Grantee
Spotlight
Catalytic Partners, Lasting Change
At Greenbridge, our goal is simply to find the right organizations at the right time. Whether that means supporting a visionary leader as they scale, helping a founder establish a proof of concept, or stepping in as an organization launches into a new market, we aim to be flexible, responsive partners on their journey toward systemic change.
We created this Grantee Spotlight to celebrate that collective impact, bringing together a rotating mix of our current partners alongside alumni whose work we remain deeply proud to champion. Though they span different sectors, approaches, and stages of growth, each shares an unyielding commitment to pushing boundaries and creating lasting, scalable change. We are privileged to stand behind them, and we invite you to check back regularly as we continue to celebrate their impact.
FreeWorld
What They Do
FreeWorld is on a mission to end mass incarceration and generational poverty by creating legitimate pathways to economic mobility. Recognizing that a lack of stable income is the primary driver behind individuals returning to prison, FreeWorld connects justice-impacted individuals with high-wage careers in the trucking industry. By streamlining the path to earning a commercial driver's license through an accessible, tech-enabled platform, FreeWorld bridges the gap between a massive trucking industry labor shortage and a community of individuals eager for a true second chance. Their holistic approach replaces a cycle of hopelessness with financial freedom and a stable future.
The Leader
Through the help of Matt Mochary, Jason Green, and Andy Bromberg, Founder and CEO Jason Wang built on top of their original concept to develop FreeWorld, largely influenced from his own lived experience. After being justice-involved as a young man and serving a 12-year prison sentence, Jason overcame the odds to earn a full scholarship and a double master's degree. Yet, despite his extensive educational credentials, he repeatedly found doors slammed in his face by employers who could only see him for his past. Recognizing that his struggle was shared by millions of returning citizens, Jason chose to use his unique perspective and first-hand understanding of the reentry system to drive systemic change. His vision is rooted in an unshakeable belief that people are not defined by their worst mistakes, and that meaningful work is the ultimate vehicle for human dignity. Today, his groundbreaking leadership is widely celebrated; Jason is a past winner of the Pegasus Prize for social innovation and recently took home the top honor at the 2025 Truist Foundation Inspire Awards in collaboration with MIT Solve.
The Impact Realized
Now in its fifth year of operation, FreeWorld is a thriving national organization that has supported over 20,000 formerly incarcerated nationwide and forever changed the lives of over 2,300 commercial drivers license graduates. Their remarkable, human-first model has achieved massive economic and systemic impact:
$543M+ created in estimated graduate lifetime earnings, completely rewriting the economic trajectory for thousands of families.
A recidivism rate of less than 5%, shattering the national average of approximately 50% and creating over $45M+ in marginal recidivism cost savings.
An extraordinary return on investment, where every single dollar FreeWorld spends generates more than $23 in social impact and $8 in government impact via increased tax revenues and reduced public assistance costs.
Greenbridge was the very first financial supporter (along with Matt Mochary) when we first partnered with Jason Wang to create FreeWorld. Jason Green has served as its Founding Chairman since inception and still plays an active Board role. We recognized something truly rare in Jason’s Wang’s ambition, leadership and vision. Greenbridge’s early bet on FreeWorld’s leadership capacity helped turn a bold vision of second chances into a scalable engine of economic freedom. Today, that investment continues to pay dividends across the country, transforming the lives of returning citizens and proving that real economic mobility is the ultimate antidote to mass incarceration.