I disagree: You caught a lucky break here, but you are the exception, not the standard.

Family/friends and money don't mix well. They will always ruin the relationship. I've seen it countless times.

My wife does the bookkeeping for my business; she has the perfect personality for it, being financially minded and very much a details person. She was second-in-command to a CFO back when we were both working for other companies, and the CFO told me once that she basically ran the entire company's finances for him. I definitely wouldn't call this outsourcing so much as a huge lucky break. Every time I see her updating our accounts software (she prefers the simplicity of AceMoney to Quicken), I feel relieved.

Lately I've thought a lot about this: If I didn't have a tax person, a bookkeeper, a good freelance web developer friend, and a business consultant, I estimate that I would have gone out of business (a third time) about five years ago. The first and second times I failed in my businesses I had none of those things. Now I'm finding even more people to share the load whenever I find myself "in the grip of my inferior function" (Meyers-Briggs talk). The alternative seems to be depression, anxiety, and everything that comes with that.

Well, currently both my mom and dad are working with/for my company. My mom manages the full book-keeping of the company). My father, because of the general economical situation in Italy, was left jobless. So, as soon a position opened at my company i simply proposed him to join. He is the warehouse manager now.

The thing in working with parents, in case they eventually are accountant, is that they can access all the figures of the company (for the good and for the bad). Another aspect to consider is dealing with weird situations. They will do bullshits and you need to tell them, as you would do with any other employee. Dealing with this is not easy and requires a lot of communicative skills and entrepreneurial experience.

I made the horrible mistake of partnering with my father on a business venture last year, and it has significantly strained the relationship. That was with a very clear line drawn between personal and business finances. I couldn't imagine dealing with the mess of mixing business and personal finances in that situation. shudder

I hope it works out. My personal rule to live by: Never hire someone you can't fire.

I tried outsourcing my financials to my wife (who works in accounting) and it did not work out. Relationship wise it wasn't good but also found out after switching back that was happier and more productive doing it myself.

We (my wife and I) hired my mom to run my e-commerce stores after she retired. She is paid an above-average hourly rate, can set her hours, and can work from home. Knowing that we would be giving someone access to a merchant account that has a significant amount of money run through it each month, we had to have someone we could trust to process refunds and occasionally charge additional amounts when orders were upgraded.

She spends 1-3 hours a day managing the stores while my dad works on his model trains. It's enough to keep her busy, have a sense of accomplishment similar to her old job, provide a little extra income - all while not cramping their retirement.

I was a little nervous at first - more about her feeling pressure to make us happy than us being satisfied with her work. However, her role is clearly defined (answer emails, return phone calls, and submitted/track orders to our supplier, etc). This reduces the chance of misunderstandings or let-downs than would be more likely to occur with a less defined role like strategy or marketing.

Thanks for the comments! Bonus stories for you wonderful HN'ers:

My dad started out as an auto mechanic and painter. He decided to setup his own shop with his first cousin and it was a disaster. They butted heads constantly. My dad sold his shares to his partner and moved on to other things. They tried it, it didn't work out, and so they moved on. Throughout my childhood our family was very close with my dad's first cousin and his family. They relationship is still strong today.

My mother and her brother had a dispute about money over fifteen years ago. They still do not speak today.

Family and friends can be tricky when it involves money, there is no question.

What I got out of article, is that when you are one person company and do not want to do something boring, become a two* person company.

* Author calls this outsourcing, but I simply can't see that. If we buy that, we might as well buy that all other companies consist of CEO and a bunch of people he 'outsources' lower level things to.

I hired your mother too, Trebek.

See:

http://rapgenius.com/51490/The-notorious-big-ten-crack-comma...

"I can’t think of a single reason you should be doing this yourself."

followed by

"But how do you outsource something as sensitive as financials?"

Sounds like a single reason.

My dad, who's run a small business successfully for 25+ years, recently retired and I've agreed to have him support me on the operations side of my business. My mom is by far the best usability study ever. She's in her 60s and doesn't get technology that well but can use pinterest. If my website is usable for her, it'll be usable for anyone.

Many business decisions require a certain level of ruthless efficiency to execute. These decisions are fundamentally incompatible the nurturing relationships established in family units or friendships.

I think I missed the part where this is a tax deductible expense for him? Otherwise I think I'd keep my family away from my startup. Its stressful enough without having to add family into the mix.

Congrats. I agree completely.

My mom is a fantastic freelance bookkeeper. The day I go at it alone, she's going to be my first "hire".

Good for you. Hope it works out again!

Six months later: "I Fired My Mom (and now our relationship is weird)"

Really interesting, though it may really vary for most based on what skill sets their immediate relations have.

this was very touching to read and it's encouraged me to do the same. I don't have a wife or a fiance but I would never entrust them with this kind of sensitive material because there's a real risk of relationships souring. With family it's easier to deal with and it's easier to communicate instead of trying to bury things in order to not ruin a marriage.

"Hey Ma, need you to stop hiding grocery purchases under company's funds, if you wanna keep your job"

"But I'm your mother"

"Okay, alright, just don't do it again"

vs.

"Hey babe, need you to stop buying expensive items under company's funds"

"fine, since you don't love me you can marry someone else"

"nooooooooo!"

You basically practice nepotism. Most of your staff and peers and people around you consider that as a form of corruption. Congratulations.

http://en.wikipedia.org/wiki/Nepotism