Authenticity Tops AI: Predicting Podcasting’s Future with Jason Calacanis
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The way to thrive in an AI future? Be authentically human.
This week on The Media Roundtable, you have a VIP ticket to SXSW 2026 for the iHeart x Oxford Road Luncheon, with a podcasting powerhouse who consistently sees over the horizon.
Dan Granger (CEO & Founder, Oxford Road) chatted with Jason Calacanis (Angel investor & Host, This Week in Startups), to break down the current state of podcasting and what’s next. What do they agree on? AI can’t outperform human connection.
The team takes on: Conversations Over Impressions, Remember the Trough, The George Lucas Alley-Oop, and more. Let’s dig in.
“ In a world of unlimited impressions, what matters? It's that authenticity and aligning yourself with the conversations that matter.”
-Jason Calacanis (Angel investor & Host, This Week in Startups)