Every business owner has stories of “interesting” client interaction; at least one harrowing tale of someone you never would have dreamed of doing business with had you not desperately needed the work! You know, the kind of clients you rarely interact with when you’re working for someone else, but who seem to come out of the woodwork as soon as you’ve set up shop on your own.

The following cringe-worthy tales are true-to-life client stories from small business owners who’ve taken on more than they bargained for, all in the name of business.

*Names have been changed or omitted to protect the innocent and quite possibly the guilty as well. **Embellishments may have also been made because not all small business owners are good story tellers.


The Wise Guy


My brother knew a guy who needed some design work done for a new product he was importing from Southern Italy. This simple fact gave me no reason to be alarmed. When the client’s “cousin” called to set up a meeting at a neighborhood Italian restaurant where a bunch of guys were always sitting out front, however, you’d think I would have been able to put 2 and 2 together. Unfortunately, however I was quite blinded by both my hunger for work and my genuine hunger from living off Ramen at the time. I needed the job.
Long story short, the restaurant was straight out of the movies and the client, with his Falcone, two-button, pin-striped suit, was a dead ringer for a Hollywood mafia boss!

He told me to have a seat and I did. For much of the rest of our meeting, however I felt like more of a decoration on the chair than a business owner pitching my services. He spent the vast majority of our time together either talking with his way-too-young girlfriend who called repeatedly asking to spend money, or one of his “family members” who’d stop by the table to share some bit of muttered news about one thing or another, obviously not for my ears.

Try as I might to keep the meeting on track, I felt as though I were a footnote to his lunch rather than an attendee of a serious business meeting. That is, until I gave him my price…

If I’d thought about it at the time, I don’t know if it would have been possible to turn away from the grip of his gaze. The moment the (what I thought fair) dollar amount escaped my lips, all time and motion seemed to stop and for the first time since I walked into the room I seemed to have his undivided, though now undesired attention.

His eyes shot into me and grabbed a hold of the prehistoric, animal instinct previously locked deep within my cerebellum that told me to freeze! I dare not move. I dare not look away. All I could do was stare back and try not to show my fear.

Across from me the client stared too, but where I had a cute, little, furry, loveable, heart-racing, prehistoric prey animal, in him I saw a vicious, hungry T-Rex that thought nothing of me but what I was about to taste like!

A long moment passed as the price I’d muttered seemed to hang in the air between us like stale smoke in an unventilated back office, and just when I thought I couldn’t take it any longer; the split second before my fight or flight instinct would propel me toward the door leaving nothing behind but my pride and perhaps a small puddle, the sound of his fist pounding the table and his thunderous voice broke the silence and rocked me to my foundation!

“That’s a GREAT price!” he yelled. “Are you sure you can do it for so little?”


The Congenial Burglar

I once pulled together a website for a guy I “sorta” knew. We never made explicit arrangements for payment, but I figured we’d get around to it. He had some intricate requests so, before all was said and done, the bill had run into a few grand.

This was just after I’d struck out on my own and I really needed the money so I shot him an invoice and prayed a little prayer, but before I heard back from him, I had to run out of town for a conference.

The conference was great. I was learning a lot during the day and making a lot of connections while essentially partying with the other attendees at night.

During a break-out session on the last day of the conference my phone rang.  Of course, the phone ringing for a brand-new business was a major event and I nearly broke my neck tripping over people to rush out of my row and the room in time to catch the call, but I managed to glance at my phone’s face just long enough to see the number. The call was from MY HOME PHONE… At the time, I lived alone. You can imagine how freaked out I was.

It turns out that my website client wanted to repay me by cleaning my house and landscaping my yard while I was away. It might have been a nice sentiment if he hadn’t legitimately broken into my house to do it.


The Tin Foil Hat Massage

I’m a massage therapist so, you can imagine the kinds of things I’ve seen especially when I was too new to choose my clientele.

Like most therapists, I’ve been hit on by naked old guys, but at least that was something I could have anticipated. It comes with the territory. (It shouldn’t, but it does.)

One of the first clients I had, back when I absolutely couldn’t afford to lose a single customer, was an elderly lady who insisted on discussing conspiracy theories while I worked. I got to hear how the moon landing was faked (she “knew” someone who helped with the broadcast), how aliens have been walking among us since 1986 (there’s proof out there for anyone who “truly” wants to know), and how the JFK assassination had “actually” been carried out by the Chinese government.

I’m not ashamed to say that I kind of liked this sweet if not slightly delusional old lady. She was nice enough and at least the conversation was interesting.

She fell asleep toward the end of her time with me and, having no clients after her, I let her lay there for a few extra minutes while I went to wash my hands. When I returned, however she was gone.

I don’t know how she got dressed so fast or managed to leave without passing me. I also don’t know what the strange metallic dust she left behind was or where that sharp smell of ozone came from…

If you have funny business stories or would like to contribute in any way to the Disorderly Ducks’ blog, drop us a note with your contact information to: support@woystermedia.com.

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Please keep in mind that the Disorderly Ducks of Woyster Media are NOT comedians by any stretch of the imagination. We want to help others by passing along this free attempt at humor, but your situation may be different from ours. You’d be freakin’ NUTS to laugh at ANYthing we say without first consulting your personal comedian or comedy writer!