
39 segments available
“The fundamental challenge of leadership is that of being a human being: living with an open heart and not seeing other people as instruments that can be used to your advantage or as obstacles in the way of something you want.” Stewart Butterfield, the co-founder of Flickr and now co-founder & CEO of Slack, was interviewed by Tylon Garrett, MBA ’20, for the decade’s first View From The Top. During the event, Butterfield discussed his journey as a serial entrepreneur, and the learnings along the way. Slack, which now has more than 12 million active users in 150 countries around the world, is Butterfield’s fourth company and reached a valuation of $1 billion within eight months.
Stewart Butterfield shares a fun anecdote about his unusual birth name, Dharma Jeremy Butterfield, and how he chose to go by Stewart. He humorously reflects on the societal perceptions of the name and the desire for normalcy during his childhood.
"[Music] hello Stewart is a pleasure to have you here today thank you how are you doing well cool so typically we would start these with a question asking the students how many of you use flat but sinc..."
Butterfield discusses the lasting influences of his parents on his life, highlighting his mother's supportive nature and his father's career in real estate development. He reflects on how these experiences shaped his entrepreneurial mindset.
"raise your hand if you think statement one is false oh wow it's a lot of people raise your hand if you think statement two is false okay raise your hand if you think statement three it's false okay le..."
Stewart Butterfield recounts his early fascination with computers, starting from the age of seven. He describes how the magic of programming and the internet captivated him, leading to a lifelong passion for technology and innovation.
"very soon when I was twelve I really wanted to be normal and for some reason I thought Stuart was a normal name like Mike and Hertz that's a pretty bad name like you'll notice this after I say it any ..."
Butterfield shares his transformative experience of discovering the internet in college during the early 1990s. He emphasizes the profound impact it had on his worldview, allowing him to connect with like-minded individuals globally.
"usually works the people incorporate a new entity for each project or each development maybe there's a management company it takes management fees but kind of isolates the the investments which means ..."
Stewart reflects on the evolution of computing technology and its role in facilitating human interaction. He discusses the transition from early computers to the internet and how this shaped his career trajectory.
"any menu screen just like you know any child any screen was a super attractive but the idea that you could control what appeared was really magical and 1979-1980 somewhere around there I got an Apple ..."
Butterfield explains his decision to study philosophy instead of pursuing a degree in cognitive science. He discusses the fascinating aspects of philosophy and its relevance to understanding human behavior and technology.
"profound way than like long-distance phone calls out or the Telugu you could find community I grew up in its going to college in Victoria British Columbia which is again on the edge of the continent v..."
Stewart Butterfield shares insights into the history of philosophy and its evolution over the centuries. He reflects on the significance of philosophical inquiry and its impact on various fields, including technology.
"it was cognate science is usually computer science psychology linguistics and psychology and so I wanted to take courses and all four to do an honours degree in psychology was like every single course..."
Butterfield discusses his transition from academia to web development during the rise of the internet in the late 1990s. He highlights the opportunities that arose in the tech industry and the excitement of being part of a transformative era.
"questions it's good to know so who was the most influential philosopher to you I have a pretty broad range and I liked all kinds of thinkers but like going back to Aristotle it was a more contemporary..."
Stewart reflects on the advantages and disadvantages of having a humanities degree in the technology industry. He discusses the diverse backgrounds of early web developers and the evolving landscape of tech careers.
"low pay and it's a sessional position so renews every nine months and I thought of how many hoops I had to jump through just to get to that point or because it was 98 and the.com thing that's starting..."
Butterfield reflects on the broad definition of technology companies, noting how many industries now incorporate technology into their operations. He discusses the implications of software's integration into various sectors, questioning what it truly means to be a tech company in today's landscape.
"think mostly what people mean is at least around the bay area is companies that receive VC backing as opposed to anything else they're not necessarily specifically technology companies and the you kno..."
Stewart Butterfield shares his experience as a web designer and his vision for his first video game, 'Game Never Ending.' He describes the game's unique focus on social interaction rather than traditional gaming mechanics, highlighting the early fascination with online communities and social connections.
"becomes increasingly hard to to make that distinction unless you mean like technology is huawei making 5g antenna chips and it's like now and then software businesses like flock thank you for that so ..."
Butterfield recounts the challenges faced during the dot-com crash, detailing the financial struggles and lack of investment in internet-based projects. He reflects on the difficulties of developing 'Game Never Ending' during this tumultuous period and the eventual pivot towards creating Flickr.
"her cig files the things she said in comments and the the idea that that kind of connection was possible was I mean this really early stage but it's like was very interesting to me you go forward to 9..."
Stewart Butterfield discusses the decision to shut down 'Game Never Ending' and the simultaneous development of Flickr. He shares the team's reaction to the pivot and the excitement surrounding Flickr's launch, emphasizing the importance of adaptability in entrepreneurship.
"commercial appeal and that's a fist like whimsical world of like absurdist humor and kind of hopefully delightful little things to discover but it's mostly like a venue for people to interact in to an..."
