This chapter discusses the need to develop financially sustainable organizations in order to ensure that Telehomecare is able to support the delivery of care. The author combines her experience in care delivery, health management, health business investment and running companies to introduce a set of challenges facing the successful implementation of Telehomecare in the United Kingdom. She suggests ways to overcome these challenges, in particular, the lack of meaningful evidence that Telehomecare brings about desired health care objectives, the need to simplify Telehomecare by making it more informatics driven and the need to focus on the needs and outcomes for individuals using the system rather than the system itself.