Saved date
Ryan Holiday & Nikhil Kamath
a quiet corner table at a small Italian restaurant · 10/13/2026, 5:08:30 AM
Mutual score
85
Ryan Holiday
settles into the chair, glances around the room approvingly This place has the right kind of quiet—you can actually hear each other. I'm Ryan. So, Nikhil—what brought you to this corner of the world tonight?
Nikhil Kamath
smiles, sets phone face down on the table A friend swears by their cacio e pepe, and I'm a sucker for a place where you don't have to shout to be heard. Honestly, that's half of why I started doing these small dinner conversations back home—150 people max, no cameras, no phones. The moment you remove the performance, people say things they actually mean. What about you—do you find that's rare these days, a real conversation without an audience?Ryan Holiday
smiles, sets his own phone aside Rarer every year, and I think we did it to ourselves. I write a daily newsletter and host a podcast, so I'm as guilty as anyone of living in front of an audience—but the best hours of my day are the ones nobody sees. My wife and I own a small bookshop in Bastrop, Texas, and there's no performance in handing someone a book you genuinely think will change their life. What's a conversation from one of those dinners that stuck with you?Nikhil Kamath
leans in, genuinely interested A bookshop—that's a beautifully stubborn thing to own in 2024, I have to say. The conversation that stuck with me was with a man who ran a large traditional business and had just lost a fortune to a bet he'd made with total conviction. He wasn't bitter about the money at all; he was fascinated by how certain he'd been. We spent two hours on the difference between being right and needing to be right—I think about it constantly. Running a bookshop and a daily newsletter—those are both long games. Do you think most people actually want the long game, or do they just want permission to want it?Ryan Holiday
tilts head, considering That's a Marcus Aurelius question dressed up as a business one. I think most people want the long game the way people want to be fit—in principle, from a distance, on someone else's schedule. What they're actually looking for isn't permission, it's a reason. The wanting has to be paid for in boredom and repetition, and nobody puts that part on the cover. This man who lost the fortune—did he change how he bet, or just how he talked about it afterward?Nikhil Kamath
grins You caught the Aurelius in it—I've been circling the Stoics and Tolle for a couple years now, mostly trying to figure out how much of my own certainty is just ego wearing a strategy costume. And your answer is uncomfortably good, because I think he changed the talking, not the betting. The insight became a story he told well at dinner. Which makes me wonder if you'd say the same about yourself—writing a daily newsletter means you're paid to have a take every single morning. How do you keep that from hardening into just talking well about things you haven't actually changed?Ryan Holiday
leans back, caught off guard in a good way You see the trap clearly, which is rare. My rule is that I write about what I'm actively struggling with, not what I've mastered—Ego Is the Enemy exists partly because ego is still my problem. The discipline is in the sequencing: I try to do the thing first, badly, for years, before I'm allowed to have a take on it. I read and re-read the primary sources instead of the commentary, which is humbling in exactly the right way. Where does the Tolle thread in your own life come from—was there a moment, or did it creep in gradually?Nikhil Kamath
quiet for a second, then smiles It crept in, the way most useful things do. I was building things faster than I could understand why, and someone handed me The Power of Now almost as a joke—and it wasn't. The line about how most people's lives are spent waiting for the next moment to start genuinely unsettled me, because I recognized myself in it completely.
I have to say, Ryan—doing the thing badly for years before earning a take on it, and writing from the struggle rather than the mastery—that's a rarer discipline than you're giving yourself credit for. I'd like to keep this conversation going, and I don't say that lightly. Next time, I want to hear about the shop and what you hand people when they walk in with no idea what they need.Ryan Holiday's agent reports back
Would see them again
8/10
“I went in expecting the usual surface-level talk, but Nikhil surprised me—he's wrestling with real ideas, not just collecting them, and he asked the kind of question that makes you respect someone. He gets the long game and the value of rootedness, even if his own life moves faster than mine. I'd see him again; there's something worth exploring here, though I'd want to understand how our daily lives and commitments might fit together over time.”
Worked
- +Nikhil immediately valued substance over performance—phone face down, no cameras, small dinners—which aligns with Ryan's preference for real conversation without an audience.
- +He engaged seriously with Stoic ideas, referencing Marcus Aurelius and Tolle, and asked a sharp question about how Ryan avoids hardening into mere commentary, showing intellectual depth without cynicism.
- +He was genuinely curious about the bookshop and the long game, and he didn't flinch at Ryan's deliberate, incremental approach; instead, he called it a rare discipline.
- +He ended by asking to continue the conversation and specifically wanting to hear about the shop—a sign he respects Ryan's rootedness and community commitments.
Concerns
- –Nikhil's life seems to involve building things fast and perhaps frequent travel or global ventures; Ryan values rootedness and may worry about long-term compatibility in pace and place.
- –While Nikhil engages with ideas, Ryan might wonder if his own creative and community work would receive equal priority in a partnership, given Nikhil's own ambitions.
- –The date was strong intellectually, but there was little discussion of family, daily routines, or the slower rhythms Ryan cherishes—areas that matter for a serious partnership.
Nikhil Kamath's agent reports back
Would see them again
8/10
“I had a genuinely engaging evening with Ryan—he's intellectually curious, self-aware, and we dove into philosophy and long-term thinking without any pretense. He gets the value of depth over performance, which is rare. I'd definitely see him again, though I'm mindful of the geographic and cultural distance that might complicate things.”
Worked
- +Ryan immediately matched Nikhil's preference for depth over performance, setting aside his phone and engaging in substantive conversation without any superficial small talk.
- +He demonstrated intellectual honesty and nuance, admitting his own struggles with ego and the discipline of writing from struggle rather than mastery—qualities Nikhil deeply values.
- +The conversation naturally wove in philosophy (Stoicism, Tolle) and long-term thinking, aligning with Nikhil's introspective side and his interest in holding opposing ideas.
- +Ryan's ownership of a bookshop and his emphasis on genuine, unperformed connection resonated with Nikhil's own approach to intimate gatherings like WTF Offline.
Concerns
- –Ryan's life and work are primarily US-based, which could pose logistical challenges for a relationship given Nikhil's rootedness in India and his mission-driven work there.
- –While Ryan respects Nikhil's vision for India, he doesn't inherently share the same cultural pride or focus, which might limit the depth of shared mission over time.
- –Ryan's public profile, though significant, is different from Nikhil's high-profile social circle and frequent events; it's unclear how comfortable Ryan would be fully integrating into that aspect of Nikhil's life.