If I can find someone who will work for an employee's salary rate as a contractor, should I hire them?

I am 1 year into my own Startup Software business and all is going well. We have enough money to hire someone and after pushing 90-130 hours a week for the last 4 months, I think it's a sensible choice.

Currently I fullfill all web needs for the company (ASP.NET MVC, App Engine, PHP, HTML, CSS, JS), manage dedicated windows and linux servers, all IT and all project management and business development tasks. I worked as PM for 5 years while at the same time turning my 15 years of computing experience into development experience.

My Partner fullfills iOS development, but not much beyond that at the moment.

Essentially, I need someone who can take support me in my technical tasks, and ideally as well, pitch in with some admin/client handling. We also have aims to work with Graphics and Multimedia in a Creative Technology direction once we have solid client income.

Not sure if you needed to know all that, but essentially I need a clone of myself.

I know the books all say that I should probably find an eager grad from a top uni, but I've found a friend of my girlfriends that there is a big personality matching on. He's 2 years into a 3 year distance learning computer science program in Java. He current company hires him on a contract basis, but at normal salary levels. He is about to go down to 3 days a week, so he can spend 2 days a week on his degree to finish it properly.

I'm strongly considering matching his offer from the other company (which is very good considering his experience level) and mentoring him as I see fit. An advantage to him is that I see he has client management capabilities, and is SO eager to change careers this is a huge opportunity to him as well. The added bonus that he doesn't have to take a pay cut should help him focus on the job at hand.

However, he has not ever worked directly with a database beyond Access (I'm amazed that a course doesn't have someone use one in the first week!) but I really don't see this as a huge problem. I believe myself a good teacher, and while this is a risk that it will take up more of my time, I believe I can mentor him through books and tutorials to get to a useful level.

Pro's

• Working as a contractor, so simple process for the business
• Excelent personality match
• Can be trusted
• Ultra keen to do cool stuff (a key goal of our company)
• Has been using computers since the amiga demo scene
• Very hard working
• Able to be client facing

Cons

• Still in uni and has that on his mind, how ever it is a flexible course and so can defer if needed
• Only knows outdated java technologies (possibly a pro, as I can mould into the new way of doing things)
• May take up a lot of my time with teaching
• May make mistakes that I need to correct
• Only working 3 days a week

Does anyone have any experiences that would be helpful in me making my decision?
- Has

I've been in a similar position. The things I look for in someone who doesn't necessarily have the computing skillset exactly are strong teamwork, good work ethics and good maths skills.

The problem with CS courses (and if that's the OU CS course he's studying this is even more true, I know because I've done a number of the components) in the UK, at least, is they mostly don't give proper fundamental grounding in computer science. For web sites and .NET, that isn't so much an issue, but it limits the complexity of software architecture he'll be able to work with.

My alarm bell there would be he's going to do 3 days a week plus will take up a lot of your time. You really need 5 days if he's going to cost you and him 2 days a week of explaining at the start.

That said, good, hard working staff are hard as hell to find. I'm pretty unhappy overall with the work ethic of UK people I've interviewed and so, even though I'm based here, not a single one of my staff are (but all in Europe).

One thing to thing about is what if it goes wrong? What if he doesn't work out (for whatever reason, you or him at fault is unimportant) what are the consequences?

• Could this effect your relationship with your GF (or your GF relationship with her friend?)
• Because of the above will this cloud your judgement? Its always mentally very tough 'letting someone go' and if you are worrying about the above on top of everything else you're likely to leave it longer than you probably should.