They're willing to put up with a niche language like Squeak because the framework is so productive, lowering the total cost of development dramatically, and improving time to market.
Furthermore, we needed to improve significantly our response time to deliver solutions in order to meet market and financial goals, while lowering our implementation costs.
By lowering his rate and starting out on contract, this candidate showed his willingness to mitigate the risk his prospective employer would be taking on by hiring him full-time.