I remember the first time I made $1,000 in a month from my website.

It felt like a breakthrough moment.

At that time I was selling Magic: The Gathering cards and I was 20 years old.

Five years later, with a different website, this time an agency selling essay editing services, I had my first ever $10,000 month.

Another revenue breakthrough, although a temporary one as my business was very seasonal.

Three years on, with my next business — this time a blog coaching company — I had my first $20,000 month, then $30,000… all the way to eventually a $50,000 month!

These numbers became far more common place and I was making really good money for the first time in my life as I hit 30 years old.

More recently we broke $100,000 a month with InboxDone.com, an email assistant agency (my current company), and we are still growing.

Again, it felt amazing… another milestone!

Dreaming Of Money Milestones

During my 20s, each milestone I set as a goal felt very far away when I fist thought about it.

Getting from $1,000 to $10,000/month seemed near impossible and required I change businesses completely.

Even when I hit $10,000 in a month, it didn’t stay at that level for long.

The idea of breaking $100,000 a year meant consistent $10,000/months, and that seemed really hard to achieve!

Then there was my dream goal: $1,000 a day.

That is $30,000 a month, every month. Consistent, reliable, significant income.

When I finally reached this result, and maintained it for more than two years in a row, it had been such a slow gradual build up I forgot this was a goal I set long ago.

I remember looking back thinking — this was not how I expected to get here!

Yet in hindsight I started to see the steps that led to the result.

Today I feel I have a much clearer understanding of the steps necessary to make your way to each money milestone, from that first $1,000 to your first $100,000 month.

While this clarity is nice, it’s also come with a realization that it’s actually far harder than I thought!

You have to get a lot of things right, and set up a lot of processes, ideally processes that other people run for you — and building a team is really hard!

3 Components For Breaking New Income Milestones

To keep things simple, I’m going to focus on high-level conceptual steps, so you can at least get a grasp of what you need to create to succeed as an entrepreneur.

I could create entire courses on each of these steps — in fact I do have many courses inside the Laptop Lifestyle Academy that go into more detail and cover more practical steps about these concepts, but I have only so much room in this newsletter.

Here we go…

1. Positioning/Market Fit: Lots Of People Spending Lots Of Money

This always seems crazy-obvious, but you have to be selling a solution to a problem compelling enough that people are willing to spend money to solve it.

The market needs to be large enough to have enough buyers, yet at the same time you have to find a way to specialize or niche down so you stand out.

It sounds so easy, but this is where most entrepreneurs fail.

They choose too small markets, or offer ‘same-same’ solutions, meaning you’re losing out to the specialists, the big players who already dominate or the sheer volume of competition results in drowning in a crowd of options.

One of the biggest lessons I’ve taken away in recent years is to see positioning as an evolution, and a castle you have to build.

I had an idea to offer a virtual assistant service that specializes in email.

The market is big — companies spend billions of dollars on virtual assistants.

It’s also VERY crowded. One search on Google for VAs will show you the river of competitors in the space.

I was clear from the start what made us different: We specialize in email.

This is how InboxDone started and the core positioning hasn’t changed.

Yet, the nuance of this specialization has evolved so much in the 7 years we’ve run the company.

Our positioning has seeped into everything we do, from every piece of marketing we produce, to how we service our clients.

We reinforce it, we have specializations within our specialization, and we know how to present these ideas to people so we can justify our higher than average price.

There’s so much more I could write about this, but we must move on…

2. Product/Service Satisfaction (Minimize Churn, Maximize Client Results)

This is the most overlooked step because it’s not as much about making money as stopping from losing money.

Yet if you really understand it, stopping from losing money is HOW you make money.

All the growth in the world can’t fix a broken product or service.

You need solid retention. You need life time value to increase. You need to use client success as a tool to get more clients.

Testimonials are brilliant marketing tools – they offer social proof and reinforce your positioning – but you have to have clients who get results if you want those amazing reviews.

This step is one of the hardest to get right because it involves less sexy things — people and processes.

You can’t instantly have amazing processes. They must be crafted and refined over time.

To do this work, you need talented people — and don’t get me started on how hard hiring is!

Finding talent, training talent, rewarding talent, this is how companies grow.

The foundation of your next breakthrough income increase will come from improving your product or service delivery.

Customer satisfaction is marketing.

Reducing churn and increasing existing client spend is more money.

3. Build An Infinite Marketing Machine

I believe people should be told this before they start a company: You will never ever stop marketing.

New entrepreneurs think that success is just one marketing breakthrough away.

If only you can get your ads to convert, or a video to go viral, or some influencer to pitch your product, then you will win.

All those things can lead to new money milestones, but they never work forever.

Marketing is a lifestyle. You can’t stop testing NEW.

Whether that’s new ad media, new channels, new formats, testing and refinement is the job that never stops.

I’ve had to truly come to terms with this as the CMO of my company.

I have two tasks I work on:

  1. Test new media using the channels that have proven to work. This is done simply to maintain the result we already have, because all existing media gets old and performance drops. 
  2. Test new channels. Each new growth milestone comes from something new working. Unfortunately most new things don’t work, so you spend a lot of money and time simply proving something doesn’t work.

When I coach entrepreneurs, one of the first questions I ask is –

“What did you do recently to reach customers?”

“What did you do to generate traffic?”

Some say things like I wrote articles, or published social media content, or I ran paid ads, or put up flyers around my neighborhood.

When I then ask for metrics to judge performance, often they just tell me they got zero sales or no one signed up.

This is the result, not the metrics.

Metrics are things like views, clicks, email sign-ups, views on content – something that shows some response.

Ideally you have a sales funnel with clear steps so you can look at the metrics at each step.

We use a really simple sales funnel for my current company. An ad takes people to our website and then people book a discovery call, then a proportion become clients.

For my coaching business, my sales funnel was more educational. From blog post, to email sign-up, to followup content sequence, to launch campaign, sales page and then sales.

A lot of the training inside the Laptop Lifestyle Academy breaks down how to set up these sales funnels.

Even my first business had a metric on the paper flyers I distributed – how many little paper tabs with our website address on it were taken off each flyer (I could find the ‘hot spots’ to put up my flyers using this metric!).

Sadly so many entrepreneurs just do one thing once, then call it a failure and stop.

One ad, one promotion, one piece of content. Done.

Maybe they keep going, trying the same thing again and again, with the same result.

They don’t look at their metrics. They don’t understand how to move people through a sales process and they don’t experiment with new channels.

Marketing is an infinite machine that you will have to maintain forever as long as your company exists.

Of course people and processes can take this over for you, but understanding it is the fuel that feeds growth is a realization all successful entrepreneurs come to terms with.

Your Next Money Milestone

As I write this I’m working towards my next money milestone: $166,666 a month.

That’s an evil looking number you might say, but it’s just the monthly total you need to make $2 Million a year.

That officially makes your company a multiple 7-figure business.

After that, you aim for $200,000 a month, and onwards.

The game continues for as long as you want to keep playing.

There’s plenty of ups and downs along the way, and in my experience breaking milestones always takes longer than you want it to.

As long as you are enjoying the journey and improving, it can help you lead an amazing life both in terms of meaningful work and financial security.

Keep breaking those milestones!

Yaro