Worst Business Ventures I’ve Ever Launched

I don’t think anyone that makes a living online has a 100% success rate. We all have projects we thought would make us millions that failed miserably. Here are some other the worst business ventures I have been involved in as well as my assessment of why it failed and what I learned.

Platinum T-Shirts An Online Clothing Store (2007)

When I first started making money in affiliate marketing my mindset was on creating other income streams. I briefly though about residential real estate and buying a laundromat, but I had my mind set on launching a shirt store.


The store was Platinumtshirts.com, it was a store selling hip-hop shirts. My first move was to launch a design contest. At the end of the contest I walked away with about 40 designs for $4000.

One of my 40 designs
Another design
I sold one of these, I swear

From that point I purchased a bunch of screen printing equipment. I figured I could teach myself to screen print in my basement.

Learning to screen print was too difficult so I went to a printer and dropped a few thousand getting my designs screen printed. From there I proceed to have a store designed.

Once the store was setup and my designs were loaded into it I went forward with my big marketing plan, which was to advertise in the Source magazine and Rolling Stone and wait for the sales to roll in. I would see people advertising month after month, to me that meant they must be making money. I was dead wrong.

After pulling in just one sale from about $1700 of magazine ads I decided to play around with Google Adwords and Facebook Ads. Not sure how much I spent before I decided to quit all together.

What I did wrong

I had six figures in the bank so I was reckless with my spending. I did not have a budget or a plan for launching the store. I went so deep into the hole before I started selling shirts that once it was time to spend money on advertising I was too scared to lose even more money.

I could have started this store for under $1,500 if I started with 5 to 10 designs and passed on the magazine ads and screen printing equipment. At that point I could have committed another $500 to online advertising. After spending $500 on ads I could have made the appropriate adjustments to move the store forward and make it profitable and successful.

I also missed the opportunity to be one of the first people utilizing Facebook and YouTube as marketing tools. Both sites were only around for a few years. I could have easily driven sales from each, but I did not notice the potential they had for driving sales.

What I learned

Their is nothing wrong with starting small. For whatever reason I felt like I needed a store with 40 to 50 designs to look professional. I thought it was a good idea to purchase two magazine ads when I could have tested one first.

Having a start small mindset is essential, especially when you have a lot of money. It is very easy to have a mindset that your money can make the success come faster and that is not always the case.

Cashbackvillage Cash Back Website (2007)

A cashback website is a site with affiliate offers. When people purchase something via your website they get cashback via check or Paypal. Basically a kickback from buying something through my affiliate link.

I was already doing affiliate marketing arbitrage so this type of website seemed like a good opportunity. It cost about $1500 to setup. After that I had to load the website with affiliate offers and set the cashback percentages.

Once everything was up and working it was time to promote the site. I know I spent money on pay-per-view (PPV) advertising and made Google Adwords. I honestly I don’t think I spent more than $100 promoting the site, I gave up on it pretty quickly.

After a while I ended up selling it for $300 in an online auction.

What I did wrong

Bad timing and lack of a good marketing plan doomed this site. I launched this website the same time I launched platinumtshirts.com. Spending $1,500 on this site while blowing over $10K on platinumtshirts.com at the same time was not a good feeling. Not to mention buying a house and car at the same time.

It was very easy to walk away and go back to focusing on the arbitrage affiliate campaigns that were working.

What I learned

Focus is important, if I work on too many things at once none of those things will develop like I want them to develop. Also it is important to have a multi option marketing plan and commit to that plan. I learned when it comes to marketing you need a plan a, b, c, d, e, f and so on. I learned I need to plan on spending a certain amount on marketing and stick to it. On future projects I can’t allow myself to give up early.


This was a free image hosting website that I setup with the plan to make money of advertisements. I saw someone selling an image hosting site that was making decent money, so I decided to hire someone to make me one just like it. It cost me $200 or $300.

I thought this would be a profitable venture because the images people upload are usually shared with third parties. In my mind that meant lots of referral traffic.

Once the site was live I started promoting it on Google Adwords and people were uploading so I was excited. Problem was the ads on my site were not making much money and people were not sharing their images like I thought they would.

I might have spent about $200 on ads before I bailed on this project. I have no clue what the site made since I don’t have any spreadsheets from 2008 when I believe this site was started.

What I did wrong

I copied someone’s site and I did it just because I thought it was easy money. When I realized the money wasn’t as easy as I though it would be I bailed.

Even though Platinumtshirts.com failed, I was into the idea of owning a successful hip-hop related shirt company. I had thought about the idea for months before launching. I like the idea of people wearing my stuff.

The image hosting site was a passionless spur of the moment cash grab that when up in flames within a few weeks of going live.

What I learned

Copying other people rarely works out. Doing stuff because I think it easy money rarely works out.


Sadly these are just three of my many poor business decisions. I think I was too desperate to build other income stream outside of affiliate marketing that I rushed into a bunch of projects with poor planning and execution. Bottom line, it doesn’t matter how good idea is you have to be patient and you have to have a detailed plan to make it a success.

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About the Author: Andre

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