Reflections on My Friendship with Bob Cringely

Back in 1996, while I was pursuing my Ph.D., I received a phone call that would spark a three-decade-long acquaintance.

"Hello?"

"Is this Paul Tyma?"

"Yes?"

Bob responded in a rapid-fire cadence: "I just read 7 Java books and yours is the best."

My immediate reaction was confusion. My second, more analytical thought was that there were 7 Java books in existence there were definitely not seven Java books on the market at that time. While I had authored one, I believed it was only the second one available—and I certainly wasn't convinced it was the superior one.

The Java Genesis

The reason I was writing about Java was my advisor, Doug Lea, who had been an integral early member of the Java project at Sun Microsystems. He introduced the language and the JVM to his graduate students. Consequently, about four of us wrote books to capitalize on the era's massive hype.

As anyone in the field knows, writing a technical manual rarely earns you a standing ovation. I had no clue who "Bob Cringely" was, but I was thrilled. I played along, eager to discuss the "greatness" of my work.

Bob likely viewed me as the stereotypical computer geek (or "nerd," as he preferred): a lonely soul in a cramped office, typing away at code while snacking on leftover pizza. He understood that people like me were often starved for recognition regarding our technical achievements.

From Author to Entrepreneur

Bob asked if I actually performed Java programming. In the 90s, authoring a technical book provided a specific kind of leverage:

• Step 1: Write a book $\rightarrow$ Get invited to speak at Software Conferences.
• Step 2: Speak at conferences $\rightarrow$ Get hired to train corporate teams.
• Step 3: Training demand $\rightarrow$ Start a Java training company with a friend.

This trajectory eventually led to Bob hiring us to develop a project codenamed Pronto.

The "Pronto" Concept

Bob's vision was a bridge between the digital and physical worlds. He didn't believe online reading would kill the glossy, full-color magazine; he just wanted to change the delivery mechanism.

The Workflow:

1. A subscriber installs a small daemon process.
2. The system monitors the dial-up connection.
3. When the line is idle, it slowly downloads a PDF (e.g., Car and Driver or Good Housekeeping).
4. At 2:00 AM, the system triggers the home printer.
5. The user wakes up to a freshly printed magazine.

A 30-Year Connection

This project initiated my long-term relationship with Bob (whom we called "Cringe"). At the time, I was unaware of his fame via Accidental Empires, and his PBS show, Triumph of the Nerds, was debuting right as we worked together.

Eventually, I was added to Bob's "idea list"—a group of people he emailed whenever a new startup concept hit him. I often found myself in threads with other fascinating tech personalities.

Communication Statistics: Over the last 13 years, I've exchanged approximately 320 emails with him. Since these are mostly long chains, the frequency is roughly: $\text{Frequency} \approx \frac{320 \text{ emails}}{13 \text{ years} \times \text{chain length}} \approx 3 \text{ threads/year}$

Bob's emails usually followed a specific pattern:

1. The Pitch: A "wall-of-text" describing a new startup.
2. The Payoff: Detailed financial projections.

I was always amazed by how he could project earnings "to the penny" for an idea that was essentially a sketch on a virtual napkin.

Collaborations and Character

Throughout my career, I actually partnered with him on two specific ventures:

• home-account
• Sonisafe

I still possess several of his pitch decks and detailed descriptions of ideas that likely never saw the light of day.

Bob was a master of charm and a gifted writer, but he truly dominated the screen. While he wasn't a "nerd" himself, he validated the nerd experience. However, he possessed an intense desire to be a superstar founder. I often suggested he start a YouTube channel to interview Silicon Valley icons, but he usually ignored me—he was too consumed by his latest venture.

Bob's persona was a blend of media savvy and entrepreneurial hunger.

When we met for meals in San Francisco, he would be recognized by fans. He always reacted with a sense of novelty, as if it were the first time it had ever happened. Watching "TV Cringe" come to life was always a delight.

The C# Incident

Around 2001, shortly after the release of C#, I spent an entire night obsessing over the language. At 2:00 AM, fueled by caffeine and sleep deprivation, I sent Bob a rambling, rough email:

"Dotnet is going to squish Java"

I woke up the next morning to find that Bob had turned my manic rant into a blog post titled:

"Microsoft’s C# Language Might Be the Death of Java, but Sun’s the One to Blame"

It was a lightly edited version of my thoughts, and I remember feeling a strange sense of gratitude that he didn't mention the state of my mind when I wrote it.