The contractor who started a business for contractors

IT contractor Dave Chaplin started a website to help others when IR35 tax legislation arrived in 1999. Here, he talks about setting up and growing the company.

Dave Chaplin is CEO of Contractor Calculator, an online portal that has been providing free advice and information to freelancers and contractors every month since it launched in 1999.

Before he launched the service, Chaplin was an IT contractor and the proposed introduction of the IR35 tax legislation in November 1999 gave him the impetus needed to help others like him. ‘We first started the website by publishing the IR35 Calculator,’ he says. ‘This enabled contractors to calculate the financial impact of being caught within the legislation. It’s still used today by our readers.’

The site then grew by providing advice and guidance across all areas of contracting, including over 35 more tax calculators for contractors.

To begin with, it was a hobby site, based on a single idea, and it provided a test vehicle to extend Chaplin’s Windows programming skills onto the web. ‘Back in 1999 web programming was in its infancy and there were very few web programmers,’ he says.

Chaplin personally built the entire website, content management system and operations systems. This has meant he has been able to heavily automate most of the operations work, reducing overheads and staff needs considerably.

Having not programmed on the web before, Chaplin enlisted the help of friends to put together a template website. ‘Learning the basics of HTML in those days was pretty easy though and not as complicated as it is today,’ he says. For the tax calculations his brother, a chartered accountant, created a spreadsheet, which was then used to build the underlying programming code. The first draft of the website was completed in a weekend.

To host the website, Chaplin hired some space on a shared server with a web hosting firm, to which he uploaded the code and connected to the domain name.

‘These days we use the Cloud based Amazon Web Services with fail safe backup and 24/7 availability. There was no plan from the start to create what we have now.’

Expanding the business

At the start of 2003 Chaplin decided to transform the website from a hobby site into a full time run-anywhere business. ‘The goal was to earn income from a business while being what is now called a ‘digital nomad’. I worked solidly on it for ten months in the mornings, evenings and weekends, while also contracting 40+ hours per week,’ Chaplin recalls.

Then in November 2003, he quit contracting, having made enough cash to last a year to make it work.

‘There was always the fallback of going IT contracting again, so the risk wasn’t that great. It actually took one year before the website was earning the same as I had been earning contracting,’ he says.

By the following year the site had doubled the visitors from 8,000 per month to 16,000 per month. ‘We continued to increase traffic each year and finally broke the 100,000 visitors per month mark in March 2008.’

The biggest challenge was the work-life balance, something Chaplin didn’t have much of at the start. ‘I pretty much worked on it every waking moment for the first five years, which meant I missed out on other non-work activities.’

In the early days paranoia about the business failing motivated him to spend as much time on it as he could. ‘It was a very creative period, and there was a long list of items on my still ever-expanding ‘to do’ list, which used to make me feel overwhelmed most of the time.’

In hindsight while the hard work paid off, in reality Chaplin says he could have done things slower and enjoyed life a bit more outside of work. ‘The upshot of it though was that I was able to ride the tidal wave of four years previous creativity and move to a better work-life balance model for a few years and travelled a great deal – provided there was Wifi wherever I went.’

Now, revenues are healthy and the company has just had its best financial year, Chaplin says. ‘We hired our first full-time programmer this year and have exciting future growth plans for the next five years.’

Advice to others starting a web-based business

Chaplin says a strong piece of advice would be to hire the best technical people you can and keep the team small. ‘Don’t underestimate the focus on technology required as your business expands. Automate as much as you can on the operations side of things (DevOps), otherwise you can spend too much time running what you have currently built, rather than spending more time building it bigger.’

Also, always give your audience what they want. ‘By becoming the expert advice site for all aspects related with freelancing and contracting, our audience knows that they can rely on us as a trusted resource. Oh yes, and try and get the work-life balance right!’

Dave Chaplin is the founder and CEO of Contractor Calculator.

Further reading on freelancing

Ben Lobel

Ben Lobel

Ben Lobel was the editor of from 2010 to 2018. He specialises in writing for start-up and scale-up companies in the areas of finance, marketing and HR.

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