My Friend Bob Cringely

In 1996, I was a Ph.D. student at Syracuse University. One evening I was sitting in my office and the phone rang,__ “Hello?”
“Is this Paul Tyma?”
“Yes?”

Bob replied in very fast English.
“This is Bob Cringely. I just read 7 Java books and yours is the best.”

My first thought was “Huh. He actually said my last name correctly”.

But my quick 2nd thought was that there were not, in fact, 7 Java books in existence. I did indeed write a Java book, but to my knowledge, mine was the 2nd on the market and even then, I’m not sure it was the best. My Ph.D. advisor, Doug Lea, had been an early member of the Java project at Sun Microsystems. He introduced Java (and the JVM) to all his grad students and I believe something like 4 of us wrote books piggybacking upon the hype at the time.

In any case, as you might know, it is not common to get accolades or even much attention for writing a programming book¹. I had no idea who this “Bob Cringely” person was, but, um, Thanks! So glad you liked it - let’s talk some more about how great it is!

I didn’t know it then, but Bob was way ahead of me. It’s likely he pictured me as some lonely computer geek (or “nerd” in his parlance) sitting in a tiny office tip-tapping away at some code enjoying yesterday’s pizza. (He was right). He also knew computer nerds like me were typically a bit starved for attention, especially around anything related to computer-centric achievements. Again, Bob knew his audience.

He continued, “Do you do Java programming too?”

Writing a programming book in the 1990’s afforded many of the same benefits as today. In other words, nearly nothing. You sure weren’t getting rich off writing books. But it did get me invites to teach Java at some Software Conferences. Which then got me invites to train Java to teams inside different companies. Because of that, my friend and I started a company around Java training. We hadn’t done any contract programming until then, but we’d talked about it plenty.

“Sure we do!”, I rather lied.

From there, Bob hired us to build him a system called (or codenamed?) “Pronto”.

Pronto was to be the distribution future of print Magazines. The big idea was for customers (who were paper magazine subscribers) to install a small daemon process on their computer that would monitor for times where their Internet connection (i.e. often dialup modem at this point) was online but mostly idle. Our system would then slowly but persistently download their next month’s issue of “Good Housekeeping” or “Car and Driver””. Once it was fully downloaded, the daemon would lie in wait until 2am the next morning and send the PDF off to their home printer. The customer would wake up to be happily surprised by a fully printed copy of their magazine waiting for them!²

Like many at the time, Bob didn’t believe that reading online would replace reading a full-color, paper magazine. But how that magazine got to your house could change, and that’s where Pronto came in.

Bob had secured funding for Pronto - from someone in Japan I think. I don’t remember, but I remember Bob paid us consistently for the time it took to develop Pronto. After we finished, I don’t know what happened to Pronto, except that it never released in any meaningful sense. But this did begin my 30-year relationship with Bob (or “Cringe” as we called him).

As I said, before this, I had no idea who Bob was. I didn’t know about his claim-to-fame book “Accidental Empires”. His PBS series “Triumph of the Nerds” was released right around the time I was working with/for him. Well after Pronto somehow I got put on Bob’s list of “People I’m going to send my next startup idea to for thoughts” email list. I was by no means alone on that list, and sometimes I got into email threads with some interesting Tech personalities.

I just took a look - and I have had 320 emails with Bob in the past 13 years. Mind you, those aren’t unique emails, most are part of long email chains so I’d estimate I’d email with Bob about 3 times a year since the late 90’s.

Usually, the email chains started with Bob emailing me a wall-of-text about his new startup idea. While the first half of the email was about the idea, invariably, the 2nd half was about how much money it was going to make. I was always impressed at how “to the penny” he got with his projections for something that was basically an idea written on a virtual napkin.

Some ideas were good, and some were not so good. Through my career, I actually joined him in 2 ventures - home-account and Sonisafe. I have the pitch decks for a few, and the detailed descriptions of a bunch more ideas that maybe no one else has seen. This was a great honor in the beginning, especially as his fame grew. But all along the way, I felt Bob was missing the point.

If you ever met Bob - or heck, just saw him in any of his TV specials, you could see Bob charmed everyone he met. He was good-looking, disarming, and curious. He was also an excellent writer, but it was on the screen he really shined. He was comforting and fun to watch. He was fearless and made people feel special. He wasn’t a “nerd” but if, like me, you were; he understood you and he made it OK. In fact, at times, he even made it look glamorous.

Despite his innumerable gifts, Bob seemed to really want to be a superstar startup founder. I’m sure if one of his startup ideas had exploded, Bob would have filled the role fine. But to me - he was a pure natural in front of the camera. I always thought he should start a Youtube channel interviewing Silicon Valley celebrities. I sent him a few emails along those lines, but Bob would mostly just ignore me. He was usually too excited about his new/current startup idea.

When I lived in San Francisco, he and I had lunch or dinner occasionally. He really was a Silicon Valley celebrity. When the inevitable person(s) would come up to him telling them they were a huge fan, he’d act like it the first time anyone ever recognized him. Every time. The TV Cringe instantly came to life and it was always a pleasure to watch.

Goodbye Mr. Cringely. I’m very sorry to see you go. I will miss you.

A few more Cringe stories

2001

Right after the C# language was released (it must have been around 2001 or so?), I spent the evening and into the morning reading about it. Finally around 2am, with bleary eyes and a racing mind I emailed Bob - “Dotnet is going to squish Java”.

I got a response 2 minutes later, “Why?”.

I spent the next hour writing an overly long and terribly rough email, in a half-awake, caffeine-induced state and sent it off. I woke up the next morning to Bob’s new blog post - a rather lightly edited version of my rant!

Sharper Than Ever. Microsoft’s C# Language Might Be the Death of Java, but Sun’s the One to Blame

I just remember being grateful he didn’t mention me. But then, he called me later that day, “Sun is a bit unhappy with the blog post. I’ve been summoned to Sun Headquarters tomorrow and you’re coming with me.”

The next day Bob and I went to Sun Microsystems. He and I sat in a room with Jonathan Schwartz (CEO) and Rich Greene (C-something-else) while they defended Java and gave me nasty looks wondering who the hell I was and why the hell I was even there. They seemed plenty interested in impressing Bob though. By the way, Dotnet didn’t squish Java but I did get a Sun t-shirt.

After that, Whenever I emailed him, I often tacked onto the bottom of my emails - “Do whatever you want with this email, but don’t mention me. And know this email could be totally wrong or silly - either way, it’s yours now”.

2004

In and around 2004 I was living in NYC and I got a forwarded email from Bob. It was a forward from a Producer at the TV network VH1 telling him they were doing a video series called “My Coolest Years” and had a special episode about “Geeks” and they needed a computer geek. They asked him if he wanted to be interviewed about what it was like being a “geek” in high school.

He replied to the Producer, cc’ing me:

“Sorry, but I got laid plenty in high school. However, I have cc’d my friend Paul who actually was a geek in high school. He also lives in NYC.”

I ended up with a total of about 8 minutes in the show alongside Mark Cuban, John Tesh, Ben Stein, and Wil Wheaton. Bob would have been way better.

2026

Randomly, a few months ago I once again watched Bob’s “Plane Crazy.” A classic. And because of the comments surrounding his death I found that his special “The Transformation Age” is also on Youtube which I had never seen (in 8 or so separate videos). It’s quintessential Cringe.

[Plane Crazy] (https://www.youtube.com/watch?v=rqxU4nnLkeA)

[Bob’s The Transformation Age] (https://www.youtube.com/watch?v=5FuUcOF0WdQ)