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Remembering My Time With Steve Jobs on the iPhone's Tenth Anniversary

Remembering My Time With Steve Jobs on the iPhone's Tenth Anniversary
Apple CEO Steve Jobs holds up the new iPhone that was introduced at Macworld on January 9, 2007 in San Francisco, California. (David Paul Morris/Getty Images)

By    |   Tuesday, 27 June 2017 10:06 AM EDT

The tenth anniversary of the iPhone’s debut seems like a good time to resurrect a fond memory of mine: the three days I spent with Steve Jobs about two years after he was ousted from Apple.

I was a management consultant with Deloitte in L.A. My client company at the time was one of the biggest players in the entertainment industry, but was battling a reputation as an old school outfit being outgunned by newer, nimbler rivals. One of the strategies for vaulting them back onto the leading edge was to computerize their front-office operations. This was at a time when the leap from mainframe to server-based computing was still in its infancy.

I don’t remember who made the initial suggestion to get in touch with Jobs and see if it might be feasible to build the new system around his radically new NeXT computer, which had not yet seen the light of commercial day. The thinking was that this would be a double-plus for the client: Not only computerize them well beyond what any of their competitors were doing, but make it a knockout punch by collaborating with one of the most captivating pioneers in the industry.

Settling in for what I was sure would be at least a week’s worth of trying to get a response, I picked up a phone and called NeXT’s Silicon Valley offices in Redwood City. Two minutes later I was talking to Jobs. After about twenty minutes, seeing that there was interest, I asked him if it might be possible for him to come to the client’s HQ in Beverly Hills.

"How’s Tuesday?" he asked.

Much has been written about Jobs’ "gravitational field," and how easily people got sucked into it. I assure you the phenomenon was real. I can’t name the client, but trust me when I tell you that the likes of Marilyn Monroe, Julia Roberts, and countless others of the biggest stars in movie history who have traipsed through those offices wouldn’t turn a single head among the jaded staff. But when Jobs and I walked down a hall, heads would pop out of nearly every doorway, and it sure wasn’t to see me. During the two days we spent meeting with key personnel trying to figure out how we might deploy the NeXT computer, people throughout the company fell all over themselves creating excuses to get in on the meetings, just to be with Jobs for a few minutes.

His vision and decisiveness were on full display. In one meeting a young staffer suggested putting a little round icon in the app we were starting to think about. "You know," she said, "like a radio button in a car."

Jobs snapped his fingers once and pointed at her. "A radio button: I love that!" And, as with Rameses in "The Ten Commandments" ("So let it be spoken; so shall it be done.") the radio button was born right on the spot.

After two days he invited my clients and me up to NeXT’s corporate headquarters in Redwood City. While the clients saw demos and toured the beautiful set of offices at 900 Chesapeake Drive overlooking a marina, Jobs and I broke off to a side room to negotiate a deal. I found him tough but reasonable, and after about an hour we only had one real sticking point.

The NeXT machine had a pretty amazing piece of technology, an optical drive that could not only read and write CDs but rewrite them as well. This was at a time when even a read-only drive for PCs didn’t exist.

Which was the source of the problem: No software was available on optical drives, and there was no way to trade data with anything other than another NeXT machine. Jobs tried to assure me that this wasn’t going to be a problem, because it was only a matter of a short time until the rest of the world came around to using optical drives.

I didn’t find this reassuring at all, and I was also not in a position to make a bet like that on my client’s nickel. I asked him if he could just attach a floppy drive, which was the standard of the day. He shook his head and refused, saying something along the lines of, "Nothing that ugly is ever going into one of my machines."

Having pretty much nailed everything else down, we agreed to hold off while I talked it over with the client back in Beverly Hills. In that meeting, I was firm in my recommendation: It was far too big a risk, and we could find ourselves dead in the water while waiting for it to happen.

During that same meeting, my client told me that Jobs had called him asking if I might be interested in going to work for him. I didn’t know if that was a sincere inquiry or if Jobs was just trying to "soften up the consultant," but given that he’d gone through the client, I assumed he was serious. In any event, I was a few weeks from becoming a partner at Deloitte and declined the invitation to talk about it, a decision that gives me pause even to this day.

That afternoon, I called Jobs and told him that we were prepared to buy 100 NeXT boxes but that we wouldn’t do it unless he included floppy drives. We debated it for a few minutes and, while he was spirited and passionate, he was also even-tempered and professional. At no time did I see any of the nasty side that has been widely reported.

"Let me think about it," he said, and we ended the call.

The next morning, I got a call from one of Jobs’ execs, who told me they agreed to add the floppy drives. I was a little surprised, because Jobs and I had been handling it ourselves up until then. I didn’t realize until later that the conversation about the floppy drives was the last one he and I would ever have. A few days later we signed the contract, which was NeXT’s largest order to date.

One interesting postscript, the kind of thing that makes you wonder if there are any true coincidences in the universe: About twenty-seven years later, in 2014, I got a call from my friend and colleague (and now business partner) Elizabeth Cholawsky, who’d just been named CEO of She asked me to come up and spend some time helping her strategize a major shift in the company’s orientation.’s offices were in Redwood City, so I thought it might be fun to take a little side trip to the old NeXT offices and have a look around.

When I asked Elizabeth for the address, she said, "900 Chesapeake Drive."

I eventually joined her staff and ended up sitting exactly twenty-seven steps from Jobs’ old office. We had a picture of him in the lobby, and I don’t think I ever walked past it without remembering my encounter with the man who changed the world not once, but several times.

Lee Gruenfeld is a managing partner of Cholawsky and Gruenfeld Advisory, as well as a principal with the TechPar Group in New York, a boutique consulting firm consisting exclusively of former C-level executives and "Big Four" partners. He was vice president of strategic initiatives for, senior vice president and general manager of a SaaS division he created for a technology company in Las Vegas, national head of professional services for computing pioneer Tymshare, and a partner in the management consulting practice of Deloitte in New York and Los Angeles. Lee is also the award-winning author of fourteen critically-acclaimed, best-selling works of fiction and non-fiction. For more of his reports — Click Here Now.

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The tenth anniversary of the iPhone’s debut seems like a good time to resurrect a fond memory of mine: the three days I spent with Steve Jobs about two years after he was ousted from Apple.
steve jobs, iphone, next, silicon valley
Tuesday, 27 June 2017 10:06 AM
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