OPINE: Farewell to Ron May, An Unforgettable Character

A crowd of more than 200 people gathered last night at the Merchandise Mart to pay tribute, and say goodbye, to one of Chicago’s most unforgettable characters, Ron May.

[Above Photo: Harper Reed, CTO of Threadless, enjoys a light moment with tech blogger, Ron May, during an interview for The May Report. (Courtesy of The May Report)]

On June 23rd, Mr. May, Chicago’s original tech blogger, succumbed to complications from diabetes that plagued him for several years. He was well known in the local entrepreneurial community as the founder and sole writer for his influential newsletter, The May Report, which reported extensively on the startup scene in Chicago. After working as a tech recruiter from 1981 to 1995, May launched his publication.

Ron was truly a double-edged sword. He could add significant value and bring visibility to Chicago’s startup community, ask probing questions, and keep his readership informed of popular networking events, influential entrepreneurs and investors, hot startups, and other relevant information pertaining to entrepreneurship in Chicago. On the other hand, more often than not, he could be rude, obnoxious, and overbearing and disrupt an event. It’s not a coincidence that he was banned from so many groups around town.

I had my own personal experiences with Ron. In October 2006, my partner, Len Bland, and I launched the BNC Venture Capital Group. We discussed sending a personal invitation to Ron but decided against it. Although he could provide us valuable publicity in his report, he could also alienate our audience. Eventually, Ron heard about us and began attending our events. Initially, he behaved himself but then I had to set ground rules:  1. If you arrive late, you walk in the back door and don’t draw attention to yourself.  2. No blurting out unsolicited statements to the room.  3. No tapping people on the leg with your cane and asking for their business card.  4. You dress appropriately in business or casual business attire.  5. When you ask a question, you ask a question and don’t pontificate.

For a while Ron behaved himself but, then, he regressed to his usual ways. Finally, I banned him from all my BNC groups when, believe it or not, he showed up at my BNC TechPitch event in his underwear, wearing nothing more than a white T-shirt and boxer shorts. He proceeded to get dressed in front of the room as I finished my interview with serial entrepreneur George Deeb of Red Rocket Ventures. He protested and offered me a number of excuses and justifications as to why he didn’t have sufficient time to get dressed before he arrived at my event. I told Ron that I would reinstate him if he could come up with the name of one entrepreneur, angel investor, or venture capitalist who walked around the city of Chicago in his underwear. For probably the only time in his life, Ron was speechless.

In my humble opinion, Ron’s legacy is that he filled a void in Chicago’s entrepreneur scene. The thousands of subscribers, including myself, to The May Report is a testament to the contribution that Ron made to the startup ecosystem in Chicago.  At the end of the dotcom bubble in 2000, The May Report reached its zenith with close to 40,000 readers. If you wanted to keep your finger on the pulse of entrepreneurship in Chicago, you were more likely to turn to the May Report, not the business sections in the Chicago Tribune nor the Chicago Sun-Times or Crain’s. Ron provided a valuable service that the major publications in town were unwilling or unable to offer. He was a networking and writing machine and typically would attend multiple events and publish his newsletter several times per week.

To his credit, he was a prolific writer. Regrettably, to the ‘dismay’ of many, Ron did not always check his facts and would publish stories or make personal accusations that were patently untrue.

In the final analysis, whether you were a friend or foe of the May Report, Ron May left an indelible mark on the startup ecosystem in Chicago with his passion for entrepreneurship and his force of personality. ❒

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