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Two common ways to get rich from shareware - by Steve Pavlina* 
There's a pattern I tend to see among shareware authors, what I believe to be a common problem that holds them back from achieving greater success with their businesses.  I think often people jump right in and create a new product without giving much thought to the size of the market for that product and the willingness of the prospective customers to buy.  If you take a look at highly successful shareware authors (to name a figure, say those who are making $10K+ per month), you may notice two common patterns that seem to prevail.  In such cases I commonly see either:  
1) low-priced product(s) with an *enormous* market or  
2) relatively high-priced product(s) with a smaller, well-focused market.   
You might also see a combination of the two for authors with multiple products.  I'm not saying that these are the only possibilities, but they seem far more common to me among the most successful shareware developers.  A variation on this pattern is to have mid-priced products with a moderately sized market, but that seems less common.  In other words, the smaller the market, the higher the price. 
On the other hand, I've seen many brilliant shareware authors who are less prosperous financially often choose a much harder approach -- they offer low-priced products to a very small market.  Generally I see these people having a really hard time growing their businesses, and they only make a fraction of what they could be earning. 
For an example, take a look at ASP board members Tom Warfield and Terry Swiers.  Tom sells Pretty Good Solitaire for $24, a low-priced product with an outrageously enormous world-wide market.  He practically owns the word *solitaire* in the search engines and his downloads and web traffic would make anyone salivate.  Terry, on the other hand, sells Atrex inventory control / POS software for $249.  His market is much smaller, but he obviously makes a nice chunk of change on every sale.  Both Tom and Terry are extremely successful shareware developers. 
Both approaches seem equally valid if your goal is to maximize your financial return from your shareware business.  When I started in shareware, I chose the low-priced mass market approach, and it has worked wonderfully for me.  In the "leveraging technology" thread, I've been exploring the possibility of also doing high-priced focused products to sell to the game developer community.  My market would be much smaller, but software that sells to this group is commonly over $1000, so just a few sales a month can make for a very nice income.  Even a low-end solution for a few hundred dollars could do very well as shareware. 
If you want to do shareware as a hobby mainly, it doesn't matter so much what market you choose.  If your goal is to build a very high income for yourself through shareware, then I think it makes sense to take time to consider the market for each product before you jump in.  There are many considerations aside from just the price and market size. 
It can be tough to separate yourself from the emotional attachment to a particular market.  For instance, through my experience with the ASP, I've amassed a great deal of knowledge about shareware and have many ideas for products and services that would be of benefit to shareware developers. 
Emotionally I would love to do this, but business-wise the decision doesn't make financial sense.  Because the average shareware developer isn't exactly swimming in cash, I'd have to price such products on the low side.  And the market is very small compared to other markets, so although I could make some money from it, the upside just isn't that high.  I would be better off making another game, where the upside is potentially enormous if the product takes off. 
* Steve Pavlina is CEO of Dexterity Software, an on-line game publisher dedicated to releasing retail-quality games through shareware channels. He was President of the Association of Shareware Professionals. You can find Steve interacting with Dweep addicts at http://www.dexterity.com 
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