The Secret to Making Money Online: Failure

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..and a lot of focused hard work. You have to learn how to GRIND!

I intentionally put the lead out front. There’s no sugar-coating it. Success requires work. And usually, it’s boring, repetitive, mundane work.

I say failure is the key to making money online because there’s not really one sole recipe to follow in order to do it. 

You have to try something, fail at it, try something else and fail at that too. Most of the time you end up trying, and failing, at several different attempts.

You fail some more. You work some more.

In my experience, it’s usually the case that success is iterative. You work at it until you find out what works – FOR YOU.

Is my way of making money online the only way to do it? Not at all.

Is my way of making money online the best way to do it? No.

Can you learn something from my methods and from my past failures? Hopefully.

That’s great news because I fail a lot!

So, Who Am I?

Let’s just get this out of the way now. I’m just some guy having a mid-life crisis. I’m nobody special. In fact, I’ve never “made it” in anything. I hit forty years old recently and I had planned on being out of the workforce by now, or at least close.

But I’m not… yet.

I’m an executive at a well-known company in a big city. And…

I Hate it.

I hate everything about working for someone else. I hate that they control my time, my pay, my focus, my commute and even the industry I’m in. I hate trading hours for dollars.

There have been many times in my life when I’ve been told to essentially “stay in my lane” at work. But that’s not how I work. It’s not how I want to work. And you know what, nobody cares how I work or what I want.

They just want me to do the job they hired me to do.

It sucks.

Why Don’t I Do Something About it?

I plan on it. My “goal” when I graduated college (the first time) was to “retire” when I was 45. I could do it on the last day before my 46th birthday, but I would retire while 45. So, that’s the plan.

Full transparency, I quit working for someone else already once in the past.

I successfully pulled myself out of the corporate world for three glorious, wonderful and terrible years. 

This is a story for another day, but it should be enough to say that I started my own business at one point. It was just after graduating with my MBA.

I thought I knew everything. Boy, was I wrong.

I started the wrong business, in the wrong place, at the wrong time, with the wrong people (most of them), and put my money & trust in something that was doomed for failure from the beginning. I failed.

But, I recovered.

And I learned a few things along the way.

My History With Making Money Online

 It was during my time at my startup that I learned how to build a website. How to sell stuff, write ad copy and write content for an audience (it’s where I found my voice as well). My business dealt in online, and print, publications. At one point I had over 50,000 visitors each month coming to my website.

But I didn’t know how to monetize. 

I was busy trying to sell direct ads to local businesses. For a site that got 40% of my visitors from outside the US altogether! I didn’t know how to monetize.

So I failed.


But in my failure, I learned that there were better ways to make money. (Sadly, by the time I learned this I had already closed my business and gone back to being a “desk jockey” in the corporate world). While the business was failing, I came across an article about monetizing your site through Amazon. 

There was this idea called Affiliate Marketing and you could build Amazon Niche Sites and using the Amazon Affiliate Program, you could make money.

I was convinced that this was my ticket out, but my wife and I were already too gun shy to do anything about it. We didn’t want to relive the past few years.

So I started dabbling in building niche websites.

How to dabble in Niche Sites – the wrong way

In early 2012 I spent a lot of time surfing the web. I came across Spencer Haws, Pat Flynn and found Reddit (which included u/humblesalesman, who has since deleted his account). There were a couple of subreddits talking about making money through websites (r/Entrepreneur was one and soon after that r/juststart “popped up”).

The idea of a case study was discovered.

Following someone else’s journey is a serious dopamine hit. I loved it. I read tons of them.

People were making life-changing money and sharing it. I loved the high of reading someone else’s journey but I didn’t want to sit on the sidelines forever. I wanted that cheddar too!

Finally, I decided I wanted to join with everyone else who was making money online. 

I bought 10 domains.

I figured if one site could make someone $5000/month, then ten would make 10X that amount. Obviously, I didn’t understand that things don’t scale that way – and that one site is a ton of work if you do it right, and ten sites would be unimaginable levels of work if I were to do it myself. 

But I didn’t get that. I got them all hosted and a clean install of WordPress on each.You have to realize that this was 2012 or 2013 when I tell you this, but then I paid to have five articles SPUN from other articles on the web for each site (they called it “re-written”). I figured that was probably good enough and I sprinkled in some Amazon affiliate links and sat back to collect the checks.

I bounced from site to site thinking that adding an article every few months would fix the lack of traffic and dollars.

Clearly, it didn’t happen.

As you can see, this too was doomed to fail. Again, I had fallen victim to looking for a shortcut and thinking the shortcut would pay dividends.

Eureka, I’m Failing Up!

