We’re kicking off Giving Tuesday early this year! Your donation today will be matched up to $10K, doubling your impact! If you donate $50 today, the Reader will receive $100.

The Reader is now a community-funded nonprofit newsroom. Can we count on your support to help keep us publishing?


All the Gossip the High-Tech Industry Can Handle

By Jack Helbig

Go to any public high-tech event in Chicago–First Tuesday or BIGfrontier or ComDex-Chicago–and eventually you’ll meet Ron May. A huge, jowly man with squinty, tired eyes and a wrinkled coat hanging open to accommodate his large belly, May leans on a cane as he limps around the room, his free hand partly extended as he shouts in his raspy voice, “Hi, I’m Ron May.”

He pushes into every conversation, whether it’s a tight circle or a loose one, interrupting whoever’s speaking and going around the group asking, “Who are you? Who are you?”

He will then collect business cards from anyone who has one, glancing at them briefly before shoving them into his coat pocket and making a few mental notes. If he has happened on someone who’s important to the Chicago high-tech community, he might hang around for a minute or so, listening or shooting in a question or two.

Sometimes he tries for a little hearty bonding conversation, though these attempts often fall flat–May is the king of the blurted-out inappropriate comment. “My God, Jack–when did you turn into such a fat fuck?” he asked me at a recent networking party. I’d known him casually in college, but hadn’t seen him since the early 80s. “I’ve got an excuse–I’ve always been a fat fucker,” he went on. “But you used to be thin. My God.” He eyed my belly accusingly.

May, gadfly and rumormonger of Chicago’s high-tech world, is publisher and chief reporter at the “May Report,” an electronic newsletter he’s been putting out since 1997 and now publishes five to seven times a week. It’s a weird collection of stories, scoops, press releases reprinted verbatim, a few ads, and anonymous E-mails from disgruntled employees and board members spilling the beans about local companies. In recent months these letters have been filled with reports of layoffs that haven’t yet made it into print and rumors of layoffs. “The ‘May Report’ is not an observer,” he says. “It is a participant in the game. I’m an actor in the game.”

May prides himself on his scoops and tries to stay one step ahead of everyone else, rushing to get stories out as soon as he has something hot or embarrassing. He was one of the first to report last fall that all was not going well at MarchFIRST, which filed for Chapter 11 protection on April 13. Last January he published in advance the access code to a private conference call set up by Mercantec’s managers to discuss possible layoffs. “The call turned into a gabfest for ‘May Report’ readers,” he says, chuckling. “There were maybe 50 of my readers on the line–all at the expense of Mercantec.”

Stunts like that have made May both loved and hated in the high-tech community. And spoofed. “Is Ron May Possessed by Satan?” was the title of an article published on indignantonline.

com. “Observation of Ron and the May Report,” the story said, “does bring up some frightening similarities to behaviors exhibited by people possessed by demons.” On March 5, when May went in for an angiogram, “ePrairie,” a “May Report” competitor, reported on the event, publishing images of his angiogram–supplied by May–and writing that he’d gone into the hospital to prove “he has a heart.”

May, who says the “May Report” is the result of “taking my neurotic Jewish family and bottling it,” claims to be descended from a long line of gossips. His paternal grandmother, he says, “was the supreme gossip. But it was vicious gossip. When I was five years old, my oma tells me she loves me more than my other grandmother. The proof? She gave me more gifts.” May, wanting to find out if it was true, repeated the story to his maternal grandmother, who fought all the time with his oma, to see how she’d react. “Ahhhh,” he says, smiling, “the ‘May Report’ is born.”

May’s oma, a German-Jewish refugee who’d fled Germany when Hitler came to power, constantly caused mischief among her relatives. She seemed to delight in finding fault with her daughter-in-law’s side of the family and in telling family secrets to the young May, knowing he would blurt them out on some public occasion. When May was eight she told him that his maternal grandmother had been married once before. May dutifully repeated this, gleefully telling his grandfather, “You’re grandma’s second husband!” When May was 19, his grandmother let slip that he wasn’t his mother’s first child, that she’d aborted a child before he was born–and she hinted that he could easily have been aborted as well. He ran to his mother and told her he was furious.

