Another good one from Daring Fireball: Pinprick.

And introducing the Gruber Theory of Software Pricing: "Don’t underprice your software in an attempt to appeal to cheapskates."

And after you are done reading that, I have three little relevant stories to share that I think back to often.

. . .

When I first started working on software to sell independently on the mac (back in the os9 days, written in realbasic and ... java of all things) I was talking with a friend of mine, Jamie Halmick, who with a partner had his own company writing plugins for Cinema 4D. He worked at home, and more importantly, didn't answer to The Man. Among the many bits of advice he gave me, the one he drove home most was not to sell your app too cheap. I of course ignored him, and he gave me crap when VoodooPad 1.0 came out for 10 bucks. "People read into the quality of the app based on price, and you'll even sell more" he said. "It's crazy, and it doesn't make sense, but it's the way it is."

When I eventually raised the price to 24.95 he asked me how things were going after the price increase. "Much better" I said.

"You should sell it for even more".

. . .

Another friend of mine (Hi Mike Marconi!) used to own a nice italian restaurant, and of course we would talk about pricing as well since he did a bit of consulting on the side. He told me a story about how his wine distributor came in and offered a couple of cases of decent, yet reasonably cheap wine for something like 4 bucks a bottle. Mike could buy that, and sell it on the tables for 8 bucks and folks could have a nice bottle of wine with their dinner.

Of course, none of them moved. Then he raised the price to 24 bucks a bottle, and bang- he sold out of them.

. . .

And the last story, and this is probably the most important piece of advice I have ever been given and is imprinted in my brain for all eternity.

In high school I worked at a local grocery store as a bagger, and eventually moved up to checking folks out when I was old enough to sell alcohol (18 in Missouri). Of all the positions, it always seemed like the guys working in the produce department were the most amusing and fun, so I would of course slack off around them when I was given the opportunity. Maybe it was because I would juggle the oranges for them.

Anyway, I remember talking to Tom, one of the produce guys, about a certain (and very cute) girl that was working there at the time and wether or not I should ask her out. My feelings were that she was too high on the ladder for me. He sort of paused and looked at me, and here's the part that's stuck in my mind forever:

We're under those crappy flickering florescent lights, and Tom is wearing a brown apron stained with random bits of fruit, restocking the celery and he's holding a stalk in his hand and pointing it at me and he says "Don't ever sell yourself short".

That's it. Those are the words that I've (tried) to live by ever since that moment. And if you haven't heard that bit of advice before, well... now you have. Don't forget it.

(The second most important piece of advice I was ever given was delivered to me as I was in my mom's car pulling out of the driveway and off to my first year of college. A friend of the family was outside of the car saying to me as we backed out: "Remember, try not to get distracted by all the work.")

Oh, And it turned out the girl had a boyfriend. Doh!