One Founder’s Journey of Championing Second Chances and Building a Future of Hope

Meet Daily Point of Light Award honoree Sebastian Tan. Read his story, and nominate an outstanding volunteer or family as a Daily Point of Light. 

As the founder of OutsideConnection, a groundbreaking online job platform built on the central tenets of hope, second chances and transformative impact, Sebastian Tan has dedicated his life to providing welcoming employment opportunities for individuals returning from prison. Sebastian’s own journey began in the humble setting of his family’s bakery, but his vision has since expanded far beyond those walls, touching the lives of thousands across the country. 

Sebastian’s early exposure to a diverse workforce at his aunt’s bakery in Pittsburgh laid the foundation for his lifelong commitment to social justice. “When I first stepped foot into our family bakery at the age of 7, I immediately became accustomed to a culture filled with a diverse range of people,” Sebastian recalls. Working alongside reentrants—individuals who have been previously incarcerated—he quickly learned that they were more than just employees; they were part of the family. This early experience shaped his understanding of the challenges reentrants face in finding stable employment, a problem that would later become the driving force behind OutsideConnection. 

The idea for OutsideConnection was born out of necessity. During and after the COVID-19 pandemic, businesses across the country struggled to find new employees. At the same time, the stigma surrounding hiring reentrants began to soften. “Taking advantage of this, I started OutsideConnection, a free second-chance job platform that has helped our business and local businesses alike employ reentrants while also supporting our local communities,” Sebastian explains. 

What began as a local initiative quickly gained national traction. Today, OutsideConnection has helped over 10,000 reentrants gain access to employment opportunities in 34 cities and 17 states. The platform boasts over 1,900 job positions from 40+ second-chance employers, and its impact has not gone unnoticed. Last year, the U.S. Department of Justice adopted the program, further amplifying its reach and potential. Despite the significant strides OutsideConnection has made, Sebastian’s work is far from finished. With over 19 million Americans holding criminal records, he is determined to expand the platform’s reach.  

“Looking forward, I imagine transformative expansion for our project,” he says. His goals include expanding operations to the remaining 33 U.S. states, hiring more staff to support the platform’s growth and increasing the number of job listings to meet the demands of reentrants across the country. He also envisions more state Departments of Corrections adopting OutsideConnection, ensuring it becomes an integral part of governmental resource programs. 

Sebastian’s journey with OutsideConnection has also been deeply personal. “As we’ve grown, so has my passion for social justice, labor economics and entrepreneurship in the reentry field,” he shares. The impact of his work is felt not just in numbers but in the lives he’s touched. “From glimpsing smiles, embracing hugs and hearing thank-you’s, I’ve become motivated by the personal impact I’ve made on each and every individual,” Sebastian says. Through these experiences, he has gained invaluable insights into the systemic barriers reentrants face and the importance of providing stable employment as a means of restoring dignity and fostering hope.

“Volunteering in something you believe in is important because it enables you to effect positive change in the lives of people as well as give you first-hand experience on the causes that are dear to your heart,” Sebastian says. His advice to those looking to make a difference is simple: find something you’re passionate about and start, no matter how small. “Something you have, the skills and knowledge stored inside you, can make a big difference—so use it.” 

Sebastian’s journey has been one of perseverance, driven by a deep-seated belief in second chances. His work with OutsideConnection is not just a professional endeavor but a personal mission that continues to shape his worldview. “My work with OutsideConnection has taught me invaluable lessons about justice, dignity and the power of second chances,” he reflects. These lessons have been integral in guiding his approach to creating long-term solutions that address the systemic barriers faced by reentrants.  

Sebastian also believes in the importance of nurturing the next generation of leaders and changemakers. OutsideConnection currently employs over 60 youth workers, a number he hopes to grow as the platform expands. His message to young people and aspiring volunteers is clear: “When it comes to volunteering, it is important to look for an organization or campaign that you are passionate about.”  

Sebastian himself is not only building a stronger community but also inspiring future leaders to continue the work he has started. His commitment to empowering others ensures that the impact of OutsideConnection will be felt for generations to come, as the platform uplifts and equips one reentrant at a time. 

Do you want to make a difference in your community like Sebastian? Find local volunteer opportunities.