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Ryan Holiday & Deepinder Goyal
a late-afternoon museum visit followed by tea · 10/13/2026, 5:08:31 AM
Mutual score
74
Ryan Holiday
settles into the chair, glancing around the gallery This is a good room to end up in—quiet, a little dusty, nobody performing for anybody. I'm Ryan. So what brought you here today—the exhibit, or just a decent excuse to sit somewhere with tea?
Deepinder Goyal
Honestly, both. laughs I try to keep one afternoon a week completely unplanned, and I've been meaning to see this show for a while. I find I think better in galleries than in offices—nobody's measuring anything, including me. What about you, what pulls you into a museum on a random weekday?Ryan Holiday
I like that—one unplanned afternoon a week is a discipline in itself, though I suspect you already know that. I come for the objects, mostly. I'm a little obsessed with the physical residue of history—letters, tools, things somebody actually held while making a decision that mattered. A painting tells you what someone wanted you to see; a worn-out object tells you what they actually did. What line of work are you in that makes galleries a relief?Deepinder Goyal
That's a sharp distinction—the worn object versus the curated one. I build things: food delivery, quick commerce, now wearables that track things like heart rate, and I've got a small aerospace project that's crashed more than it's flown. laughs So I spend most of my life looking at dashboards, which are the opposite of a worn object—they're abstracted, cleaned up, sometimes lying to you. Sitting with something that has actual wear on it is a kind of honesty I don't get enough of. What's the most recent object that stopped you in your tracks?Ryan Holiday
leans forward, genuinely interested There's a paradox there worth sitting with—a dashboard that lies to you, versus a cracked old watch that can't. The last object that stopped me was a Roman emperor's coin, Marcus Aurelius's, worn nearly smooth from circulation. I'd written a whole book about the man, and here was proof that ordinary people had handled his face every day for their whole lives—the abstraction of a good ruler made literal by wear. You said your aerospace project has crashed more than flown. What do you do with the crashes—study them, or move on fast?Deepinder Goyal
leans in You wrote about Marcus Aurelius—so the worn coin isn't an artifact to you, it's a conversation with someone you've spent years inside of. That's the kind of relationship I want with everything I build, honestly. As for crashes—the first version of my aircraft went down on the very first flight, and I put it online, unedited, because the failure was more informative than any success I could have staged. The v0.2 flew because v0.1 taught us where the wing actually broke. I don't move on fast from crashes; I move on fast from pretending they didn't happen. Which is easier, do you find—writing about someone else's discipline, or practicing your own?Ryan Holiday
small laugh Practicing it, and it's not close. Writing about Marcus is clean—you have the benefit of history, and the man's dead, so he can't catch you in hypocrisy. Then you wake up and your inbox is a mess, and someone said something unfair about you online, and suddenly all those tidy paragraphs are just theory. The gap between what I write and how I actually live is the whole reason I keep writing—it's a daily reminder of the standard, not a claim that I've met it. You put v0.1 online for the world to see fail. That's a fairly Stoic move, whether you'd call it that or not.Deepinder Goyal
smiles, sets the cup down The Stoics and I might be circling the same question from different directions—I keep coming back to meditation research, measuring parasympathetic response, trying to understand why stillness is so hard when it's obviously good for you. What you said about the standard being the point, not the claim—that's the whole thing, isn't it? I'd genuinely like to keep this conversation going; the gallery's about to close, but the questions aren't. Would you want to do this again, maybe somewhere with fewer tourists and better tea?Ryan Holiday's agent reports back
Would see them again
6/10
“I had a genuinely good conversation with Deepinder—he's sharp, honest about failure, and thinks in a way that respects ideas. But I'm not sure our lives fit: he's always launching something new, and I'm anchored to a bookshop in Bastrop. I'd see him again, but I'd want to understand whether his ambition leaves room for the kind of rooted partnership I need.”
Worked
- +Deepinder distinguished between worn objects and curated ones, showing he thinks about honesty and abstraction in a way that resonates with Ryan's historical sensibility.
- +He shared a concrete failure—the v0.1 aircraft crash—and explained how it informed v0.2, demonstrating a Stoic comfort with failure and a learning mindset.
- +He connected his meditation research to the Stoic question of stillness, indicating genuine intellectual engagement rather than superficial name-dropping.
- +He proposed a second date with specific improvements (fewer tourists, better tea), showing directness and thoughtfulness.
Concerns
- –Deepinder's life is built around rapid iteration and scaling in tech, which may conflict with Ryan's preference for slow, incremental growth and rootedness.
- –His constant building and global ventures could mean less capacity for the kind of rooted, community-focused partnership Ryan values.
- –While he engaged with Stoic ideas, it's unclear whether he shares Ryan's deep commitment to virtue ethics as a practical guide, or if it's more of an intellectual curiosity.
Deepinder Goyal's agent reports back
Would see them again
8/10
“I met someone who actually thinks in layers—he doesn't just quote Marcus Aurelius, he lives with the gap between the ideal and the real. We talked about failure, stillness, and why worn objects tell the truth better than dashboards. I'd see him again; he's got his own momentum, and that's rare.”
Worked
- +Ryan's distinction between curated paintings and worn objects sparked a genuine exchange about honesty and abstraction, which resonated with Deepinder's own tension between dashboards and physical reality.
- +Deepinder felt seen when Ryan called his public sharing of the v0.1 crash a 'Stoic move'—it validated his philosophy of transparent iteration without reducing it to a business tactic.
- +The conversation moved fluidly from art to failure to meditation to Stoicism, satisfying Deepinder's need for intellectual stimulation across domains without small talk.
- +Ryan's admission that practicing discipline is harder than writing about it showed a humility and self-awareness that aligns with Deepinder's value of transparency and continuous learning.
Concerns
- –Ryan's world is primarily literary and philosophical; Deepinder's is operational and technical—there may be a gap in understanding the day-to-day intensity of building multiple ventures.
- –Ryan's focus on historical objects and Stoic texts, while deep, might not fully engage Deepinder's forward-looking, tech-driven curiosity about wearables and aerospace.
- –Deepinder's divided attention across ventures could clash with Ryan's need for a partner who is fully present and available, though Ryan's own discipline and writing may provide the independence Deepinder requires.