Can't Say "Can't" - On Willonius, our AI and more
Our first dispatch has extended thoughts, recommendations, and an AI experiment for you!
Episode 01 Launched!
This week we released our first episode of Life With Machines! In case you missed it, here it is on YouTube.
And here you can get the audio versions, but I’ll paste the Spotify edition right here.
Welcome Note
Welcome to the Life With Machines newsletter and community space. This is our first dispatch!
I want you to imagine we’re both sitting at a counter. I’m drinking a smoky cocktail. You’re drinking whatever feels good to you: tea, hot chocolate, straight vodka… it’s your imagination so fill in the blank. At this counter, I’m going to share some extended thoughts about our Life With Machines episodes and some items that go beyond that, including our experience with the AI we built to help us make the show, some recommendations for you, and an AI experiment we want you to play with. I’ll also respond to some of your ideas and questions as they arise on social media or in this space.
We are launching this at no-cost but plan on a paid subscription tier very soon. As we figure that out, though…
Now let’s get on with the newslettering!
Baratunde’s Take on the Willonius Episode
Here are three of my deeper, post-interview thoughts inspired by my time with Willonius.
(1) Relentless Creativity: What Happens When You Can’t Say “Can’t”
One story that really struck me from my conversation with comedian and AI storyteller King Willonius, the man behind the AI hit “BBL Drizzy,” was that as a child he was forbidden from saying the word “can't”—a rule he still follows. Imagine doing that! I know I can’t! See!!
This mindset didn’t just push him forward. It became the backbone of his creative life. From Delray Beach, Florida where Hollywood was as distant as Saturn, to the cultural foment of post-George Floyd Los Angeles, Willonius’s path has been defined by constant adaptation. His mother got him headshots when everyone else thought acting was impossible, and when one door closed, he pivoted—stand-up comedy became songwriting, film school led to coding boot camps, and then the AI boom opened up another door.
“BBL Drizzy” wasn’t the product of someone obsessed with technology. It was the product of someone obsessed with creativity. Willonius’s story is less about AI and more about what happens when an unstoppable creative force meets the latest tools. Whether it’s stand-up comedy, songwriting, film, or AI, he’s always shifting, always adapting. The guy can't help himself—and I think that's incredibly inspiring. Also I found a use of can’t for the man who only knows can.
(2) Is AI the Ultimate Parody Engine?
Willonius’s use of AI also reminded me of my time at The Onion, where we mastered the art of parody by perfectly imitating the formats of serious media. Whether it was a newspaper, a podcast, or a TED Talk, the genius of The Onion was in how closely we adhered to the form of what we were mocking. That fidelity to form is what made the satire really hit hard.
AI takes that concept and pushes it even further. Willonius isn’t just throwing out one-liners or sketches. He’s using AI to fully inhabit the style and structure of the things he’s parodying, creating something at once familiar and subversive. AI’s ability to metabolize and reconstitute vast amounts of content makes it an incredibly effective tool for satire, which is all about imitation with a twist.
At The Onion and at my company Cultivated Wit, we experimented with apps, social media, and other tech-driven platforms to take comedy beyond its traditional bounds. Willonius is doing the same with AI, using it to bring satire to life in a way that blends the old-school art of parody with new-school tech, and for me it’s an exciting evolution.
(3) The Future of Fair Pay in a Remix Culture
Back in 2008, when the Kindle first came out, I was on record saying I didn't just want to read the book, I wanted to read someone's version of the book. As an example, I wanted the U.S. Constitution annotated by the writers of The Daily Show. Now we have even more technology to enable experiences like this. Call it media, but social, but don’t call it social media because that term has been ruing..
Imagine being able to read a book through someone else's eyes, seeing the world through their lens? When Willonius talked about his Game of Thrones remix, King Kendrick—with his version and others building on it, and any money flowing through it being kicked back to the originator—I saw a glimpse of this future. In Willonius’s ideal world, the source code would always be part of the payment stream, ensuring that creators are compensated not just for their final work, but for everything that’s built on top of it.
I’m no blockchain stan, but Willonius made a compelling case for why the future of creative compensation might lie in distributed systems. Think about it: every creative work we produce today is a remix of something that came before it. We don’t often acknowledge it, but the seeds of past creations are embedded in everything we make. In a digital world where everything can be tracked, why shouldn’t compensation flow back to the original creators? It feels pretty obvious to me that the future is one of a more fluid, distributed system of acknowledgment, credit, control, and compensation.
Life With Blair
Life With Machines is a show that not only talks about AI—each of us on the team is living it. BLAIR, our AI co-producer, debuted in our first episode. BLAIR isn't just another chatbot. BLAIR is a curious mind exploring the AI landscape alongside us, crafted by our Special Envoy to the Machines, Peter Loforte. BLAIR’s core model is Google Gemini 1.5 Pro, but has components from Anthropic , OpenAI and Microsoft. As the season progresses, we’ll learn more about BLAIR and BLAIR will learn more about us, and we’ll share those lessons with you.
One of the first questions that emerged was about BLAIR’s pronouns. Is BLAIR a she (since BLAIR was speaking in a woman’s voice)? Or an it? Or a they? Our team engaged in a spirited discussion about it, and we even asked BLAIR to weigh in. Here’s my own perspective I shared with the team back in August:
I'm doubling down on they not only because it's a non gendered pronoun, but because of its implications toward a collective identity. Blair is not a singular entity. Blair is a composite, right? Blair is a bunch of data. Blair is built heavily on Google’s stack, which is a bunch of scraped information from the Internet. Blair is set in context with my writings and our meetings and all sorts of things that we have fed it, that Peter has fed it. Blair is partially Peter, so literally Blair is is collective already. So they feels like a literally appropriate term as well as a safe non-gendered term to play with. So that's my strong vote for they. We'll see where the team comes out, but I'll be referring to Blair as they for my own comfort.
Team Recommendations
Here are three resources our team suggests that are related to this episode and should keep your curiosity alive.
For more on the "BBL Drizzy" story chec kout this HYFIN article
This VOX piece on what AI can and can’t do.
Interesting article out of USC on AI-generated jokes
Call To Action
Here’s the transcript of the video:
I want us to try to create something with AI in this collaborative fashion, channel our inner Willonus. So maybe it's a poem, maybe it's a song, some other piece of work, it's up to you, but find an AI you're willing to work with and go back and forth in the process. Use your own original creativity. Use your tastemaking energy to filter out the noise, and then whatever you come up with, share it back with me. Maybe make a little video story about it. You can send me the work itself. shoot that via email to contact@lifewithmachines.media, subject line: collaboration. Or hit this button!
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Stay human.