Slack CEO Stewart Butterfield: "It Sucks To Be the CEO of a Startup That's Doing Super Well"

“It sucks to be the CEO of a startup that’s doing super well,” argued Slack CEO Stewart Butterfield, adding "the stakes just get higher and higher." The quote, shared with interviewer Andrew Braccia of Accel Partners and the Startup Grind Global Conference audience, earned both gasps and laughs. But Butterfield's Slack is doing better than well: founded in January of 2013, the company is already all the rage at companies like Adobe, The New York Times, HBO and Expedia, while Slack’s valued at just under $3 billion. Yep, must definitely suck.

The History of Computing, According to Butterfield

You can’t really understand Slack, says Butterfield, without understanding the history of computing. 

At first, humanity began by making devices that were designed for a narrow purpose. Take calculators - a prime example - built for the specific purpose of solving arithmetic problems, without the possibility of repurposing. Butterfield calls this the phase of application-specific computing.

The next phase of computing, led by dominant work software like MS Office used by both businesses and consumers, became document-specific computing.

Following document-specific computing, ushered in by networks like Twitter, Linkedin, and characterized by flexible, dynamic units of communication like voice, text, and video, we've entered the third phase: relationship-based computing

“Today, most CPU cycles are spinning to facilitate people talking to one another,” Butterfield observed, and he's in the right position to grow relationship-based computer into an entirely new phase of evolution.

Does Slack mark the next stage in the development of computing? The philosopher in Butterfield is careful not to go this far, but he does believe that Slack is a new kind of operating system, in two senses:

First, it provides a new kind of structure to the ways we communicate through our devices. Conversations can be controlled in a granular and socially-intelligent way by participants, just like real-world conversations. 

Second, Slack is an action engine that helps people measure, track and manage the goals they’re trying to achieve.  

What Inspires Butterfield?

Butterfield is a philosopher at heart, and like all philosophers he values clear thinking and rigorous analysis. He holds both bachelor and master degrees in the subject, and focused on cognitive science and the philosophy of mind during his graduate studies at Cambridge University.  

How does this training impact Butterfield today? For starters, his philosophical training informs how he deals with internal challenges at Slack, from tough internal debates around pay transparency to broader concerns with how to optimally motivate his team.

According to Butterfield, philosophical training is essential because “there will always be a demand for understanding human beings.” That desire to understand those around him is paying huge dividends at Slack.

As the company faces all kinds of scaling challenges, Butterfield has found that it’s extremely hard to scale a business “without the wheels coming off” for one simple reason: “Get a bunch of people together, and it’s like Lord of the Flies.”

Perhaps that’s the key takeaway: If you try to understand what makes everyone on your team tick, and if you lead with integrity and empathy, you’ll be able to build a truly world class company. That company won’t be perfect, because it will be a reflection of the imperfect people who built it. Yet despite its imperfections, companies like this are more likely to undertake “the work they are meant to be doing,” as Butterfield would say.

Read Startup Grind's highlights with Stewart Butterfield and Andrew Braccia here, and watch the full talk.