Pentorship is an organization with a mission rooted in providing incarcerated, and formerly incarcerated people access to programs that promote entrepreneurial thinking, innovation, and personal development. Today, the organization acts as a private foundation whose primary focus is to support the alumni of its former programs and the returning citizens community at large.



Our goal at Pentorship is to “Reinvent The Will”. We believe returning citizens deserve an opportunity to change the outcome and trajectories of their lives with dignity. The “Reinvent The Will” mini-grant was established in 2019 to support individuals with a small investment that can be used towards their professional development endeavors as they reestablish their new lives.

Grant DEtails

Grant Amount: $500.00

Award Frequency: Monthly (1 grantee)

Grant Cycle: Accepting applications on rolling-basis


Applicant Requirements

  • Pentorship Program Alumni (SquareUp In-Person Course)

  • Formerly incarcerated individuals who have completed the SquareUp Course offered via (

  • Formerly incarcerated students who have completed the SquareUp Course via *partner organizations.

Grantee Responsibilities

  • Must be willing to review future applications and select prospective grantees.

  • Must be willing to use the fund towards professional development expenses.

Examples of Possible Uses:

  • Startup/Small Business Investment

  • Industry Conference/Professional Networking

  • Education/Training Courses

  • Professional License/Certification

  • Resume Help/Personal Branding

*If you are unsure as to whether or not your course was offered through a qualified partner organization, please contact us at