In a candid conversation on "20 Minutes VC," Harry Debbings interviews Stuart Butterfield, the founder and CEO of Slack, exploring his journey from a web developer in the early internet days to creating Flickr and ultimately Slack, which transformed business communication. Butterfield shares insights into leadership, decision-making, and the importance of a clear vision. He emphasizes the value of continuous product iteration and the role of intuition alongside data in making strategic choices. Butterfield also discusses Slack's future, highlighting Slack Connect's growth and the platform's evolution as a systems integration fabric. Throughout, Butterfield reflects on the nuances of leadership, the challenges of tying identity to a company, and the impact of wealth on personal happiness and motivation.
"In 98, I got my first dot job, which I quit in the very beginning of 2000, actually quit in kind of mid late February 2000. So just before the crash and convinced one of my coworkers to start to take his side project, which was a website called Gradfinder.com, which is a competitor to classmates. And this is many years before Facebook. So many people used to organize high school reunions. I convinced him to let's make that a company. We raised a tiny bit of money and it got acquired a couple years later, started another company called Ludicorp to build a web based, massively multiplayer game called Game never Ending. That didn't work, but we made Flickr instead. Flickr got bought by Yahoo, spent three years at Yahoo, and then most of that original Flickr team got back together to start another company called Tiny Spec to build a web based, massively multiplayer game. That didn't work and then we ended up with Slack."
The quote outlines Stuart Butterfield's entrepreneurial journey, highlighting the transition from various startups to the eventual creation of Slack.
"Well, money alone does definitely not make you happy. I know some people who have a lot of money and are fairly miserable. It definitely makes things easier, though. So while it doesn't magically make you happy, it creates the conditions where a lot of stress has gone from your life."
This quote emphasizes that while money can remove stress, it is not a source of happiness in itself.
"People who have a lot of money want more money, not because they're going to do something with it, generally they're going to give it away, but because it's how you keep score."
Here, Butterfield explains that for many wealthy individuals, accumulating wealth becomes a way to measure success rather than a means to an end.
"In the case where vision is talking more about the values or aspirations in the broad general sense, I think it's probably a good thing. A vision of a very specific outcome, like a state of the world, I think is probably less valuable."
This quote underlines the distinction between a broad vision and a very specific one, with the former being more advantageous.
"It's not something that just is happening in the external world and we're passersby observing it. It's something that we actively cause."
The quote indicates that the speed of market adoption is not merely a passive observation but an active outcome of the company's efforts.
"Yeah, it's very difficult, to be honest. So it's hard not to take it personally when things aren't going well."
This quote reflects the challenge of not internalizing the company's performance as a reflection of personal worth.## Company Growth and Cultural Development
"Probably haven't put enough effort into instilling or building a culture that's powerful enough that it has a lot of momentum."
The quote emphasizes the challenge of developing a strong company culture amidst rapid growth and expansion.
"I'm constantly worried about the things outside of the company when I'm focused on the company, and constantly worried about the company when I'm focused on anything outside."
This quote highlights Stuart's perpetual concern for both his personal life and his company, indicating a balanced yet worried mindset.
"Yeah, all the time. And it depends. It's really funny because there's certain things I'm quite certain about... I don't second guess on the management and leadership style. It's a totally different problem..."
This quote reveals Stuart's confidence in certain business decisions but also his self-doubt and the unique challenges he faces in leadership.
"As the leader, not any one person. And there's kind of an array of people... Different board members at different times, but they've always been people that I can come to with big questions and get good advice."
The quote shows Stuart's reliance on a diverse group of advisors for leadership guidance rather than a single mentor.
"I think that's just my natural disposition... The things that are going well are good... But for me, listing all the challenges or the problems or things that aren't going well is an expression of optimism, because I believe that we can do something about them."
This quote explains Stuart's approach to board meetings, focusing on challenges as a way to foster problem-solving and optimism.
"That's really ingrained... leadership, totally different... I've just tried it so many times to lay out thoughts or to explain them, and I find that they always end up kind of causing more confusion than benefit."
Stuart discusses the difficulty of applying logical decision-making processes to leadership, which often results in confusion rather than clarity.
