taking the leap

Jamie Costello left a career at Microsoft Research to co-found payroll and workplace pension platform, Paycircle. Here, he gives his top tips on making the leap from a secure job with a tech giant for life as an entrepreneur.

It’s very cool to found a tech startup. But it’s not a panacea – there’s a huge amount of work involved.

When I left Microsoft, I had no idea what to expect. My job was an engineer’s dream but I wanted to dream bigger.

So I jumped ship and started Paycircle. That’s where the fun really began. Here are a few things I wish I’d known at the time:

Think you work hard now?

Most of the background things are taken care of when you work for a huge corporate.

With a startup, you have to wear an awful lot a hats. Who’s going to configure the wi-fi, chase the invoices and do the paperwork?

Unless you have funding, you need to make lots of decisions. Should you get a managed office or run your business from your bedroom? What about staff? These all take time, taking you away from the main job of running your business.

Writing the code is probably about how 30% of how your time will be spent. I used to think that a 10-hour working day was long. Now I regularly clock up 15-hours.

It’s not for everyone

There’s no safety net, which makes the financial side tricky.

If you’re in a corporate environment and good at what you do, it’s unlikely you’ll ever be asked to leave.

With a startup, you might have an idea but you can’t be 100% sure it will make money. If you’re worried about paying the mortgage, then maybe it’s not for you.

Worrying about money can really work against you.

With contracting, there are no guarantees but at least you’re receiving an income. Founding a startup is a bit like contracting on steroids.

Do the basics and put together a proper business plan before leaving. We’d already built some of the systems and tested the market before I left my job. But that means working weekends plus doing your normal job.

Otherwise, it’s a step into the unknown!

Don’t worry about failure

It’s of more value to prospective employers that you have the self-confidence and belief to go out there and do something.

The closeted world of the corporate means you’ll probably never talk to customers.

The exposure you get to the wider world at a startup is invigorating. Your product or system probably won’t succeed at first but then you’ll get feedback from customers.

The key is not to worry about failure. It’s par for the course. A lot of engineers worry about losing their skills but if you keep them up to date, you’ll never be out of a job.

Choose your business partners carefully

This is one of the most important decisions.

Seek out people with different skill sets and experience – it’s important that you strike a balance in terms of skill set.

More importantly, make sure you get on. There will be times when things become very stressful and pressured.

You need to be very honest with each other and communicate immediately if there’s a problem. If not, you’re storing up problems for later.


The biggest challenge we face is recruitment – it’s hard.

The big corporates have teams of people who do this but for entrepreneurs, who have gone solo, this is time-consuming and can be expensive.

Pick who you employ wisely; the engineers need the startup mentality and to understand it’s going to be hard work. They’ve also got to fit your company culture and don’t underestimate the power of word of mouth recommendations.

Location is another important thing to consider; where you set up shop can really have an impact on you recruitment plans, so think wisely!

Making the jump

For me, the biggest challenge was making the decision to actually leave

It’s important to make that decision, stick with it and believe in your ability to succeed.

Once you’ve left the comfort of the arms of a big tech corporate and all the health insurance and other benefits, don’t panic.

What you gain is exposure to the wider world and the satisfaction of building things. Being your own boss is the best thing because you get to work with people you like.

At Paycircle, my co-founders and I are doing something we believe in – trying to level the playing field for small businesses, which means that when I get up in the morning I don’t feel like I am going to work: it’s a hobby, my passion.

I work 15-hour days because I want to. I personally love it, it’s massively empowering.

My business partners are also my friends. Is there a better way to spend the day?

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