Techweek took over the Merchandise Mart last week. Credit: Ryan Smith

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?

“The free drinks and the women,” he confessed.

Every summer, thousands of badge-wearing members of Chicago’s growing digirati class (here labeled “entrepreneurs, corporate professionals and thought leaders”) gather on the eighth floor of the Merchandise Mart for a week of connecting, commiserating, and imbibing. It’s an ironic spot for the event since the art deco behemoth of a building that embodies the city’s old economy of physical goods; in step with a place that has quickly shed its manufacturing base and blue-collar workforce, the House That Marshall Field Built is increasingly being taken over by companies that deal in data rather than objects. When it arrived in 2011—for better or for worse—Techweek signified a triumph of the new economy in Chicago.

But four years after its debut, it’s difficult to decide if Techweek is much more than a loud, self-important symbol of local tech’s might. Is it a useful utility for the local high-tech and start-up community or a tone-deaf bacchanal with the same oversunny utopianism native to the digital gods that rule Silicon Valley?

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.

“The error that evangelists make is to assume that the Internet’s open, decentralized technology naturally translates into a less hierarchical or unequal society,” he wrote. “But rather than more openness and the destruction of hierarchies, an unregulated network society is breaking the old center, compounding economic and cultural inequality, and creating a digital generation of masters of the universe. This new power may be rooted in a borderless network, but it still translates into massive wealth and power for a tiny handful of companies and individuals.”

Techweek and many gatherings of its ilk like to push the power of new apps and digital platforms to “creatively disrupt” industries—destroying inefficiencies and remaking them in a leaner and meaner fashion. But what that often means, argues Keen, is that lumbering old industries that employ tens of thousands of employees making middle-class wages are replaced by a handful of highly paid techies. Keen himself travelled to the once-glorious headquarters of Eastman Kodak in Rochester, New York. The king of the analog camera once employed tens of thousands in it’s heydey. But those clunky things have been supplanted by the tiny miracle-like smartphone with a camera we all have in our pocket at all times. As a result, those jobs and pensions at Kodak have vanished and the midsized rust-belt town has become a mini-Detroit-like ghost town. Meanwhile, when Instagram got purchased by Facebook for $1 billion in 2012, all that money got spread amongst only 13 employees.

Interestingly enough, some of these old industries have tried to attach themselves to Techweek. I’m guessing it’s part of a strategy to “rebrand” and help avoid Kodak’s fate. One of the main sponsors is Harley-Davidson, the old-school motorcycle manufacturer based in Milwaukee that mostly appeals to a rapidly aging demographic of white male baby boomers. Harley threw money at Techweek to put on a private screening of Avengers: Age of Ultron because, the young people like those comic book movies, I guess? It also set up a tent outside the Merchandise Mart where attendees could try out a sleek new electric motorcycle that the signage labeled “the Livewire Experience.”

The leather-vest-wearing Harley people certainly stood out from the tech bosses at Techweek, who are certainly of a different cloth than the ruling classes of yore—sometimes literally. They eschew the Don Draper-style three-piece suit and tie for the so-called “business mullet.” The blazer is there, sure, but they sport a colorful T-shirt underneath paired with denim jeans and sneakers that say “we’re professional, but, like, cool and casual, dude.” They don’t play golf at the country club and probably didn’t vote for Bruce Rauner for governor. They drink craft cocktails and slip Star Wars or Game of Thrones references in casual conversations and support gay marriage.

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.

One of many panels
One of many panelsCredit: Courtesy Techweek

It’s 11:30 AM. on Friday and I’m standing in a meeting room watching a talk by Dr. Jennifer Jones, a self-proclaimed shrink for executives and entrepreneurs. This is an event called EntrepreneurShift, described as an “experiential summit where you’ll learn what it takes to shift from status quo to psychological superhero.” At Techweek everyone already has the keys to great success lodged in their brains—they just need a “thought leader” to help you open up their vast potential.

Dr. Jones is trying to expound on a Power Point slide that reads “Affirmation + Action = Permanent Change.” I don’t understand any of it.

“You’ve got to imagine your dreams and tap into the unconscious and subconscious mind. Ten years from now, we’ll all be saying ‘Goddamn, why weren’t we doing that before? It’s like we’ve been eating McDonald’s cheeseburgers for every meal.” Later in the session, OKCupid and CEO Sam Yagan joins Jones for a question-and-answer session to help enraptured attendees find their own financial success by, you know, trying really hard.

