Finding Your Path: Lessons Learned from an Investment Banker Turned Social Entrepreneur

By Gerald Chertavian

Right after college I started my professional career on Wall Street as a banker. I decided to volunteer as a Big Brother in New York City and I was matched with an eleven-year-old boy named David. David lived in a housing development on the Lower East Side that was one of the most heavily photographed crime scenes in New York. During my Saturdays with David, I quickly noticed he was a gifted, passionate artist, although he lacked the knowledge and the support to pursue his dreams. I learned that his potential was being limited by a lack of opportunity that was in part driven by his zip code, his socio-economic status, his skin color and the school system he attended.

In fact, many of the people I met in David’s housing development were extremely motivated and talented – although they lacked access and opportunity. With his hard work, commitment and a bit of my support, David graduated from college, the first in his family to do so. His dedication and abilities eventually earned him a position as an animator in Los Angeles. He now runs his own business, owns his own home, and is happily married with two beautiful children. But I never forgot about the other people in David’s neighborhood, especially as I began to hear more and more about a lack of skilled employees in the country.

Year Up was born from this experience. From 22 students in 2000, we will serve 1,900 students annually in 2013. Our mission is to "close the Opportunity Divide by providing urban young adults with the skills, experience, and support that will empower them to reach their potential through professional careers and higher education". In my journey from banker to social entrepreneur, I have been lucky enough to learn some great lessons from mentors and peers. Below are four that have guided our growth at Year Up from a small, local nonprofit to a national organization.

1) Accept you don’t know, what you don’t know

The biggest trials in launching a social venture will not be the obvious gaps or issues that you know need to be addressed. The primary challenge is figuring out what is not on your radar. The best way to solve this issue is to surround yourself with a diverse group of people with different backgrounds, experiences and point of views. They will be the ones to point out the big holes and issues in your thought process and plans.

When looking for our first rental space, I was determined to locate Year Up right in the middle of a low-income community. I wanted to meet the students where they lived. My understanding from my experience with David was that public housing complexes were insular, and I wanted the students to feel comfortable. Then came Linda Swardlick Smith, an experienced and passionate Master in Social Work, who I was thrilled to hire for my team. Linda made it clear to me – in a conversation that wasn’t easy – that locating Year Up in the Financial District of Boston was the better option. This would allow our students to begin feeling comfortable in a professional setting, and help them walk into a corporate building with their heads held high. In addition, she pointed out that we would not be dealing with one type of student, and our location needed to accommodate a diverse population. If we were to set up shop in Roxbury, it may be difficult to attract students from East Boston or Chelsea.

So we opened our first site in Downtown Crossing instead, in close proximity to all the major transit lines and that made it convenient for all groups. And moreover, the central location proved in time to be vital for hosting visitors, including the investors and corporate partners who fueled our growth.

2) Put the right people in the right seats

When hiring, it is important to look for people who are emotionally fulfilled by the mission. Making sure they are willing to go the extra mile for your cause is more important than being sure they have the perfect set of skills. Skills can be worked on and improved, especially in someone who is motivated. But an unshakable passion for the mission cannot be taught, and when times are tough and late nights are the norm, you want your staff to really believe in the work that they are doing.

I learned this lesson from the first instructor I hired, Richard Dubuisson. Richard began his childhood in Haiti, and after moving to Miami he was held back because he did not speak English. He had trouble adjusting and dealt with severe prejudice. He applied for our first open teaching position knowing I was looking for a teacher with five to ten years of experience and a master’s degree, none of which he had. But in his interview, Richard made an intriguing promise that convinced me he was the right hire: he said he would be the best teacher I would ever have, because he had been one of our students. His unwavering passion and experience led him to be the perfect fit, and one of our very best instructors for over a decade.

3) You need to be a fanatic

As Winston Churchill once said, "a fanatic is one who can’t change his mind and won’t change the subject." When starting a social venture, you are constantly selling your product, and are talking to people every day about the work that you are doing. You must have an unwavering passion, because doing that is not easy. When I started Year Up, I was out three to four nights a week just trying to connect with the right people. I would try my best to meet the "movers and shakers" in Boston and to explore whether they had an interest in getting involved in our mission. It was exhausting and thrilling at the same time.

Having said that, I’ve tried hard over the years to achieve work/life integration, which is different from work/life balance. The work at Year Up doesn’t stop at 5pm and so it has been really important to figure out how to integrate work with life outside of Year Up. It helps a great deal to have a support system around you. In my case, I have been extremely fortunate to have had a "quiet co-founder" with me at all times, my wife Kate. She was there from the beginning and has been deeply involved ever since. From setting extra plates at dinner for staff or graduates, to mentoring countless students, to interviewing potential hires, Kate helped make Year Up a reality and helped us to achieve an integration that has worked well for our family.

4) Dream big and then go to sleep, wake up and dream even bigger

Entrepreneurs are in the right position to dream big. If you are not dreaming big to solve the problem, then who is? When I wrote my first business plan, my dream was to reach 10,000 students. As we welcomed our first class of only 22 students, this goal seemed overly ambitious, and several people laughed when we told them about our aspirations. Well, we will hit the goal of reaching 10,000 students in a few years, and so we have shifted our gaze to having a national impact. To advance our vision of a country in which all 6.7 Million "Opportunity Youth" have access to meaningful career opportunities, we are adapting our program and piloting new models that are capable of reaching 100,000 people a year. We are also working to impact the systems and policies that perpetuate the Opportunity Divide. With this plan, we will reach many more young people in search of a chance to prove themselves.

Social entrepreneurs are dealing with some of the biggest issues of our day. Your ideas can dictate what our future country will look like and I firmly believe that you will be at the forefront of solving some of our most pressing social challenges. We need you more than ever and I am humbled to walk alongside you on this long road towards a more just and equitable society.

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