What It’s Really Like to Make Your First $1000 Online

Jay West
22 min readApr 18, 2019


A few days before Christmas 2018 the US government began a partial shutdown and in the weeks that followed nearly 800,000 workers helped to confirm an alarming statistic, that nearly 4 out of 5 American workers live paycheck to paycheck.

To make matters worse, 70% of them claim to be in debt.

It’s no surprise then that so many people are looking online for a second income and while the online money making industry is flooded with get-rich-quick schemes and scams, wouldn’t it be nice just to make an extra $1000?

Of course, it probably won’t change your life but it could definitely take a little pressure off.

You may have bills to catch up on and $1000 could go a long way. It might even stop a bill collector from calling.

You could fill your kitchen with groceries.

What about swimming or music lessons for your kids? Even if it’s not life changing for you, it could be for them.

You could also blow $1000 on having fun. A weekend away or a new TV. A thousand bucks is a nice night out with friends or a loved one.

And, if you can make $1000 online, then you can make $2000 online or more, right?

While the “gurus” talk about 10K, 100K, or more, it’s easy to forget how much you can do with just an extra $1000.

Let’s go one step further. Imagine what you could do with $1000 per month.

You could drive a new BMW off the lot and not worry about the payment. You could afford to live in a different neighborhood.

With an extra $1000 per month you may be able to upgrade your education or start a home business.

It all begins with that first $1000 though and as great as that would be, making your first $1000 online might not be what you expect.

What Most Gurus Won’t Tell You

If you’ve been searching for ways to make money online, you’ve probably run into the “guru” systems where they show you “proof” of their 6 and 7-figure incomes online.

As you know, things are rarely what they seem. What they’re not showing you are the thousands of dollars they’ve spent on paid traffic (ads), the years they’ve spent building their email lists, and the times they lost money.

Some of them may be making millions today, but let’s take a step backwards.

Long before you can make millions, you need to make your first $1000, and for anyone starting out, that’s a far more important story.

I’m going to share with you a real example of what that journey looks like. My journey…

My First $1000

At some point during May of 2017 I had made my first $1000 online.

What you’re not seeing in this screenshot is the date my journey started. If I told you it began in December 2016 as shown in the screenshot, it would seem plausible. But it was actually in October of 2016, nine months prior, that I signed up for the program that taught me how to make money online.

And still, that’s just a small part of my story.

We can go back another year and half to the summer of 2015 when I actually started to learn the skills that allowed me to make that $1000 online.

For anyone trying to tell you that making money online is quick or easy, the truth is not what they want you to know. And I get it — the last thing I want to do is discourage you.

The point of this article though, is to show you that despite the challenges you’ll face and how long it may take, you can still do it.

For those who are truly committed though, who not only want to escape the rat race but absolutely need it, you’ll have a far greater chance of success knowing the full truth, which is…

What looks like an easy few months from the screenshot I showed you, is actually a 2 year adventure and a lot more work than you might think.

And even after 2 years, my journey had only begun.

Why My First $1000 Almost Destroyed Me

It would be easy to imagine I was excited about the money I had made but as I mentioned earlier, things are not always as they seem.

You may have noticed in that screenshot (above) why I was anything but excited, but just in case, here it is again.

This time I’ll point at something different — actual sales.

When you look at the sales that led to my online income, they are from January, February and March.

April and May were complete failures.

The only income I really had coming in were recurring sales from previous months which carried on for much of 2017, along with a random sale here and there, so with my first $1000 in the bank… I was the exact opposite of excited.

Even though I still made a few bucks that year, whatever I did to make in those first few months of 2017 turned out be a mystery.

And my financial situation only got worse.

By mid-April when I realized whatever I did in the month before was no longer working, I panicked. Afraid of losing momentum I started buying more courses, tools and gimmicks.

Not only was I barely making any money, I was burning through piles of it.

As you can see below, my income in 2017 was not what dreams are made of.

A year after joining this particular program, and despite my early success, I was back where I started. Zero sales.

By the end of 2017 I had spent far more money than I’m willing to admit — many thousands. In addition to the courses, push-button systems, tools and gimmicks… I also spent a ton of money on paid traffic.

I tried sales funnels, dropshipping, e-books, social media marketing and blogging. After countless hours of trying to make money online, aside from my earlier success -I pretty much made nadda.

To say I was depressed and frustrated is an understatement. I can’t even count the failures.

Way back in March when it appeared my online career was about to take off, I had my dream life mapped out. For a brief moment it felt real, but then it was gone and the letdown was far worse than it would have been if I hadn’t made anything at all.

