My 5 Biggest Failures as a Marketer and Entrepreneur (Cost Me 15 Years)

I have loved internet marketing and the whole idea of creating something out of nothing ever since I was a kid. However, I think as more and more websites pop up, there is a huge misconception about what it actually takes to succeed online. There is no such thing as overnight success. Being successful online takes a lot of hard work and most important: failure. Yes, it usually takes many failures to succeed!

Today I’m going to share with you some of the many failures that I’ve gone through to get to where I am today. Fair warning, there are a lot.

It Started Like a Drug

If you’ve ever read my bio, you already know that I’ve been an entrepreneur since around the 6th grade. I started reselling CDs and DVDs on eBay and this allowed me to buy my very first laptop in cash. This was back in the good ole days of Netzero dial-up. 😂 Boy, I don’t miss those days. Now we live in an age where we just tether our phones when our cable goes out. Crazy!

The feeling of paying for that first laptop with nothing other than my skills on the internet was a feeling that even today is like a drug. Only other entrepreneurs or internet marketers will probably be able to relate. I truly believe entrepreneurs and internet marketers are born with a certain mindset that you just can’t turn off. Trust me, some days I wish I could. Some of my family growing up probably did too haha.

Drugs are bad
Drugs are bad (Image source: imgflip)

First Failure (It Didn’t Last)

By the time I was in 8th grade, I was reselling CDs and DVDs on eBay full time (or as full time as you can get while going to grade-school). I started dropshipping items from Deep Discount, which at that time had two separate sites, Deep Discount CD and Deep Discount DVD. I made $1,500 alone just on reselling The Cheetah Girls Original Soundtrack CD when it first came out. Deep Discount CD had it for $4.25 and I was selling it on eBay for over $15 a piece + charging for shipping. Well over a 250% markup. I also had great success reselling the Lonesome Dove DVD.

During study hall, my classmates would be in the library goofing off on MySpace while I was busy checking my eBay listings and researching new products to resell. 🤑 But unfortunately, all good things have to come to an end… especially in internet marketing. People started to catch on to what was happening and others started replicating my results. Within a few months everyone was doing it and therefore my strategy no longer worked. This was my first online failure.

Although looking back now, I consider it my first learning experience. In internet marketing, nothing lasts and you have to know when and how to pivot.

Second Failure (Burned Out in the 10th Grade)

Now in 9th grade, I was frantically looking for something else I could do to make money online. I knew the itch or rather urge wouldn’t go away. I loved computers and started to wonder how they worked. So I ordered some parts and built my first computer. Upon completion of my first build, another light-bulb 💡 went off and within a week I had a business license (co-signed by my Dad since I was underage. Thanks Dad!) and a website up (highwirepcs.com) to sell custom built computers.

I sold the computers on my website and eBay, quickly achieving PowerSeller status. Back in those days, custom built computers on eBay were still hard to find and the competition was low, unlike the reselling space. I would sell a computer on eBay, order the parts from Newegg, and build their computer to order. I would then pack it up and ship it off to them. We are talking sometimes a 2-week turnaround. Crazy, as this wouldn’t fly today. People get impatient now when their Amazon package takes more than a day to arrive.

I sold computers to countries all over the world. I remember my Mom helping me by picking up custom boxes, 10-15 at a time from a local box distributor, taking the scale out to the kitchen, and packing it up for shipment (Thanks Mom 🙏). This is what I did for most of the 9th and 10th grade. My feedback profile on eBay proves it, 1,601 and still going strong at 100% positive feedback. While other kids were playing video games, I was building computers.

But then the day came… I burned out in the 10th grade. Yes, it’s kind of hard picturing a kid burning out so soon. But between going to high-school, building computers, fixing them, and managing the shipping and returns; it was just too much for me at the time. For those of you who are fellow IT nerds, you’ll remember that back in those days, a lot more went wrong with computers. We are talking bad PSUs, bad sticks of ram, bad thermal paste on CPUs, faulty motherboards, you name it. Computers back then required a lot of hand-holding and patience.

Burned out
Burned out (Image source: GIPHY)

So I decided to call it quits to the computer building business. This is what I would consider my 2nd big failure.

Third Failure (Couldn’t Figure Out How to Scale)

Then came the 11th grade. This time around I was wanting to figure out how to do something less stressful where I could just sit at my computer. No ordering, shipping, packing involved. 😉 I took a job as the network administrator’s assistant at my high school and I started to learn everything I could about web hosting in the evenings. I already had a website and branding from my previous computer adventure (HighWire PCs), so I rolled with that as it kind of worked for the hosting space as well.

I spent my weekends and nights browsing forums and starting up conversations with people who were looking for hosting. Participating on Web Hosting Talk was, in fact, a big part of how I got a lot of my first customers. Basically, I was renting dirt-cheap servers and running WHM on them. I was throwing as many clients on to one box as I could to ensure the most profit possible. Yes, I know… shame on me. I was helping create something which today I now despise: shitty shared hosting.