Butterfield shares a vivid account of attending a conference on law and virtual worlds in New York, where he faced food poisoning. He humorously describes the challenges of that trip and how it led to the development of the first version of Flickr, showcasing the unpredictable nature of entrepreneurship.
"enough money to finish it and we tried to cast around for something that we could do with the technology we developed that would create a commercially viable product that turned out to be flubber yeah..."
Stewart Butterfield reflects on his leadership style during the transition from game development to Flickr. He describes a democratic decision-making process among his team, illustrating the challenges of consensus-building and the importance of team dynamics in startup environments.
"just kind of migrated so that wasn't that bad it's good so you realize you have to shut down the game but not before flying to one last video game conference in New York what happens next so it was a ..."
Butterfield discusses the lessons learned from his time at Flickr and how they shaped his leadership approach at Slack. He emphasizes the difficulties of executing ideas within large organizations and the importance of maintaining momentum in a competitive environment.
"actually very good that got us going so I've and yet to have a battle with food poisoning be so productive so kudos to you there you decided to focus on Flickr when you made that shift did everyone on..."
Stewart Butterfield reflects on his departure from Yahoo and the challenges faced during his tenure there. He humorously references his resignation letter and discusses the impact of organizational size on innovation and decision-making, setting the stage for his next entrepreneurial venture.
"it was you know the game was play as a pre-tax or social interaction Flickr was photography as a pretext for social interaction is the first actually one of the we got bought by Yahoo and one of the d..."
Butterfield shares the emotional challenges he faced when shutting down his second company, Tiny Speck, which developed the game Glitch. He discusses the impact of this decision on his team, particularly on individuals who relocated for the job. This segment delves into the personal responsibility leaders feel when their decisions affect the lives of their employees.
"and like it's there's definitely not something that stands us like the thing that I learned there other than how hard it is too hard it is to get something done or how hard it is I mean maybe that's t..."
In this segment, Butterfield explains how the lessons learned from the failure of Glitch paved the way for the successful launch of Slack. He discusses the evolution of their communication tool, which was born out of necessity during the development of Glitch, and how it transformed into a billion-dollar company within eight months.
"are for all practical purposes impossible okay so with fast forward to 2012 you have left Yahoo which by the way if you have not read the stewards resignation letter from Yahoo please google it he lik..."
Butterfield describes the technical foundations of Slack, including the use of IRC and the importance of message logging and search capabilities. He emphasizes how these features were crucial in creating a communication platform that teams would rely on daily, setting the stage for Slack's rapid adoption and success.
"much more experienced it was very easy to raise monies look if you could just like look at any factor in a giant matrix of like things that would lead this to be a good plan or to be successful we had..."
Butterfield reflects on the emotional toll of making tough decisions as a leader, particularly when it involves layoffs. He shares a poignant story about informing an employee who had relocated for the job, highlighting the personal connections and responsibilities that come with leadership.
"everyone we we are now as a group in a switch were working on because there was animators and musicians and writers and illustrators level designers a whole bunch of people who just didn't have skills..."
In this segment, Butterfield discusses the process of shutting down Tiny Speck and the steps taken to support employees during this transition. He shares how they managed to help team members find new jobs and the importance of handling such situations with care and empathy.
"look that was very sad but obviously for me the video it's personal it's embarrassing I did all this press and they made all these claims I had to convince all these people to calm and it convinced an..."
Butterfield explains how the experience of shutting down Tiny Speck led to the creation of Slack. He discusses the initial challenges of convincing companies to adopt the new tool and the importance of effective communication in marketing a novel product.
"was very very difficult in Indiana needs like a little bit of positive news because we had five and a half million dollars left of that money we were able to shut down in a relatively elegant way so w..."
In this segment, Butterfield reflects on the competitive landscape as Slack gained traction. He discusses the challenges of positioning a new product in the market and how the arrival of competitors like Microsoft Teams validated Slack's concept while also presenting new challenges.
"record-setting pace of eight months that worked out super well I mean we had developed the system that was the proto slack again ninety-two I mentioned one of the software network tools that I used wa..."
In this segment, Butterfield reflects on the launch of Microsoft Teams and how it validated Slack's concept. He shares insights on the relationship with Microsoft and the initial lack of concern about competition, highlighting the innovative edge Slack had at the time. Butterfield explains how the introduction of Teams changed the competitive landscape and the implications for Slack's growth.
"get anyone to even try it and the incursian thing was once people started trying it they all mostly variably stuck with that they've logged in every day it became like it was for us the foundation of ..."
Butterfield elaborates on the unique needs of Slack's large enterprise customers, such as IBM, and how Slack's features cater to those requirements. He contrasts Slack's capabilities with Microsoft Teams, emphasizing the limitations of Teams for large organizations. This segment underscores the importance of understanding user needs in product development and maintaining a competitive advantage.
"relationship with a guy named Qi Liu who was a software exactly yeah who was the CTO of Microsoft left around then to go be to take over Baidu but weren't especially worried just because when it was t..."
