In an embarrassing and preemptively apologetic presentation by its $1-a-year chief marketing officer, the city of Chicago presented a new plan to "rebrand" itself -- by highlighting its past sins of racism and segregation, neglecting its greatest strengths, and promoting its struggling mayor as a superstar.

Sounds like a surefire winner for attracting suburbanites and tourists back to town. Maybe the CMO is overpaid.

Yes, we have some issues in Windy City. So do all the world's big cities. But you don't hear Paris advertising the fact that there's a demonstration every other day that ties the city in knots or devolves into violence on the Champs-Élysées. So inviting the world to visit Chicago as a place with great sports and cultural institutions, fabulous food, and blues as good as Basin Street seems a lot smarter than asking visitors to "experience diversity," as the new campaign plans to do. What's the point? We're a great city that has been inhabited, proudly if unevenly, by a wide variety of people and cultures for more than a century.

The current campaign feels a lot like a forlorn and desperate mixing of messages conceived by a committee of tone-deaf and highly defensive folks without a clue as to how to overcome the public's anger and fear following massive unrest, as well as a surge in murders and nonstop shootings of children by crazy teenage gangbangers. Here's a hint: You can't apologize for the criminals.

In a way, you have to feel sorry for the team taking on the campaign. It feels like a turkey accepting an invitation to Thanksgiving dinner. Chicago's marketing agency is trying to serve an unknown and largely unknowable mayor in Lori Lightfoot as well as too many other masters and being asked to address too many issues all at once. Not even Superman, or a tiny mayor dressed as a masked superhero -- as she did recently to promote safe Halloween protocols -- can leap obstacles this tall in a single bound. And worse yet, because the city is almost broke, please try to do it as cheaply as possible using staged "emotional tentpole" events like Halloween and Christmas amplified by powerful social media that has already allegedly transformed Mayor Lightweight into a celebrity because millions saw her memes. But frankly, seeing -- even on the web -- isn't remotely like believing. Calling this mayor a celebrity is like calling Trump a statesman, which may be one of the few things our mayor hasn't called him.

Mayor Lightfoot will be the cornerstone of the campaign because she's so "authentic" and intriguing. Yet she comes across as cold and callous, without any particular personality, sense of humor, or empathy. Snobbish, stilted, and superior are common adjectives for this novice politician, who's managed to make the memory of Rahm Emanuel's reign seem like a good time in Mr. Rogers's neighborhood. It's gonna be quite a heavy lift, all right.

Authenticity is a lot like sincerity. Once you can fake that, you've got it made. It's not easy, and it doesn't help that this mayor, with neither business nor much government experience (she's a corporate lawyer by trade), was elected in a contest where basically nobody came to the polls. But the most colossal mistake is the underlying assumption that anyone cares about her. In politics, as in business, people don't care about you; they care about what you can do for them.

There are so many lessons here for startups and entrepreneurs that it's actually hard to know where to start. But be sure to watch this sad adventure roll out, because even if it's not a good example, it can always serve as a horrible warning.

Lesson One: A Hashtag Can Become a Bashtag Overnight.

Basing a branding campaign on the prospect of obtaining broad and favorable social media -- especially in today's world of trolls and deep fakes -- is simply naive and a little nuts. There are no more critical and fickle places to try to tell your new story and no more precarious places to be when the wind shifts against you for no good reason than the messy world of the web. Viral isn't always virtuous, and traffic means next to nothing compared with real connection and active engagement with the right audience. Authenticity and celebrity almost never mix successfully.

Lesson Two: Don't Try to Do Something Cheaply You Shouldn't Do at All. 

Relying on free branding efforts is like eating cheap food -- there are always hidden costs and unforeseen consequences. A far better and more effective approach is to focus your efforts on a finite number of known channels, an identified population of target consumers (visitors, voters, volunteers, etc.), and a unified and single message rather than trying to be all things to all people, doing a little and mediocre bit for everyone. You get what you pay for, but even more important, you demonstrate that you'd rather do a few important things well than a lot of things poorly. This message is far broader and more important than any ad or banner -- it's a statement and a demonstration of your philosophy that permeates your entire business.

Lesson Three: A Brand Is a Promise -- Not What You Say, But What You Do. 

Maybe it's always a mistake to announce that you are setting out to create a new brand or rebrand a place or a product. (Hello, Wells Fargo.) Maybe there's a problem when the place you've decided to rebrand is more than 180 years old and has a proud history and a persistent past and shared stories of remarkable accomplishments that many residents aren't prepared to casually discard in the haste to move forward.

Sure, there are warts, but it feels a bit abrupt to summarily talk about tossing out the old before this mayor has done much of anything concrete for the people of this city other than offer herself as the personification of the new Chicago. Praise without purpose and worthless attempts at admiration have more to do with politics and personality quirks than with promises made and kept. Authentic brands aren't bought or manufactured. They're built through hard-earned trust and collaborative efforts rather than fits, foul language, or fiats. They have delivered demonstrable results.

The brand called Chicago needs real leadership and real change. This is not an easy fix -- it certainly can't be a cosmetic one. And the fix won't happen overnight for sure. But if it doesn't start out from a smart place with a solid foundation, the whole exercise will only end in further tears. As unhappy as the tourists in New York City who buy knockoff Gucci handbags from street vendors. The handbags are original and real. It's just the brand that's fake.