Shame on me
Shame on me (Image source: Meme Generator)

By the time I graduated high school I had a couple dedicated servers in a data center and was hosting over 700 domains, still under the “HighWire PCs” branding. I was off to a private University and things were looking great! The sky was the limit I thought.

Freshman year I took a job at the HelpDesk at Walla Walla College (now Walla Walla University). Thankfully due to my network administrator job I had learned some valuable skills. I pretty much knew the ins and outs of Novell and Active Directory. Since tuition cost $30,000 per year, my hosting company profits weren’t going to cut it quite yet. Actually taking that job was one of the best decisions I have ever made. Who knew I would be working there for 6 more years and gain work experience that was literally priceless.

But then things started to fall apart again. About halfway through my freshman year, I realized I couldn’t keep up with the support and maintenance of all my web hosting clients. Going to class full-time, working 30+ hours a week at the helpdesk, and managing my company late at night just wasn’t working. I tried to hire outside help and failed miserably. I couldn’t figure out how to scale properly. So I ended up selling my company, HighWire PCs, along with all the clients.

Fourth Failure (I Cashed Out Too Soon)

It wasn’t long after selling my company that my entrepreneur blood kicked back in. I think it was about a week lol. 😂 I always loved building websites so I decided to start a blog where I could share what I was learning at my job at the University. By this time I had moved into the role of PeopleSoft Security Administrator for the department. So I started the IT blog theitbros.com, along with my brother, who was also attending the same University.

Things were going great for a while. The IT blog was making money on AdSense and I was enjoying blogging in the evenings. Later that year I packed up everything I owned and without a job lined up (risky I know), and moved to sunny Scottsdale, Arizona. I had just gotten sick of the constant rain in Washington state. Fortunately, by the time I arrived in Scottsdale, I had a few job interviews and took a job at the HelpDesk at Partners Rx, a health insurance company.

An opportunity then came along and I decided to sell theitbros.com on Flippa for $7,000. At the time this seemed awesome. I had a few sites, but getting over $7,000 for one was beyond exciting at the time!

Free money
Free money (Img src: Giphy)

However, fast forward a couple years and this turned out to be a huge mistake. Looking back now at all the time I had invested in it, I should never have given it up. Most people don’t realize, when it comes to niche authority sites, if you just keep at it long enough it’s almost impossible to fail. Obviously, there are exceptions to this, but I seriously undervalued my site and cashed out too soon.

Fifth Failure (Striking Out on My Own Didn’t Work)

Working HelpDesk at Partners Rx soon got very tiring. It was pretty low pay for working a lot of hours. I remember still having to run back to the office many times because the VPN failed or the Exchange Server went down. So I decided to strike out on my own and start Scottsdale Computing, a remote computer repair shop. I had some money saved up for about 6 months worth of rent and expenses so I wasn’t too worried at first. However, I hadn’t done my research. I soon found out that Scottsdale already had huge players in the computer repair space and it was almost impossible to break into it.

I started online advertising and housecalls did start picking up here and there, but running around in the 100-degree heat lugging computers back to my apartment to fix them soon got tiring. I then made a decision that there was no way I was ever going to work IT again in my life (even though that was where most of my experience was). IT is stressful and exhausting. So once again, I failed.

I hate my life
I hate my life (Image source: Meme Center)

First Sign Of Success (But Met With Life Hurdle)

My brother had recently moved to Arizona and was working as a web developer for a local company. I was looking for a new job and had always dabbled in marketing. After chatting with them I took a job at Pain Doctor as their AdWords and SEO Specialist. I was excited. No more fixing shit, no more phone calls from clients at 10 PM. I was finally free!

A couple weeks into the new job I decided of course that I wanted to start blogging what I was learning. So I started blogging on brianjackson.io. It took a little work but eventually, I hit 10,000 visitors a month without any advertising (all organic). I started to see something clicking and a lightbulb kind of went off. 💡 Soon things at my job were showing huge results and I started putting those things into practice on my own websites.

Fast forward one year and brianjackson.io was getting over 35,000 visitors per month! Things were looking up. I had a good paying job, I was finally figuring out what people wanted to read online, and how Google worked. But nobody said life was easy. In 2014 I suddenly started having stomach pain. Long story short, I was diagnosed with Ulcerative Colitis, an incurable autoimmune disease.

It took me about a year to figure out that doctors weren’t going to be my savior. I finally went 100% gluten-free and have been ever since. This literally saved my life. So much so that I launched a site called No Gluten where I blog about eating gluten-free. If you’re curious about my struggle with Ulcerative Colitis, you can read the long version here: An Entrepreneur: Living with Ulcerative Colitis.

