The Other Side Academy
Geography:
U.S.A.
Type:
DEBT INVESTMENT
Mission
Rebuilding lives through peer-led training and accountability.
The Problem: Cycles of Incarceration and Addiction in the U.S.
Across the United States, millions of individuals exit prison each year only to face the same forces that led them there—addiction, poverty, homelessness, and lack of opportunity. These systemic challenges make it difficult to truly start over, particularly for those with lengthy criminal records and histories of substance abuse.
Traditional rehabilitation programs often fall short. Many offer short-term fixes, lack accountability, or fail to provide meaningful work and support. As a result, recidivism rates remain shockingly high, with upwards of 70% of formerly incarcerated individuals reoffending within five years.
The Solution
The Other Side Academy (TOSA) is breaking this cycle by offering a long-term, cost-free residential program for individuals seeking real transformation. Instead of relying on therapists or state funding, TOSA uses a powerful peer-led model that fosters behavior change through honesty, accountability, and hard work.
Students live together for a minimum of two and half years in a peer-led community, working in self-sustaining social enterprises like The Other Side Movers and The Other Side Builders. These businesses do more than generate revenue—they are the very mechanism by which lives are rebuilt. Participants learn job skills, leadership, and integrity, all within a community committed to personal change.
The Outcomes
The Other Side Academy firmly believes that no nonprofit should exist if they don't clearly outline and measure their goals. TOSA has defined their success to be keeping individuals drug free, crime free, and employed. TOSA measures these goals.
100% of TOSA students are employed upon graduation
84% of all graduates are still employed
83% of all graduates are still crime-free
74% of all graduates are still drug-free
The Investment Opportunity
To support TOSA’s expansion and long-term financial sustainability, UI Charitable is offering a debt-based impact investment opportunity. Through your donor-advised fund (DAF), you can invest in TOSA’s continued growth while preserving your philanthropic capital.
By refinancing high-interest commercial loans with lower-interest, mission-aligned capital, TOSA can reduce its annual financing costs and redirect those savings into direct services—helping more individuals transform their lives.
Use of Funds: Property acquisition, renovation, vehicle and equipment financing
Loan Size: Starting at $50,000 (money can be pooled among several investors to reach the minimum)
Terms: 5-year loan at 4% interest, repaid quarterly
* Loans are secured by real estate or equipment assets
How to support
To learn more or make an impact-aligned investment through your DAF, contact us at impact@uicharitable.org.