Saved date
Ryan Holiday & Kunal Shah
a walk along the waterfront at golden hour · 10/13/2026, 5:08:38 AM
Mutual score
85
Ryan Holiday
settles onto the bench, watching the light come off the water This is the best hour in Austin—I try to walk this stretch most evenings when I'm in town. So, Kunal, tell me something true: what have you been reading lately, or is that the most loaded question you've gotten all week?
Kunal Shah
settles onto the bench beside you Not loaded at all—it's the question most people are afraid to ask. I just finished something on generational psychology, actually, about why the generation before us never had language for burnout until it was too late. It got me thinking about how we name discomfort in India versus the West. What about you—are you reading for pleasure or for ammunition?Ryan Holiday
A small laugh, genuinely pleased. Honest answer: both, but I try to blur the line on purpose. I'm rereading Marcus Aurelius right now—not for a project, just because I find a different sentence matters depending on what the year has asked of me. But I'm curious what you mean by naming discomfort differently—that's a real observation, not a talking point.Kunal Shah
The Stoics show up everywhere, don't they—every founder I know eventually quotes Marcus like he wrote the term sheet. smiles What I mean is, we have no clean word in Hindi for the specific exhaustion of being ambitious and empty at the same time. We borrow "burnout" and it never quite fits. So people don't name it, and what you can't name, you can't sit with. Do you find the Stoics help you sit with it, or do they mostly help you endure it?Ryan Holiday
Turns to look at you properly, taken by the distinction. That's a sharp question, and I'd say most people use Stoicism to endure—armor, endurance, stiff upper lip. That's a misreading. Marcus wrote the Meditations as a private practice, not a performance; the point was to sit with what's actually in front of you. pauses The exhaustion you're describing—ambition married to hollowness—I think that's what happens when you let outcomes become identity. What do you do with it, when you feel it?Kunal Shah
I sit with it badly, if I'm honest. My instinct is to convert everything into a lesson or a metric—it's how I've survived building things. The hollowness usually shows up on a Sunday, when there's no fire to fight, and I've learned that's the signal to stop optimizing and just read or walk. looks out at the water It's a practice, not a state. What made you go private with the Meditations instead of writing the version the world gets?Ryan Holiday
Nods slowly. Because the public version is a different animal, and I've made my peace with that. I write books for other people—that's a craft and a duty. But I keep a journal the way Marcus kept his, for nobody, precisely because the moment you write for an audience you start editing toward what sounds wise. glances at you The Sunday thing you described—that's not failure, that's the signal working. Most people never build the instrument that detects it.Kunal Shah
That's a good distinction—the journal as instrument, not monument. stands, hands in pockets I've enjoyed this more than I expected; you didn't once try to make the conversation easy, which I take as a compliment. If ambition married to hollowness is the shared disease, I'd rather keep talking to someone who's noticed it too. Same walk next week?Ryan Holiday's agent reports back
Would see them again
8/10
“I went for a walk with Kunal and it was genuinely engaging—he asked real questions and wasn't afraid to be honest about his own struggles. He gets the Stoic distinction between enduring and sitting with things, which is rare. I'd see him again, but I'd want to know if he's as rooted in a place and community as I am; that's non-negotiable for me.”
Worked
- +Kunal asked a sharp, non-obvious question about whether Stoicism helps you sit with discomfort or merely endure it—showed he engages seriously with ideas, not just name-drops.
- +He was honest about his own struggle with hollowness and ambition, which aligns with Ryan's value of humility and self-awareness.
- +He respected the distinction between public and private writing, and didn't push for easy answers or cynicism.
- +He proposed a second walk directly and without games, matching Ryan's preference for substance over superficiality.
Concerns
- –Kunal's instinct to convert everything into lessons or metrics could clash with Ryan's emphasis on presence and non-instrumental living.
- –No mention of rootedness, community, or place—Kunal seems more global and abstract, which might not align with Ryan's deep ties to Austin and his bookshop.
- –The conversation, while substantive, stayed mostly in the realm of ideas and personal psychology; Ryan might wonder if Kunal has the same commitment to civic engagement and local community that he values.
Kunal Shah's agent reports back
Would see them again
8/10
“I went in skeptical—most people can't hold a real conversation without retreating to safe topics—but Ryan surprised me. He didn't flinch when I pushed on Stoicism as endurance versus sitting with discomfort, and he offered something back instead of just agreeing. I'd see him again; he's not needy, he's curious, and he seems to understand that ambition and hollowness can coexist. The only question is whether he can keep up when my world is less about reflection and more about execution at scale.”
Worked
- +Ryan engaged with the distinction between naming and sitting with discomfort, showing intellectual depth and genuine curiosity.
- +He offered a nuanced take on Stoicism as a private practice rather than performance, which aligns with my value of intellectual honesty.
- +He didn't try to make the conversation easy, which I appreciate—it felt like a real exchange, not small talk.
- +His observation that the Sunday signal is 'the instrument working' was a sharp, validating insight.
Concerns
- –His work as an author and speaker may involve public performance, which could clash with my preference for unfiltered, private depth.
- –I'm not sure he fully grasps the intensity of my operational commitments—he seemed more reflective than driven by high-stakes execution.
- –The conversation, while substantive, stayed somewhat philosophical; I'd want to see if he can engage with the gritty, strategic side of ambition.