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Rest in Peace, Ron May

Ken Gaebler

Ron May - Chicago Tech Journalist and Gadfly
Ron May was ever-present on the Chicago tech scene. A character to the end, we will miss him.

Ron May died yesterday.

Although some might disagree, this is a not insignificant loss for the Chicago tech community.

It struck me personally for some reason; I have to admit  that I cried minutes ago when I heard that he had died.

In her coverage of Ron's death, Wailin Wong described him this way:

May preceded the current renaissance in the Chicago startup scene, having become a well-known figure during the first dot-com boom. In the late 1990’s, he launched an email newsletter called The May Report that was stuffed with his commentary on Chicago tech news; emails from readers and sources reprinted wholesale, sometimes without their permission; rants against companies or people with whom he took issue; and musings on his personal life, including details on his deteriorating health in recent years. 

As a Chicago tech entrepreneur, I got to know Ron in 1994 when I was raising a venture round for VREAM, a software company that I co-founded that was later acquired by PLATINUM Technology. It was a time when US Robotics was Chicago's only big tech success story. It was before the Web had emerged as a popular medium. Nobody had websites. Chicago-based Spyglass was licensing NCSA's Mosaic around then and Netscape Navigator would be coming out a few months later.

Since then, Chicago has matured as a tech city. Groupon and other success stories have overshadowed the early tech entrepreneurs. We participated in the dot com boom, and we have done reasonably well in the latest tech boom.

Throughout all those years, Ron May was there, relentlessly looking for a scoop. He was at every networking event, always and incessantly asking for the business cards of attendees. Give Ron your card and you were added to his newsletter mailing list. Any tidbit of tech or startup news was relayed to the masses via The May Report.

I was a target of Ron's obsession for many years. He occasionally would get obsessed with specific entrepreneurs, and I was one of those that he keyed in on for a small while. At one point, years before I started tech PR firm Walker Sands, I attended a local PR firm's seminar on media relations, and I was one of about 100 attendees in the audience. Ron May was of course there -- I swear he was at every event.

Near the end, the panel leader opened up the discussion for questions and Ron May immediately stood up and said: "Are we allowed to ask questions of the audience? Because I have a question for Ken Gaebler who I see sitting in the back. Ken, I'd like to ask you what you are up to these days?" It was about then that I stopped going to networking events -- the idea of being hounded by Ron May was a bit off-putting.

That was the downside of Ron May. As much as he brought together the tech community and kept us informed, he also scared many of us away from participating actively. We didn't want to be in his limelight.

With a vast network of sources, he gathered news at light speed. When the dot com bubble started to burst and my firm,, had to layoff employees, we held a meeting to let employees know. Within 20 minutes of the meeting's end, the news was in The May Report!

At some point, his coverage took a turn for the worse. Whereas his early "scoops" were about who had raised a seed round or who had been bought out, his later scoops were about who had had an affair or who had been fired for an ethics breach. In a world where people are innocent until proven guilty, Ron was happy to report rumor as if it were fact. Many people were damaged by his reporting, and he would go after people relentlessly if they got on his bad side.

Truth be told, I stopped reading The May Report years ago. It continued to come to my inbox but I never read it. I only looked at it when somebody mentions to me that Ron had mentioned my name, an honor he bestowed on me just a week or two ago with regard to our sponsorship of TechWeek.

We all watched Ron struggle with diabetes. His health was horrible, which made it all the more amazing that he could get to so many of those networking events. Eventually, his body just gave up.

Now, he's gone. I'm going to miss the guy. Love him or hate him, you cannot argue that he has always been a player in the Chicago tech scene. When we needed it, when many of us wondered if there were any other tech entrepreneurs in town, Ron was there to connect the dots and let us know that we were not alone.

Somehow, Ron managed to posthumously send out a newsletter, entitled The May Report: Final Report – No Really with lines typical of Ron, such as this one:

There are no doubts that many of you are a breathing a sigh of relief that they'll never be the subject of another snarky headline or personally intrusive investigation.  You know who you are; I don't have to remind anyone of my favorite subjects.

Briefly, I was one of Ron's "favorite subjects" -- like I said, I'll never forget the guy. At the end of the day, it's my take that he was net positive for the Chicago tech scene.