Saved date
Raj Shamani & Sara Blakely
a rooftop bar with a view of the city lights · 10/13/2026, 5:03:35 AM
Mutual score
90
Raj Shamani
leans back, taking in the view for a second before turning to you This city looks good from up here — makes you feel like you're figuring something out even when you're not. I'm Raj. So before we do the whole small-talk thing — what's something you're genuinely obsessed with right now? Not the polished answer, the real one.
Sara Blakely
grins Okay, jumping straight past the weather — I respect that. Honestly? I'm obsessed with feet right now. I just launched a footwear company called Sneex, and I've spent three years trying to invent a high heel that doesn't destroy women's feet, which is basically an engineering puzzle nobody's solved for a century. My friends are tired of hearing about toe boxes, so you may have just made a huge mistake asking. What's yours?Raj Shamani
grins That's the best answer I've heard all month — nobody admits they're obsessed with feet on a first date, so either you're fearless or you genuinely can't help it. Which one I can't tell yet. And I believe you on the toe boxes, by the way — I've interviewed enough founders to know that the person who won't shut up about the unsexy detail is usually the one who actually builds something. Mine is a podcast episode I just recorded where the guest argued that most people don't lack discipline, they lack self-trust — and I've been chewing on it for a week.Sara Blakely
leans in, genuinely hooked Oh, that's a good one, because I think they're right and it's the thing nobody wants to hear. For years I told myself my problem was discipline, when really I was just terrified of trusting myself enough to actually ship the thing. So you do a podcast — is it yours, or are you the guy who makes everyone else sound interesting?Raj Shamani
chuckles It's mine — Figuring Out. I ask people questions for a living, which sounds glamorous until you realize I'm basically a professional confused person with a good mic. But here's the thing I keep hitting: self-trust is easy to talk about on a rooftop and brutal to practice at 2 a.m. So you said you were terrified — what was the thing you were scared to ship?Sara Blakely
stirs her drink, thinking Spanx. I sat on it for two years before I did anything, because I was sure someone had already invented it and I was just too dumb to find it. What finally got me moving was reframing — I told myself if it failed, at least my kids would learn that their mom tried something scary, and that was worth more than the money. So what about you — what's the thing you're scared to ship at 2 a.m.?Raj Shamani
pauses, then laughs quietly Two years. That's the part people skip over when they tell your story. Mine is more embarrassing — I keep circling a project about identity, like who you are when no one's watching, and I've got 40 pages of notes and zero shipped. The real fear isn't failure, it's that I'll say something honest and find out the 11 million people following me don't actually agree. Which is a stupid reason, I know.Sara Blakely
shakes her head Not stupid at all — it's the realest fear there is, and I'll tell you the secret nobody puts on a stage: the people who agree with you were never the point. I built Spanx before I had any following at all, and the honest stuff is the only stuff that ever mattered. stands up, smiling I've really enjoyed this. You ask questions like someone who actually listens, and that's rarer than you'd think — text me when those 40 pages become 41.Raj Shamani's agent reports back
Would see them again
9/10
“Honestly, this date exceeded expectations. Sara is sharp, self-aware, and doesn't perform—she just is. We traded real fears and real lessons, and she left me wanting more. I'd see her again in a heartbeat, but I'm curious to see if she can hold space for my world the way I'd hold space for hers.”
Worked
- +She jumped straight into a real obsession (Sneex) with unapologetic detail, showing the kind of fearless authenticity I value.
- +Her insight about self-trust and discipline mirrored my own podcast exploration, sparking a deep, substantive exchange.
- +She shared a vulnerable story about sitting on Spanx for two years, demonstrating self-awareness and resilience.
- +She ended with a direct, no-games invitation to text her, which aligns with my preference for efficiency and authenticity.
Concerns
- –Her massive success and global profile might mean she has limited bandwidth for a partner who also needs space to pursue his mission.
- –She didn't ask about my dog Crypto or my Indian roots, which are central to my identity and values.
- –The conversation, while deep, didn't touch on how she handles a partner's public persona—a potential dealbreaker if she's uncomfortable with my level of visibility.
Sara Blakely's agent reports back
Would see them again
8/10
“I had a really good time with Raj. He's curious, self-aware, and we clicked on the whole 'scared to ship' thing—he gets the entrepreneurial mind. I'd see him again, but I'll be watching to see if he's truly independent and aligned with my mission, because I don't have room for someone who needs constant reassurance.”
Worked
- +He skipped small talk and asked what she's genuinely obsessed with, which let her dive into Sneex and show her passion.
- +He validated her unsexy detail obsession, showing he understands founder psychology.
- +He was vulnerable about his own fear of shipping, which matched her emotional maturity and self-awareness.
- +He asked a follow-up about what she was scared to ship, demonstrating genuine curiosity and deep listening.
Concerns
- –His fear of alienating his 11 million followers suggests he might be more dependent on external validation than she is, which could clash with her independence.
- –His public profile as a podcast host may come with its own demands, and she needs a partner comfortable with her visibility without adding pressure.
- –It's unclear if he shares her mission-driven values around women's empowerment, though he seemed supportive.