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When Ron May Ruled Chicago’s Tech Scene

Two decades ago, at the peak of the dot-com boom, one internet impresario had all the city’s startup world in his sweaty grip.

Ron May in 2008, at an AOL-sponsored conference
Ron May in 2008, at an AOL-sponsored conference Photo: Chicago Tribune

“I have all the sources and all the connections,” Ron May boasted to me in a raspy whine. It was the summer of 2000. We were at a West Loop nightclub called Drink, surrounded by lanyard-draped PR reps in stacked heels mingling with ponytailed entrepreneurs from now-defunct startups like Gazoontite.com (“disintermediating the hypo-allergenic pillow market”) and investors from Divine InterVentures (Chicago’s self-styled “internet zaibatsu”). May popped another hors d’oeuvre into his mouth and kept talking. “Here’s the thing, pothead: You can’t do this business unless you have passion, but you’re more interested in chasing skirts than stories and you don’t put in the work like I do.”

May’s forehead was glazed with sweat, his tie loosened, his shirt partly untucked. In his non-eating hand, he gripped a plastic bag full of business cards. Resting between us on the banquette was the tape recorder he’d been thrusting into people’s faces all night and, next to that, the cane that he used to get around — he’d lost a toe years earlier to diabetes — and to whack the legs of sources who wouldn’t go on the record for his gossipy e-newsletter on Chicago’s nascent tech scene, the May Report.

Later that summer, a splashy New York Times profile of the 44-year-old May would liken his newsletter — which, by May’s estimate, reached some 15,000 subscribers, many of whose email addresses he’d manually entered from business cards after long nights of schmoozing — to the Drudge Report. It also quoted one industry observer’s description of May’s modus operandi as “shoot first, think later”; another insider called May the “town tattler of the high-tech community.” No rumor seemed too ill founded for May to publish — this CEO’s a cokehead, that one’s about to lay off 300 people — and no confession too personal to air. Among his favorite topics: his seesawing weight and his interactions with women. “I couldn’t get it up in a million years so don’t sue me for saying that you have nice melons,” he claimed to have said to one female tech professional.

Me? I was the competition, a Birkenstock-shod 25-year-old reporter for a fledgling industry publication predicated on a more conventional journalistic model. But, really, how could I compete with a guy like May? If you were in the dot-com world in Chicago, the only thing that terrified you more than showing up in the May Report was not showing up in it.

Earlier that day, I’d published a long interview with an up-and-coming, earring-sporting software entrepreneur. I’d considered it a big get. But here was May, a smudge of Buffalo sauce on his cheek, calling my article “the ultimate puff piece.”

“Our problem in this town is that there is too much evangelism,” he continued, his words muffled by the mozzarella stick he’d just bitten into. “We have to get back into truth telling.”

This sentiment struck me as odd — coming from a man who’d falsely reported that Old Navy was about to get the naming rights to Navy Pier — and I said so, stammering something about fact-checking and journalistic best practices. May swiped a napkin across his lips and tossed it on the table. “Let me say this: I believe everything is relevant. If you’re abusive to cabdrivers and waitresses? That’s relevant. I don’t think you can leave anything out.” He leaned in close and added, “My real core belief is that we’re all better off as a society for sharing information.”

If this wasn’t dot-com evangelism, I didn’t know what was. But I held my tongue. The crowd was thinning out, many of the guests heading up the street to a VIP dinner being hosted by Microsoft and Comdisco at Ghost Bar, and I was eager to follow them.

As I started walking east on Randolph, I looked up from my Nokia to see May racing by in a cab — entitled to disability taxi vouchers, he never walked — accompanied by several young women. When I arrived at Ghost Bar, May was arguing with the hostess. “I guess this is one of those gated communities!” he shouted in her face, gesturing upstairs toward the private room where the dinner was being held. It seemed May was on the guest list but his entourage wasn’t, and so now he donned the mantle of champion of the people. At length, though, after emptying himself of vitriol, he shrugged to his friends and started laboriously ascending the stairs alone, the tip of his cane landing noisily on each step.

The choice of entrée that night was lobster or steak. May, seated next to me, ordered both, citing a need to maintain his blood sugar. As the evening wore on, he seemed to grow self-reflective. “There is evil in me,” he said resignedly at one point, acknowledging his occasional regret at not having followed in the footsteps of his father, an academic, or his brother, who made a handsome living in corporate recruiting and had married the Channel 9 lottery girl. Occasionally, in an elegiac tone, he referred to himself in the third person: “The thing that drives Ron May is instant gratification.” At other moments his boastful self would resurface: “People have no qualms about calling me up and giving me all the stories about what is going on. I’m switchboard central! People come to me and say things they would never say to you or the other ‘journalists’ ” — here he inserted finger quotes. “All of you just kiss ass and publish press releases. It’s not really a story until it’s in the May Report.”

Toward the end of the night, after I’d left Ghost Bar for a rave I’d heard about nearby, May called my cellphone, determined to continue our conversation. From the sounds of it, he was in a fast-moving cab, maybe on the Drive heading back to his Lake View apartment, which I’d heard had once been condemned, or maybe to the gyro shop he frequented at the end of long nights. “My job is to talk to people who think of themselves in an exaggerated or self-aggrandizing role,” he said. “But some of these people will have a legitimate role to play.”

That turned out not to be true for most of the would-be moguls May skewered in his newsletter, but the fact is, before the bubble burst, we all fancied ourselves potential kingmakers. It’s just that May, who died in 2013 at the age of 57, inhabited the role more fully than the rest of us. What’s more, well before the age of social media, he proved that anybody with an internet connection and an ego could enter the fray.

That may have been his biggest scoop of all.

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