What I, and thousands of others, fail to realize is that a case study cuts out 99% of the WORK that’s involved with building a money-making site. All the case studies are formatted like this:

  1. Get niche idea
  2. Buy website
  3. Add some content
  4. ????
  5. Add affiliate links and/or ads
  6. Profit

Step 4 is the part they leave out. It’s the part that they gloss over. It involves work & time… on repeat.

The reality is that it’s a GRIND. That’s the hidden secret. There’s no easy way to say it and it’s even harder to get the point across in print.

Grinding out content and doing things you don’t feel like doing is the only way to make this work**.

Day in, day out.

With only a few hints that it’s even working. It takes focus. A certain level of stubbornness.

And a pinch of blind optimism.

And that was my issue. I was so desperate to make something work, I never focused on one thing long enough to see it through.

**Technically, if you have the money you can pay someone else to grind for you but you have to get the money first.

Way Leads on to Way

Life happened and I kind of let my websites just sit there. I renewed them each year. I occasionally added an article or two. And multiple times I started some “BHAG Case Study” post on Reddit to try and motivate myself to make them work.

They never worked because I didn’t work on them. Tons of excitement and motivation didn’t fill in the blank.

I just thought that somehow the “????” would be filled in with dumb luck.

It wasn’t and it won’t. And I didn’t learn that until I found something that I actually wanted to make work.

This is when I learned the secret to success online… 

Something Finally Hit – But it Wasn’t What I Had Planned

In 2017 I stumbled upon Amazon Merch from a post that Neil (u/W1ZZ4RD) made in r/juststart. I didn’t know that would change the direction of my online hustles and ultimately change my life.

After 8 months of waiting, I was accepted into the program. I uploaded designs right away and a few sold. I came up with more ideas, made the designs and then uploaded them.

Some of those sold. I got excited.

Other people were making real money doing t-shirts and sharing their journeys on Reddit.

I wanted the same thing. I tried to take it seriously and treat it like a business. Businesses set goals, so I set goals.

Designing funny and unique ideas fed my creative side. I enjoyed it so I kept creating and uploading.

The more I uploaded, the more I sold. It was acting like a real business and I was starting to make real money. But I kept finding myself frustrated the more it grew. I didn’t feel like I had control (the fact that it’s Amazon’s platform is a totally different control issue).

For me, the frustration had to do with the goals I set.

I tried to set sales goals and I never hit them. I tried to “pick” which design would take off or be a hit.

I couldn’t figure that out either.

I’d say “I’m going to sell $2,000 in shirts this month” and I’d sell $1800 and feel like a failure.

Why? Because I couldn’t control how many sales I made. Setting that as a goal was stupid. There’s nothing I could do to directly change the number of sales I made each month. 

I had to break down the business into its simplest tasks. What things did I have in my control? Which “levers” could I pull directly? What moved when I pulled those levers? Which ones were the important ones?

Here’s what I learned: uploading designs was how to feed the beast. This was an activity I could control. It had a direct correlation to the number of sales I’d make. If I had more designs live, I’d sell more designs.

It was also something I could set goals around.

This was a “lightbulb moment” for me. I could control how many uploads I made. I couldn’t control much else.

…the key to success is work. Not just any work, smart work. Work on things that actually matter.

Goals should revolve around what we can control. Nothing else.

Money, sales, traffic, RPMs – those are all by-products of the things you do that you can actually control. These are what I call “Targets”.

The vision I have for my company will shape the targets I set for the year. Then I back into the actionable tasks required to reach those targets. I set goals around these tasks.

For Merch, I set goals around uploads.

My upload streak at one point was 5 months. I uploaded at least 20 designs each day for over 5 months (full disclosure, I took Sundays off but frequently loaded 40 on Saturdays). I met my goals.

I had started the conveyor for my t-shirt business.

And I was forming good habits.

I was learning to GRIND.

And, the awesome by-product was sales. Lots of sales.

But it was still moving too slowly for me – and there was always the fear that Amazon could take it away. I didn’t have control over the traffic or the buyers. I had built my home on someone else’s property.

Buying My Own Land

By 2019 I had slowed my uploads to try and figure out how I could begin to control the traffic I was getting.

I realized that most of my designs were in a few niches that I had always been interested in. In fact, most of my designs were in niches that I already owned domains for and had started to build websites around.

I think you see where this is heading.

In 2020 I started the year with the vision that I would focus on the websites related to my niches and build them up to the point where I was directing TARGETED traffic to Amazon to buy my shirts. Of course, they’d have affiliate links so I’d make a small commission on everything in the basket.

It was a good plan. But it was poorly executed because I was trying to build seven sites at the same time.

And, sadly, we all know what happened in 2020, on top of my bad plan.

Ironically, this part of the story doesn’t have a sad ending. In fact, it was the best years I’ve ever had with my online ventures (so far). And it had nothing to do with what I DID in 2020. It had everything to do with what I did in 2018 & 2019.

The work I put in GRINDING at the beginning paid off.