“I said at her funeral, ‘Oma wasn’t built for peace,'” he says. “If you needed to survive Hitler you wanted someone like her on your side. But you didn’t need someone like that in the normal course of affairs.”

May’s father was a professor of marketing with a PhD from the University of Michigan who couldn’t get tenure. So every five years or so the family uprooted and moved to another college town; May spent his childhood in Columbia, Missouri, in Austin, Texas, and in Saint Louis.

Always overweight and unathletic, he had trouble fitting in wherever the family moved. It didn’t help that he was always one of the smartest kids in his class or that he loved to shoot his mouth off. In high school he became notorious among debaters in suburban Saint Louis for his aggressive, flamboyant style–and for his tendency to throw tantrums if he didn’t win. For several years in the mid-70s the debate team at a rival school commemorated his whining by giving out a Ron May Good Loser award, which, in the interest of full disclosure, I won in 1974.

After graduating, May went to Knox College but dropped out in the spring of his sophomore year. “I spent all my tuition money on pizza,” he says, smiling. “And then I made up a story that my oma bought hook, line, and sinker. I told her that I really needed to leave school and go to a fat farm. I had her looking all over the country for a good fat farm.”

May took a year off, finished a year at Knox, then transferred to the University of Chicago, where being bookish and unathletic were badges of honor. He threw himself into his studies, taking advanced classes and even graduate-level courses, but his ambition outran his ability to cope with the pressure. “I took a class with Edward Levi. Edward Levi had been president of the university, the dean of the law school, and attorney general under Gerald Ford. I had problems writing my paper for him because there was a huge expectation gap.”

He didn’t finish many of his papers, preferring to take incompletes in hopes of writing better papers later. By 1980 he’d become a Hyde Park cliche–well past his fourth year of college, but still taking classes and still buried under piles of unfinished papers. His father gently suggested it was time for him to find work in the real world.

“My first job was selling tools to farmers on the phone,” May says. “Then I got a job as a headhunter.” He quickly discovered he was good at calling people up and persuading them to consider a new job or field, though he never felt completely comfortable doing it. “I was advising other people in their careers,” he says, “which was the one damn thing I couldn’t do for myself.”

As the computer revolution gathered steam in the 80s and early 90s, May found himself doing more and more head-hunting for high-tech companies. In 1993 he began to contribute a column to Computer Guide, a local newspaper; he called it the “May Report” and used it to write about local high-tech deals. “I was a real deal junkie,” he says. “I was always writing about venture capital or angel finance deals. I was always trying to find out what people didn’t want to reveal. I was already functioning in my obstreperous way.”

He found it increasingly difficult to maintain the contacts he needed to be a successful headhunter–“I pissed off a lot of people”–while doing the sort of no-holds-barred reporting he loved. So in February 1996 he quit writing.

A year later his oma died, and suddenly he realized that what he loved most was writing and playing the gadfly. He gathered material for another “May Report” and approached the folks at Computer Guide. “The editor said, ‘I can’t publish this. This is too controversial.’ I said, ‘Fine. I’ll send it out by E-mail to people I know.'”

He prepared an on-line version, figuring he could sell enough ads to scrape together a living, and sent it to 60 people on his Rolodex. The next morning he had 20 responses. Now he has 20,000 subscribers–and last year the newsletter grossed $330,000. “I love the Internet,” he says, “because it gave a fuckup like me a second chance.”

The “May Report” now completely consumes his life. When he isn’t out chasing down a story, trying to get an interview with a beleaguered dotcom CEO, or gathering gossip, he’s home writing his next column or pacing the narrow path that runs between the innumerable boxes and books and piles of loose paper that fill his Lakeview apartment.

The place clearly hasn’t been cleaned in years–in his kitchen is a pile of burned-out lightbulbs he hasn’t gotten around to throwing out. He doesn’t care. “I’ve been given a gift–being able to work at something that I’m passionate about,” he says. “Never mind that I’m passionate about it because of sick things–like I love causing trouble.” He pauses and reconsiders what he’s just said. “I really do honestly want to help the high-tech community. People think that I’m just a gossipy guy. Not at all. I like to gossip–but it’s gossip with a purpose.”

Art accompanying story in printed newspaper (not available in this archive): photo/Lloyd DeGrane.