How to fail 10 times at online business and what to learn from it

I’ve failed a few times, tried to build a business and earn money online (and offline) in every conceivable way and I eventually found something that worked. So I want to share what I’ve learned in that time and give to you the benefits of my failures

I steer away from treating failure as a friend as some say, quite the opposite in fact; and now get into the habit of using prior micro mistakes (controllable factors) as huge red flags and signposts for future kinks in the online entrepreneur’s road.

If you’re in business (even if its just you, trying to make it work online) this list is for you. You should care about continually correcting your course, cataloguing prior micro mistakes, rolling up your sleeves and ultimately minimising failure.

By seeing this post through to the end you’ll get a handle on where I went wrong, how I fixed it and how you can fix any red flags you can see in the 10 controllable failpoints below. I’m 100% sure I’ll have lots more over the next 5-10 years but here’s where I’m at so far, so here we go.

1. Too much faith in the magic bullet

This is a biggie, something I encounter a lot when I speak to subscribers. There was a time when I was on 27 mailing lists, probably 5 or 6 direct mailers and I’d enrol on some online wonder-programme or other almost on a monthly basis.

What I quickly realised that even though each probably had some merit it would be physically impossible to action everything, I was chasing the magic bullet, the quick win, the never never… resulting in getting quickly nowhere nowhere.

How I beat it

I unsubscribed from all lists, installed a kick-ass anti spam and began my list amnesty. Anything I missed I resubscribed to and I put more emphasis on actually finding my own information, only following content creators who spoke my language.

I succeeded at only seeking expertise when I needed it rather than being forcefed information which only distracted me from my vision. This enabled me to work out my own solutions with good old trial and error backed with only credible guidance.

Your own beaten path is much more reliable than an off the shelf “insert-superlative-here-profit-power-flood-programme”

How you can beat it

Commit to getting better, not consuming every hot new system. Take yourself off the drip feed, use your intuition and follow credible voices who won’t try and ram a programme down your throat at every opportunity. Then you’ll finally be able to save yourself from drowning in content you’ll never be able to action.

Some picks to rebuild after ‘list-amnesty’ – Corbett Barr, Adii Pienaar, Rand Fishkin, Jonathan Mead, Kristi Hines, Chase Reeves, Scott Dinsmore

2. Lack of self control

So this one probably applies to Liam v1.0 (incidentally I’m at Liam v2.8 right now). Aged around 18-21 I took the “lifestyle business” to the extreme, to a point where it was all lifestyle no business, I mean who wants to think accounts and revenue forecasting after a 5 day weekend?

But I was young, finding myself and some of that stuff helped the creative juices flow which took me on the perennial path I’m still meandering down today.

If you’re aiming for the business which supports your lifestyle you should double down on strategy & efficiency to ensure you are able to physically “cap” your working week. When you add in a dash of self control you won’t squander the working time you’ve set forth, preventing that sinking feeling you get from not putting in the work.

How I beat it

Oddly enough things started to change for me when I actually “went to work”. Previously I always had a home office.

I hired a desk in a shared startup environment which enabled me to divide my business/personal life in a more physical way.  The nice sidenote is that in the 2 years that followed the floorspace I occupied increased by a factor of 20 and we’ve now got our own custom build in the premium area of the same building with 16 desks at last count.

How you can beat it

Try to channel friends with high self control & will power. We all know the guy who refuses to midweek drinks, who always considers how decisions affect tomorrow and the next day or the guy that hits the gym 4 days a week no matter what. Study what makes them tick and see if you can mould it to your own personality.

3. Ambiguous goals

This is something I pound the drum about a lot. The fact of the matter is some entrepreneurs go into business to make money without clearly understanding and defining what makes for success.

I tend to analogise it as “if you don’t have a map, compass or destination how do you intend to get from A to B?”

When I started out alone aged 19 I knew I needed to make enough to pay the bills. In the end I did, but as I didn’t have a clear vision for success I stuttered into a plateau which, combined with failpoint 1 preceded a recession in my fortunes.

Had I been able to track performance against my milestones I could have taken more decisive action to stop the rot.

How I beat it

For each new venture I’m now doubly clear on what I want to get out of it. Its time sensitive and very specific, right down to the roadmap of employee responsibilities to make it a reality.

