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Jan 30, 2020 · 15m · how-i-built-this

Live From The HIBT Summit: Stewart Butterfield

Stewart Butterfield · 11m spoken Guy Raz · 3m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Recorded live at the How I Built This Summit, Guy Raz interviews entrepreneur Stewart Butterfield on how he steered two failed gaming projects into tech giants Flickr and Slack, sharing key lessons on startup pivots, product explainability, and empathetic leadership.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 25.9% of the talking time here. How this is scored →

Guy as informed peer 2.8 Guest teaching 3.0 Guest disagreement 1.3 Guy pushing back 1.5
05100:0010:001:06–5:09 · Guy as informed peer 3/10 Pivoting from Game Neverending to Launching Flickr Guy questions the standard entrepreneurial advice regarding grit versus knowing when to pivot. Stewart explains the pragmatic reality of running out of money and losing belief before reflecting on early internet history.5:10–8:00 · Guy as informed peer 2/10 Why Glitch Failed in the Mobile Era Guy asks how Glitch failed and probes incredulously on how funding was raised for an absurd concept. Stewart explains the standard two-by-two positioning matrix in video games and how technological shifts to mobile sealed Glitch's fate.8:01–10:49 · Guy as informed peer 2/10 The Emotional Toll of Shutting Down Glitch Guy inquires about the personal and emotional toll of letting down a team when closing a startup. Stewart shares a poignant story about relocating an employee with a new baby and making sure all laid-off employees found new jobs.10:49–15:12 · Guy as informed peer 4/10 Navigating Pivots and the Importance of Explainability Guy brings in case studies like Tofurky and Stacy's Pita Chips to ask about pivot timing. Stewart checks the premise by attributing it to survivorship bias and disagrees with Guy's assertion that Slack was easy to explain.1:06–5:09 · Guest teaching 3/10 Pivoting from Game Neverending to Launching Flickr Guy questions the standard entrepreneurial advice regarding grit versus knowing when to pivot. Stewart explains the pragmatic reality of running out of money and losing belief before reflecting on early internet history.5:10–8:00 · Guest teaching 4/10 Why Glitch Failed in the Mobile Era Guy asks how Glitch failed and probes incredulously on how funding was raised for an absurd concept. Stewart explains the standard two-by-two positioning matrix in video games and how technological shifts to mobile sealed Glitch's fate.8:01–10:49 · Guest teaching 1/10 The Emotional Toll of Shutting Down Glitch Guy inquires about the personal and emotional toll of letting down a team when closing a startup. Stewart shares a poignant story about relocating an employee with a new baby and making sure all laid-off employees found new jobs.10:49–15:12 · Guest teaching 4/10 Navigating Pivots and the Importance of Explainability Guy brings in case studies like Tofurky and Stacy's Pita Chips to ask about pivot timing. Stewart checks the premise by attributing it to survivorship bias and disagrees with Guy's assertion that Slack was easy to explain.1:06–5:09 · Guest disagreement 1/10 Pivoting from Game Neverending to Launching Flickr Guy questions the standard entrepreneurial advice regarding grit versus knowing when to pivot. Stewart explains the pragmatic reality of running out of money and losing belief before reflecting on early internet history.5:10–8:00 · Guest disagreement 1/10 Why Glitch Failed in the Mobile Era Guy asks how Glitch failed and probes incredulously on how funding was raised for an absurd concept. Stewart explains the standard two-by-two positioning matrix in video games and how technological shifts to mobile sealed Glitch's fate.8:01–10:49 · Guest disagreement 0/10 The Emotional Toll of Shutting Down Glitch Guy inquires about the personal and emotional toll of letting down a team when closing a startup. Stewart shares a poignant story about relocating an employee with a new baby and making sure all laid-off employees found new jobs.10:49–15:12 · Guest disagreement 3/10 Navigating Pivots and the Importance of Explainability Guy brings in case studies like Tofurky and Stacy's Pita Chips to ask about pivot timing. Stewart checks the premise by attributing it to survivorship bias and disagrees with Guy's assertion that Slack was easy to explain.1:06–5:09 · Guy pushing back 1/10 Pivoting from Game Neverending to Launching Flickr Guy questions the standard entrepreneurial advice regarding grit versus knowing when to pivot. Stewart explains the pragmatic reality of running out of money and losing belief before reflecting on early internet history.5:10–8:00 · Guy pushing back 2/10 Why Glitch Failed in the Mobile Era Guy asks how Glitch failed and probes incredulously on how funding was raised for an absurd concept. Stewart explains the standard two-by-two positioning matrix in video games and how technological shifts to mobile sealed Glitch's fate.8:01–10:49 · Guy pushing back 1/10 The Emotional Toll of Shutting Down Glitch Guy inquires about the personal and emotional toll of letting down a team when closing a startup. Stewart shares a poignant story about relocating an employee with a new baby and making sure all laid-off employees found new jobs.10:49–15:12 · Guy pushing back 2/10 Navigating Pivots and the Importance of Explainability Guy brings in case studies like Tofurky and Stacy's Pita Chips to ask about pivot timing. Stewart checks the premise by attributing it to survivorship bias and disagrees with Guy's assertion that Slack was easy to explain.

