Things look pretty good for the Smalltalk business, even in the beginning phases of a fairly nasty looking financial mess. Here at Cincom we had our best year ever, and things look good going forward as well - we have a nice mix of new business and growth in our existing customer base.
One of the very cool things that's happened over the last few years has been the growth of Seaside. It came out of the open source (Squeak) community, and every vendor either has support now (like Cincom), or has announced that support is imminent (like Instantiations). This means that anyone building a web app in Smalltalk can feel pretty confident about their options: it's no longer a one dialect game.
Interested in taking the plunge? Just head on over and download Cincom Smalltalk now - we offer free, unlimited trials. Don't take my word for it - give it a try yourself, and check out Smalltalk Daily for help.
Don't let the Enterprisey types confuse you - Smalltalk is the real thing.