Here's How Chicago Can Keep Its Top Tech Talent From Leaving for Other Cities

April 30, 2018 6:04 pm

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I’m sure you’ve heard by now that pretty much every metropolis in the country is claiming to be the next Silicon Valley. In a previous Inc piece I wrote, titled The Advantage Chicago Has Over Silicon Valley, I threw Chicago’s hat in the ring to be considered next in line.

Many Chicagoans have responded positively to the piece, validating Chicago’s entrepreneurial excitement. A handful of people, however, responded with some resistance to the constant comparisons to to Silicon Valley, like this Medium post by Jason Fried, CEO of Basecamp: Chicago, be Chicago

And for good reason–following another city’s playbook limits the space for originality. But on the other hand, resisting to target other cities is problematic and, to a some extent, dangerous.

Why? I’ll get to that in a second, but first I need to share a small part of my story:

I’m a twenty-something entrepreneur born and raised in Chicago. I founded MSTQ, a Chicago-based design and innovation firm, which has afforded me the opportunity to have a hand in some of Chicago’s most exciting tech startups. My work has given me a front row seat to Chicago’s growing tech scene, seeing first-hand this city’s immense potential for innovation. 

But there was once a time where I felt a deep sense of wanderlust. Not too long ago, I had dreams of packing a single suitcase and buying a one way ticket out. Admittedly, I felt like there was something bigger than what Chicago had to offer, that Chicago wasn’t forward-thinking enough and that I had outgrown it.

The problem is I’m most definitely not the only aspirational, bright-eyed entrepreneur that has felt this way. Many of my most talented friends–friends with incredibly promising creative potential that I admired–have left Chicago for cities like New York, Los Angeles and, you guessed it, Silicon Valley. 

Moreover, Chicago’s population has decreased for the third straight year. Meanwhile, urban populations are increasing everywhere else. While Chicago is still the third-most-populous metropolitan area in the US, it was the only one in the country’s top ten cities that saw a decrease rather than an increase in population, according to the Census Bureau.

So when influential figures in Chicago like Jason Fried resists comparisons to the very cities that are siphoning Chicago’s best native talent, they’re maintaining the status quo.

The crazy irony is that it was Fried himself who once preached the value of illuminating comparisons to competitors. In his book REWORK, here’s what he had to say about “picking fights”:

“If you think a competitor sucks, say so. When you do that, you’ll find that others who agree with you will rally to your side. Being the anti-_____ is a great way to differentiate yourself and attract followers. Taking a stand always stands out. People get stoked by conflict. They take sides. Passions are ignited. And that’s a good way to get people to take notice.”

So, why then, would you shy away from picking a fight with the biggest competitor?

The reality is, Silicon Valley is regarded as the tech and innovation capital of the world, bar none; it’s the modern day Rome of technology and innovation. And you know what they say–all roads lead to Rome, including the one from Chicago.

Insisting that young, ambitious Chicagoans like me ignore the success of the Valley hinders the ability to stand out and develop a sense of pride–a key ingredient in motivating the next generation of talent to stay in Chicago. 

Shouldn’t there be a target to aspire to? A vision to rally around?

Look, I get it. Let’s build something that’s our own. Let’s stop copying other cities. Let’s be original. Let’s not inflate our rent prices. Let’s make Chicago winters cool.

But instilling the belief that Chicago can be better than the best requires learning from and acknowledging the best. If today’s leaders in Chicago are going to preach a philosophy to its next generation of tech leaders, let it be Kobe Bryant’s perspective on comparisons to Michael Jordan:

“When you’re looking at players out there now, you’re saying, ‘OK, there’s not a next Michael Jordan.’ It’s not about the surface stuff. It’s about: Are they approaching the game the way he did?”

That way, the next generation of tech talent can not only better understand the formula for success, but also the Chicago’s unique strengths in comparison. And in Fried’s words, picking a fight with the best might inspire them to rally around the potential for the Second City to be first in innovation. 

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