How you can beat it

This doesn’t need to be such a mammoth project, you just need to work backwards from your monetary goal and understand what that looks like in terms of customers,  prospects, visits, online visibility.

You also then need to be specific about what your lifestyle looks like so you can continually be auditing yourself, ensuring you’re not sacrificing living the life you want by chasing it.

As a simplistic example, if you want to make $10k per month and your product/service sells for $100 you know you need 100 customers. If 10% of your opt-in prospects go on to buy you need 1,000 prospects to hit your funnel.

If your conversion rate (visit-to-prospect) is 5% you can start putting specific plans in place to amass the exposure and visibility required to realise 20,000 visits every month by your target earnings date.

4. Overcomplication, start small

In my should-be entrepreneur research experiment “the fear” I analysed just why people don’t start in business. Don’t get me wrong some people just aren’t built of the right stuff to go all the way with a business but as my over arching concept dictates “everyone is a nerd at something and anyone can start, own and grow a business”

The ones that don’t make it (or don’t start at all) look at it as an all-or-nothing endeavour which simply isn’t true, this manifests itself in a phenomenon I call “the fear”

I have tried lots and lots of stuff, putting my neck on the block on a daily basis in the early phases of my journey. I over complicated ideas and gave up on some as a result. This is a waste of time in the long-run so I’m here to tell you to scale down the complication, start small and test it.

How I beat it

I made myself known in the freelancer marketplace, part-time at that, which enabled me to work with pretty much bare bones until I proved the concept.

Once the concept is proved jump in with both feet, until then don’t over invest in it.

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How you can beat it

Definitely think part-time alongside your current activity, definitely leverage a remote team, definitely start small and really pin down your owner:nerd intersection before fully committing and you’ll beat the fear and beat overcomplication.

5. Poor grasp of time value / leverage

This is huge. So much so I wrote a book and video programme on it. This was one of the major catalysts in my recent years’ business growth.

I won’t go too much into it here as I’ve got tons of extra resources on the topic you can go through but essentially you need to understand this:

As a business owner you wear lots of hats. Doing everything yourself for ‘free’ is false economy; damaging to the well being of you and your business.

Understand that everything in your business can be mapped out into a process and you can leverage a remote team to get things done to deliver on that process.   I put a quick video together on the time-value concept here.

How I beat it

Again, far too much to explain here and I’ve got lots of free resources on the topic here but the penny dropped when I devised a yes/no flow (which you can follow yourself here) building a team which helped me deliver items which didn’t immediately require my attention.

How you can beat it

Start to track your time understand the processes going on in your business and develop a team structure to help you deliver those using a service like Elance.

6. Sacrificing vision in face of difficulty

So here’s the thing. I’m a sucker for great branding, culture development and really clear, unbridled vision.   But what happens when times get tough? What about when you need to cut costs, do things faster?

I found myself pawning out my brand and quality of delivery in return for quicker revenue or lower costs. This is something that Rand Fishkin ( got into recently on his blog.

How I beat it

It’s a real tough one and I’m not sure I fully have but at least I’m aware of it when it rears its head. The one benefit I have though is ability in every area of my business interests. That is to say if everybody who worked at the businesses disappeared I could probably manage, even stripping it right back to me and my laptop.

I’m very aware this flies in the face of the distributed workforce and lifestyle business but I guess the learning point for me on this one was to always have a plan B and to know enough about what you’re doing to be able to survive.

How you could beat it

In some of my content I talk about “devise the what, outsource the how” that is to say you make the big calls, devise the processes and have an arms length understanding of every point of your business but your team deliver on that vision.

If you make your team members accountable for documenting their work too you’ll be in a much better place to safeguard against disasters.

7. Lack of software availability

I used to spend 15+ hours per week on activities such as:

  • managing accounts
  • calculating payroll
  • approving diarising staff holidays
  • collaboration with teams by email alone
  • sharing files by snail mailing CDs / USB (yes, really)

This is something that couldn’t really have been avoided at the time as most didn’t exist beyond the realms of $10k / month enterprise software but current technology allows huge timesavings by really getting good at software.

How I beat it:

Almost all of the above is automated and second nature now, I use mostly free software (link to a post on Under30CEO where I outline everything we use) which represents a great opportunity for the small (one person) business keeping up with larger competitors.

