On a surface level, information system development (ISD) consultancies adopting entrepreneurial and minimalist characteristics offer a disruptive alternative to software professionals. These companies typically minimize company overhead costs, and their workers maintain entrepreneurial status, enabling e.g., staff augmentation workforce to keep a larger portion of their billable hours to themselves. In this study, we examine this emerging form of employment through interviews with company founders. Through reflexive thematic analysis we discover the following tensions within the workforce who have migrated to the new work arrangements: (1) while workers are looking to maximize the compensation for their work, most still require and seek job security; (2) while workers do not wish to spend money on social gatherings, they still value a sense of belonging at their workplace; and (3) while workers gravitate towards working with skills they already have, most still feel a need to develop themselves as programmers.