Katie Sullivan with Benjamin Project Students

Katie Sullivan, founder of Streamline Family Office, will be recognized as a special honoree at the Adopt-A-Student Foundation Gala on Thursday, October 26 at Boston Seaport Hotel. When Katie is […]

Katie Sullivan, founder of Streamline Family Office, will be recognized as a special honoree at the Adopt-A-Student Foundation Gala on Thursday, October 26 at Boston Seaport Hotel. When Katie is not serving her valued clients, she can often be found at Cathedral High School in Boston’s South End, working with teens enrolled in the Benjamin Project – a bold initiative that explores the complexities of money while doing her part to level the playing field. Read more about the Benjamin Project, Katie’s brainchild fueled by unparalleled generosity and love, and why Katie’s work is so meaningful and deeply important to students in the below article.

To join us in celebrating Katie Sullivan’s contributions, visit our Gala page. 

The Benjamin Project Teaches Students About Finances Through Compassion – and Cash 

By Dan Carmody, President of Cathedral High School  

Schools, when at their very best, should serve as incubators of ideas, beacons of creativity, centers of student empowerment. They should change lives, transform lives, and even save lives. But a school alone is nothing but a building. The driving force behind successful schools are the selfless, visionary, and determined leaders who will stop at nothing to make a difference. At Cathedral High School, Katie Sullivan is one of those leaders. 

When Katie, founder of Streamline Family Office, first stepped into Cathedral High School, she did so with a self-described bold, kind-of-crazy idea, but an idea that she thought might just shift the pendulum of opportunity. Holding her right hand high and indicating, “all the money is up here,” and gesturing her left hand down low to indicate, “but it needs to get here,” Katie had a vision of how she could create change, one $100 “Benjamin” at a time. Through what seemed like a divinely sent combination of humility, wit, compassion, humor, love, generosity, and determination, the Benjamin Project at Cathedral High School was born – and Katie Sullivan began a mission that is empowering young minds in ways never imagined. 

Cathedral High School’s mission is to provide a strong, Catholic education for families who would otherwise not have access. They do so by reducing a $20,000 a year education to less than $2,000 on average per family, and for many, much less. Through the generosity and philanthropic spirit of the school’s donors and partners, no child is denied the opportunity to excel through a transformational education. Consisting of 99 percent black and brown students, most coming from some of Boston’s most disadvantaged and marginalized neighborhoods, Cathedral provides hope, opportunity, and unparalleled paths to success for every student in their care. We provide the mission. People like Katie Sullivan help us live it. 

The Benjamin Project represents Katie’s uniquely personal way of imparting knowledge, confidence, belief, hope, and, most importantly, love, on Cathedral students through a cohort model of six weekly classes.  Bringing together ten students at a time, Katie engages the group in conversations around money, and does so in a non-traditional model. Rather than a rigid financial literacy class, Katie emphases the intrinsic and tangled web of emotions, impacts, outcomes, and complexities of money: how money impacts relationships, decisions, success, failures; how it empowers or derails us; how money motivates us; how we feel with money, and how we feel without money.  And at the end of every single session, each student leaves with a full belly, an open heart, and a $100 bill in their pocket.  Unconditional, no restrictions, no strings attached – only the ask that the students commit to bringing an open mind and open heart to each class. 

Why the $100 bill if the class is really about so much more? As Katie explains, “if you want to teach someone to play basketball – and there’s no ball, and no hoop, and no court – what can they really learn? If we’re going to talk about the impact and emotions of money, it needs to be real.” 

While the content and conversation of the Benjamin Project are compelling and captivating, make no mistake about it, the energy and deep impact of the program is fueled by Katie.  Be it through her raw vulnerability to open herself up for the benefit of others, her wit and sense of humor, or her passionate repetition that “you are loved,” Benjamin Project sessions are filled with emotion, honest conversations, and an ability to trust, love, and learn.  As one Benjamin Scholar indicated, “being with Katie during the Benjamin Project was the first time I truly felt seen for who I am, not for what I look like.” 

The Benjamin Project has impacted more than 70 students at Cathedral to date, with a waitlist of students eager to participate. It is not the $100 they receive that motives the students. It is the unconditional love they receive, from one remarkable person with a bold idea to make a difference.