It seemed my first $1000 online was just luck.

If You Think it Gets Better From Here, You’re Wrong!

Have you ever felt like you’re being kicked when you’re down? Of course, who hasn’t right?

In my case, the same month I ran out of money, the company I worked for finished their biggest project and I was laid off.

How awesome is that?

Look, I admire people who can comfortably talk about their rock bottoms… but I’m not one of them.

What I can tell you is this. Starting over in your mid-40’s is not fun. It’s as if everything you’ve worked for up until that point had been erased. Of course, that’s not entirely true, but it feels that way.

You can treat it like a downward spiral or a hard reset. One an empty pit of despair and the other an awakening. I chose the latter.

There were no illusions here. It wasn’t bad luck that led me here, or a universe out to get me. It was 100% my own fault.

In gambling terms, I went all in andcame up short. C’est la vie.

Now, I’m not saying your journey will look like mine and you do NOT have to “start over”. In fact, the reason I’m writing this is so you can learn from my experience and not make the same mistakes.

But chances are, if you embark on a similar journey, it’s going to be tougher than you expect. If you truly want to succeed, then remember — it’s not your problems that hold you back, it’s how you deal with them.

When You’re in Deep, The Best Thing To Do is Dig Deeper

As I said, starting over feels like everything you’ve worked for is being erased, but the truth is, situations like these are a gold mine.

“Every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.”

I was reminded of a quote I read more than 20 years ago from Napolean Hill…

To be clear, that doesn’t mean an equal or greater benefit is going to jump right out at you. But if you think back to your challenging moments you may find that what seemed like a set-back at the time was instead a path to something better.

Sometimes you have to dig a little deeper because the equal or greater benefit is less obvious.

  • First, I had acquired an education that few people will ever get.
  • Many try to make money online, but few get the opportunity to learn from countless failures of their own. Few get to experience what it’s like going broke in the process.
  • As crazy as it sounds, if I had to do it over again, I’d probably do the same thing because I wouldn’t know half of what I know now about making money online if not for that experience.
  • Second, I discovered just how awesome my family is. They knew I was working hard towards building a better life for all of us, and my wife had my back.
  • Third, I learned I could be just as happy, even more, without all of the “stuff” I had desperately tried to hold onto. Aside from the obvious necessities like food, shelter and ice cream 😀 … I learned that a comfortable place to sit, my laptop and a coffee was all I really needed (although there is one thing I really miss).

No… not my daughters. I mean, I miss them when they’re not with me (like right now) but for the purpose of this article, I’m talking about my car. I really miss my car and a new one just like this is at the top of my shopping list 🙂

In my case, I didn’t have to dig too far to find a treasure trove.

Why Your Only Choice is Failure

How do you approach failure? Are you afraid of it? Do you welcome it?

Whatever your think of failure, there’s one thing you should never do.

Never a let a good failure go to waste. A failure is only a failure if you don’t learn anything from it and wow, I learned a lot.

I’m as dumb as a stump about many things, but one thing I do know is that you will never get what you want in life if you ignore your failures or play the victim.

And that’s for those who are at least playing the game. Most people don’t even try, they tippy-toe through life avoiding failure.

Your only choice if you want a better life is to get in the arena, play the game, and fail. Fail as many times as it takes and learn everything you can.

With no money left, my only option was to go back over everything I had tried, all my failures, and everything I had learned to figure out how to make this work.

If you’ve been trying to make money online, then you already know that traffic is what you need, and since I was broke, buying traffic was out of the question.

That left me only one option, free traffic, and since my first $1000 was made with free traffic it was obvious what I had to do.

I had to go back to what worked the first time which led me back to my first mentor, an online entrepreneur from Victoria BC (Canada) named Kyle Loudon.

His diagnosis was quick and spot on.

I lacked patience, I was looking for shortcuts, I was focusing on money rather than learning new skills and getting good at them- in other words, I had a condition called Shiny Object Syndrome.

You’ve probably heard of it. You may even have it, and while I’m not a doctor, my suggestion (as it was prescribed to me) is patience.

Like learning to play a guitar or earning a black belt in Karate, making money online doesn’t happen overnight, and that was my biggest mistake.

I had made money online but instead of getting better at what I was doing, I quit and tried something else. When that didn’t work, I moved onto another thing, and then another, and another…

To use the martial arts analogy again, it’s like winning a big Karate tournament and thinking, “I’ve got this!”. Then, getting your butt kicked and saying, “screw this, I’m switching to Jujitsu.”

