From time to time I get asked for advice on starting a painting service. There is no surer sign of my being here on TMP too much, than being asked for advice on how to do things I've never done myself. (Hint: Longevity is not the same as wisdom). On the other hand I have used (and recommend) a number of painting services. Plus, I flatter myself that I'm not an idiot
but herewith my unsolicited advice presented in no particular order. Consider the source and what you paid for this advice.
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Schedule time to answer e-mail and calls every day. Once in the morning and once at night as a minimum. If you only check e-mail once a day, put that on your web site and as part of your signature, etc.
Keep your web site simple and full of eye candy. No one cares if you have a great looking web site. It should be clean, easy to navigate and loaded with photos. Don't even consider starting it without at least 2 dozen different minis in the gallery. Nothing makes me more suspicious than seeing 87 photos of the same 26 figure Flames of War platoon
or 26 out of focus, dark, badly shot photos of 87 different commissions.
Don't overcommit.
Schedule time to send an update to every customer at least once every two weeks. Let them know to expect this. Even if all you say is "Last time you were 19th in line, now you 14th" or "we're on schedule for completion on June 20." Be honest. If you're falling behind, say so. Gamers are patient to a fault but they'll love you if they know what is going on. Give them an option to cancel if you're going to miss their "must have by" date so they can go to whatever plan B might be.
Be careful of which web sites you become known to hang around. People will often treat posting there as the same as an e-mail. It's not hard to suddenly have a couple dozen sites, forums, groups etc. you find you need to check daily.
Consult a tax professional. A real one, nit just some guy who plays one on TMP. Find out everything that is tax deductible if you work from home. Supplies and ads, sure, but can you get a break for Ospreys you bought last year before you decided to start a business? Is it worth taking the home office deduction? What about furniture, utilities, etc.?
Do the math. Be realistic. How many 15mm French Napoleonics can you paint in 8 hours (I'm assuming a 10 hour day with 2 hours of breaks). What about 28mm Samurai? Mounted figures? There could be no worse disaster than you fill your order book only to discover you're only making $0.02 USD an hour. There are 52 weeks in a year. After a few sick days, personal days, and vacation, how many actual working days are there?
Fill your down time by painting and selling on E-bay, TMP or your own web site. It will give you an excuse to paint stuff you enjoy and you'll be able to add them to the gallery, practice taking photos etc.
Do you really want to be in business or do you just want to paint for people you know on the side. When I hire someone who is doing it "on the side" I have on set of expectations. But if they have a web site and business card I expect professionalism. Not saying they won't have issues, but I expect them to contact me proactively, not make me hunt them down. So be in business or don't. Don't go half way.
Have a contract. Have a disaster recovery plan for jobs gone bad. Put it in writing and make people agree to it. I suggest having a simple invoice/contract that spells out all these kinds of details. Just have some empty space where you fill in what figures, how many, prices etc. This is a contract – put it in writing. You may eventually dispense with it for good regular customers but it will save you a lot of grief in the end. (One such: You hate the work I did? Send it back. I sell it and reimburse you the cost of the unpainted lead or equivalent. )
Consider always using tracking or insurance when sending finished goods. Unpainted lead is cheap your time ain't.
Find a good way to ship painted figures – including fiddly fragile bits like gun barrels, pikes, thin horse legs, etc. Road test it with unpainted figs first – mail it around to a few friends then open it and look at it. You'll learn a lot that way.
Get some free business cards at VistaPrint.com and carry them with you especially to local game days, shows etc.
Think about a free sample program. Pick up some decent but cheap figures off E-bay and paint them. Give them away to the first 25 people who ask. I do this with new (unpainted) miniature ranges as a way to promote them and they have always done very well for me.
Have some money in the bank. Some time, some where you will get paid slowly or not at all or will lose two weeks to the flu. You'll need that rainy day fund.
Be realistic about what you do/don't want to paint. If you hate doing shields don't take those jobs. I guarantee that if the one and only thing you hate to paint is white horses, your first big commission will be for 1000 Arabian Knights all on white horses! (For me it would be tanks and terrain).
Don't overcommit.
Don't say "I specialize in historical, sci-fi and fantasy figures from 2mm to 200mm." Uh, in other words, you don't specialize in anything. If you specialize okay. I know a number of services that do mostly 6mm work. Or only WW2. Or only bigger the 20mm.
Be very clear about historical reference. Will you provide it or should the customer do so? This can get expensive (but take advantage of your local library – you'd be amazed what you can get if you plan ahead). Get good at painting one then sending photos to get client approval. That way there's no argument about what "Bavarian Blue" is. If you have to just send a good photo of a color swatch. Use common paint references where available (as in "I'll paint them a green like Vallejo 666 but a touch lighter.")
Don't overcommit.
Get good at taking photos of your finished minis. Work at it until you have a set up (e.g. light box, tripod, lamps, whatever) that you can get reliable results from. If you can leave it permanently set up somewhere all the better. Never post bad photos with an apology for the bad photo. They do more harm than good. ("The chef says to apologize that he is sending you a sauce that tastes like feet. Enjoy.")