In this part, Butterfield discusses the challenges Slack faces in user adoption, particularly among those who are already integrated into the Microsoft ecosystem. He highlights the importance of brand perception and the hurdles Slack must overcome to attract new users who are accustomed to Microsoft Teams. Butterfield emphasizes the need for Slack to differentiate itself in a crowded market.
"structure so wouldn't work for them and there's many other things that are not very very fundamental limitation so for 5,000 people you can have 200 channels if you want to add a 200 first you have to..."
Butterfield analyzes Microsoft's aggressive strategy in promoting Teams and how it affects Slack's market position. He discusses the implications of Microsoft's integration of Teams with Office 365 and the challenges this poses for Slack in attracting new users. This segment highlights the competitive dynamics in the collaboration software market.
"you don't have any idea and and you hear that there's two alternatives one slack and ones teams and because you're an office 365 customer teams is already free and integrated with all the Microsoft to..."
In this segment, Butterfield reflects on the competitive pressures Slack faces from Microsoft and the broader market. He discusses the importance of maintaining a strong brand presence and the challenges of being perceived as a viable alternative to Teams. Butterfield shares insights on how Slack can leverage its unique strengths to navigate these pressures.
"of importance like the Financial Times Person of the Year was such a novella and so there's a big write-up of that and there's six consecutive paragraphs that are about slack and there's like there's ..."
Butterfield shares his insights on the importance of diversity and inclusion in the workplace. He discusses Slack's efforts to create a diverse workforce and the challenges that come with it. This segment emphasizes the significance of starting early in building diverse teams and the misconceptions surrounding hiring practices.
"hmm so despite selling out and actually becoming a consultant I studied mechanical engineering and undergrad and as a black engineer I really appreciate what slack has been doing on from the perspecti..."
In this part, Butterfield elaborates on the advantages of hiring diverse candidates and the unique challenges they face. He argues that diverse individuals often bring valuable perspectives and resilience that can enhance a company's performance. This segment highlights the importance of recognizing and valuing diversity in the tech industry.
"there's a really pervasive and incorrect belief that you would have to lower the bar to hire someone who isn't but the canonical candidate look the archetypal candidate for this role I think that's us..."
Butterfield reflects on how his leadership style has evolved as Slack has grown. He discusses the challenges of leading a larger organization and the impact of his words on employees. This segment provides insights into the complexities of leadership at scale and the importance of being mindful of communication.
"archetypal presentation oh it's amazing thank you for sharing that I'm sure I hope people were taking notes so we've gone through the journey of your career you started as a web developer you found in..."
In this concluding segment, Butterfield discusses the complexities of leadership as companies grow. He emphasizes the need for leaders to adapt their communication and engagement strategies to maintain a positive work environment. Butterfield shares his ongoing journey of learning how to lead effectively without overwhelming employees.
"microphone on at all the time so if anything's negative or critical if I have a relationship with someone then we work together for a long time it's not really a big deal if it's someone that you know..."
In this segment, Butterfield articulates the fundamental challenge of leadership as being akin to the challenge of being a human. He emphasizes the importance of living with an open heart and viewing others not as tools or obstacles, but as individuals with their own lives and ambitions.
"been learning this whole time is is how to do that without like crushing people how to do that without creating an environment where it's entirely top-down like Iron Fist from above and it can be toug..."
Butterfield shares a personal anecdote about the instinct to view others as obstacles in daily life, using the example of a crowded flight. He discusses how this mindset can hinder genuine human connection and the importance of recognizing the humanity in others.
"leadership is is the same as the fundamental challenge of just being a human being and I think that's so sound a little bit weird perhaps but like living with an open heart and not seeing other people..."
Butterfield answers a question about Slack's early product design, emphasizing the importance of making life easier for users. He discusses how thoughtful design choices, like simplifying login processes, contribute to a better user experience and reflect a host-guest mentality.
"in that moment they're just a potential pain in the ass that might take the middle seat next to you and that that's pervasive and when you're really trying to accomplish something it can be very tempt..."
In this segment, Butterfield draws parallels between successful businesses and the importance of basic fundamentals, such as clean bathrooms in restaurants. He highlights that success often hinges on simple yet essential elements that enhance user convenience.
"for aspiring entrepreneurs yeah so I'm not sure I want to like slice it up by who gets more credit but I think the fundamental approach was how much easier can we make people's lives and when I look a..."
Butterfield reflects on his journey through various mediums of communication, including video games and photography, leading to Slack. He discusses the unique challenges of designing software that facilitates group interactions and the social dynamics involved.
"actually is like a challenge so there's some some real fundamentals but the things that we did that were most successful were those things which made life more convenient for people and one of those w..."
In a light-hearted lightning round, Butterfield shares his thoughts on philosophical questions, culminating in his view on the meaning of life. He emphasizes the importance of love and connection, providing a thoughtful conclusion to the discussion.
"system are much more difficult to to design for and therefore much more interesting amazing thank you all for the questions Dharma you had a pleasure chatting with you it's not often that we get time ..."