I grew tired of listening to the talk, so I walked around the crowded conference floor seeking Techweek’s positive aspects—especially since I mostly saw a lot of colorful booths with plucky PR people from companies like T-Mobile handing out branded swag upon my first lap around. It didn’t help that one of the first exhibitors I talked to—a tall, well-scrubbed guy in a blue collared shirt—put the brakes on our five-minute conversation about his “innovation lab” after I revealed the nature of my employment.

“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.

But I didn’t give up. I spoke to Carolyn Blackman, who works in public relations for Avant—an up-start loan company based here. Techweek sponsors a hiring fair and she said her company leaned on the event for recruiting purposes. They employ 650 people and will be hiring 300 more by year’s end “Finding top tech talent can be tough in Chicago,” she told me.

I also appreciated my time chatting with Craig Douglass and Tom Buchanan, recent college graduates from Syracuse University who’ve made a device that sounds like something out of a Matrix-like sci-fi movie. It’s a robot glove called Contact and it acts as a virtual-reality control device by mimicking everything the user’s hand does and simulates the sensation of holding what’s on the screen. If you grab a virtual coffee mug, for instance, you’ll feel increased pressure on your hand as you tighten your grip. Amazing stuff—and the pair have come to Techweek to help find capital to help make their prototype a reality. For them, Techweek’s contest that lets young start-ups pitch capitalists and investors, and grants the winner $50,000 is extremely valuable.

If nothing else, this was also the year that Techweek shed some of its frattiness and casual sexism—the kind of culture that has put the tech world as a whole under the media microscope. Two years ago, Techweek hosted a tacky bikini fashion show and last year organizers of a “Black Tie Rave” promoted the event with photos of a pair of scantily clad women in sexually suggestive poses. The ad prompted some big-named techies to request their names be pulled from the Techweek100 list of business and technology leaders and Crain’s Chicago yanked its sponsorship of the event. Techweek’s execs responded by apologizing on its blog, canceling the rave, and hosting a round-table discussion on “how we can better communicate positive and exciting events in the future.”

In May, the Chicago-based company took its image rehab a step further by sidelining previous CEO Iain Shovlin and promoting 30-year-old social-media star Katy Lynch to the top position. Lynch announced plans to expand Techweek’s reach from six cities to 11, which currently include Chicago, New York, Los Angeles, Miami, Detroit,and Kansas City, while simultaneously shrinking the footprint of Chicago’s Techweek. They’d trim the show-floor hours from three days to two and cut some of the fat from the extracurriculars. (“The old CEO spent a lot of money on entertainment, not so much this year,” a friendly tech guy I spoke with told me. “Last year, I heard Grammy winners were hired to play at private parties.”) The conference this year opened Thursday morning with much more female-friendly programming, including a women-in-tech panel discussion and Q&A session. The roster of speakers included more women and the marketing materials appeared fairly gender neutral.

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.

Or how about promoting a nonprofit “global venture fund” working for better global water quality with a three-hour cruise on Lake Michigan on a yacht where attendees wore blue (for water, duh!) while sipping booze at an open bar and dancing to a DJ? And why was a Chicago startup hosting a brogrammer-friendly beer-pong tournament on the conference floor?

Yup.Credit: Ryan Smith

I don’t have an answer, but I also can’t answer this: What is the alternative to Techweek and this superstar economy of app-loving entrepreneurs and massive tech titans like Amazon and Facebook that keeps hollowing out the middle class? In The Internet Is Not the Answer, Keen hopes for top-down reform. An antitrust crusade to break up Google, whose founders have a private air force, including a pair of Boeing airliners and a decommissioned fighter plane. Or for world governments to adopt economist Thomas Piketty’s suggestion for a global tax on wealth.

But that’s unlikely to happen—especially considering that tech is the engine driving so much job growth and productivity in America in 2015. Our leaders are unlikely to take the car keys away, and maybe they shouldn’t. It’s possible that my fear that within a decade Google will be more powerful than world governments and all of our jobs will be performed by intelligent robots and algorithms is just a mutation of the same thing we’ve already heard for 50 years. In 1964, a committee of scientists and activists sent an letter to president Lyndon Johnson claiming that “the cybernation revolution” would create “a separate nation of the poor, the unskilled, the jobless.” Five decades later, that still hasn’t happened.

So maybe, like them, I’m just a Luddite. Maybe I need to put on some sneakers and a blazer and play some goddamn beer pong.