Part of the problem is that selling to small/medium business sucks, unless you can make it very transactional (the cheap model above, just scaled per-seat). Any

Part of the problem is that selling to small/medium business sucks, unless you can make it very transactional (the cheap model above, just scaled per-seat). Anything that needs to be hands on costs you almost as much in labor costs as big company ... without the high-price point to justify it. My very first personal ISV "hustle" was a classified ad product for desktop publishing. I priced it at $750, and discovered that my cost of sales and support made this untenable. Now I know why small desktop publishers were doing classified ads by hand, and the really big companies had mainframe- and minicomputer-based systems costing five or six figures in the 80s and 90s. Same dynamic, and all it took was my car being repossessed to make me realize there was something wrong with my business model.