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Gerald Chertavian, CEO and Founder of Year Up

Gerald Chertavian’s BIO

Gerald Chertavian

Gerald Chertavian is dedicated to closing the Opportunity Divide that exists in our nation. Determined to make his vision a reality, Gerald combined his entrepreneurial skills and his passion for working with urban young adults to found Year Up in 2000.

An intensive one-year training and education program that serves low income youth ages 18-24, Year Up provides the technical, professional and communication skills needed to empower urban young adults to make successful transitions to careers and higher education. With its annual operating budget exceeding $50M, Year Up is one of the fastest growing non-profits in the nation. It has been recognized by Fast Company and The Monitor Group as one of the top 25 organizations using business excellence to engineer social change. Year Up has also been named one of the nation’s top 50 non-profits to work for by the Non-Profit Times.

Gerald’s commitment to working with urban youth spans more than 25 years. He has actively participated in the Big Brother mentoring program since 1985 and was recognized as one of New York’s outstanding Big Brothers in 1989. He is the recipient of the 2003 Social Entrepreneurship Award by the Manhattan Institute and the 2005 Freedom House Archie R. Williams, Jr. Technology Award. In 2006, Gerald was elected as a Fellow with the Ashoka Global Fellowship of social entrepreneurs, and in 2008, he was appointed by Massachusetts’ Governor Deval Patrick to serve on the MA State Board of Elementary and Secondary Education.

Gerald began his career on Wall Street as an officer of the Chemical Banking Corporation. Following graduate school he co-founded Conduit Communications and fostered its growth to more than $20M in annual revenues and more than 130 employees in London, Amsterdam, New York and Boston. From 1993 to 1998, Conduit ranked as one of the UK’s fastest growing companies. Following the sale of Conduit to i-Cube in 1999, Gerald turned his full attention to opportunities for others.

Gerald earned a B.A. in Economics, Phi Beta Kappa, summa cum laude, from Bowdoin College and an M.B.A., with honors, from Harvard Business School. He has received honorary doctorates from the Massachusetts School of Professional Psychology and Mount Ida College. He is on the Board of Advisors for the Harvard Business School Social Enterprise Initiative, a former Board member of The Boston Foundation and an Emeritus Trustee of Bowdoin College. His 2012 book, A Year Up, was a New York Times best seller.

More information about Gerald Chertavian can be found here:


1. Please share with us what prompted you to create Year Up?

Gerald: My first job out of college was on Wall Street, and I tried to find some balance in my life by volunteering as a Big Brother on Saturdays. I was matched with an eleven-year-old boy named David, who lived in the Rutgers Houses on the Lower East Side. At the time, the neighborhood was considered one of the most heavily photographed crime scenes in the world. The crack epidemic had hit David’s neighborhood hard, and I can vividly remember stepping over empty vials on my way into the building. When I first started going, I was legitimately afraid every time I walked into projects.

But I quickly learned that some of the people who lived in the Rutgers Houses, who had been written off by society as economic deficits, were among the most talented people I’d ever met in my life. David, I discovered, had a gift for art and a passion for animation. During the Saturdays I spent with him, it struck me that the talent and potential of so many people around him were going to waste, at a time when our country didn’t have any talent to spare. I started dreaming of a school that would help connect the talent that was lying overlooked in our urban neighborhoods to the mainstream economy that was in dire need of it, and wrote my admissions essay for Harvard Business School about that goal. I never let go of the idea, especially as I watched David grow into a successful animator in Los Angeles. When I sold Conduit Communications in 1999, I found myself with the opportunity to dedicate the rest of my career to making it a reality.


2. There is no typical day in the life of an entrepreneur. Please share with us a sample of your day, start to finish.

Gerald: I spend about 60% of my time working with external stakeholders and/or visiting with Year Up sites around the country. I spend a lot of time building relationships with corporate executives, philanthropists, and public officials who are interested to get involved with our mission. The balance of my time is spent with our national staff and Board members, helping to guide the organization forward and realize our strategic plan. If I am on the road, I might meet with four or five different individuals throughout the day, starting with breakfast and finishing around 5pm, and I try to squeeze internal calls in between while leaving me enough time to get some work done. If I am on the East Coast, I usually try to get back to Boston that evening to see my family. It takes a fair bit of coordination, although I am fortunate to have a great team that helps to make my days smooth.