I made more revenue in 2020 in t-shirt sales than I made at my day job. I guess people used their stimmies to buy my shirts!

The situation didn’t change much, and the year could have been even better. Merch shut down for the entire month of April.

But I made lots of dollars.

And as far as website building, the year was a bust. Sort of. I made a lot of extra money, then spent it.

Looking for Shortcuts Again

In the summer of 2020, I decided I was going to take the money I had made and start to hire writers to create actual content for my sites.

I purchased 15ish articles. And posted them.

I primarily focused on one site that was showing that it was favored in Google. Things were going well with it. I was making a steady $100 each month with only 5 articles on the site at the beginning of the year. 

By June I was making $250 with 8 articles. This was one of the sites I had started around 2015 but let sit.

I tried to grow it multiple times but I only ended up with 4 published posts and 30 drafts to start 2020. It was hard to write for the niche because it was about a hobby that I’ve tried but I’m not really “into it”.

Then I came across a website in the same niche that was for sale. I bought it.

My new plan began to develop. I would take these sweet, sweet, monies I was making selling t-shirts and invest that into websites that were already making some money. 

Buying content and traffic. I thought it was a great plan.

I found and purchased two more existing sites in the niche and found one “ready-made” site that was already producing some revenue. I bought that too. All in I purchased around 140 articles and 3000 pageviews each month.

But when I put it on my site it showed the true power of an aged, topically relevant domain (even if it lacked a lot of content, the existing content that I had written before was really good).

Within two months I was getting over 1200 visitors a day. I made $1800 in December 2020 and $2200 in January 2021! Was this the secret of success? Had I had found a shortcut?

You just needed money and knowledge of 301 redirects.

What were my goals for 2021?

Again, I decided to pursue my lazy path of least resistance (instead of the path that involved GRINDING again for months).

I was going to shortcut the whole process and just buy, and merge, my way to affiliate website success.

Sarcasm Warning:

I was going to play it smart and only allow myself to pick three of my existing sites and focus on them for the year. You know, only three, so I didn’t overwhelm myself by trying to do too much too fast.

They were the three sites that were showing the most promise at the beginning of 2020.

make money online with websites traffic and posts chart

Oops, I did it again…

My plan lasted just longer than the date when I finally decided to do it.

The traffic to the best-performing site dipped in February. It dropped some more in March. I tried to figure out what went wrong.

I read some of the transferred articles for the first time.

Oh my, they were crap. Here’s where you can’t judge me. At least not too harshly. I didn’t have time in 2020 to go through all the articles before moving them. And I REALLY didn’t have time to train someone how to do it – exactly the way I wanted it done.

So I just moved them over. And now I had around 160 articles that needed to be reworked entirely (more than I bought because I had blindly published several of the articles I outsourced without editing them either). Epic fail.

Now I get to waste the time to go through them since I didn’t make the time to do it right in the first place.

I was still being stubborn so I decided I’d hire someone to edit them for me.

But then I got hung up on writing the SOPs.

I procrastinated so long that recently got smashed again by the August/September Google update and I’m down to around 200 pageviews a day.

So where did I screw up? What did I forget that I had already learned?

Shortcuts don’t exist in this. Work, patience, time and repetition are the key to success.

What has been my problem this whole time?

In August I finally sat down to assess what I was doing wrong. I had to break it down into the tasks that I can control and what brings the lion’s share of the results (hint: it’s content).

So, what’s my problem? I started by identifying where I’m weak & where I continually fail. Here’s what I discovered about myself:

  • I’m overly optimistic. My dreams are often bigger than my abilities or time to manage them.
  • I lack focus. Call it stress, distraction, lack of sleep or ADD – I was having a hard time focusing because I was too busy looking at the “whole elephant”.
  • Accountability. I didn’t have to hold myself to anything I set out to do. I left room for excuses. I had an out.
  • Lack of time – we all have this, or don’t have this, today don’t we?!?
  • I try to find too many shortcuts
  • Not productive work. I was doing a lot of things that kept me busy but weren’t really moving the needle. I built spreadsheets and color-coded stuff. I think I’ve been in the corporate world too long. I was just killing time.
    • In fact, I considered not doing this case study at all because I’ll feel like I’m doing something but I’m actually not making any real progress.

What case study?

You might be asking this question after reading that last point. Well, let me quickly explain then wrap this essay up.

I’m officially launching a case study because of the findings from my “soul searching session”.

I’ll be putting into practice the lessons learned over years of trying and failing, to build a money-making portfolio of websites.

But I’m only starting with one. I’m going to focus, grind and do those things that matter.

I’m going to do the “one thing” that will bring me internet success – WORK.

…and probably a lot more failure along the way. Because that’s what I said it takes in the first sentence.

I’m going to finally get there and I’ll be retiring at 45.

I should after all – because it only took me nine years to finally get to month one!