Gerald Chertavian

Gerald Chertavian


Year Up

Chicago, IL USA

You have to believe you can do it before you can do it.


By Roadtrip Nation

Gerald Chertavian


My road in life has been direct.
I grew up in Lowell, Massachusetts, and went to one of the toughest high schools in the city, where the idea of being a good student was met with ridicule from other students.
When I went to college and got good grades, I realized that there’s a whole world of people out there who will be happy for you when you do well and succeed.
I started working with the Big Brothers program in college to help mentor and care for young boys who don’t have father figures.
After college, I was working on Wall Street and mentoring a boy from a rough neighborhood in New York—it opened my eyes to the lack of opportunity people face based on their upbringing or skin color.
I made it a personal mission to eventually start a program to help close the opportunity divide in the U.S. and give urban communities access to the training needed for secure career opportunities.
I went to graduate school for my MBA and then co-founded a technology consulting and software development firm.
After six years, we sold the firm and I founded Year Up, a workforce development organization that provides young adults with the skills and training needed to reach their professional potential.
I’ve been running Year Up for 20 years, raised a family of my own, and still actively participate in the Big Brothers mentoring program.
Keep following my journey



I help run a workforce development organization with a mission of closing the opportunity divide.

Career Roadmap

My work combines:
My work combines:
Teaching / Mentoring

Day to Day

Half my time is external with donors, corporate partners, and other key stakeholders. The other half of my time is spent internally on culture, strategy, management, and people.

Advice for Getting Started

Here's the first step for professionals

Work for a great social entrepreneur as their assistant, even if it is a job you think you are over-qualified to hold. You will do and learn a bunch of interesting things, get great exposure, and make some awesome contacts.

Recommended Education

My career is related to what I studied. I'd recommend the path I took:


The Noise I Shed

From Family:

"Your nonprofit idea is laughable."

Challenges I Overcame