My Outsourcing Horror Stories

Outsourcing Horror Stories

Dumb ChoicesThe following stories, while showcasing horribly incompetent individuals, are painful failures on my part.

I was the biggest screw up in these stories.

I should have known better. Now I do, and I hope that these help you avoid similar mistakes as well!

Ok, grab some popcorn, lock the doors and turn all the lights on…

The Web Site from Hell and How I Paid $150 to Look Ridiculous for Weeks


I paid a freelancer $150 to design a website for me that, if done correctly, was worth much more than that. I went cheap thinking “what’s the difference?”

There was a difference, a big one. The freelancer made the site, seemed pretty clueless the whole time and when I saw the end product, I realized, he was in fact, clueless.

The site was laced with typos, formatting errors, non-functioning buttons, it wasn’t responsive and overall, it was a complete eyesore. It looked read like it was designed by the Nigerian Prince who contacts you every so often letting you know that he is giving you 6.8 million USD.

The worst part, the site remained that way for days (which seemed like years) and bounced potential visitors from my site deep into the stratosphere.

I eventually paid someone a reasonable rate ($400 I believe, which was a ton for me back then, but this was a disaster, food could wait) They fixed it and it looked great, but the damage was done. I was out $150 dollars + the $400 I should have paid from the beginning and had my launch set back weeks.


The Social Media Saboteur and How I Paid Someone to Destroy My Brand


This is the worst outsourcing mistake I have ever made, even though it “cost” me less than $100. It was a black eye to my reputation for a long time.

I found a freelancer who marketed himself as a “Social Media Expert.” First mistake: You don’t pay $0.70/hour for “Experts”.

Yes, you read that right. 70 cents per hour.

I had no money back when this happened. I paid what he asked, but would never hire at that rate now (upwork has a $3.00/hour minimum wage anyway). This was back when it was still Experts charge way more than this guy was asking, so that should have raised red flags.

I assumed “hey, I don’t need an expert, but if he says he is, he must be at least decent…”


I made the unforgivable mistake of giving the reigns to my social media management to someone who I didn’t know and who had no clue how to actually provide value on social media.

His idea of social media marketing was Commenting with 3 canned responses on every single one of my past posts from 4 different profiles he had made. Each name was a ridiculous attempt at a traditional American name and could not have looked more spammy if he tried.

It was a freaking disaster.

“This is a great article not only for someone interested in this topic, but also others as well!” – My Social Media “Expert”

 Now, take that piece of crap comment and repeat it with different users…on every post I had ever made!

Smooth Alip (my expert), very smooth…

The freelancer here wasn’t the moron, I was! What was I thinking? How could I let someone else I didn’t know represent my brand?!?

Trusting a Party Animal to Meet Deadlines


If you read my article The Ultimate Guide to Outsourcing with Fiverr, you know you shouldn’t hire freelancers you haven’t built rapport with for high level importance, time sensitive work.

I made this mistake and it bit me hard.

One of my businesses involved 3-4 virtual assistants, working Monday through Friday 8+ hours each day. The biggest mistake I made was hiring only enough labor to meet the needs of my clients, and had little protection if any of the employees was absent.

We had 25 paying members at $147/month. It wasn’t something with room for error.

As I was reviewing the weekly production, I noticed that one of my VAs hadn’t worked that day. I immediately contacted her and was genuinely worried about her wellbeing.

She didn’t respond for a week, I assumed the worst and that she was in an accident or something really bad.


Here is the actual correspondence…

Horrible freelancer






Oh, after ending this contract, she also gave me a one-star review…

Crazy Freelancer





I always recommend avoiding over the top criticism of your former freelancers, but you should say exactly what happened, tactfully.

2.5 stars was pretty generous in my opinion, but she was still “very frustrate with my behave.”


 The Worst Logo of All Time


There isn’t much to say here…pretty much speaks for itself.

Worst logo ever



How about you? Do you have any outsourcing horror stories? Comment below!


About the author

Nate McCallister

Nate is the founder and main contributor of He is a lifestyle entrepreneur who spends his time building businesses and raising his two kids Sawyer and Brooks with his beautiful wife Emily. His main interests include copywriting, economics and piano.


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