Authenticity Tops AI: Predicting Podcasting’s Future with Jason Calacanis

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 & All-In), 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 & All-In)

Conversations over Impressions – You can get your fill of impressions almost anywhere, but you should know you’re encouraging the conversation wherever you are investing your dollars. It’s a luxury to have so many shows to support; you can actually find some you believe in that can also be successful for your brand. And it’s more futureproof too. Jason believes there’s always a place for  “people who can create new things in the world.” Support the creators bringing new things into the world that align with your values. Their fans will support you too.

The George Lucas Alley-Oop – You miss 100% of the moments you’re not present for. Skilled interviewers (like Jason, who studied Charlie Rose, Howard Stern, and Oprah) can sense when the moments audiences crave appear. That’s when they go off-script and discover something new. Stay on the old track, and you’re like the interviewer who asked George Lucas about merchandise, ignoring an alley-oop about Lucas’ life-changing car accident. Marketers: this is paramount for host-reads. Let the experts shape the moment for their audience; just find ways to support them.

Remember the Trough – The most valuable journeys you take in life are often marred with a trough of strife somewhere along the way.  Expecting that dip means you’ll be more prepared to stick it out. This advice applies to Y-Combinator, Tim Ferriss studying Mandarin, and Jason learning to play pickleball with his daughter. In an AI future, many tasks could be easier. The things that are still hard will be valuable, and will need practiced resilience to succeed.

See the future in Jason’s crystal ball by tuning in to the full episode below