2025-12-05
In this episode of the High Functioning Podcast, host Jason Reposa sits down with Boston comedian and content creator Gary Bolles (@boyfromboston617). Gary talks about growing up in South Boston, getting clean after a rough run of bad decisions, and finally committing to stand up after his sister passed away in 2017. He shares how therapy, open mics and reps turned into paid shows, crowd work and a late-blooming comedy career. They dig into how social media actually works for comics, from clubs that want 50,000 followers to using Instagram Reels as ads to move tickets, and why you still need to crush on stage or you will not be invited back. Gary also talks about cannabis as part of his creative process, chasing laughs in a healthy way, and why he is okay being a “late bloomer” who is still living at home at 44 while he builds a real career in comedy. 00:00 Intro: The $95,000 Cat Video 02:43 Censorship Wars: Getting Banned on TikTok & Instagram 05:31 The Raw Truth: From Opiate Addict to Bank Robber 06:50 Robbing the Same Bank Twice: Why He Did It 09:50 Driving the "True Crime" Trolley in Boston 11:02 Growing Up in Southie in the 80s & 90s 15:20 Confronting Rejection: Starting Stand-Up at 43 18:40 Social Media Hacks: Why You Should Purposely Misspell Words 23:45 Watching the Pros: Mentors in the Boston Comedy Scene 30:52 Is Comedy the New High? Replacing Addiction with Laughter 36:23 Monetizing Snapchat & Facebook: How Creators Actually Get Paid 43:51 The Art of Crowd Work & Handling Hecklers 50:41 Cannabis as a Muse: Writing Jokes While "Melted into the Couch" 57:34 Why Spontaneity Beats a Script Every Time Website with all episodes: https://www.highfunctioning.show/ 21+ where legal. Nothing for sale.