In this episode of Startup School Radio, host and Y Combinator partner Kat Manalac sat down with Solomon Hykes, who is currently the founder and CTO of Docker.

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Docker, which is an alum of Y Combinator’s Summer 2010 class, is an open platform that lets developers build, ship, and run distributed applications using what’s known as “containers.”

The company originally launched out of YC as dotCloud, a platform-as-a-service startup, and in 2013 shifted to fully focus on its homegrown container technology to become Docker.

One particularly interesting aspect of Solomon’s hour-long interview was hearing him discuss the process of how Docker grew out of dotCloud, how he decided it was time to pivot the company’s focus entirely, and why it succeeded in large part because the team went all in on the pivot. This portion begins at minute 35:00:

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Solomon Hykes : We did build a business, we had paying customers, and dotCloud was by no means a failure, but it wasn’t succeeding fast enough, basically. We had plenty of money in the bank.

There was no dramatic, horrible situation. It was more like a slow-boiling frog situation, where you’re making progress every month, but you can’t help but think, “Could it be better?” But you don’t really have a reference point, so you keep going. Because what are you going to do? You’re not going to give up. And so that’s where that seed was planted that it would eventually lead to the pivot, to Docker.

Kat Manalac : So when was that moment that you were like, “We are boiled. We need to move.”

Solomon Hykes : Right. So that moment was the beginning of 2013, basically. At the end of 2012, I kind of made a call with myself that, “Okay, the frog is boiled. I repeat, the frog is boiled.” But that was a difficult moment. Because, well, if you act on that conclusion, then it’s not an easy thing to do, right? You have to tell people that their hard work is — you have to tell engineers, “All the stuff you’ve been building for the last few months, we’re canning it.” In our case, we had to lay off people because we couldn’t afford to do something new and keep doing the existing thing at full speed. So you’re not sure. But you kind of have to make that call and go all in.

…There was a core team around me, and it was not an easy conversation. We were evaluating all these options, right? The general approach was, “Okay, we have this thing, it’s working, it’s making progress. We know it’s got to be better. So let’s keep doing it, but on the side, let’s start thinking about version two.” And so we went through a lot of ideas over many months and…

Kat Manalac : And was it mainly your core team making these decisions, or did you have advisors, who helped inform this?

Solomon Hykes : We had advisors, and we had a board that turned out to be very helpful in mostly pushing us, but in the right way. I can’t say enough about picking your investors and your board members carefully. Not just the firms and the brands, but the individuals. Because they end up really being part of a team, and they’re the only part of the team that you can’t fire. So you’ve got to be really careful. And fortunately I received that advice and I took it to heart, and we were lucky in that we ended up having a great board. They’re the ones who said, “Your suspicion is correct, Solomon, that this could be better,” because they’ve seen other companies, so they have this kind of pattern. “This is good, but it’s not great. So yeah, you definitely should be thinking about fixing that.”

Kat Manalac : So how did you know, out of all the possibilities, that Docker was the correct path to take? Was it based on that feedback from advisors?

Solomon Hykes : No. Definitely from advisers came the frame that, “Okay, you should be looking for something,” but then what that solution is, you’re totally on your own, because there’s no objective correct answer. And actually, we wasted time. Docker was maybe the sixth attempt at doing something to solve that problem. And the previous five obviously failed. I think the reason they failed, really, is because we weren’t all in. We tried to do both. We tried to say, “Oh, we’ll keep doing this, and we’ll also do this on the side, and we’ll ramp up…” The kind of strategy that a conglomerate would apply, like, “Oh, we’ve got this super successful brand, and let’s start building another brand.”

But [as a startup], you’re 15 people. And no one cares about your first product. So it doesn’t matter. What made Docker succeed, I think — well, we got lucky in a bunch things, it was the right thing at the right time. But mostly, what gave us a chance to succeed is that we went all in. Basically, it was a screw it moment: “Okay, forget it. If we’re going to fail, then let’s fail doing something that we really are excited about.” That was my motivation.

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