Ron May: Digital Social Pioneer

Ron May, 1956-2013

Ron May Digital Social Pioneer, and the notorious Chicago hightech commentator and analyst, died on 23 June 2013. Since I knew Ron longer and better than many people, I’ll reflect on what I knew of his life and considerable gifts and contributions. Above all, I’ll try to convey what Ron taught me about the digital world, where he was a pioneer among pioneers.

I met Ron in late 1996 in Dick Reck’s office at KPMG, when The May Report was fledging. It was obvious that he was unusually smart and passionate and motivated, and I learned that these traits were the foundation of Ron May the person. Ron May cared, and he had strong opinions. He had a brilliant inquisitive mind and indefatigable energy. I had a few conversations with Ron about his health over the years, and I suspect that it had a large impact on how he felt and interacted in public.

Ron had encyclopedic knowledge about (especially) Illinois hightech entrepreneurs, angels and venture capitalists. I can’t tell you how many times he asked the most compelling questions at Chicago hightech events and elevated the conversation. Yes, sometimes his comments were sardonic and rude, which got him barred from some events over the years—not to mention sued. Ron proved to be incorrigible, so often people and events adjusted around him because his willingness or ability to adjust himself socially seemed limited.

Ron was notorious in the hightech community, but I counseled dozens of people over the years to not be afraid of him. Underneath, Ron had his own sense of ethics, as we all do, but he didn’t hesitate to use his cane and pen as a weapon when some person or organization aroused his ire. This earned him a unique reputation in the hightech community. I had less contact with him in later years as I spent less time at hightech events.

In most cases, though, he was attracted by people and organizations that were intellectually interesting, full of themselves or trying to hide things.

I think his strongest motivator was exposing things that people were trying to hide or gloss over. He was also fascinated by technology or business models he liked. He didn’t sugar-coat things, to say the least. He was also unpredictable and seemed to engage in personal vendettas, so many people were afraid of him.

Over the years, I was intermittently the subject of his ire, but overall Ron and I were okay with each other. I have known people that were gravely injured by Ron and The May Report. Underneath, I don’t think that Ron wanted to hurt anyone in most cases. I felt that Ron was a very social person, although he did strike out at people and hurt them, sometimes seemingly intentionally. However, he also helped people and companies by publicizing what they were doing, and often his insights were valuable and unique. He added dynamism to the Illinois hightech scene.

The May Report broke a lot of rules, but it was a pioneering publication. Ron published everything people sent him via email, automatically. Sometimes he honored “do not publish” requests, but I learned to not email him anything that I did not want published because Ron didn’t give guarantees. But it provided information you couldn’t find anywhere else. It was read by people worldwide.

Ron May taught the world about transparency, way before many-to-many Web 2.0 apps were in use. Transparency doesn’t mean nice. It means nakedness. And because we humans are mortals, we all “distort” reality in accordance with our points of view. Social mores are complex, but they govern how people and organizations use transparency. Ron May broke a lot of those, sometimes vehemently, so he was admired and derided for that. The May Report offered information that one couldn’t get anywhere else. It reflected humanity and the Web in general: everything from brilliant analysis and reporting to abject lies, distortions and backbiting. But I think it was more positive than negative overall.

Transparency confronts people, and most people don’t like confrontation. The May Report shared a lot of information, and the reader had to filter. Its lack of orthodoxy hurt it as a business, so it was clearly a work of passion. TMR was a (mostly) one-man Glass Door, TechCrunch, blog and community because Ron was not easy to work with. Most people like transparency about other people, not about themselves, but it doesn’t work that way.

In his own gruff—and sometimes perverse—way, Ron May was a booster of the Chicago hightech economy. The May Report gave the world a unique view into Chicago’s hightech community and economy. It was idiosyncratic, opinionated, hard-hitting, and gossipy, all at once. Ron may have struggled socially, but he gave the world the gifts of his reportage and analysis as well as snarky comments. The unevenness of the report hurt its credibility, but that’s just the way it was. Here is his last post and Chicago Tribune obituary.

Lastly, I will miss Ron May the person. He was passionate, curious, rough and very smart. His raspy voice, unyielding cane and alternately incisive and twinkling gaze will always be a part of Chicago hightech events in my mind, and I’m sure in many others’. I am very glad to have known Ron May, and I’m sorry he is gone.