YouTuber Jason Trimond opened up about his turbulent past, content creation journey, and the backlash he faces for covering crime-related topics during an appearance on The Bounce Back Podcast with host B. Luke.
Growing up in Rockport, Massachusetts, Jason described his upbringing as relatively stable but shadowed by alcoholism in the household. Despite his family’s blue-collar background, he always had creative ambitions. However, drug addiction led him down a destructive path, resulting in incarceration at a young age.
Jason’s YouTube career started as a hobby, initially focusing on pop culture before shifting to crime stories tied to New England’s underworld. His deep dives into mafia history, unsolved cases, and street culture quickly gained a loyal audience, but success also came with criticism.
Despite occasional backlash, Jason remains committed to filling a gap in YouTube’s crime journalism space. “If it’s in newspapers and magazines, why can’t I talk about it?” he questioned, addressing the double standards he faces.
Jason also detailed his frustrating experience with YouTube’s copyright and monetization policies. He has received multiple copyright claims and community guideline strikes, often without clear explanations.
“YouTube doesn’t tell you what words or images get flagged,” he said, recalling how a video on detox centers meant to help those battling addiction was demonetized for no clear reason.
At one point, his entire channel was demonetized without warning, leaving him scrambling for answers. Despite submitting an appeal, YouTube took 10 days to respond, reinstating his monetization within 20 minutes—but never providing a reason for the initial strike.
While Jason initially focused on mob-related crime, he has expanded his coverage to Boston’s modern gang scene. Discussing Boston’s rap industry, he highlighted the struggles of artists trying to transition from the streets to mainstream success. Many, just as they start gaining traction, face legal troubles, referencing recent RICO cases involving Heat Street and Troy YJizzle.
Even for those attempting to leave the streets behind, past conflicts don’t always let them move on. Jason noted how social media fuels street violence, where maintaining a certain image has become essential for credibility in the rap industry.
Beyond true crime and music, Jason is dedicated to documenting the changing face of Massachusetts. He and his team plan to expand coverage to Lowell, Brockton, Holyoke, Springfield, Lynn, and Lawrence, providing historical and contemporary perspectives on these areas.
With gentrification rapidly altering Boston, Jason sees an urgent need to preserve authentic local stories.
“Boston is changing so fast. If we don’t tell these stories, they’ll be forgotten.”
Despite the challenges of independent content creation, Jason takes pride in building his platform organically. His final message to aspiring creators?
“Believe in yourself, silence the doubters, and chase your vision with conviction. Usually, the closest ones to you will try to talk you out of it. But if you have that burning desire, trust that it’s there for a reason.”
His mantra remains simple yet powerful: “Make good choices. It’s all we have.”
