Prashanth Venkataramanujam

Prashanth Venkataramanujam is a stand-up comedian who started performing in high school before rising through the Chicago comedy scene - eventually building a career that spans live performance, digital content, and executive leadership in sports media, including work with major platforms like NBA digital. In this episode, I sit down with Prashanth for a conversation that starts in stand-up and quickly spirals into everything else in the best way. We talk about how he literally built a comedy scene in his friend's basement as a teenager, turning living room open mics into packed high school shows, and how that early momentum pushed him into clubs and the broader Chicago circuit. From there, we get into the psychology of being a comic, the pressure of expectations, and why good news can sometimes feel like bad news when you care too much about what comes next. There's a ton here on identity, ambition, and the weird mental math that comes with chasing something creative while trying to build a stable life. We also bounce through everything from hip-hop debates to existential questions - what it means to "make it," how you define success, and why Prashanth believes there's no real red tape in life, just systems we choose to accept or push against. Follow Prashanth Venkataramanujam: Website IMDb Instagram Facebook X (Twitter)