Everything I Know I Learned From Steve Jobs

By Andy Cunningham, Founder and CEO of Cunningham Collective, an Innovation-to-Market Consultancy
October 27, 2015

It is hard to believe that after all these years, the work that I did with Steve Jobs from 1983 to 1987 would have made it into the biography that Walter Isaacson wrote and the major motion picture written by the famous Aaron Sorkin and directed by the equally renowned Danny Boyle.  My character is played by the talented actress Sarah Snook and in the movie I am his publicist throughout the timeframe of three critical product launches: Macintosh, NeXT and iMac. In real life, I held that role for the launch of Macintosh only and then worked with him on his exit from Apple, the formation of NeXT and the acquisition and launch of Pixar. I did not actually do the public launch of NeXT or the iMac once he was back at Apple, as is portrayed in the movie. But such is Hollywood where storytelling trumps fact, and for good reason.


Two years older than I, we were both Baby Boomers in Silicon Valley. I was working at Regis McKenna, Inc., a storied PR firm, leading the Apple account. For some reason, Regis, a long-time friend and mentor of Steve's, thought I would get along with him and be able to manage his difficult personality. And somehow, I did. I am forever grateful to Regis, for the confidence he had in me to do so, and to Steve, for going along with it and bringing me into his inner circle.

When Steve left Apple, I decided to leave Regis McKenna and head out on my own. It was a good time to do so, as I had established myself in the “Steve camp” at Apple and that simply wasn’t the best camp in which to reside. I formed Cunningham Communication, a public relations firm dedicated to helping high technology companies get traction for their innovations. I was in business only a few weeks before Steve called and asked me to help him with a press conference at which he intended to announce the formation of NeXT.

I drove over to his house in Woodside to find dozens of business press reporters milling about his yard. I made my way into the house to find Steve and seven deserters from Apple sitting on the floor in his kitchen. He looked up at me and said thanks for coming, he was just about to announce to the world that he was leaving Apple, forming NeXT and taking these people with him. Oh, and he was also going to tell the world that Apple and its management team could go to hell.

At this point, I wasn’t working for Steve or Regis or Apple, so I had no allegiances to protect, no conflicts of interest to worry about. So I did what I thought was the right thing to do and told Steve he would be a fool to go forward with this press conference and I told him why. He had not completed his separation from Apple, he had not worked out the exit of his team and he certainly did not want to tell the world that his former employer and its management team could go to hell. NeXT wasn’t even formed yet. What was the product? Did it compete with Apple? Who would the customers be? None of this was formed.

He paused for a moment to think and then said, “OK. But you have to tell them all to leave.” I sighed with relief and proceeded to go outside and deliver the bad news to the throng of reporters who thought they were going to have a chance to talk with Steve about Apple. Needless to say, I was the enemy of the Fourth Estate that day. But this act of defiance cemented my role with him as his new PR counsel and made my agency famous.

Steve hired and fired me several times over the next three years that I worked with him and when our relationship ended for good, it was because after he had fired me for the fifth time, my public relations firm had taken on a competitor called Taligent which made our reunion impossible. I remember him being very annoyed with the fact that I had chosen to work with Joe Guigliomi, an ex-IBMer, and CEO of Taligent.  I told him I could not represent NeXT and Taligent at the same time and that Taligent was a very big client. I could not depend on Steve as a regular and I was by that time running a relatively large PR firm. After we hung up, I didn't realize that I would not speak with him again for many years, until, in fact, he became sick and reached out over email to me with a kind note about a job change.

Those were high-impact growth years (for both of us) and I learned so much from him and the times we were experiencing. The fact is, in those five years, Steve molded me into the professional I have become. Since then, I have guided my life and my teams by the light of three basic principles I took from Steve Jobs based on vision, differentiation and quality. He never spoke of them as principles, but he embraced them in everything he did and in fact, they were his very gestalt.

The Vision to Package Technology

While Steve was building computers inside Apple, he preferred to think of his products as appliances, or bicycles for the mind, or songs in your pocket, or intelligence in the palm of your hand. He saw them for what they could do for those who used them and preferred not to call them users or even customers, but rather simply people. He had the vision to package technology for the benefit of people and in so doing, his grand plan was to change the world--make a dent in the universe--by giving people a radically better way to do what people do. I guess you could call him one of the early pioneers who disrupted some of the common tools of the day like the mini-computer, the Walkman, the telephone, the television. The beauty of Steve's vision is that it was so personalized. What he wanted to do with technology was to make people's lives better and do it simply and elegantly. He had a capacity to ascertain how technology might be used in this way and then the will to make it so. 

But I noticed other benefits to vision like his. Not only did he "tell the future," but the mere idea of changing the world, leaving a legacy or simply making a difference in some way seems to be a visceral human need and by providing it, his team performed miracles for him. And the effect seemed to be multiplied in the presence of a common enemy. Steve created one in IBM that inspired the famous 1984 ad depicting skin-head-like automatons taking direction from “Big Brother” only to be disrupted by a young woman in a Macintosh tank top taking a sledgehammer to the screen.

The David and Goliath story that he coopted for Apple championed the little guy, the creative force, the disruptors of the early 1980s and acted as a rallying cry that united a group of people to a common cause. And in 1983 throughout Bandley 3 in Cupertino with a pirate flag flying high above, tee shirts worn to threads by the Mac team bore the evidence: 90 Hours a Week and Loving It!  This really showed me that if people think they are contributing, making a difference, fighting a common enemy, they work harder and longer and love it more.

