Tales of A Ozy Faker Who Tried to Make It and an Apple Maker Who Sometimes Faked It

By Eugene S. Robinson

In Silicon Valley, there’s a long continuum along the spectrum of visionaries — some of them hailed so by peers and the press, some simply self-anointed — and all along that line you’ll find marketers, reality distorters, hypesters, hucksters, all the way up to rank criminal. Some of them actually get shit done; some try to fake it til they make it; some are just on the make. There might even be a few true mad geniuses sprinkled around. But they’re not what this story is about. 

I’ve worked with a couple of the largest-of-life of these characters who, at first glance, you might say are on opposite ends of the spectrum. But in the Valley, the ends aren’t as far apart as this place’s apologists would have you think. 

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Let’s start in 1998. It was fear, and fear was afoot.

“Listen, I need to tell you” – Chris Gulker was an Apple evangelist and a big brain in the Valley. His early death I would later ascribe to him having spent inordinate amounts of time on the early cell phones telling people about how Apple, post-almost bankruptcy, was on its way back now that Steve Jobs was back. “Steve is a screamer.”

Gulker knew me from outside of Apple. A longstanding family friendship with his stepson and casual dinners had cemented a convivial relationship. Being the best boss I ever had, it was largely all about him telling me how it is: “You have one job, and one job only: to make me look good. You do that for me? I’ll do anything for you.”

But he knew how this screamer bit would hit. I’m a notorious not-taking-any-shit type and it was as much a warning as it was a gentle push.

“Does he care if people scream back?” I asked, and he pushed his way back from his desk and swiveled to face me.

“Let me tell you a story.” One of his team spent a few seconds in an elevator with Jobs and expressed some doubt about a task at hand. The team member was unemployed by the time the elevator had stopped.

Mental note: stay away from Steve Jobs.

Which is easy if you’re someone else. Not so easy if you’re me. Because, as luck would have it, part of making Gulker look good had everything to do with reviving the company website. In the early days when no one knew what websites were good for anyway, apple.com was little better than the Yellow Pages. And five of Gulker’s marketing folks had failed to get any traction. 

Which is why Gulker suggested bringing in a real world media type. He had worked at the LA Times, and suspected that I was the type of animal that could make it happen. And I did. Five articles a week, all on people doing cool shit with Apple products. Heavy emphasis on cool. 

Frank Kozik graced the first week’s edition, he of the dancing rats and electric post-punk angle of attack for his art. During our interview, Kozik started sobbing when he explained what Apple meant to him. Letting me know, in no uncertain terms, that I had hit gold.

Even more so when not even a month in I got an email from Steve Jobs: “This is great. Keep doing it.”

Which is about all I needed to get the Apple seal of approval and Gulker’s sign-off on trips to the UK to cover the cats at hot-as-shit record label Ninja Tune. To Japan. To Germany to interview the guy who signed Rammstein. No marketing meeting after marketing meeting necessary. This was status conferral and cool products make cool people happy. Connecting Apple to that cool was easy peasy.

And since no one has ever convinced anyone that they were cool by saying that they were cool, the sleight of hand connection had been made: Apple was cool because cool people said it burnished their cool. Jobs might have spun up one hell of a reality distortion field, but he didn’t do it out of nothing. 

From distortion to dissonance

Years later, now deputy editor at OZY, I tried to pen a piece on the man. it was killed; in literary terms, let’s call this “foreshadowing.” I also happened to be at the Valley’s newest wunderkind on the block, a digital newsmagazine funded by the deepest of Silicon Valley pockets, first and foremost among them Laurene Powell Jobs. 

Carlos Watson, the founder of OZY, had a television career significant enough to get him some Emmy noms as an on-air personality, but in the aftermath he had been looking for a way back and found it in digital media when digital media was supposed to ride in and save the day. Vice’s valuation was in the billions, and the media world was abuzz about connecting to twenty-somethings. Watson played on that, with a twist: twenty-somethings and specifically, people of color.

It was perfectly constructed for 2012 and as Employee No. 1, courtesy of OZY chairwoman Louise Rogers (previously my boss at EQ Magazine), I was perfectly poised to make the most of my previous “make your boss look great” dictum.

Except for the fact that Watson was a boss unlike any other. “It’s like he asked me to paint his house yellow,” I once complained to Rogers. “And on presenting him with a yellow house he says ‘yellowier’.”

Watson didn’t know what he wanted, but he often knew he didn’t want what he had, especially with a hardcoded MO: if a cursory Google search revealed that any of the top 10 publications had already covered it, it was out. We were to focus on the “new” and the “next” and that was it.

Or really, it wasn’t. What had been promised of Jobs — the screaming, the firing, the imperiousness, all of which never happened with Jobs if you were an A-team player — happened with Watson. On the regular. Whether or not you were an A-team player. His paranoia meant that A-team players were really just B-team players faking it.

Something that built up to his firing me two months after being on the job. The infraction: taking a weekend off that I had scheduled when I took the job.

