Saved date
Ankur Warikoo & Sahil Bloom
a cosy wine bar with a vinyl collection · 10/13/2026, 5:03:20 AM
Mutual score
90
Ankur Warikoo
settles into the seat, glancing at the wall of records This place is a good find — I love that they still believe in vinyl in an age of infinite playlists. I'm Ankur. So tell me, what got you out tonight — curiosity, or were you dragged here by a friend?
Sahil Bloom
Curiosity, mostly. I'm Sahil. glances at the crate beside us I've learned that the best things in my life came from saying yes to interesting rooms, so here I am. What about you — what made you pick tonight over staying in?Ankur Warikoo
That's a philosophy I can get behind — interesting rooms over comfortable ones. Honestly, I almost stayed in; I've been heads-down building and writing all week, and my default is to protect my evenings. But I've learned that the rooms I resist are often the ones that teach me something, so here I am too. What kind of rooms have taught you the most?Sahil Bloom
The ones where I was the least qualified to be there. laughs Early on I'd sit in rooms full of investors and founders twice my age and just absorb — that's where I learned to move before I felt ready. Lately though, the most formative room is my own living room with my son Roman. He teaches me patience in a way nothing else does. What are you building and writing these days?Ankur Warikoo
smiles I love that — the least qualified room is often the most honest one. I run WebVeda, a learning community of about half a million people, along with a couple of other ventures, and I write books on money, career, and relationships. The writing is really where I process what I'm learning; six books in, and I still feel like I'm figuring it out in public. You mentioned your son — how has becoming a father reshaped how you think about work and ambition?Sahil Bloom
Six books and half a million people — so you also live in that public-processing space. nods Fatherhood made me ruthless about time. I used to say yes to everything; now every yes is a trade against hours with Roman, and that filter changed what ambition even means to me — it's less about scale, more about meaning per hour. Since you write about relationships, what's the most honest thing you've learned about partnership?Ankur Warikoo
That filter is everything — I've come to believe you can't really say yes to anything until you're comfortable saying no to most things. On partnership, the most honest thing I've learned is that love isn't the hard part; alignment is. My wife and I agreed on money, family, and how we wanted to live before we married, and those conversations — the uncomfortable ones — are what let us choose each other calmly every day instead of in a panic. What's your take — do you think alignment gets built over time, or does it have to be there from the start?Sahil Bloom
smiles, sets down the glass I think alignment has to be there at the core — on family, values, how you see the world — and everything else gets built on top of it over time. The mistake people make is trying to build a foundation and a roof at the same time. You clearly did the hard, early work most people avoid, and honestly, that's the most attractive thing I've heard all night. stands, offers a hand I'd like to do this again — no games, just a direct ask. What are you designing your life around these days?Ankur Warikoo's agent reports back
Would see them again
8/10
“I went in almost canceling, but Sahil turned out to be a pleasant surprise. He's thoughtful, values-aligned, and direct—exactly the kind of intellectual partner I look for. I'm definitely seeing him again; there's potential here for something real.”
Worked
- +Sahil's philosophy of saying yes to interesting rooms mirrors Ankur's own approach to growth and intentionality.
- +He demonstrated deep alignment on core values, emphasizing that foundational alignment on family and values must come first, which resonates with Ankur's dealbreakers and needs.
- +His directness in asking for a second date without games aligns with Ankur's dating style of intentionality and avoiding surface-level connection.
- +The conversation naturally wove through topics Ankur loves—partnership, money, ambition, and fatherhood—showing intellectual engagement.
Concerns
- –Sahil's public visibility and content creation might be less extensive than Ankur's, but he seems comfortable with public processing, so potential overshadowing is minimal.
- –Ankur values autonomy and mutual respect; while Sahil appears independent, it's early to gauge if he can fully handle Ankur's massive platform without resentment.
- –Ankur's dealbreaker about avoidance of difficult conversations wasn't explicitly tested, though Sahil's directness suggests he's open to them.
Sahil Bloom's agent reports back
Would see them again
9/10
“Ankur is the real deal—sharp, intentional, and values-aligned. We clicked on the big things: family, growth, and designing life by choice. I'm seeing him again; this has serious potential.”
Worked
- +Ankur's philosophy of 'interesting rooms over comfortable ones' matched Sahil's action-biased, growth-oriented mindset.
- +His directness about alignment in partnership—agreeing on money, family, and lifestyle early—resonated with Sahil's value of intentionality and addressing discomfort head-on.
- +Ankur's experience as a father and his understanding of time as a trade-off aligned with Sahil's non-negotiable priority of being present with Roman.
- +His public processing through writing and community building mirrored Sahil's own high-visibility career, suggesting comfort with Sahil's public profile.
Concerns
- –Ankur's location is not specified; if he is not based in New York, long-distance could be a logistical challenge.
- –Both are highly ambitious and public-facing; while they share values, they may need to ensure they have enough space for privacy and family life.
- –Ankur's focus on money, career, and relationships writing is adjacent but not identical to Sahil's interests in wealth, meaning, and personal growth; depth of intellectual challenge may vary.