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WANTED: Your Jerkiest, Most Unprofessional, Inappropriate Business Emails. (You Can Keep The Sender.)

In: Hard Stuff,

You ever get an email that just pisses you off?

All you’re trying to do is go about your day, maybe fire off a few invoices, maybe do a little creative work, maybe try to avoid having a mid-day myocardial infarction.

And then it arrives.

You can’t tell if it’s an email or maybe somebody laid their elbow on the wing ding button. You scan it and see a wall of exclamation points, capital letters, and percent signs and asterisks flying all over the screen. It’s Symbols Gone Wild, Gmail edition.

At first your internal alarm goes off: Heart starts racing, adrenaline starts flowing, eyes start widening. You instantly take all the blame, telling yourself you must be as horrible a human being as they say you are; obviously strangers who email other strangers and say mean things are surely in the right. THEY MUST KNOW SOMETHING YOU DON’T. And because: *%!!$#@!

But then, after the fourth line or so, your balls drop and all the sudden you’re all, “Wait a minute, what the hell is this? Whhhhhhat? What is wrong with them? I did nothing of the sort!” (Yelled in your best 16th century accent.)

…and then you go get some ice cream. Because ice cream works for this kind of thing.

Shortly thereafter, you settle in and queue up to write your reply.

Dear Rumpelstiltskin,


Too aggressive.

Maybe if you hadn’t insisted on a CAN’T! MISS! RUSH! DEADLINE.

Don’t stoop to their level.


Too personal. Also: Vin Diesel.

Dear Rumpelstiltskin,

Rot in hell.

And then, and only then, after you’ve written and subsequently deleted at least four versions of imaginary emails you’d love to send, do you queue up to write the real one you do send:

Dear John,

I’m so sorry to hear you weren’t satisfied. What can I do to make it up to you?

Because that, folks, is the life of a small business owner.

No matter who spits in your face, you can’t spit back, because you apparently have an adult-child relationship with every client in the history of clients, and what kind of adult spits on children?

I know. That’s some imagery right there.

Then again, so is having a child spit in your face…

…and letting them get away with it.

What’s the jerkiest, most unprofessional, inappropriate email YOU’VE ever received?

Visit (and vote on!) the jerkiest email business owners around the world have gotten, and even upload a screenshot of your own to automatically be entered to win an exclusive license for access to the newest (and biggest, most important) product we’ve ever developed, LOVE, BUSINESS OWNER, a place for business owners who suck at saying the hard stuff (including new peer-to-peer “what do you do in THIS situation?!” support forums), launching Tuesday, November 11th. Let the cat get your competitor’s tongue.


Spill it!

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3 thoughts on "WANTED: Your Jerkiest, Most Unprofessional, Inappropriate Business Emails. (You Can Keep The Sender.)"

  1. David McDougal says:

    Dang this one would have been fun. I usually delete the truly fantastical ones just so I can move past them and try and save the relationship. I do recall though early in my web design time of two clients.

    1. We created a 100% original artwork and site. The site was for a music festival (blues) and we did the site navigation like a giant sax and each of the note keys on the stem were a menu item. You click on the name or key and it opened the page, and then it faded to the background to show the content of the new page. The client loved it and in good faith w put the site up for them and they dragged their feet in paying. Finally the event was over and they told us to take a flying leap and that they would never pay the asking price for the site (their visitors loved the site based on feedback). So, we got stuck with a 2K loss of work.

    2. We designed a site for a client and all was perfect. Then one day they get hacked (we were hosting them) and so they said something to us (as they should). We checked everything under the sun and there was no breach on the server, no other clients hacked and because we had great backups were able to restore the site quickly with no loss of data. Client threatens to sue us for loss of business, character etc. Thankfully we had a contract in place that had provisions for this. After nearly 20hrs of investigation and almost 1K in expenses on our side to figure out what happened we asked to see the clients machine. Come to find out that they had nearly 40 viruses on their computer, and despite EVERY warning we gave them they would edit live files via ftp and the editor on their site (we now remove this access for clients to protect themselves). Well needless to say they did not like that explanation (we sat in a conference room and cleaned the clients machine in real time for them). Thankfully he dropped the suit proceedings.

    I have had some other doozies but those are the two that stick out in my head the most. Mostly as they were people we trusted, and it hammered home the contract and insurance thing for us with such clarity. Today we still do things a little bit unorthodox but we have learned from each of these examples and know better how to address things.

    Cannot wait to see some of the fun ones coming though! 🙂

    1. Ash Ambirge says:

      Oh my goodness @davidmcdougal:disqus! Both of these are horrendous, though the issue in #1 is particularly disturbing because I know this kind of thing happens to business owners every day. I’m not sure how those folks can sleep at night – truly.

      And the fact that you’re very thorough with your FTP procedures – all makes sense! 🙂 Jesus.

  2. Love the part sbout having an adult-child relationship with your clients! Fortunately most of our clients are sweethearts…. but I DEFINITELY have a couple that need parenting…