Millennials are the youngest generation to hold any considerable spending power (generation Z is just starting to enter the workforce). Millennials, while they weren’t born with the miracle of the internet and smartphones, have to think back quite a ways to a time when they didn’t have them. Millennials are a much coveted demographic because they spend an estimated $200 billion annually. But marketing to them is perilous. For one, they’re savvier that the average consumer having adopted smartphone use from the very beginning. And for two, they’re active on social media and will mock brands mercilessly and publicly when they make a marketing mistake. What follows are a few examples of how not to market to millennials and lessons that can be learned from them.

Chevy’s “Real people not actors” focus group commercials

If you’ve ever watched any of Chevy’s “Real people, not actors” commercials, and rolled your eyes at how accurately they portray millennials, you’re not alone. To Chevy, millennial men are bearded, tattooed, and pierced with lumberjack-style flannel shirts and skintight jeans. Millennial women sport unusual hair styles with one side shaved and strange colors. Both men and women are characterized by their nomadic, non-conforming lifestyle. The stereotypes are so apparent, someone actually made a parody of Chevy’s focus group commercials. The problem with portraying millennials in this manner is that you’re actually portraying a small minority of the millennial demographic. Millennials aren’t always bespectacled, bearded, hipsters who prefer outrageously overpriced coffee shops. In fact, only roughly 26% of millennials fit this description. Stereotypical portrayals of millennials actually distance the common, non-hipster variant of millennials. Millennials are a diverse generation so brands need to take care not to oversimplify them through offensive stereotypes.

Hillary Clinton

Many political analysts say that the primary reason Clinton lost the 2016 election was her inability to relate to millennials. She once famously asked millennials in a tweet to share their feelings on student loan debt with three emojis or less. This might not seem too problematic on the surface when you consider how much millennials love to communicate with GIFs, memes, emojis, and textspeak. But there are right and wrong ways to capitalize on this tendency. Dominos made it possible to order pizza by tweeting a pizza emoji at the pizza chain’s twitter handle. It doesn’t get much simpler than that, and it was a huge success. Student loans, on the other hand, is a very important and serious topic to millennials, they don’t want to discuss in using emojis. Using emojis in advertising for anything other than convenience suggests that millennials are too lazy or illiterate to speak using actual words.

Microsoft’s intern recruiting tactics

A university recruiter for Microsoft sent out the following email to college students hoping to drum up excitement for their internship:

“Hey bae intern! <3… we’re throwing an exclusive after party the night of our event at our San Francisco office and you’re invited. There will be hella nom noms, lots of dranks, the best beats, and just like last year, we’re breaking out the Yammer beer pong tables! Hell yes to getting lit on a Monday night!

As with emoji use in advertising, attempts to sound hip by using slang and improper grammar and spelling usually does the opposite. Chances are the slang you use stopped being cool last month and it just makes you look unprofessional. You see this mistake a lot with SMS marketing campaigns when brands lapse into millennial slang and textspeak to try and sound cool but end up sounding like they’re poking fun or talking down to their audience.