When a few months go by and you’re not a Jujitsu master, you quit and try Kung Fu. And when then doesn’t work, well… you get the point.

Everyone wants to be great at something, but few have the patience to let themselves get great.

They follow the steps and go through the motions for a short while but give up long before their mind and body can absorb everything they’ve learned. They quit before it becomes as natural as walking, running or breathing. And that where you find success.

A great runner doesn’t think of her every stride.

Why Being Smart is Really Stupid

In addition to having patience, another critical step on your journey to greatness is accepting you have more to learn. Or, to put it another way, admitting you’re not as smart as you think you are.

And I thought I was smart.

I had spent so much money, taken so many courses and tried so many strategies. How could I not be an expert, right?

I had even made money online, so what was my problem? As it turns out, my arrogance was the problem. I didn’t know jack****!

You probably have one or two things you think you’re really good at. Mine was understanding people, or so I thought.

With nearly 20 years of sales and management experience, there’s one thing I was certain of. I knew people, and I knew what they wanted.

So, every time I read or listened to an expert say,

“You must understand your audience and know what they want”, I thought to myself, “yeah-yeah-yeah, I know that already. Now get to the good stuff. “

I was too arrogant to realize that was the good stuff. Know your audience.

What I thought I was really good at, turned out to what I was really bad at.

If I told you that you that suck at the very thing you think you’re good at, you probably wouldn’t even believe me. And why would you?

How would I know, right?

But what if it were true?

It’s almost impossible to imagine because the thing we think we’re good at is part of our identity.

To witness this in action try telling someone you know who loves to drive that they’re a terrible driver. It doesn’t matter if they’re suck behind the wheel, they believe they’re a good driver.

Humble pie is tough to swallow.

I can’t put my finger on the exact moment I realized I sucked at the thing I thought I was good at, but it was true, and I spent a long time in my head playing past situations in this new light.

When it came to making money online though, the reason was now obvious.

I wasn’t giving my audience what they wanted.

I didn’t even know what they wanted because I didn’t understand them. And, I didn’t even try to understand them, I just assumed I did. It was one of my strengths after all.

Like I said, you can follow the steps and go through the motions, but certain things only become apparent once the thing you’re doing becomes part of you.

A guitarist will never be good if they have to stop and think about every note and chord they play.

Likewise, if you’re still trying to earn your first $1000 online it’s NOT because you can’t, it’s because you haven’t acquired (and absorbed) all of the skills and knowledge you need to do it.

Give it time and have patience.

Your “blindspot” or challenge may be different than mine, but either way, you need to keep moving forward, learn from your failures and let your process of discovery play out.

So, Was My First $1000 Online Really Just Luck?

Yes and no.

I was lucky when I first earned money online because the campaign I was running turned out to be exactly what my audience wanted.

But matching the perfect audience to the perfect product was a complete fluke.

I just happened to stumble upon a good keyword that people were searching for and I used it to drive traffic to the exact thing they wanted.

This might seem like an obvious thing to do, but it’s not as easy as it sounds. It’s not just matching the perfect audience to the perfect product. Your audience must also be ready to buy.

Most audiences don’t even know what they want yet. Others are still kicking the tires.

Timing is everything.

Marketers and copywriters spend years getting good at doing this deliberately. I did it accidentally and had no idea what I had done.

Or how to do it again.

I knew it worked because I started making money, but I had no idea why it worked and what’s worse, I couldn’t replicate it.

So, the fact that it worked was not lucky. Blindly stumbling onto it was lucky.

Why You DON’T Need Money to Make Money

So, you thought this would just be a simple story about making your first $1000 online, eh?

I’m sure there are many thousands who have made their first $1000 online and never looked back, but obviously, I’m not one of them.

Your story will likely have ups and downs of it’s own, and hopefully you can avoid the same mistakes I made. The more important lesson here though, is that even if it takes longer than you want it to, and it probably will, there’s no reason to give up.

Not even if you’re broke.

Remember, I was selling everything I owned to cover the bills and buy groceries. That didn’t stop me though.

You don’t need a ton of money to make money. In fact, running out of money turned out be a benefit not a burden, and here’s why…

Why Quitting was The Best Decision I Made

Throughout 2017 I tried so many ways to make money online and all of them, except for one, failed.

If you’ve tried and failed multiple times too, I don’t need to explain how exhausting it is. By the time 2018 rolled around, depressed and broke, I decided to quit.

I didn’t have it in me anymore. I wasn’t going to create another funnel and have it fail again. Not another eBook, no more Facebook Ads, pop-ups, email opt-ins or offers of any kind.

