meet rsyp staff:

Ananda Timpane, Executive Director
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AnandaAnanda is Executive Director at Railroad Street Youth Project (RSYP). Ananda grew up in South County, attending the Stockbridge Plain School, the Great Barrington Steiner School and Hawthorne Valley High School in Ghent. She graduated from Oberlin College in 2002 and is a Masters candidate in the Social Justice Education Program at the University of Massachusetts Amherst. From 2004-2009, as an Outreach Educator at the Berkshire Violence Prevention Center, Ananda worked with South County youth to prevent sexual harassment, relationship and sexual violence. While at UMass Amherst, Ananda was the Education and Prevention Specialist at the Center for Women and community where she taught and supervised their Educator Advocate program until 2012. In her current role at RSYP, Ananda continues to support youth with the behind the scenes work it takes to run a small youth organization day-to-day. When she is not at RSYP, Ananda hangs out with her dog, Stella, reads, and keeps tabs on current pop culture trends with a healthy dose of TV watching.

Jocelyn VassosApprenticeship & Mentoring Director
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JocelynJocelyn was born and raised in the Berkshires, graduated from Monument and has spent a lot of time hanging out on Railroad Street. After high school she left town for college, then came back to the Berkshires, then left again, then came back, left again and now back again (for good)! During her time away she worked at Academy of Swift River as a residential counselor and alumni counselor. Six years ago she decided to take a turn in her career and pursue a long-time passion of photography and went back to school to become a professional photographer. As serendipity would have it, at the same time Jocelyn was planning her move back to the Berkshires, Railroad Street Youth Project was hiring. Understanding first hand some of the struggles that Berkshire living presents for youth, Jocelyn was thrilled at the opportunity to be an advocate for the youth of Berkshire county. She has been with RSYP for  2 ½ years and some of her favorite moments have been impromptu games of Apples to Apples, spray painting leaves and playing Dance-Dance Revolution (to name a few).

Luisa Leija, Deputy Director
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LuisaLuisa is a California Native- born and raised in THE BAY where she made her mark in the Non-Profit and Youth Development fields.   In Oakland, Luisa worked with Bay Area Community Resources as a site-based After School Coordinator and a regional After School Programs Manager.  In these two roles, she led the strategic design and implementation of new out-of-school time programs for youth, K-12.   Luisa has also worked as a Teaching Artist, Teacher Coach, and Director of Programs with Streetside Stories, in San Francisco.  Aside from that, her work as a community organizer has led her to gather people of all ages around traditional Mexica & Native American rituals to connect with teachings that have been suppressed over generations of conquest and colonization in the Americas. In her spare time she writes, trains for ½ marathons, learns about nutrition, TCM, practices yoga, watches movies, holds women’s circles, rides her bike through the rolling Berkshire Hills, and looks for pretty much anything to be fascinated about.

Will Syldor, Jobs & Careers Coordinator, AmeriCorps MA Promise Fellow
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Will_SyldorWill Syldor is the current AmeriCorps Massachusetts Promise Fellow serving at RSYP. His role is the Jobs & Careers Coordinator. He’s a Brockton native and has found himself going farther and farther east. He identifies proudly as Kiskeyano, slang version of Quisqueyano, which is a Taino name for the Island of Haiti/The Dominican Republic. Will spends his free time playing baritone ukulele and working towards social justice. He has worked for a stadium, a camp, a dining hall, and as a driver, becoming a pretty well-rounded person. In his role at RSYP, Will works with young people concerning jobs, careers, and academic support, believing that it is not youth who are maladjusted to society, but society that does not care to meet many youth where they are at. Will teaches how to maneuver for survival, not how to destroy yourself in order to become more palatable for employers and school systems. This is rooted in his belief in critical reflection and teaching for social change. The red star on his hat is from the Zapatista flag.

Alex Lenski, Mentoring Coordinator
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Alex at Open MicAlexander Lenski joins the team as the Mentoring Coordinator. He recently served a year as an AmeriCorps Ambassador of Mentoring, a collaboration between Child Care of the Berkshires, Inc. and the Mass Mentoring Partnership of Boston. At RSYP, Alex is the “matchmaker” for the qualitative and enjoyable relationships entrusted between youth and adults. Graduating from the Massachusetts College of Liberal Arts with a B.A. in English/Communications and B.S. in Middle School Education, Alex wound his way co-founding its Education Club, serving as a peer mentor with Barrington Stage’s Playwright Mentoring Project, and joining a family of rugby players. Alex is excited to return to the inspiring work of empowering youth with more resources to enjoy life, and find their niche in the world.

Leandro (Leo) Rosa, Counselor


Leo was born and raised in NYC to Dominican parents. He has a Bachelor’s of Science in Physical Therapy from Springfield College and completely changed careers obtaining a Master’s Degree in Social Work from Hunter College in NYC. While at Springfield, Leo was the president of the Student Society for Cultural Diversity and comes to RSYP with over 11 years of experience in Social Justice and Social Work. Leo is also on the Board of Multicultural BRIDGE, works at Eagleton School and continually works on spreading himself thin. In his spare time, Leo loves to read, dance Salsa, Merengue, Bachata and eat food from all over the world. He is continually adjusting from “city-life” to “country living” in the Berkshires.

Luiza Trubka, YOB & Drop-in Coordinator
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LuizaLuiza is the Youth Operational Board Coordinator. She was born in New York City but raised in Berkshire County. After attending two years at Monument Mountain High School she attended four years at Bard College at Simon’s Rock where she studied Cross-Cultural Relations. During her senior year at Simon’s Rock Luiza served as an intern at RSYP helping to organize community events. In the spring of 2013 Luiza was hired to be the RSYP staff organizing the 411 in the 413 Youth Development Conference. In the summer of 2013 she took on the responsibility of the Youth Operational Board Coordinator. Together with her two youth interns, Luiza co-facilitates the weekly YOB meetings; a group of youth and community members who meet once a week to discuss current issues, bring youth together, and provide funding for youth inspired projects. Luiza loves to travel, read, dance, make art, and has learned all she knows about Ping Pong at the Drop-In Center.

Stella, Puppy in Residence

StellaStella joined the RSYP team as the Puppy in Residence this past summer at 10 weeks old. She is currently attending Real Life Obedience School in Egremont, MA, while completing her on the job residency. Stella works directly with youth and staff to bring laughter and fun to the Drop-in Center and conduct outreach to youth around town. In her time off, Stella enjoys hanging out at the dog park, long walks and playing tug with just about anyone.