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I’ve had a fair few of businesses in the past and some were even successful! But I have had some clangers too ?

Here’s a whistle stop overview and a couple of lessons learnt on the way.


It all started when I left Uni and wanted to have my own web design company ?

It was 2000 and the internet was still built on hand coded pages and there was a smidgen of CSS. I wasn’t bothered about that, I just wanted to have my own business ?

Living up North had it’s benefits back then. Business Link wanted to give me *all* the training courses. I walked to the other side of town every week to sit with other wannabe business owners and was taught “business” ?

The first contract fell through and it hurt. I was crap at coding and I couldn’t solve the problem the company hired me to solve ?

My first business failure was that I focused on building a business without having a sound product. Fucksticks ?

I ended going back on the dole then getting a job at the Early Learning Centre… and I hated kids ?

2003 — I had another go at business. I thought that getting a Masters in Online Business ?? would help. It did ?

I was reasonably successful in building a clothing company ?

I did everything! I built the website, I designed the t-shirts, I got in magazines, made some great friends and met my heroes ?

But I didn’t make enough money for it to grow past a bedroom business ?

My second business failure was that building lifestyle brands could get you fame but fame doesn’t mean money. (Translate this to the modern day equivalent — Having a massive social media following is shit unless you can turn it into cash.)

Another job and a go at being a career girl commenced and I retreated back into the work force ?

2010 — I ?? moon walked out of my corporate job and started in business again. I followed the freelancing route and built websites for DJs ? and Lifestyle Companies.

My third business failure was that I ended up being a dogs body and it smashed my confidence. Pricing yourself correctly is essential. I had no idea how to position myself as an expert and I became another web designer ? Fail!

2012 — Tried my hand at selling on EBay and Amazon. Pure sales copy and marketing 101.

I made money on my first day! ? I did this for three years. Every day, I packed and posted products, and sold over 5,000 units ?WHOA!!!

My fourth business failure was not picking a product that enough people wanted and the product didn’t retail for much cash. I made pocket money not mortgage money. Another fail!!! ?

2015 — Another stab at web design. This time I had a great product, a problem was being solved, I got clients, priced myself correctly, I was an expert and made some money! Yippee! ?

My fifth business failure was doing it ALL myself and becoming a Technician as Michael Gerber puts it. Bollocks! I hit the earnings ceiling and I was working hard to do that. ?

2016 — Productise my services… YES! Solving the problem of pressing the buttons myself was done by selling courses on web design! This was IT! ?

I sold ONE! One course. I worked my arse off for £100. ☠️

My sixth business failure was not being everywhere. You can have a great product but unless it gets in front of the right people, it’s useless.

Spring 2016 (I’m failing faster!) — I ditched the product idea and went back to web design.

Someone released a similar course and made five figures. ?

My seventh business failure was not being patient. Nuff said.


Summer 2016 — Today — Here’s my list up to now…

1 — Have a decent product.
2️ — Focus on the selling not the fame.
3 — Price it correctly.
4 — Ensure it makes enough money to fund your lifestyle (cos that’s why most people are in business!)
5 — Build and outsource your business systems as soon as possible.
6 — Get it in front of the people who want to buy it.
7 — Be patient.

Now hustling hard to make it eight lessons.

✨ And I guess that’s the eighth lesson — You’re always gonna fail but my GOD, you’ll learn how to do it better next time ✨


Carolynne Alexander is a battle-hardened web designer and business Mistress for female entrepreneurs who are more about working on their business instead of in their business.

As a recovering Fortune 500 employee, she realised that “business as usual” was killing her soul so she flipped the bird, moon-walked outta there, and went back to building stuff.

And when she’s not knee deep in Squarespace, you’ll find her serving up a Dose of Realness about entrepreneurship over at kicksmith.com