Things Finally Started Working

I kept blogging on my personal domain and figured that I should really move it to a business name. There are things to be said about personal branding, but what if I ever wanted to sell it down the road? Of course, being more careful this time about undervaluing it. So I acquired the woorkup.com domain in 2015 and started sharing marketing strategies pertaining to SEO, SMM, WordPress, and web performance; along with in-depth SaaS reviews. I moved all my content from brianjackson.io and 301’d it to woorkup.com.

During this time I realized I didn’t want to be sitting in a cubicle anymore. So I quit my day job and after looking around online I ended up with a remote position at KeyCDN as their Inbound Marketer. This was a great fit as it was easier to manage my health and I got to do what I now loved: writing and SEO. Two things which I had become really good at throughout all these past failures.

Fast forward one more year and I decided that WordPress was calling my name. I had always used WordPress for my own sites so I was already used to using it on a daily basis. I was at that time hosting my sites at Kinsta and had gotten to know Mark, the CEO, and Tom through Skype. I was, in fact, one of Kinsta’s first customers. Long story short, they were looking for someone to help take their marketing to the next level. I’m happy to say it was a perfect match from there on out. It’s awesome to no longer sell shitty shared hosting, but a service I’m really proud of. 👏 Not to mention the team at Kinsta is the best group of people you’ll ever meet.

Hooray
Hooray (Image source: Meme Generator)

In June 2016, my brother and I decided to go 50/50 business partners on everything and formed forgemedia LLC. We launched our first WordPress plugin, WP Coupons. Fast forward a year, and we launched our second premium WordPress plugin, perfmatters. If you’re interested to learn more about my niche site or things we learned during the launch of our plugins, here are a few posts you should check out:

Summary

I’m happy to say that 2017 was our best year yet in terms of income from our sites and plugins. 2018 is already on track to significantly to surpass the previous year.

Earnings
Earnings

The point of this post wasn’t to gloat, it was to show that not all internet marketing success comes overnight, as some might have you believe. If you read the back stories of many of the successful internet marketers you follow today, you’ll most likely discover that they’ve been hustling at it for years.

It took me fifteen years of failure to finally figure out how internet marketing works, or at least a way to make good money from it. Without all of these failures I wouldn’t have the knowledge I do today and also, wouldn’t appreciate it as much.

For some of you younger folks, it might not take as long. Remember, I started back in the days of dial-up and Windows 98/XP. Everything moved slower back then. Today you have the entire internet at your disposable with an unlimited source of knowledge. If you’re currently struggling to make that first dollar online or the first $100 a day mark, just keep at it! It’s possible and I can tell you it’s worth the wait.

My brother and I are now both debt free and planning our early retirements. Speaking of which, we also have a blog about that. Check it out at pennybros.com. Haha, you see I can’t help myself. 😜

I would love to hear your thoughts. Have you failed over and over again online like me? What have you learned?

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21 thoughts on “My 5 Biggest Failures as a Marketer and Entrepreneur (Cost Me 15 Years)

  1. Hey Brian – I have always enjoyed your articles and content (mainly wp and kinsta stuff before). This one was awesome too – thanks for sharing all this – bookmarked!

  2. Hey Brian,

    You’ve already gone through so much and I admire how you kept thinking of new ideas and working on it day/night.

    And Pennybros.com shows how intrigued you’re with the word “bros”

    Keep shining.

    • Thanks Shafi! Never stop hustling. Haha, and yes… for some reason a couple of our projects have included the term “bros.” My brother and I tend to be two peas in a pod… marketing/SEO + coding.

  3. Thanks for the motivative article Brian.

    I have been failing since 2014 in blogging, changing from niche to niches with one particular domain, but now i think i have found a good niche for myself.

    I am highly motivated to continue working on my blog, and now i believe so much in it once again

    Thanks once again Brian… you’re a real hustler

    • Thanks Doronize,

      Glad my post was of some inspiration. Ya niche blogging can be very hard as sometimes you have to continue to fail (even after researching) until you find one that works really well. Sounds like you’re on the right track. Keep at it!

  4. Hey. May i know the inspiration behind the word “Woorkup”. does it stand for “work up” or what was the thought process behind it.

    Really inspiring work. I am a fan of perfmatters plugin.

    • Hey Hitesh!
      So I acquired the woorkup.com domain as it had some authority behind it already. So I didn’t create the word woorkup. But I link to think of it has “work smart” or always work with the idea of moving forward/up.

      Glad you like the perfmatters plugin. You’re probably gonna love the next feature we are launching. I won’t give it away, but it’s a great one.

  5. I love your story and am on a similar path, different track. I have to say, I was chuckling because you talk about doing stuff on dial-up. I wish I had that AND eBay when I was a kid.
    Cheers

  6. A truly inspiring story :)

    Our biggest fault is that we underestimate our power. We should never underestimate our own potential.

    That gif on free money made me laugh. Actually I can relate that with one of mine incident. ;)

    Thanks for sharing your valuable experience.

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