"It is being very explicit about the things that I either don't have an opinion on, or don't have a strong opinion on, or I'm sure about, or I just have no expertise and nothing to contribute."
The quote illustrates Stuart's approach to leadership by openly admitting his limitations and encouraging others to contribute their expertise.## Deductive Decision-Making
"I feel like the process of convincing myself is very deductive. And when I say deductive, I mean proceeding according to known rules from premises to conclusion, and there's not a lot of room there."
The quote explains Stuart's method of reaching decisions through a logical and structured process, which he believes doesn't easily allow for alternative solutions once a conclusion is reached.
"But just decide and keep your eyes open. And then when you're wrong, you change things."
This quote summarizes Stuart's philosophy of decisiveness in product design, emphasizing the importance of adapting based on real-world feedback and results.
"If you enjoy cooking and you're kind of enthusiastic about it, you start making something and you just constantly make adjustments."
This quote illustrates the iterative nature of the creative process, whether in cooking or product design, where constant refinement is key to improvement.
"So a lot of times, deep into a discussion about something, someone will say, well, that's a two way door, meaning we can just stop debating this."
The quote reflects the idea that some decisions can be easily reversed (two-way doors), allowing for more experimentation and less deliberation.
"I'm a big fan, and the model that's evolved from kind of technical operations, teams of blameless post mortems, I think is really important."
This quote highlights the value Stuart places on objective and blame-free analysis of failures to facilitate learning and improvement.
"Governing a large state is like boiling a small fish."
By quoting the Tao Te Ching, Stuart conveys the idea that leadership actions, like cooking a delicate fish, require careful handling to avoid negative outcomes.
"It's very rare that anyone just takes my word for anything, really."
This quote acknowledges that despite his success, Stuart's opinions are still subject to scrutiny and debate within his company, reflecting a culture of critical thinking and collaboration.## SPAC vs. Direct Listing vs. IPO Debate
"There's certainly no general rule today. About whether direct listing is better than a traditional IPO or a SPAC is better than either of them."
This quote underlines the lack of a universal rule in choosing the method of going public, emphasizing the importance of assessing individual company needs and circumstances.
"I think that we started three years or so before, maybe four years before we went public for what we called public company readiness."
Stuart Butterfield explains the significance of preparing for being a public company well in advance of actually going public, highlighting the acronym PCR used internally to denote this phase.
"For listeners of this podcast, I would recommend one of three leadership and self deception, crucial conversations, and the courage to be disliked."
Stuart Butterfield provides book recommendations that he believes would be beneficial to the podcast's audience, particularly those interested in leadership and self-improvement.
"I think more space for art or things that have traditionally been characterized as the creative disciplines."
This quote expresses Stuart Butterfield's desire for a more inclusive Silicon Valley environment that embraces art and creativity alongside technology.
"I mean, if it had the benefit of the knowledge of how everything went, then, God, I would do every single thing differently."
Stuart Butterfield reflects on the journey of Slack and acknowledges that with the knowledge he has now, he would approach the building of Slack differently.
"The problem is almost always comprehension, but we treat it as if the problem is friction."
Stuart Butterfield explains the misconception that the main obstacle for users adopting a new product like Slack is friction, when in fact, it is often a lack of understanding of the product's purpose and benefits.
"If I had to choose this one, I would say Andrew because of that consistency."
This quote highlights the value Stuart Butterfield places on long-term consistency and support from board members, exemplified by Andrew Bracha's tenure.
"The slack from five years from now, I think, will continue to iterate and improve on the core user experience and the way that we deliver the service and the excellence in support and all that."
Stuart Butterfield outlines his vision for Slack, focusing on continuous improvement and expansion of services to facilitate better integration and communication across organizations.
"Hello Sign is an effortless esignature solution used by millions to securely send and request legally valid digital signatures and agreements."
This quote illustrates the success of Hello Sign, emphasizing the importance of building a product that prioritizes user experience, leading to significant funding and acquisition outcomes.
"Pendo, the product cloud company, is expanding rapidly throughout Europe and recently released a version of their product, which is designed and priced specifically for startups."
The quote showcases Pendo's growth and its commitment to supporting startups through tailored product offerings, demonstrating the value of catering to the unique needs of different market segments.