I was done.

At least, I was done trying to make money.

I was NOT done with online marketing and blogging though. Not even close. In fact, armed with this new perspective I was never more serious.

The problem with most people trying to make money online (myself included) is that we’re connecting the thing we’re doing directly with the money we hope to make.

It doesn’t work that way.

We’re like med students on our first day asking the professor how long it’s going to take to make money.

Who knows? Maybe never if we can’t get through school without quitting first.

So I stopped worrying about money and accepted what the journey is really about. Learning, gaining experience and improving my skills.

Hey, that doesn’t mean money isn’t important, or that it’s not the ultimate goal. Maybe it is, maybe it’s not.

But if money is your only measure of success, you’re in for a frustrating adventure.

I decided to set non-monetary goals instead, like building traffic.

Being broke, I focused on free traffic through SEO (search engine optimization) and social media, and since money was no longer my distraction, I was able to laser focused on that goal.

Now, if you’re just getting started I know you want to make money fast, but if you look closely, this was not overnight. This screenshot represents a full year of effort going back to April of 2018.

This is what happened in 2018 and 2019…

47,000 Monthly Users

And, it was another full year prior to this (April of 2017) that my brief moment of success had collapsed.

I know these traffic numbers won’t knock most bloggers socks off, many have millions of visitor every month, but I’m happy with them. These numbers are a lot better than zero, which is what they would have been if I had quit and spent my spare time watching Netflix.

Why My Second $1000 Was Better Than My First $1000

Two years, many thousands of dollars, and countless failures later I made my second $1000. It was different this time around though, because my third $1000 was close behind, followed by my fourth, and so on…

The reason it was different is because I knew what I was doing. Well, that’s not entirely true.

I had a better idea of what I was doing, but to say I knew exactly what I was doing is definitely not true.

I’m still learning, testing and racking up my failures.

But rather than making money, simply learning and getting better is still my goal, and making money is just a byproduct of that goal.

I also learned along the way the that even audiences with similar problems are usually interested in different solutions, so it’s a good idea to diversify and provide more than one.

As my traffic grew and the calendar rolled into 2019 all of my time and effort started to pay off. The following screenshots are from various sources.

If you’ve never heard of affiliate marketing, you need to learn because it’s one of the most powerful ways to make money online.

The first is an affiliate program that provides tools, training and one-on-one coaching for aspiring online entrepreneurs.

Income Source #1

Hundreds of thousands of companies from Apple and Amazon to small independents who create digital products like apps and production software have affiliate programs that pay commissions when someone buys something based on your recommendation.

I struggled with affiliate marketing for the longest time.

In theory it sounds simple and every now and then you get lucky (as I did with my first $1000), but turning a profit requires an intuition that takes time, effort and patience to develop.

Some people pick it up quickly, others (like me) take longer.

This is why it pays to find a mentor, and speaking of mentors, one of mine recognized a missed opportunity.

I had become so obsessed with trying to understand and connect with my audience that I forgot how diverse they were. This is what my mentor pointed to me — how I was ignoring a big percentage of my readers and at the same time leaving a ton of money on the table.

This next screenshot shows income from CPA offers, or cost per action. CPA is a form of lead generation where companies pay for someone to perform a specific action, which may include anything from downloading and trying out a program to filling out an application or submitting an email.

Income Source #2 (YTD represents Feb and Mar)

Well, not literally a ton. But a lot!

Just because people have similar goals and desires does not mean they are looking for identical paths to achieve them. People are at different stages in their journey.

What I didn’t realize, was that a big part of my audience was at the very beginning of their journey, kicking tires as I mentioned earlier, and they were not ready for the serious training or one-on-one coaching that some of my other recommendations were providing.

Oh, and another hidden benefit to going broke buying all of those systems, courses and gimmicks is that you learn first hand which ones suck and which ones don’t.

Some of your audience will be further along, but they’re not exactly ready for anything serious either.

They may not want or be able to spend money, and that’s perfectly okay. CPA offers can provide an alternative path for them to get closer to their goals, and it’s another source of income for you.

I signed up for this particular program in late January and started running full campaigns in February. It started earning money right away and even though I haven’t fully implemented it across my entire site yet, as you can see in the screenshot above, $1287 in the last couple months is not too bad.

Now, I’m not about to retire on it but this is income I wouldn’t even have if I hadn’t reached out to someone for help and advice.

How One Simple Question Turned Into (at least) $650 Per Month

While we’re talking about mentors I should explain that a mentor doesn’t have to be someone you find locally and follow around 24 hours a day. A mentor can simply be someone you connect with online who is doing what you’re doing but is further along the journey.

