Billion pound company to bootstrapper: Why I left Microsoft to start a business

Jamie Costello gave up financial security, structure and the kudos of working for a tech giant to pursue his start-up dream. So, was it worth it?

In my previous company, Microsoft, which has a market capitalisation of well over $500bn at the time of writing, you could always take certain things for granted.

Suffice to say that, in a global conglomerate of geeks, IT support was pretty good. You also never had to explain who the hell Microsoft was to friends in the pub; Microsoft and ‘that Bill Gates guy must be worth a few quid’ are words and phrases that are hard-wired into people around the world.

And, as a company with a market value higher than the net worth of many nations, it goes without saying that there was structure and great financial security.

Put it this way, at Microsoft – where I was fairly senior systems architect – nobody worried about not being paid.

So, it struck many of my friends and family as a surprise when I jumped ship from the ivory tower of ‘research’ in one of the world’s biggest companies with all the job security, not to mention kudos, that the role entailed, to a bootstrapper.

From super yacht to paddle boat

To continue the nautical metaphor, it was equivalent to jumping off a Russian oligarch’s super yacht onto a hand-powered paddle boat with a mini kids’ slide on the back. And yet I wouldn’t have it any other way.

At Paycircle, the company I co-founded, I’m no longer just a systems architect but get to wear countless other hats: finding new clients, raising and chasing invoices, ensuring the Wifi works, recruitment (argh!), attending strategy and board meetings, finding and kitting out a new office, and taking the staff to the pub (quite a lot of that).

Building a website for your business idea is easier than you might think. Our online tool ranks the top website builders that offer free trials.

Your business becomes your life

No day is the same and no day is easy. Oh, and no day is short, either, come to think of it. At Microsoft, it was always pretty intense but we’d at least work fairly regular hours. And when you left for the day, you could switch off.

At Paycircle, it’s not unusual for me to work 15 hour days and, even when I’m not working my brain is still thinking everything through. Your business becomes part of your life. Or as my wife says to me occasionally “It takes over your life”.

As the lead systems architect at my business, there’s a lot of responsibility too. After all, when it comes to the product — specifically whether it works and successfully pays thousands of people’s pay each month as it needs to — the buck stops with me. That level of responsibility can be quite scary. Terrifying, in fact.

The rewards of going it alone far outweigh the benefits of working for a big firm

The product I left Microsoft to create (and excuse the brazen plug) is a cloud-based payroll and workplace pensions platform. In plainer English, we’ve created a business tool that enables small business owners to run their own payroll, saving money and time, and also set up a pension scheme in as little as an hour — and then run it with minimal effort.

Essentially, we’ve ‘automated’ vast amounts of incredibly dull tax, pensions and payroll rules and legislation so that even the most numerically and tax challenged people out there can take ownership of such an important part of their business.

Put it like this: if the owner of our PR company can use it, then anyone can. He or she may have the payroll and PAYE know-how of a ham sandwich but they will now be able to pay their company without hitch every month in a matter of minutes.

While there have been moments of doubt while creating this product, and while running your business can be a white knuckle ride, I much prefer working for myself. I also like being able to choose the people I want to work with, all of whom are also my friends rather than people you’re obliged to work alongside.

There are all kinds of risks and uncertainty in running your own business, but the rewards, independence and sense of achievement far outweigh them. Hand on heart, not once have I regretted making the move.

On that note, I’ll have to wrap this up as I need to reset the office router and chase some unpaid invoices…and buy some flowers for the wife. Ah, the challenges of running a start-up!


(will not be published)