It’s just like how many marketing, sales, and creative teams often don’t talk to engineering. Too many numbers. Too black and white. Too many geeks in one room geeking out.

But I wanted to understand the squishy stuff and the geeky stuff. And I liked all of it. I could also translate back and forth—explain the squish to engineers, translate the 1s and 0s to the creatives. I could synthesize all the pieces and keep the whole company in my head.

I spent nine years at Apple. It’s the place where I finally grew up. I wasn’t just managing a team anymore. I was leading hundreds, thousands of people. It was a profound shift in my career and in who I was. After a decade of failure, I finally made something—actually two things—that people actually wanted. I finally got it right.

But it didn’t feel like success at first. Or even in the end. It was still work, every step of the way.

We organized our time into bigger chunks—weeks, months. We started taking a macro view of our projects. And that enabled us to build the V1 of Velo in about eighteen months. Then we handed it, gleaming and new, to sales and marketing.

And they had absolutely no idea what to do with it. They’d never seen it before. They didn’t know how to sell it, where to sell it, how to advertise it. They had been an afterthought to us, and now we were an afterthought to them.

We had figured out our internal heartbeat, but had never synced it with any other team. Nobody else could keep up with our rhythm. We were dancing to our own beat, sure that all eyes were on us, and our dance partner was across the room getting punch, thinking about electric shavers.

It’s between $1 million and $10 million that the team needs to focus on cash. Growth sucks cash, and since this is the first time the company will make a tenfold jump in size, the demands for cash will soar.

I [Jeff Killeen] found I had to be precise and resist my natural temptation to use too many superlatives when describing the accomplishments in the business. John would say, ‘You spin things all the time. You make everything sound good.’ I’d say, ‘John, that was good.’ And he would say, ‘But you make it sound like it’s even better than it is. We’re engineers. We don’t use words like terrific and outstanding. We say, “You did your job.” When you say that the team did a terrific job, they don’t believe you.’ We finally agreed that whenever he thought I was spinning, he would tell me. And whenever I thought he was underwhelming, I would tell him.”

Killeen elaborates on how he learned to communicate in an engineering culture. “The perspective from which John comes to the business is obsessive in a wonderful way. He harks back to the philosophy that he’s building a bridge and that a bridge cannot fail. I said, ‘John, but we’re not building a bridge, and failure is okay if we fail fast and incorporate that learning so that we can grow as fast as possible. It’s preferable to me to get eight things done well and fail a two versus doing three or four things to perfection.’ John said, ‘We’re not trained to accept a lot of failure or welcome it into the process.’ I said, ‘That’s a management concept we have to work on.