My Four Failed Businesses And How They Led To Over 10 Years Of Success

I recently posted a message to the members of my Laptop Lifestyle Academy asking them what their most common concerns were when it comes to succeeding with their online business.

I received a bunch of replies and one of the repeating themes were issues related to mindset, especially in the face of failure.

Here are some of the common issues:

  • “How do you stay focused?”
  • “How do you stay motivated when things aren’t going great?”
  • “I’m not getting any traffic.”
  • “I’m having trouble choosing a topic.”
  • “No one buys my stuff.”
  • “I keep feeling overwhelmed because I have to do too many things.”

All these issues are things we face as part of the entrepreneurial journey.

If you know my story, the one I share in podcast interviews, webinars and when talking on stage, then you’ve heard about my successful projects – a magic: the gathering card game business, essay editing company, investing in websites, and of course, blogging and digital products.

What you probably don’t know about, are all the other projects, websites and businesses that never went anywhere, which I spent many hours on during the first seven years of my entrepreneurial life.

I too faced all the issues listed above, getting lost in the emotions and thoughts that come with feeling like you’re just failing, and frustrated that things are moving incredibly slow.

By explaining to you some of my failures and also how they impacted my mindset towards successes, I hope you can see the connection to help you get through whatever situation you’re dealing with at the moment.

My Journey Of Failures

My first successful business was an eCommerce and content site about the card game Magic: The Gathering.

After several years of running that site, I grew bored of the card game and was looking to start new projects.

This is when I started to experiment with new website ideas, leading up to the creation of my next successful project, an editing company

However, along the way I had a string of failures that I’ve never really talked about before. I am going to reveal these to you now, starting with my attempt at an MP3 music download website from back when MP3s were brand new.

In my early twenties, I registered a domain name, It was meant to become an MP3 music sharing website.

At the time MP3s were really starting to take off. This is when Napster first arrived, but it was still hard to find music online, so people started sharing MP3s on websites.

To cut a long story short, my website didn’t really go anywhere.

I finished the design, opened up and launched the site, and very quickly realized I was getting into an area that had a lot of lurking legal issues.

I also didn’t really have a plan to make money besides hoping for enough traffic to profit from advertising. Although most people would just come to sites like mine to find an MP3, then quickly leave, so even the advertising strategy was flawed.

The key lesson I want to share with you from this experience is the legal aspect.

Why make your life harder by starting businesses where you could succeed, but because you succeed you get shut down due to legal trouble? I’ve seen a number of friends focus on business ideas that as soon as they started to make money, were hit with legal troubles and were forced to close.

This is exactly what would have happened with my MP3 site. As soon as it attracted enough attention that I could have built a business around it, I would face the same legal challenges as all those other music download sites did back in that era of the Internet.

Instead, I said to myself “this is nuts” and shut my site down. It proved to be a fun website to build, but not a business I wanted to pursue.

After the MP3 experience, I went in a very different direction with my next project.

At the time I felt a lot of passion for subjects like the environment, health and making the world a better place. I knew there were many other people my age also interested in these subjects, yet they were not well catered to on the Internet at this point in time.

My idea was to hire some writers and build up a community around topics related to being a young activist, a person who wants to make a difference in the world. Hence I purchased the domain name,

Using HTML skills I’d learned from my previous websites, I spent many nights building my activist website and designed a logo using my very basic graphic design skills. I was a mediocre designer at best, but I went through the process, finished the website and I did actually publish a few articles.

Needless to say, it fizzled out very quickly.

No one else got involved, I was having trouble getting any traffic, I had no momentum, and I realised that even if I had all these things in place, I didn’t have a business model that could work.

I didn’t have a direction or strategy in place where money could be made. Even with advertising, I would have needed a lot of traffic to generate much income. On top of this, I was targeting young people who have no money to spend because they’re too busy being activists and studying.

The key lesson I took away from this project, is I need to have a better plan to eventually profit from my website.

The next project actually started on a trip to Canada.

I was around 24 at the time, already running both my card game website and essay editing company.

I woke up in the middle of the night with an idea — I was going to start a new Craiglist. This is how silly it sounds in retrospect.

I figured I could start up a trading based community focused on students, as I was already attracting a similar audience with my essay editing company.

I was really excited about this project because to me, the fact that Craiglist worked using such an ugly simple design, meant that I didn’t have to worry about how my website looked. I just needed users.

Once again, I threw in a bunch of my time and energy to build an entire website and then attempted to get people to start listing their second-hand stuff for sale.

I got a tiny bit of traction with two people listing things for sale on my website, but that’s as far as the project went.

The problem was no matter how many listings I got, I simply didn’t have enough people seeing those listings, so products never got purchased, and thus people never came back. I also didn’t have enough people listing things, so there was nothing to see when people first arrived at my website.

It was a classic Catch-22 problem. I needed a critical mass of users to create listings of things for sale and people to buy those items.

I was crazy to think I could somehow attract enough people to my craigslist-ripoff site and get a regular user base despite the fact that there were already established players in the market — and there was nothing new or different about what I was offering.

The lesson from this experiment was not to jump in to a new business idea without properly thinking it through, even if you can see a connection with your current business.

Around about 2003, I was putting up posters to advertise in a Korean restaurant when my eyes glanced over another ad.

It was about English tutoring – helping international students in Brisbane learn English.

I started thinking about teaching English on the side to make some extra money. I printed up some posters offering one-on-one tutoring and put those up too.

