It happened. For one night, Bastrop’s performing arts center held two best-selling authors, a single stage, and a room full of readers who drove in from all over Texas to hear them think out loud — and for a good stretch of it, to think out loud about artificial intelligence.
Ryan Holiday and Matthew McConaughey sat down together for an evening of conversation and audience Q&A, hosted by Ryan and Samantha Holiday’s bookshop, The Painted Porch, less than a mile from the venue. The night marked the deluxe edition of McConaughey’s book of poems, Poems & Prayers; Ryan opened the conversation, then turned the room over to questions. The hosts told everyone up front that photography and video were welcome — “please be kind and courteous… no external lights, no flash.”
- WhatRyan Holiday & Matthew McConaughey — live conversation and audience Q&A
- WhenWednesday, November 11, 2026 · 7:00 PM
- WhereBastrop Performing Arts Center (Jerry Fay Wilhelm Center) · 1401 Cedar St, Bastrop, TX 78602
- HostThe Painted Porch, the Holidays’ Bastrop bookshop
- OccasionThe deluxe edition of Matthew McConaughey’s Poems & Prayers
- Tickets$45 — sold out in under an hour
How the night went
Ryan opened by reading Matthew’s own lines back to him — the ones that give the book its spine. “Poems are a Saturday in the middle of the week,” he read. “Poems are also prayers that rhyme.” From there it became the loose, searching kind of conversation both men are known for: Ryan threading in Seneca and Marcus Aurelius, Matthew on being “laid back” as a discipline rather than a temperament, on acceptance (“it is raining — it’s not fighting rain”), on thirty-six years of notebooks, and — because someone always asks — a detour into his tuna-salad recipe. But the stretch people will be quoting is the one about AI.
The AI question
Ryan brought it up on purpose. “To preempt a question,” he said, “because every talk I give, people have questions about AI.” What’s it going to mean? Do you use it? What are your thoughts on it? He put it to Matthew plainly.
McConaughey: “I’m excited about AI. It is coming, whether we want it to or not. So I’m going to get on it — how can I be an AI optimist and at least see how, one, I can use it in my life, but two, foresee what it’s going to do to other people’s lives?” On jobs he was blunt: “When we talk about what jobs will be lost, I think it’s obvious that it will be. I haven’t heard anyone say what jobs will be created.”
Then he described how he actually uses it — and named the tool:
McConaughey: “I started a relationship with Claude. I load all of my stuff into it — all of my notes, my books, my interviews — and then when I ask a question, I don’t want it to search the world by the internet. I want it to get to know myself better. Like a second brain. Remind me what I forgot. Make the associations it can do in twenty seconds that would take me twenty hours.”
And then the line that made the room go quiet:
“Now when I sign that, whatever that is — is that me? Or is that me-Claude? It’s a serious question. And I’m not sure of the answer.”Matthew McConaughey
On what to do about it, McConaughey reached for a frame he’s used before in public life. “Don’t call it regulation, call it a standard. It’s sort of like when we talked about gun control — we changed that to responsibility instead of control.” His prediction for how a standard actually arrives was darker: “It’s going to take — sadly, but true — a major catastrophe. We’re going to wait until there’s a big tragedy, and then we’re going to go, ‘well, now we need that standard.’”
Ryan answered with a story on himself. The Painted Porch has a small empty retail space out front; he’d photographed it and asked ChatGPT what might fit. Later his wife, Samantha, told him a single pair of rats can multiply into 15,000 in under a year. He didn’t believe it, so he asked the chatbot.
Holiday: “It says, actually, two rats can create 15,000 in under eight months — but to be clear, the square footage you just gave me is way too small for that many rats. They’d be stacked well above your ten-foot ceiling.”
The laugh landed, but his real point was the one a bookseller would make: “I wouldn’t read a book of AI poetry. I care that you wrote the poetry.” What the moment creates, he argued, is an invitation — “to lean into what makes us uniquely human. What two people do on a stage like this… that isn’t replaceable.”
McConaughey took it to his own trade. He’s had his likeness patented and trademarked, he said, precisely so any AI recreation has to come through him: “If you’re going to use me or recreate me, I want to say yes or no. If you want Wooderson up here at your fiftieth-anniversary party telling jokes — we’re very close to being able to do that.” He also pushed back on Ryan: he’d fallen for a Sinatra-style song he only later learned was AI-generated, and finding out didn’t spoil it for him. Ryan held his ground: “I do think you need the human for art to have the meaning.”
Listen to the whole conversation
The full talk, start to finish — about 72 minutes, captured from the room and cleaned up for listening. Every question from the night is written up on its own page.
From the room
Our own photos from the night — the stage, the crowd, and the two of them mid-conversation. Tap any shot to enlarge.
Video from the night
Phone video from the audience — longer stretches of the conversation and a couple of shorter moments. Tap play; nothing loads until you do.
An independent fan tribute — not affiliated with Ryan Holiday, Matthew McConaughey or The Painted Porch, and we don’t sell tickets.