Boston comedian and creator Gary Bolles (@boyfromboston617) joins Jason to talk about growing up in Southie, getting clean, and finally committing to stand up after his sister’s death pushed him to change his life. He explains how therapy, endless open mics and reps turned into paid shows, crowd work and a late-blooming comedy career, and why he is okay living back at home at 44 while he builds something real.

They dig into how clubs use follower counts to pick comics, how Instagram Reels act as ads to sell tickets, and what it looks like to balance cannabis, creativity and social media guidelines in 2024.

Listen now on Apple Podcasts, Spotify, YouTube, or at https://www.highfunctioning.show/.

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