After high school, Evan diverged from his family's legal tradition and pursued a career as a comedy writer. The entrepreneurial spirit within Evan Samlin led to the founding of REIL Capital in partnership with his cousin Ian Samlin, on March 16, 2017. During the challenging times of the COVID-19 pandemic, Evan and REIL Capital demonstrated their philanthropic commitment by donating over 200,000 masks to local small businesses, aiding their survival and resilience.