License to Differentiate

But Steve had a chip on his shoulder. He was smarter, more visionary, more clever—different from his counterparts in the industry. He saw himself as an artist and admired those who took artistry and commercialized it into beautiful things that people would love. Hartmut Esslinger. Paul Rand. Mick Jagger. Katherine Graham. His intent was always to build simplicity and elegance into his products and to do that, he had to think differently about what they did, how they looked and how they felt.

So he built things that were different. Sometimes they were so different that they didn’t catch on in the market. Macintosh was a rectangular “portable” box that contained the screen and the guts all in one unit. It had a separate keyboard and mouse and looked so very Picasso-esque rendered in simple, colorful Japanese brush style in the first Macintosh posters. A thing of beauty and adorable it was—quite different from anything else in the market. But it didn’t do very much. In fact, it didn’t sell very well and ultimately landed Steve on the outside looking in.

Everything about Steve was different, rather counter-culture, actually. He didn’t want to wear shoes, he didn’t have furniture in his house, he refused to wear a jacket to a dinner with Bill Joy at Windows on the World, he wouldn’t lean on a desk to be photographed by Fortune Magazine, he insisted on Calla lilies in the middle of the night in New york and fresh strawberries with cream in a separate bowl—incessantly listening to Billy Jean by Michael Jackson during a photo shoot, sitting on the floor at home and at work, installing a Bosendorfer grand piano in the atrium of Bandley 3, building a wide wooden staircase twice at NeXT on Deer Creek Rd., believing he was what he ate, locking Apple people out of the Mac project, insisting engineers could perform miracles, turning the music industry on its ear, parking in handicapped spaces, and on and on and on.

All of this created an image, a cult, that gave him license to differentiate. If corporate America was doing it, Steve wasn’t. Yet his original dream for Macintosh was to topple IBM in the enterprise. When he realized this wasn’t going to happen, he embraced the cult that was forming around him and turned his attention to the “creatives” who were buying the computer and bringing it to work through the back door. These creatives became the every man for whom the product was built and they were celebrated in the famous Think Different campaign that better than any other, captured the essence of Steve Jobs and the cult of Apple.

Maniacally Focused on Details

None of this would have come to life, though, if Steve hadn’t been maniacally focused on details and the quality level of every single thing that passed through his hands—and practically everything did. He believed that the entire experience

of a computer or a poster or a brochure or a room was made up of the little details that comprise it and the environment in which it existed. He was looking to create a particular reaction or emotion and he did it by maneuvering the details.

When it came time to build a factory for Macintosh manufacturing, Steve treated it like any other environment. He designed it. He took the best thinking from just-in-time manufacturing and combined it with a look and feel. He bought an automobile factory in Fremont and proceeded to turn it into a place where visitors and workers would have an Apple experience. He painted it the bright colors of the Macintosh renderings and provided guide posts for the inevitable tours he would conduct there. He put Debi Coleman in charge who managed with authority and finesse the workers who built the computers and raised her up as the spokesperson for Apple’s different manufacturing. She was amazing. He was brilliant.

And Me

His mantra was always “Great artists steal” and so I stole his principles and apply them to all my endeavors. At Cunningham Communication, I declared our vision to redefine public relations and that our enemy was the status quo. We became a renegade troop with a common cause to change our industry and make PR into an integral component of business strategy.  With this rallying cry, we attracted the best and brightest of the field and proceeded to make our own little dent in the PR universe.

We were swimming in a pond with a lot of other PR firms, so we knew we had to differentiate ourselves. We structured the firm opposite our competition: we offered clients senior people rather than the usual trove of junior account executives and we charged and received above and beyond the industry norm for it. We focused on strategy rather than publicity and worked with a vengeance to “help our clients win in the marketplace.” We were different from the rest and I asked my people to prove it by challenging the status quo and thinking beyond the press into the business.

We got so wrapped up in delivering quality products to our clients that we gave every human being at the company the right to stop a document from being delivered if he or she noticed so much as a typo in it. This maniacal focus on quality became a source of pride in the company and a hallmark of our work in the industry.

I learned from Steve that you can get people to move mountains for you if they believe in the cause, a vision of how the world will be different because of what they are doing. I also learned the rewards of thinking outside the box and examining all the different ways a problem could be solved. Standing out among a sea of sameness is exhilarating. Both employees and customers see the power in it. I learned not to be afraid to think different. I came to understand exactly what he meant by “insanely great.” World-class. The simplicity on the other side of complexity. A mother in every box. A dent in the universe.

Because my world is about helping companies bring their innovations to market, not about making innovations from scratch, we have to be able to provide clients with the very best “think different” advice and the ability to articulate and realize their visions. To do that, we have to have an environment at Cunningham Collective that encourages and enables all of that. I have tried throughout my career since my days with Steve to take the best of him and re-use it for my own leadership style. I don’t bully. I don’t demand. I don’t invoke a reality distortion field. I try to inspire. To think different. To set a higher bar. A miracle a week is all I ask.

©First Republic Bank, 2015

The views of the author of this article do not necessarily represent the views of First Republic Bank.