Great analysis! I've been working on a startup merchandising site (StartupThreads) so I think about this a good deal. A few tips from working with companies:<p>1) Make it interesting - Tie your design into the ethos of what your customers care about. This can compelling beyond just your logo/brand (An Example by CloudMine: <a href="http://on.fb.me/MD9E0W" rel="nofollow">http://on.fb.me/MD9E0W</a> and AngelHack <a href="http://on.fb.me/Mmn8CM" rel="nofollow">http://on.fb.me/Mmn8CM</a>)<p>2) Fit & Quality Matters - Spend the extra few dollars to get a decent American Apparel shirt, as it will fit better and stand out amongst the bargain bin shirts that most startups hand out (order womens sizes, guys). Increases the likelihood that they will wear it more than average shirt.<p>3) Make It Exclusive - There are varying strategies on this, but it is my observation that giving it out to those who really care about your company is the best way to go. You don't want the receiver to feel like you are bribing them to try their service/product. It works better if you are thanking them for their loyalty, as you help to solidify that relationship.<p>4) Reduce Your Colors - Most t-shirts that you are going to put out are screen printed and the cost varies based on the amount of colors used in the design. You can get great results with a one color shirt (see stripe: <a href="http://on.fb.me/MHG7Hp" rel="nofollow">http://on.fb.me/MHG7Hp</a> or foursquare: <a href="http://foursquarestore.com/shop/product/SH_MayorCrown" rel="nofollow">http://foursquarestore.com/shop/product/SH_MayorCrown</a>). Even if you have a multicolor logo, there are likely ways to represent it with less colors and still communicate the same things.<p>5) Ask If The Printers Save Screens - If you are screen printing, have your printer save the screens they use, as it is a fixed cost that can save you money on subsequent runs<p>6) Vector Artwork (!!!) - Make sure your designer creates vector versions of your logo for print (bonus points if they do different versions for varying amounts of colors). You do not want your logo to look jagged when printed, so the best bet is to play it safe with a vector version of all artwork. (I spend most of my time dealing with this, actually)<p>Working on a full post on this, will get it out soon!