What it was really like to work for Steve Jobs

Above: Andy Cunningham (right) with actress Sarah Snook, who plays the role of Cunningham in the movie “Steve Jobs.” Top: Steve Jobs in 1985. Above: Andy Cunningham (right) with actress Sarah Snook, who plays the role of Cunningham in the movie “Steve Jobs.” Top: Steve Jobs in 1985. Image 1 of / 4 Caption Close What it was really like to work for Steve Jobs 1 / 4 Back to Gallery

So what is it about this man that captured the loyalty of so many who never met him? And how did he inspire a generation of entrepreneurs?

Having worked closely with him during his formative years — the launch of Macintosh, formation of NeXT and acquisition and reinvention of Pixar — I saw him as an inspiring and fearless, if irascible, leader who really “thought different,” made the impossible possible and ultimately enchanted the world with his products. These outcomes made the maniacal attention to detail, the rudeness, the blunt assessments and the complete absence of patience tolerable.

No one expected changing the world to be easy or smooth. No pain, no gain. And we were all in.

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His vision was to build computer products he called “appliances” that would make people’s lives better — appliances that he would want to use. During the run-up to the Macintosh launch, he told me he wanted “to put a mother in every box.” To him, that meant when you unwrapped a Macintosh, it would appear to be doing things for you, just like Mom. If you were lucky enough to be on his team, it was because he needed your help. He made you feel that you were an important part of something much bigger than yourself — or even bigger than the company.

With confidence in Steve’s ability to do the impossible, we did not question anything he asked. We were young, exuberant and extremely inexperienced. He trusted us to perform miracles, and we simply did. Our limits were stretched right before our eyes, whether the request was filling a vase with fresh calla lilies in the middle of the night or writing software modifications to make a Macintosh speak on the fly.

We were admitted to the Steve Jobs “reality distortion field” and glad to be there. His use of harsh language, humiliation and intimidation were simply hardships to be endured.

I remember a late-night moment with him in early 1984 at the Carlyle Hotel in New York after a grueling evening of briefings and preparation for journalist meetings the next day. Was the room set up for the best possible outcome — the right flowers, the fresh strawberries, the baby grand piano? Were the messages perfectly crafted? Was the background arranged to support photographs that would illuminate just a touch of rebellion while signaling a new way for corporate America to work? Did the hands-on demo operate? Was his clothing right for the next day? Did the schedule allow enough time to eliminate overlap in meetings? And so on.

We closed up the suite and headed to our rooms around 3 a.m. I did not want to be in the elevator alone with him, but there it was and there he was, so we both got in. We were exhausted. He closed his eyes and sighed. I ventured some empathy: “I know how you feel.”

He snarled: “You don’t have any idea how I feel.” And we were silent for the rest of the ride. He was right. I had no idea how he felt. I wasn’t there for empathy. I was there to get him and the room ready for a Macintosh experience that would eclipse all other news. And that’s what I did.

Since then, I have worked with hundreds of other CEOs, many of them young entrepreneurs and many Fortune 1000 industry leaders. Only a small percentage have what it takes to change the world, to be insanely great. Who are they, and how do they do it?

Netflix CEO Reed Hastings changed the world by thinking differently about entertainment. He was considered mad when he split his business into two (Netflix for streaming content and Qwikster for the original DVD mailing service) and began charging more for DVDs than streaming. Met with customer revolt, he killed Qwikster before it launched, but then masterfully transitioned customer delivery from the Postal Service to the Internet. He bet on the future of streaming and redefined how we watch television.

What if your idea made travelers feel as if they belong anywhere? Brian Chesky, founder and CEO of Airbnb, has done just that. He was not deterred by the hotel system. In fact, he didn’t even consider it a competitor. He wanted to travel and noticed there were a lot of empty couches around the world. He thought: What if couches were for rent? People could travel more freely and inexpensively, and those with couches could make money and meet new people. Couches turned into beds, which turned into rooms, which turned into apartments and homes. He saw possibility where others didn’t.

Josh Tetrick is doing the same with food at Hampton Creek, trying to upend mainstream food companies with plant-based products. His vision starts with the question, “What if we could start over? What would our food system look like?” Tetrick is reimagining food to make it better, more affordable and accessible for the 9 billion people who will inhabit planet Earth in this century. By thinking of food as a platform to create change on social issues such as the lack of good nutrition for lower-income families, childhood obesity, Type 2 diabetes, energy efficiency, pollution and others, Tetrick has set about building a food system that is healthy and sustainable.

Innovation happens when you change people’s behavior. But you have to corral a team to work tirelessly on a mission, accept a think-different approach, move the impossible to the possible and at the end of the day, enchant a customer with the result. You have to be crazy to try to change the world. And in Silicon Valley, we call that insanely great.

Andy Cunningham is founder and president of Cunningham Collective. She previously launched and ran two PR and communications strategy agencies — Cunningham Communication and CXO Strategies. She moved to the Bay Area in 1983 to help Steve Jobs launch the Macintosh.

Editor’s note: Ideas, a new essay series, lets Bay Area leaders share their insights into business topics every other Monday. To submit an essay, send a proposal to business@sfchronicle.com.