speaking balance: gold is Guy, purple is the guest (3 minute bins)

0:00 · Guy 69.6% · guest 30.4%0:00 · Guy 69.6% · guest 30.4%3:00 · Guy 8% · guest 92%3:00 · Guy 8% · guest 92%6:00 · Guy 14.9% · guest 85.1%6:00 · Guy 14.9% · guest 85.1%9:00 · Guy 20.6% · guest 79.4%9:00 · Guy 20.6% · guest 79.4%12:00 · Guy 1.4% · guest 98.6%12:00 · Guy 1.4% · guest 98.6%15:00 · Guy 83% · guest 17%15:00 · Guy 83% · guest 17%
Sharpest disagreement ▶ 12:43 Pushing back on Slack's explainability

When Guy claims Slack is simple to explain, Stewart quickly counters that it is actually very difficult and remains an ongoing internal debate.

 Hardest push from Guy ▶ 6:48 Incredulous question on funding absurd pitch

Guy interjects with disbelief to ask how Stewart could possibly raise investment money for a bizarre game about milking butterflies and squeezing chickens.

 Biggest teaching moment ▶ 11:26 Dismissing pivot intuition as survivorship bias

Stewart reframes Guy's question about pivot instincts by comparing his own advice to a lottery winner giving tips on number selection due to survivorship bias.

 Guy holds their own ▶ 10:49 Guy cites Tofurky and Stacy's Pita Chips pivots

Guy displays deep domain knowledge from past interviews by detailing specific pivot mechanisms from Tofurky and Stacy's Pita Chips.
the scores for every segment, with the reasoning behind each
ChapterTopicGuy as informed peerGuest teachingGuest disagreementGuy pushing backWhy
Pivoting from Game Neverending to Launching Flickr 3311 Guy questions the standard entrepreneurial advice regarding grit versus knowing when to pivot. Stewart explains the pragmatic reality of running out of money and losing belief before reflecting on early internet history.
Why Glitch Failed in the Mobile Era 2412 Guy asks how Glitch failed and probes incredulously on how funding was raised for an absurd concept. Stewart explains the standard two-by-two positioning matrix in video games and how technological shifts to mobile sealed Glitch's fate.
The Emotional Toll of Shutting Down Glitch 2101 Guy inquires about the personal and emotional toll of letting down a team when closing a startup. Stewart shares a poignant story about relocating an employee with a new baby and making sure all laid-off employees found new jobs.
Navigating Pivots and the Importance of Explainability 4432 Guy brings in case studies like Tofurky and Stacy's Pita Chips to ask about pivot timing. Stewart checks the premise by attributing it to survivorship bias and disagrees with Guy's assertion that Slack was easy to explain.

Statements from this episode (7)

Assertion Contradicted
Grateful Dead newsgroup was the most popular community on early internet
“In fact it's kind of mind-blowing, but rec.music.gdead, the Grateful Dead news group, was the most popular thing on the entire internet. It was like, in terms of traffic, it was the Netflix of its day, just like the text postings going back and forth”
Stewart Butterfield Jan 30, 2020 ▶ 4:09
Insight
Butterfield: Internet's Significance Will Match the Invention of Written Language
“And I think when we look back tens of thousands of years to this time, it will seem as significant as the development of written language, because it just allows this accretive knowledge allows the accessibility, it allows this instant communication and coordi…”
Stewart Butterfield Jan 30, 2020 ▶ 4:28
Disclosure
Butterfield: Glitch had capital left over when the company shut it down
“In fact, we had money left over when we decided to shut it down, but it was apparent that it wouldn't work”
Stewart Butterfield Jan 30, 2020 ▶ 5:21
What-if
Glitch might have survived if it had not bet on Flash
“And we had made a bet On Flash as a technology for delivering the game, which wasn't going to work on mobiles, and I think in the end that, that really was the nail in the coffin. If it hadn't been for that, I think it would have been worth trying a little bit…”
Stewart Butterfield Jan 30, 2020 ▶ 6:52
Insight
Butterfield: Shutting an online community is like ending a small civilization
“Any of you who have participated in online communities, especially in the early days, where, like, the online community was the nexus of all of these friendships and all these relationships, when they disappeared, that's it. Like, people can say, we're gonna m…”
Stewart Butterfield Jan 30, 2020 ▶ 9:38
Assertion Not checkable as stated
Only 8 of 45 Glitch employees stayed to build Slack
“So there's 45 people at the company, and eight of them were going to stay on to work on Slack. So for the other 37 people, we did kind of career coaching. We wrote reference letters. We set up interviews for them. We ended up getting everyone a job”
Stewart Butterfield Jan 30, 2020 ▶ 10:28
Opinion
Slack's biggest challenge is creating a brand-new software category
“I think we still face that as a major challenge for Slack, because it's like a brand new category of software that doesn't really replace anything specific that you were using before.”
Stewart Butterfield Jan 30, 2020 ▶ 12:10
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