The TMZ of Tech

Rick Ross, the founder of Java Lobby, called me one day and said, “I want to introduce you to Maureen O’Gara.

I think she should write for you.”

I told him I’d drive out and meet her.

I had never heard her name before.

* * *

That week, I drove to Long Island and walked into Maureen’s office.

After that first meeting, we started publishing her weekly newsletter on our Linux site, Linux Business News.

Almost immediately, it took off.

Only then did I understand who she really was.

Maureen wasn’t just a reporter.

She was wired directly into Silicon Valley.

She was on a first-name basis with Bill Gates, Steve Jobs, Larry Ellison—people most journalists only saw from a distance.

She broke stories aggressively and fast, and she didn’t worry much about who she offended along the way.

Together, we became something like the TMZ of technology.

Around that time, we licensed the LinuxWorld brand from IDG. Pat McGovern ran the LinuxWorld conferences but didn’t have a print publication. He sent Colin Crawford from California to negotiate the deal.

Colin was IDG’s vice president of new business development and operations, and before that, he’d been president and CEO of Mac Publishing, the publisher of Macworld magazine.

* * *

Colin came to our Montvale, New Jersey, office with a one-page acquisition offer from IDG to buy SYS-CON Media.

Instead of selling, we ended up licensing the LinuxWorld name and launching the magazine in both print and online formats.

We paid IDG ten percent of top-line revenue.

LinuxWorld quickly became the most widely distributed Linux magazine in the world.

That was the only meeting I ever had with Colin Crawford.

I used to visit Maureen regularly.

We’d meet early in the morning, grab breakfast at the diner next door to her office, and then I’d drive back to New Jersey.

One morning, I walked into her office and saw a man asleep on her brown leather sofa.

* * *

He slowly got up, washed his face, opened a fresh package with a white shirt inside, put it on, tied his tie, and joined us for breakfast.

“This is Ken Crone,” Maureen said casually. “Interim CEO of Computer Associates. He’s in the middle of a divorce. His wife has the twelve-bedroom mansion, so he’s crashing here.”

We didn’t talk business over eggs.

* * *

Ken was extremely sharp.

He had come from the publishing world and had single-handedly structured CMP Media’s $920 million sale to United News & Media.

Despite that, he told me he never received a single dollar for his efforts.

The Leeds family, who owned CMP, walked away enormously wealthy.

Ken walked away disappointed.

Not long after, Computer Associates became a Diamond Sponsor of our CloudEXPO events and stayed one for years.

That’s how business often worked in those days—relationships first, contracts later.

* * *

Another story Maureen broke involved Oracle co-president Charles Phillips.

His former mistress rented billboards in Times Square, Atlanta, and San Francisco, displaying photos of the two of them together and linking to a website documenting their eight-and-a-half-year affair.

The story exploded.

Phillips told Maureen that Larry Ellison had paid for the billboards.

She ran with it.

The article pulled in more than two hundred thousand reads over a single weekend.

* * *

At the time, Phillips was widely viewed as a potential successor to Ellison at Oracle.

Not long after the scandal, Oracle hired Mark Hurd as co-president, and Phillips stepped down.

He soon resurfaced as CEO of Infor, where he later became one of our Diamond Sponsors—paying double for the CloudEXPO opening keynote and taking the slot Oracle had held since the show’s inception.

* * *

While all of this was unfolding, Maureen got into a public war with Pamela Jones—known online as PJ—the anonymous author of Groklaw.

Maureen attempted to unmask her identity publicly.

It was a disaster.

* * *

Groklaw’s readers came after us in force.

Advertisers threatened to pull out.

Editors threatened to resign.

Our websites were hit with denial-of-service attacks.

We couldn’t keep the servers online.

SYS-CON Media was suddenly collateral damage in a war I never asked to be part of.

The controversy spilled into mainstream media, including a Forbes cover story titled “Attack of the Blogs.”

SYS-CON and the entire mess were now on display for the business world to analyze.

In the end, to protect the company, we pulled the article and stopped publishing Maureen’s work.

I never asked her about her sources, and she never offered them.

But years later, I strongly suspected they were tied to Microsoft, which at the time was quietly backing SCO’s legal campaign against Linux and IBM.

Whether that was true or not almost didn’t matter.

What mattered was the lesson.

When you build platforms at scale, you don’t just publish content—you inherit consequences.

Intent doesn’t protect you. Distance doesn’t protect you. Once you’re big enough, everything sticks. That chapter taught me something I’d keep relearning: You don’t get to choose which fires come with growth.

You only get to decide which ones you put out.