I booked my first student, printed out English lesson plans from the Internet, and we met at a cafe for our lesson. I sat down and helped them go through the tutorial handout and had practice conversations.

After spending some time learning about the English tutoring industry, I noticed that most schools catered to large classes of 20 to 30 students. What was missing was a tutoring service where students received individual attention in small groups or one-on-one and the opportunity to practice English with locals.

At the time, my company was growing. It was a hundred percent online and very hands-off for me to manage. A true laptop lifestyle business.

I decided to go ‘all-in’ with my new English tutoring business. I searched around for a few months and eventually found an office near the downtown center, which I leased for $1,200 dollars a month on a 3-year term. My office had three small classrooms and a reception area. The only job left was to fill it with students.

I also purchased the domain name, and once again built an entire website myself for my new business.

Unfortunately, this is where things stalled. I struggled to get anyone through the door. After a few months of running AussieTutor, I had maybe 5-6 students actually visit us and even fewer paid lessons. On top of this, I copped a $500 fine for placing a signboard on the street advertising my business (apparently this was against city council laws).

I spent a lot of time that year sitting in a very quiet office by myself on the internet working on my editing company or just wasting time browsing and feeling depressed.

I realised I had created the very thing I was trying to avoid. I had created a job for myself, an office I had to go to every day just in case we had potential students show up.

After nine months I decided to shut down the tutoring business. I managed to break my lease early, suffering a two month rent penalty fee, which I was happy to pay if it meant I was free.

I learned a huge lesson from this experience – don’t start a business that will just be like a job. I came to value the freedom of having a pure Internet business so much more after leaving this failed business.

Seek Out Failure As A Means To Answer Questions

The most important mindset lesson I took from all these experiences, is to look at everything you’re doing as a process of trying to find answers to questions, and not simply as failures or successes.

Some of these projects taught me things about myself that I would not have known so clearly if it wasn’t for the experience  (for example, Aussie Tutor teaching me I never wanted to work in an office).

It’s easy to be hard on yourself and see failures like these as reasons why you will never succeed. It’s a lot smarter and helpful to see failure as simply an experiment, a stepping stone to eventual success.

In order for this idea to work, you need to be excited by the process of discovering failures and using them to create awareness. To create moments of clarity about what didn’t work so you can take that into your future and focus on what works instead.

Whenever you’re thinking about doing something, rather than focusing on the outcome and whether it will turn out to be a failure or success, simply do it with the mind of a curious child. Be excited about finding the solution to the questions you’re trying to answer.

A good example is running a webinar to sell an online course for the very first time.

It’s something you’ve never done before, so you’re probably going to have a lot of fear about it. You might even have thoughts like:

“I don’t know how to get anyone to show up on the webinar”

“I don’t know what to put on the webinar to get people to buy”

“I don’t know how to get people from buying to receiving the product”

You can see those as reasons to not do it. To get afraid, to give up, to turn away.

Or, you can choose to see those obstacles with a curious mind and think —

I’m curious. If I ran this Facebook ad campaign will it get me the kind of traffic I need to fill my webinar with attendees?

Of course, you don’t go into it completely blind.

You educate yourself. You take a training program on Facebook Ads if you’re going to do Facebook Ads, or you take a course on building content and creating email funnels like what I teach in Blog Mastermind if that’s the strategy you want to focus on.

Once you have the knowledge, you enter the execution phase purely thinking:

I wonder how this is going to work?”

“I’m going to do the best job I can to make this work”

“Let’s see what happens”

If you’re curious about it and not just thinking about the outcome, then you’re giving yourself a dynamic situation that you can’t help benefit from.

So, the next time you come across failure or procrastination because of fear of failure, exchange those fears for feelings and thoughts of curiosity.

Always remember – There is no such thing as failure. Only growth through experiences.


P.S. The only cause of true failure is not taking action.

If you spend all your time planning or waiting for perfect conditions or to feel the right emotions — that’s a big problem because you’re not doing anything.

I can show you the exact actions you need to take to build an online business based on content. All you have to do is take my free live webinar — The Platform Launch Plan.

It’s 100% free and will take you less than two hours of your time to learn all the exact steps you need to get started.

All you have to do is be curious enough to take action.

Book your seat for my workshop using the link below:

Free Live Workshop With Yaro: Learn How To Launch Your Online Platform, Grow Your Email List Without Buying Ads, And Turn Your Knowledge Into A Real Business. Reserve Your Seat »

About Yaro

Yaro Starak is the author of the Blog Profits Blueprint, a report you can download instantly to learn how to make $10,000 a month, from only blogging 2 hours per day. You can find Yaro on Facebook, Twitter and .

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  • Hi Yaro,

    Thank you so much for this perfectly timed reminder that we’re only “done” when we decide we’ve failed and will NEVER succeed. Remembering that each misstep gets us closer to eventual success if we see it as a step and not a bottomless pit.

    Best always,


  • Hello Yaro,

    We all have faced failures in our lives & careers, specially in the beginning, it was tough, but all those failures turned into experience and it has helped us grow.

    By the way, Great to be back reading your posts.

    ~ Donna

  • Love this post. I’m sort of known for quitting when the going gets slightly more than bumpy; the why of that is something I’ve been exploring lately. (Hence, me finding this article…!) It’s great to hear about failure from those who have succeeded.
    It’s also lovely to see someone who believes in the oxford comma. Thank you twice!

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