Last Tuesday I got an offer to sit on the board of a media company, but it was hard to take the pitch very seriously. I’d only been mingling at the so-called “TechMixer” in a loud River North club for an hour and had been acquainted with the smooth-talking CEO for all of five minutes. Not only that, he was heavily intoxicated and worked in advertising, not tech. So why come to Techweek every year?

As an outsider, I’d lean more toward the latter conclusion—but then again, I’m a skeptic. That’s especially true after recently reading Andrew Keen’s anti-Silicon Valley screed The Internet Is Not the Answer. In the book, the former tech evangelist turned doomsayer questions our popular narrative about the Brave New World of Web 2.0, that it’s a democratizing force that informs, empowers, and liberates humanity. The Internet can and does accomplish that in some measure, Keen argues, but it simultaneously acts as an economic hurricane that leaves vast inequality in its wake.

Plus, the corporate bosses that populate Techweek aren’t just here to make lots of money. They here to preach and spread a gospel of self-actualization and the TED Talk is their tent revival sermon. 

“Are you interested in entrepreneurship?” he asked. “Nope, I’m a journalist,” I said. He then turned and immediately tried to initiate a conversation with someone else.

That’s great, but Techweek undermined its progressive breakthroughs with other moments of breathtaking cluelessness that made me wish there was a Chicago edition of HBO’s techie-skewing show Silicon Valley. How else to explain that Techweek celebrated an announcement that the organization was expanding into impoverished Havana, Cuba—one of the first American organizations to do business with them since President Obama lifted the long-held embargo—with a tropical-themed party that mandated men wear fedoras and Hawaiian shirts while women donned grass skirts. It was held in the moneyed part of the city at celebrity-hangout Parliament, a nightclub that features a members-only lounge called the House of Lords, complete with a glass elevator leading to a rooftop deck. When you’re in a place literally called the House of Lords, introducing your future economic colonialism to a poverty-stricken island while sipping fancy cocktails and wearing hilariously misappropriated ethnic garb, maybe it’s time for a bit more self-awareness.