Here is my transcribed interview with dynamoe.tumblr.com aka creator of the Mad-Men-Yourself application!!
> When did you receive your professional commission and how did your client > come into contact with you?
It's a slow process from doing things for friends as a favor to friends insisting on giving you something for your work which starts as a picking up a tab at the coffee shop to a fist full of cash money to getting an agreed amount of money from a stranger. I'm not sure which was the first professional commission. I assume it was a flyer for the UCB Theatre after a year of doing posters and flyers for free because I was in the shows the posters were advertising.
> How do you come into contact with most of the clients you make work for > currently?
The internet. I try not to have to meet anyone in person or have to talk to them on phone. I want clients to be faceless text-on-a-page. Clients find me, I don't do any promotion and don't have a manager.
> What kind of work do you get asked to do the most?
It depends what the last big project I did was. When my Mad Men drawings first got a lot of viral attention, I got a rash of people who wanted their portraits done in that style. When the AMC Mad Men Yourself web toy came out, a bunch of websites wanted applications exactly like that (people have no imagination; I turned all these down not only because of conflict-of-interest but because I am not a programmer), but I ended up doing a similar web thing for the Marc Jacobs site (since taken down). When Hipster Animals got a burst of media attention, I was getting 4-5 requests a week to draw pets or draw people-as-animals from that site. Right now, no one is asking for anything... it's pretty dead.
> Do you have a preference of what kind of work you like doing the most? Poster design? website layouts? personal portraiture? etc?
I don't do web at all. People specialize in that and my web skills date to about 1996. It's way too much work. Anything else is good.
> Do you mind doing commercial work, and is there a certain kind of company > that you'd never make work for?
You mean as opposed to personal portraits? As long as I get paid, I don't care. A lot of big companies find ways not to pay you. I would avoid working for the flagrantly dishonest ones.
> How long are you usually given to make something for a client, or how long > do they usually give you? Do they typically set a deadline or do you?
I depends on the job. Most cases I ask if there's a date they absolutely need it by and give a broad frame of when it's coming. I wouldn't turn an illustration around in under a week unless the client paid a rush fee.
> What is your work schedule typically like when you're working on a > commission?
I avoid doing the work for as long as possible and then get it all done in one go. I procrastinate and have insomnia.
> Are most of the clients you work with agreeable about the finished product?
In all but discounted jobs, I say up front that I include three rounds of revision. If they're unhappy, they have stages to vent their frustrations and ask for changes or pay for more revisions. Only two clients in memory have still been discontent after three (and I delivered a great many half-stages between those) stages were never going to be satisfied, so I refunded their money and told them to find someone else. I'm not a therapist or a mind-reader and I wasn't getting paid enough to become one for these clients. I'm not sweating my "integrity" on some a job I took just for the money; I'm worry about my sanity and frustration.
> Do you ever revert back to traditional media to make or to assist on a > digital piece?
No. I'm 100% digital.
> Do you think that digital media measures up to physical media? Do you think > it surpasses it, even?
I don't use paint, ink, etc. and never have. I doodle with a pen on diner placemats and that's it.
> Do you have a full or part time job in addition to doing freelance?
I taught regularly at the Upright Citizens Brigade Theatre this year but that was similarly unstructured. Not sure which one counts as the "day job."
> Who is your favorite illustrator/artist currently?
I haven't thought about it. Probably Daniel Clowes.
> Who were the artists that influenced you when you first started > drawing/making artwork?
Who influenced me professionally? Luc LaTulippe is a Canadian illustrator who also works in vector and had a big web presence ten years ago (and still does) when I was starting to become a "professional" instead of a dabbler. When feeling my way through Adobe Illustrator I was looking at his techniques as a guide. He's not famous, just a solid working illustrator. When doing work for Mad Men I was specifically looking at illustrators who worked in the era the show is set (and slightly before since photography had all but taken over ad work in the 60s), which included Aurelius Battaglia, Alice & Martin Provensen, Art Seiden, Miroslav Sasek and J. P. Miller. Looking at Richard Scarry's early work lead to his later work that inspired Hipster Animals.
> Do you feel like the internet has made being an artist easier or more > difficult? or both?
I couldn't work without it so I assume easier. I haven't been an "artist" in the time before email was widespread so I can't compare it. It would be harder to avoid phone calls with no email.