“I can’t tell whether Eugene doesn’t give a shit or is just acting like he doesn’t give a shit,” he said to Rogers, unhappy that I hadn’t tried to get my job back after being separated from it. At Rogers’ urging, Watson and I spoke on the phone right before Thanksgiving 2012. Right after Thanksgiving 2012 I was hired back. No explanation why. Or even what was now expected of me.

In the roiling waters of OZY, it was all about what remained hidden under the surface. Explaining a lot of the workplace toxicity, extreme even for Silicon Valley but maybe not the least of what should have been expected by former Goldman Sachs folks, which Watson and his right hand man and COO Samir Rao had been, was audacious criminality. Goldman is a well-known meat grinder, and moving on from there Watson and Rao might have imagined there was no need to change it up. Goldman was, after all, “successful.” 

In October 2021, a New York Times article revealed that in a finance call with Goldman Sachs and Youtube someone had been using a voice-changing device to gin up OZY. And that someone was Rao, being fed prompts, Cyrano De Bergerac style, by Watson via text.

Flood gates opened; much more flowed out: documents attesting to a vastly inflated worth rolled out to potential investors. Fake contracts, signed by fake people, claiming wider television deals that did not exist. Chicanery so audacious that a resigning CFO called it what it was before she quit: criminal.

Watson still felt secure enough to fire me — again — this time for starting a Substack that I had been told I could start. And bold enough to deny me severance after almost 10 years of service on account of a negative Glassdoor review that he believed I had written. 

Craziness followed: lawyers in the bushes in front of my house, FBI interviews, film companies trying to get first dibs on the story and signing me to development deals, all eventually leading to an arrest, guilty pleas by his co-defendants, and in December 2024, a nearly 10-year prison sentence. 

So take that, Elizabeth Holmes and Sam Bankman-Fried. 

Leading up to Watston’s conviction and 10-year term, things got even crazier: he refashioned the OZY site into a criminal defense site with the claim that he was being some version of high-tech-lynched, on account of being a Black entrepreneur, all undergirded by facts and figures that showed Justice Department bias in finance prosecutions.

So, let’s see, it’s not that he didn’t do those crimes, but that what he did was an industry standard — and why should he be held to a different standard? If not for race.

In this defense, Watson throws Vice founder Shane Smith (who also owes me money) under the bus as a fellow traveler. He then sued Ben Smith and his new publication Semafor, claiming Smith had shitcanned OZY so he could lift OZY’s business plan.

All business as usual in Silicon Valley? The OZY charlatanism spurred a few media reminiscences of Steve Jobs faking his way through a PR show of the first iPhone. Or a seat-of-his-pants debut of everything from the iMac to the iPod.

All seeming to miss the salient point that the iMac, the iPod, and the iPhone were actual things, things you could lay hands upon and that would change how we did business and lived our lives.

OZY did some things too. The part that was real was just good old solid journalism. There was a lot. But a lot less toward the end, when the entire company had bent to the mission of making Carlos Watson a household name. Quotes on billboards, kiosks, and buses proclaimed Watson the second coming of Oprah and Anderson Cooper on the basis of his wooden The Carlos Watson Show. 

Plastered all over the place, the quotes came from other publications. Except, no: they were written by Watson and Rao. That’s not just bold. That’s insanely audacious. Very different from Jobs’ insanely great yardstick to measure the ways in which he moved culture along.

In a conversation with an early investor, a team of Silicon Valley who’s-who that included the likes of Ron Conway, Larry Sonsini, and Laurene Powell Jobs herself, the dismay and anger at what Watson wrought was palpable: “Racism held him back? Disgusting that he would claim that when people were stumbling over themselves to give him money,” said one on background.

To the listed tune of $83 million. 

That Watson would claim to be “Black” media, when Black media stalwarts like Roland Martin were lambasting him for using his blackness like a cloak of protection, was lost on no one. Least of all the Justice Department who, minutes before I wrote the sentence you just read, had prosecutors seeking to put him in jail for allegedly using confidential documents in the aforementioned suit against Smith, Semafor and BuzzFeed.

You read that right. While staring into the face of questions regarding lies, prevarications, and fraud, here was Watson’s best move: To disclose documents that were not his to disclose. The Feds pushed for his trip to the slammer because his behavior, they said, was part of a larger pattern to intimidate and retaliate against witnesses.

Which brings us up to now. At press time for this article, written on a very real and tangible MacBook Pro, the media world continues to wash Steve Jobs stories over us: biographies, biopics, and last fall, odes to the 12th anniversary of Jobs’ death. Most with nary an extended mention of any of his failures to be anything other than correct with the facts and figures.But also at press time, OZY, refashioned as panegyric to Watson’s genius and to raise funds for his legal defense, limps along – or rather stands, like the Ozymandias it was named after, a tribute to faking it without making it.

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Eugene S. Robinson’s work has appeared in the Los Angeles Times, GQ, The New York Times, Ad Week, Alta Magazine, The Wire, LA Weekly, Vice Magazine, Hustler, and Decibel, among many others. He has also been editor-in-chief of Code and EQ. His Substack is:  https://eugenerobinson.substack.com.