How you can beat it

You probably already are but using the yes/no chart from point 4 you should be able identify where else you might use software to get more out of the time you have available.

8. All optimism no realism

Part of the entrepreneur’s makeup is ambition and optimism. On the surface the two are the same but in the past I’ve been guilty of allowing my ambitious streak to out-run realism, when it comes to decision-making.

That is to say I’m using my ultimate goals, my vision and ambition as a guide instead of cross-referencing with straight-up realism, potentially quite dangerous.

How I beat it

I now put together a ‘what if’ analysis for each major decision. For minor (mainly financial ones) I do a quick cashflow forecast to find out worst case scenarios. These aren’t huge exercises, I’ve just developed a few simple questions to get to the core worst case but the point here is to understand the wide spectrum of consequences for every major decision to protect you from any potential failure.

How you can beat it

You’re probably doing this already but at the least, take no decision lightly – you should be able to make each decision with a couple of questions:

  1. Is this purchase/hire/contract/etc a contribution to my roadmap or a distraction?
  2. What is the worst case scenario of making that choice

By using the steps above you’ll be much more informed and be less reliant on your ambition or instinct.

9.  Not being proud of it

As I’ve said above I’ve tried lots of business models. From flipping domains to electronics dropshipping, from EMD affiliate sites to margin stock trading.  You name an Internet lifestyle ‘trend’ I’ve probably tried it.

The traits the above have in common is that they were each:

  • pretty darn ugly
  • a failure ultimately

They all existed as a plot to make quick money, nothing more. I wasn’t proud of them. I soon realised that the key to making business work is to be proud of everything you put your name to, and to use value as your shining beacon.

If you’re proud of what you have achieved and can be sure you’re providing value to a market sector you’re on the right track.

How I beat it

Well, I was a creative at heart and knew what looked good so I pretty much self-taught Photoshop and started to take control of the branding of any new business ventures.

I also found that sharing via my own immediate social circle (think close friends & family) enabled me to check and double check what I was putting my name to.

How you can beat it

Find a good creative minded partner or freelancer. If you can provide the detailed vision, direction and product/service you can work together to package that up into something you can be proud of.

Further reading: Adii Pienaar (founder of Woothemes) talks about what makes him proud of his business and branding in this pro q&a

10. Not finding my voice

This is a pretty recent one thanks to some wise words from Chase & Corbett on the Fizzle podcast and in some way goes back to the point on chasing the magic bullet. In the early days I was mimicking other bloggers and web entrepreneurs rather than finding my own voice and personality.

I pretty much hid all reference to my age, my background, my face and everything that would allow the visitor on the other side of the screen to connect.  The result was lots of copycatting, no fixed idea of my market, no engagement and pretty much no impact.

Your personality should come through in everything you put your name to and you should be able to provide strong points of view that reflect your own personal experience and outlook. Combine that voice with your market passion (finding your Owner:Nerd intersection) and you’re on to a winner.

How I beat it

I guess this came with time and experience. As I was able to (over time) develop my own experiences rather than channeling someone else’s I became more confident in what I was saying and a little more relaxed in my approach.

How you can beat it

You can begin to look at which styles of content / presenting feel natural to you. Is it long, deep, data-filled posts? Is it short opinion pieces? Are you more curator and do you provide more value that way?  Are you better talking via a screencast? Or on video in front of a whiteboard?

Try stuff, see which firstly feels right, then once you’re in a comfortable place see what resonates best with your audience.

At that intersection you’ll find your voice.


So by following the steps above you’ll be able to counter-punch any hint of failure, allowing you to carve your own path and learn from my steps to catalogue your own micro mistakes enabling you to be more productive, earn more and ultimately succeed.

There are a ton more which just come from ‘time in the game’ and general experience which are more difficult to put down in black and white as I’m sure you’ll agree but if you drop your email into the box below the post I’ll be sure to send you all I know over the next couple of weeks.

I am by no means perfect though, I’ve just mustered the endeavour to keep going, learning as I do. This is a journey and I’ve not yet reached the end and as the old Churchill quote goes:

“Success is not final, failure is not fatal: it is the courage to continue that counts.”

Winston Churchill

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