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This bonus episode of Insider Interviews: With Media & Marketing Pros came together super spontaneously at On Air Fest in Brooklyn, where podcasters, creators, and technologists gathered recently to talk about the future of audio and, no spoiler alert, the future of AI.
After a keynote session that talked about living WITH machines by keeping humanity present I had to grab Baratunde Thurston and Terry Rice to keep talking about how creators, entrepreneurs, (and parents) are navigating exactly that. Both of these conversations landed on the same core idea as my previous episode with Jack Myers:
The real differentiator won’t be the machines—it’ll be the humans using them.
Baratunde Thurston, author, speaker, comedian, and “thought leader of interdependence,” has been thinking about this balance for years and created his podcast Life with Machines to really explore that. As he asks:
How do we live well with technology, instead of just enduring it?
Living Well with Tech per Baratunde
He’s experimenting with AI directly in his own creative process—even creating an AI character named “Blair” as a kind of co-producer on his show. But he’s also clear that there’s a line between assistance and authorship.
#AI can help with research, feedback, or execution. But the deeper creative work, like ideas, voice, perspective, still needs to come from a human.
“There’s something slower and messier about crafting things yourself—but there’s also a pride of creativity that I want to maintain.”
Baratunde, and not surprisingly after him Terry Rice, also raised an issue that’s only going to become more important: authenticity.
As generative AI content becomes harder to identify, the industry may need new ways to verify that a real person is behind what we’re seeing, hearing, or reading. Some technologists are already exploring ideas like “proof of humanity.” But Baratunde’s take was refreshingly simple:
“I think the thing we’re going to trust the most is this: I feel you. We’re sharing the same air.” (He grabbed my arm to illustrate, saying “THIS is what matters.”)
In other words, real-world presence and connection may become even more valuable in a digital ecosystem increasingly filled with synthetic content.
My second conversation was with Terry Rice, entrepreneur, speaker, and host of The Signal, a podcast designed to help entrepreneurs cut through the noise and focus on practical strategies for growing their businesses.
Terry uses AI in his own workflow, like generating prep guides before interviews (which I wish I had done for these spontaneous chats!) or organizing research.
He also got so inspired by his kids that he built a way to help parents, with a way to build their own app for their kids!
Trust me, you have to listen and hear what he did.
But he made an important distinction: the value isn’t letting AI do all the thinking. It’s knowing what good looks like.
“The real skill isn’t producing every answer yourself—it’s recognizing when something is good and when it isn’t.”
That was one of those lightbulb emoji comments. It’s also a mindset that he’s already teaching his kids. In fact, his ten-year-old daughter summed it up in a way that might be the most useful rule for all of us navigating AI right now:
“It’s okay to fight with AI.”
Out of the mouths of (this generation’s) babes. Question it. Push back. Refine the answer.
Through lines? AI will absolutely change how content gets made and how businesses operate. But creativity, judgment, curiosity—and yes, a little humanity—are still very much part of the equation.
And for now at least, that’s something machines can’t replicate. (But props to Chat GPT for helping me summarize some of this brilliance!)
Key Moments:
01:36 – Baratunde Thurston on the philosophy behind Life with Machines
02:40 – Experimenting with AI as a co-producer
03:20 – Where creators should draw the line with AI
06:43 – The emerging concept of “proof of humanity”
07:55 – Why physical presence may matter more in an AI world
10:13 – Should AI try to imitate humans?
11:10 – Could real human experiences become a luxury?
12:18 – AI’s environmental impact and future possibilities
15:54 – Build With Them AI Parenting
17:18 – A Brand Marriage: The Signal and Fiverr
19:54 – Vulnerability Builds Trust
22:47 – No Guilt Using LLMs
23:52 – Teaching Kids to Challenge AI
Connect With:
Baratunde Thurston — Author, comedian, cultural thought leader; host of Life with Machines Podcast
Terry Rice — Journalist, entrepreneur; host of The Signal and founder of Build With Them
On Air Fest
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