3. What are your ‘can’t live without’ Smartphone or desktop applications?

Gerald: When I am traveling, I use 3 different weather apps (weather underground, accuweather and The Weather Channel) and try to triangulate on what is actually going to happen. For news, I love the HuffPost app on my Ipad as it has the best interface by far. And as Thursday rolls around, I am always looking at AllSnow in the winter and Surfline in the summer to see what the weekend is going to hold.


4. What are your tricks for time management?

Gerald: I´m always looking to get better at this and don´t claim any magic tricks. Every quarter, I take stock of my priorities and look hard at where I am spending my time and how it’s helping me to reach those goals. I also try to cut down on email by sending everything I am cc’d on to a different folder, which I only look at every few days. I take the subway to and from work and clean up my inbox during that time. At the end of the day, I still find that most nights I get back on my PC after the kids go to bed to close out things from the current day. Perhaps my best time management trick is being fortunate not to need a lot of sleep!


5. What was the best advice you received when you started your career?

Gerald: Reputations are earned very slowly and lost very quickly. It was given in the context of the 1980s on Wall Street, but it’s something I’ve kept front of mind throughout my life since then.


6. Given the current economic climate, what has been your strategy for building awareness of Year Up for short-term and long-term growth?

Gerald: The single greatest strategy for our success is the continued success of our students and alumni. Helping them to reach their potential doesn’t just help them; it helps our corporate partners to grow their businesses. That’s why 250 of America’s leading companies are eager to hire our interns; their sitting on a mountain of cash, have millions of vacancies, and are in dire need of talented employees, even in a time of high unemployment.
We meet a real business need, and I think that speaks to people; it certainly speaks to businesses. We do also have a small marketing team, as well as great people working on our development team and on our systems change work, but the core of our messaging is always the strength of our alumni and the value they add to their companies.


7. What is your proudest achievement as an accomplished entrepreneur?

Gerald: The success of each of our alumni is what makes me proudest. There are more than 3,500 of them now, and that number will continue to grow in the years to come. Each of those alumni has a ripple effect on their community; imagine the total impact of creating thousands of new role models. There have been other triumphs along the way – hosting President Obama at our Washington, DC site in 2009, and receiving results of an independent randomized control trial that found our students to be out-earning their peers in a control group by 30%. But ultimately, helping our alumni to reach their potential is my proudest achievement.


8. How do you achieve balance in your life?

Gerald: I put all of my kids´ school commitments in my calendar at the beginning of the year and then schedule my travel around that. I also avoid sleeping away from home unless I am traveling to the west coast. That means 4am starts, but also means I read a lot more bed time stories. I rarely work on weekends and tend to head to either the mountains or the beach with the family on Friday night. Lastly, for the last twenty years, my wife and I have had a standing Sunday night movie date.


9. Your top 3 book recommendations?

Gerald: I´m a self-help guy so The 7 Habits of Highly Successful People is something I recommend to a lot of young professionals. For parents, I absolutely love the book Children Are From Heaven, and have probably given it to 50 people already. Also, if you are trying to manage a company, I think Daniel Pink´s book, Drive, is very thought provoking.


10. What are your most rewarding charitable involvements?

Gerald: Year Up takes the majority of my time, although outside of that I have been an active Big Brother for 25 years and always try to support the Big Brothers Big Sisters organization.

Year Up also puts together a team of cyclers each year to ride in the Pan Mass Challenge, and so far we have raised more than $700,000 for cancer research. It’s an extremely challenging and rewarding weekend for us every summer and one that I’m very proud to take part in.


11. Who has influenced your career the most?

Gerald: My Little Brother, David Heredia. Year Up exists today because of him and the time we’ve spent together. I’m so grateful to have been matched with him twenty-five years ago.


12. What is your advice for someone interested in entrepreneurship?

Gerald: Learn on someone else´s dime before you risk your own. When you come out of school, don´t worry about your title or the perceived prestige of a job. Rather, focus entirely on the quality of the people you are going to work with, and who is going to really push your learning/professional development. If you can establish those two things, and the company is growing fast and is high performing, then go for it! You will be richly rewarded and grow a lot more quickly than many of your peers.

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