My 12 Business Failures

I have failed often in business. Much too often. 12 total failures in my life by the age of 29. You could say I never learn. To top it all off, I even quit two secure marketing jobs just to work on these business dreams.

Each business I started was about something different. I had a wild idea, a spark of imagination, and I was good at acting on it in the heat of the moment.

Here is my list of business failures and what I learned from each one:

Textbook reselling

At age 20, I decided to start selling textbooks while attending university. I would find international copies of a textbook from Thailand or India, and I would bring them in at $40-60 a pop.

Textbooks at the retail level were expensive, with some selling above $200. I thought this was outrageous to pay, on top of astronomical tuition fees.

I would sell books at $80-100, helping students save their hard-earned money. Compared to the university bookstore, my textbooks were unbeatable in price.

The only difference with the international versions of the textbooks were the covers. You would have softcover books from Thailand, while the university’s books would be hardcover. Most students would want to lighten their backpack load with a softcover book anyway.

I stopped selling textbooks after a year of doing the business. I decided it was odd to be carrying books to campus and selling them right across from the higher-priced bookstore.

I was profitable for the entire time I ran the business. This fueled my entrepreneurial spirit, realizing that success is attainable with the right attitude.

This led to my next project.

Eye research nonprofit

Due to my history with eyesight, I wanted to start a nonprofit and help scientists cure eye diseases. I managed to raise a few thousand dollars in funding from friends and family.

After two years, I decided my heart wasn’t in the project. I shut the website down for good. Anytime I decide to donate going forward, I will do so privately.

Clothing brand

For my next venture, I sold t-shirts, hats and accessories. Every design was created by me, with a portion of profits donated to mental health initiatives across the world. Carss Clothing Co. was born.

Starting a clothing brand online takes less than a day now. WooCommerce is my platform of choice. It’s free to start, and you have a great selection of custom website themes to choose from.

I paired my WooCommerce site with a platform called Printful. They handle all of the printing and shipping of my designs, on-demand.

Although the clothing fabrics were high-quality and made in the USA, I couldn’t get past Printful’s slow shipping times and no-refund policy. For any clothing brand looking to seriously grow long-term, it may make sense to find an alternative supplier overseas. You will have more control on your shipping times, materials quality and manufacturing processes.

I shut the clothing business down before committing to any overseas investment.


It was time to start earning some real money with freelancing. I hopped on Upwork to look for clients that I could do marketing for. I made over $10,000 in my first few months! It helped that I had a specialization in marketing.

If you would like to succeed on Upwork, watch this video about profile optimization.

When freelancing, my advice is to go high. Find clients who will pay you more per hour. The marketing effort to find one client is the same, whether you are charging $5/hour or $100/hour. Go high. With all of the low-cost freelancers out there, it’s best not to race to the bottom.

I liked freelancing, but from a passive income standpoint, I would still be trading all of my time for money. I wanted to figure out how I could make real money while sleeping, which led to my next project.


I love creating stories. It was time for me to unleash my inner creativity by writing and illustrating a variety of books and publishing them on Amazon. I have over a dozen books on there now, and plenty more on my website.

Here are a few of my books on Amazon.

Amazon has so much worldwide traffic that I thought it would be a cinch to get noticed there. I was wrong. Even after publishing your books, you need to market the heck out of them to get any exposure. In the end, I decided to stop my marketing efforts, feeling like a better solution should be created.

My solution was Fuzzery.


I created a marketplace to help children’s authors sell their books. The authors would get 80% of every sale, which is 10-50% better than Amazon’s royalty rates. This worked out well for authors, because they could publish their books in any format (not like the restricted formatting on Amazon).

What I learned is that Amazon’s publishing platform is quite appealing to many authors. With the sheer traffic heading to that website, I found it challenging to build a scalable infrastructure that could beat it. From a niche, small-player perspective, Fuzzery certainly had potential in the children’s book arena. What I really preferred was selling my own books, rather than spending all of my marketing effort promoting others.

Then something interesting happened.


From my blog articles, a startup founder reached out to me to ask for advice. The founder was interested in paying me hourly to help grow her business! I decided to get into coaching entrepreneurs.

I have so much to learn still. I decided that I would not be suited to give advice just yet. This coaching practice never really took off due to my sheer lack of self-confidence. Someday things might change.

Affiliate marketing

I started an Amazon Associates account many years back to become an affiliate marketer and promote books that I had read and reviewed.

After only a week of trying, I decided to stop this venture. I made $0.55 and felt like a snake-oil salesman. It didn’t feel genuine to be recommending books that I was opposed to. Now I only recommend products that I use, whether I get affiliate income or not.

Chromebook review site

Along the lines of my affiliate marketing business, I started a Chromebook review site to share my passion for computers. Most people might not know what Chromebooks are because they are such a niche product, typically reserved for the education industry.

I did videos on YouTube and top 10 lists on a blog. Then I ran out of things to talk about. The Chromebook website never really gained traction, so I decided to shut it down. I wish these computers were more popular, then there might be better business opportunities to talk about them.

Facebook group

I started a Facebook group to educate entrepreneurs on success, motivation and passion. I managed to recruit over 1,100 members in the span of 45 days.

Here is an article on my growth strategy for Facebook Groups.

My vision was to promote courses and marketing books with this community, but I ended up giving away everything for free to help as many people as possible. I couldn’t sustain this approach. I stopped growing the community.

YouTube channel

Growing a YouTube business is downright difficult, but so much fun if you’re into video creation. I started to film tutorials and vlogs, with links to business courses that I had created.

I never really saw traction or interest in what I was putting out, and decided it wasn’t right for me at the time. Maybe when I become more relaxed and confident with entertaining others, I could revisit this business.


Lastly, I tried out podcasting. It is so easy to start a podcast, I’m surprised more people don’t do it. All I used was my Chromebook and red microphone, and I was off to the races!

I had the idea of talking about marketing, business and life on this podcast, but quickly noticed that most people do it for fun. I also ran out of things to talk about after over 200 recordings.


Today, I’m still experimenting to see what clicks with me. I love building things, and who knows what my next venture will be.

For those of you who are worried about failure: don’t be. Failure is learning, and I’ve been fortunate enough to learn from all of my mistakes thus far.

If you have a business idea in mind, I would encourage you to give it a try. Later on, you might regret not taking action. The right time is now.

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