Data were collected by means of a mail questionnaire survey of 174 inmates of nine prisons ranging from young offender institutions to high-security, local, and open prisons. Responses came from 87 inmates in seven prisons, as well as the 57 inmates in the pilot survey of Leyhill open prison. A similar survey of probationers received only one response; therefore, a followup survey was conducted that received responses from 52 probationers. Surveys were also conducted of prison education officers and probation officers. Results revealed that prisoners may be more entrepreneurial than other occupational groups, although probationers are not. Findings suggest that a high proportion of both groups of offenders had worked in their own businesses in the past and thus may benefit from specialized small-business training or support that can address their particular needs. Although prisons generally offer training, probation agencies do not, and little coordination of this training appears to exist between agencies. Tables, notes, and 23 references (Author abstract modified)