They can point out things you may have missed and help you avoid potential roadblocks, which can all be done through things like email and social media groups. There’s no reason not to have a mentor, or several mentors.

I implemented ads on March 5th and it took another week or so to see optimal placements and RPM’s (revenue per mille… or revenue per thousand impressions) and I still earned $650.98 for the month.

April is on pace to exceed $800.

Here’s more money I was leaving on the table. The next screenshot is ad revenue for March.

Income Source #3

Again, this is not retirement money, but it’s a lot better than the pennies I was led to believe ads were worth.

“Hey, is it worth it to have ads on your site?”

It pays to ask someone who knows first hand what they’re doing instead of relying on information that’s incomplete or handed down. Half the advice you read on line is nothing more than uniformed opinions and hearsay.

This $658.98 is the direct result of reaching out and asking another blogger who has ads on their site just one simple question,

That one question will be worth thousands of dollars by the end of the year.

Don’t be afraid to reach out and ask questions.

Now, to be fair, there are situations when ads don’t make sense and in a lot cases, the advice you get may be right for someone, but not right for you.

Legitimate situations when ad revenue might not make sense include people who are using a paid traffic strategy. For them, ad revenue will not be profitable.

Likewise, if you have no traffic or very little traffic, trying to earn money with ads is a terrible idea.

On the other end of the spectrum, bloggers or online marketers in the six-figure per month income bracket may not bother with ads either because they’d account for an insignificant percentage of their overall revenue.

How A Poor Attitude and Bad Memory Became A Great Surprise!

The best money you’ll make online is the kind that comes as a complete surprise.

Back in January I had applied to another affiliate program and like all of my attempts to make money with affiliate programs, this one seemed to be a dud too.

I checked the stats a few times in the first week or two and while it was getting a few clicks, there were zero sales. No surprise. I had gone down this road a hundred times before.

Another $636.30 for the month of March!

What’s another failure, right? Who cares.

With that attitude I gave up on it and completely forgot I was still sending traffic to it from a post I wrote nearly a year ago. When I woke up on April 4th, I was reminded with this email.

Income Source #4 (This one is my favorite because it came as a complete surprise. It’s from an affiliate program I had forgotten about.)

Now, if you follow any of the “make-money-online GURUS” out their, you may be disappointed that what I’m showing you is not Private Jet and Ferrari money.

I don’t know what to tell you.

Maybe those gurus drive Ferrari’s because people like me keep giving them thousands of dollars for their push-button systems and secrets, but as I mentioned earlier, things are rarely what they seem.

In my opinion, a moderate income you can earn from home (or wherever you want) with a laptop and an internet connection is still pretty good, and worth the effort.

Of course, I won’t lie. I still dream of buying a Ferrari and who knows, maybe one day I will, but it’s no longer my goal. Learning and getting better at what I’m doing is my goal.

Now It’s Your Turn!

The best lessons are learned from experience, but that doesn’t mean you should torture yourself. You can also learn from other’s experiences.

I mean, if you’re driving down the highway and the car in front of you hits a giant pothole, you don’t have drive into it yourself just to make sure it’s real, right?

Of course not.

Let my story be that pothole.

If you’re trying to make money online, don’t panic if it’s not working. And, whatever you do, don’t start throwing money at the problem. Paid traffic is particularly dangerous by the way.

Treat your journey as you would if you were going to school or getting a black belt in Karate. Be patient and focus on the skills you’re learning, not the money you’re not yet making.

I get it. Most of us are here because we want a laptop lifestyle — to kick back on the beach while money flows into our bank accounts. And it’s possible, it just takes time to learn how. Give yourself the time you need because it’s worth it.

It only takes a few hundred bucks each month to move into a bigger home or a new neighborhood. Another few hundred bucks might pay for a new car so you no longer have to worry about fixing your old one.

You could put your kids in a better school, go back to school yourself, or put some extra money in the bank for peace of mind.

And you can do it all from home. If you’ve already started your journey to make money online, focus on the skills you’re learning. If you haven’t yet started, there’s no reason to wait.

There are mountains of free resources online and there’s never been a better time. Learn exactly how I did it HERE. Actually, scratch that! The last thing you want to learn is to do it “exactly” how I did.

What you want is to learn how I did it, minus the mistakes.

Now, I’m going to give you a step-by-step beginners guide to making money online and how you can connect with me personally. Grab it for free HERE and let’s get started today!

Originally published at https://gighustlers.com on April 18, 2019.