Sebastian Tan is a Sewickley Academy junior who already can be proud of many accomplishments, including being captain of the varsity tennis team and leading the school’s DECA career and technical club.

And this spring he’s in a new class — the Prudential Emerging Visionaries, a group of 25 exceptional students ages 14 to 18 from across the country “who have created innovative, bold solutions to financial and societal challenges in their communities.”

Sebastian was 15 last year when he began building a solution that would connect previously incarcerated people with jobs at employers seeking to hire them. Using skills he learned in computer science class, he launched OutsideConnection — — about a year ago, and he says it’s already offered access to jobs to more than 10,000 people returning from local, state and federal correctional facilities.

His family’s business, My Sweet Lilly bakery in the Strip District, was hiring previously incarcerated individuals “before I was born,” he says, because his aunt who owns it “wanted to give back.” When he started working there, he learned firsthand how those jobs help those workers as well as provide the business tax benefits.

During and after the COVID-19 pandemic, he recognized, such connections could be even more beneficial for employers having difficulties finding people who wanted to work, and so that pushed him to build out the site. So did the connections he made with other groups working to help “reentrants,” such as the Allegheny County Anchored Reentry Coalition.

Now OutsideConnection works with many other agencies, including the Department of Justice via its National Reentry Resource Center, and Tan, amid everything else he’s doing, is working to grow and improve it.

For instance, although he runs it now as a free nonprofit, he’s looking into how some employers might pay an annual fee to hire these employees.

For a high school student to be so into something like this is “remarkable,” agrees Kevin N. Tyler Sr., who is the executive director at Re-Entry Coaching Academy, or ReCA, that works with Sebastian and OutsideConnection. They met at an ACAR summit in Pittsburgh and wound up having Sebastian speak to people in a ReCA career wellness program here.

Sebastian Tan presents his OutsideConnection nonprofit at the 2023 summit of ACAR, the Allegheny County Anchored Reentry Coalition. (Robin Roop)

“Boy, I was so impressed,” Tyler says. “He’s doing some amazing things,” including helping to keep some men and women from going back to incarceration.

“My hope is that more kids look at a Sebastian and say, “Wow, it’s OK to be smart. It’s OK to be impassioned,’ ” Tyler adds, noting that, “We look forward to continuing the partnership and growing with him.”

Tyler, who is in the Baltimore area, plans to come to this year’s ACAR summit, which is on April 26 at Community College of Allegheny County on the North Side. But Sebastian is going to miss it, because Prudential Financial is sending him and the other Emerging Visionaries — 20 Societal Solutions for a Changing World Award winners and five Financial Solutions for a Changing World Award winners — to another summit at its headquarters in Newark, New Jersey, that will be three days of coaching and networking. Not only are all expenses covered, but also Prudential is giving each student $5,000 to “take their projects to the next level.”

Five financial solutions winners will pitch their ideas to a panel of judges to win a grand prize of an additional $10,000. And Prudential employees will vote to name an Employees’ Choice Award winner, who will receive an additional $5,000.

Tan plans to use his money to improve his site’s back end, which is “complicated” for how it finds and presents thousands of jobs from dozen of employers. Otherwise, “Right now, the main thing is adding more people” to help him run the service — perhaps other high school students who share his interest in social entrepreneurship.

“I do this work because I enjoy it,” he says. “I find it fascinating when solving large problems, whether it be in reentry, mass incarceration or in other areas like poverty. It’s cool to think of new solutions to old problems. It’s certainly a struggle sometimes when working on difficult things, but that’s expected when some issues haven’t been done before. It’s a combination of diligent work and small payoffs that keeps me going. The journey will always be my favorite part.” 

He plans to study sociology and public policy in college, and he’d like to do it at Stanford, which would be another accomplishment.

It’ll be a lot of hard work, but he also knows that sometimes you just get lucky. Mail from Harvard’s alumni association to a former tenant of his family’s house is how he learned about Ashoka, an organization that finds and creates changemakers like him with the help of partners such as Prudential.

Tan is entering some other such competitions. Stay tuned.

“It feels pretty good to win this award! However, even without the recognition, I would do stuff like this anyway.”

All the winners were chosen based on four main criteria: Their solution is innovative; it will create meaningful impact and can grow beyond the student’s community; it demonstrates a deep understanding of the issue it addresses; and the student is passionate about making change and inspiring others to take action. Read about all the Emerging Visionaries here.

For more information about ACAR and its April 26 reentry summit in Pittsburgh, visit

Sebastian Tan. (Robin Roop)

Bob, a feature writer and editor at the Pittsburgh Post-Gazette, is currently on strike and serving as interim editor of the Pittsburgh Union Progress. Contact him at

Bob Batz Jr.

Bob, a feature writer and editor at the Pittsburgh Post-Gazette, is currently on strike and serving as interim editor of the Pittsburgh Union Progress. Contact him at