seamless and efficient communication, we enable teams to work more effectively and achieve their goals. Communication is also vital in managing relationships with employees, customers, and other stakeholders, which can contribute to the overall success of the company.


Stewart Butterfield's entrepreneurial journey is marked by resilience, adaptability, and a focus on communication and community. He recognizes the power of the internet to connect people and build communities, which has been a common thread throughout his career. Butterfield's experiences with failures and setbacks have taught him the importance of perseverance and learning from challenges. He also emphasizes the role of luck in entrepreneurship and the need to balance high expectations and pressure. Building a strong company culture based on values such as empathy and curiosity is a key driver of success. As Slack grows, its ecosystem and platform potential make it a powerful tool for work communication and collaboration.

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