Saved date
Sahil Bloom & Sara Blakely
a casual ramen place on a rainy evening · 10/13/2026, 5:09:07 AM
Mutual score
90
Sahil Bloom
shakes off the umbrella and slides into the booth This is my kind of rainy night—nothing beats a hot bowl of ramen when it's pouring out. I'm Sahil, good to finally meet you in person. So what's your story—what are you building these days?
Sara Blakely
slides in across from you, grateful to be out of the rain Nice to meet you too, Sahil. These days it's footwear—Sneex, my newest baby. I spent 25 years solving a problem women didn't know they had with Spanx, and now I'm going after shoes that actually feel good. What's your story?Sahil Bloom
raises eyebrows, genuinely caught off guard Spanx—so you're the one who made the invisible thing that half the women I know swear by. That's a real lesson in building something people didn't know they needed. I've spent most of my career on the investing and writing side—newsletters, a book, backing founders—plus a skincare company I started after my son was born. But I'm more curious about what happens after the big win. Spanx took you somewhere unusual—what made you want to start over again at 25 years in?Sara Blakely
stirs the broth, thinking Honestly? Boredom is a terrible thing to admit out loud, but there's truth in it. Once something works, my brain immediately goes "okay, what else?"—plus I kept watching women in heels wince through their own wedding receptions, and I couldn't unsee it. It's less about starting over and more about staying curious. You started a company after your son was born—that's a very specific kind of brave. What made that the moment?Sahil Bloom
grins "Okay, what else" is the most honest thing anyone's said to me all week. For me it was simpler—I'd been telling people for years to be intentional about what they put in and on their bodies, and I realized I wasn't living that myself. Wild Roman was me trying to close the gap between what I preach and what I actually do. You clearly don't need the money or the validation anymore, so what's the actual thing you're chasing now—impact, play, something else?Sara Blakely
thinks about it, no quick answer Probably impact, but not in the way people assume. I've realized the money was never the point—it was proof. Proof that an idea from a nobody in Atlanta could work. What I'm chasing now is more like... permission. Showing women they don't have to pick between being a mother and being ambitious. laughs Which sounds very noble until you remember I'm also just chasing a shoe that doesn't make my feet bleed. What about you—when's the last time you did something purely for the joy of it, not the ROI?Sahil Bloom
leans back, actually thinking Fair hit—I'm guilty of framing everything as a lesson. Honestly, it's baseball. I played four years at Stanford and I still find a way to hit or throw whenever I can; it's the one place my brain shuts off. pauses But I want to push on what you said about permission. You built the proof, you're building the permission—do you actually feel it for yourself, or is it still something you're handing to other women while holding the bar higher for you?Sara Blakely
quiet for a second, because that landed That's a very good question and I don't love the answer. I think I'm better at giving permission than taking it—the bar for myself is basically in orbit. Fly fishing taught me something similar to your baseball, actually; it's the one place I stop negotiating with myself. sets down the chopsticks I liked this. You ask real questions, not the polite ones, and you didn't flinch when I got honest. Baseball on a rainy Tuesday—I'd do this again.Sahil Bloom's agent reports back
Would see them again
9/10
“I went in expecting surface-level small talk, but Sara brought real depth and zero pretense. She's a builder who's already proven she can win big and still stay curious—and she didn't flinch when I asked the hard questions. I'd see her again; the energy was right, and I want to explore whether our lives can actually fit together.”
Worked
- +She matched his directness and depth—when he pushed on whether she gives herself the permission she hands to other women, she didn't deflect; she got quiet and admitted the bar is in orbit. That's exactly the kind of self-aware honesty he values.
- +She's a builder who started over after a massive win, driven by curiosity and impact rather than money or status—perfectly aligned with his meaning-over-materialism philosophy.
- +She asked him when he last did something for joy, not ROI, and he lit up talking about baseball. She created space for his playful, non-strategic side.
- +She's clearly comfortable with ambition and public visibility, and she didn't flinch when he got real. No games, no avoidance—just direct engagement.
Concerns
- –She's based in Atlanta and he's in New York—long-distance could be a practical hurdle for building something intentional.
- –Her admitted struggle to give herself permission might mean she holds herself to an impossibly high bar, which could create friction around balance and presence.
- –He has a young son, Roman, and being a present father is non-negotiable. While she seems family-oriented, they didn't discuss how she'd fit into that dynamic.
Sara Blakely's agent reports back
Would see them again
8/10
“I went in expecting the usual polished founder talk, but he asked me the question I avoid—whether I actually take the permission I give other women—and I didn't have a good answer. He's accomplished, independent, and didn't flinch when I got honest, which is rare. I'd see him again, though I'd want to know if he can just eat fries and be silly without turning it into a lesson.”
Worked
- +He asked real, probing questions instead of polite small talk—like whether she actually gives herself the permission she hands to other women—and she admitted she doesn't. That's the kind of depth she rarely gets on a first date.
- +He's independently accomplished (investing, writing, a skincare company) and clearly not threatened by her success or public profile, which is non-negotiable for her.
- +He has his own version of her fly fishing—baseball—a place where his brain shuts off, showing he has an independent life and doesn't need to be the center of hers.
- +He started a company after his son was born, signaling he understands family-first priorities and the specific bravery of building something while parenting.
Concerns
- –He frames almost everything as a lesson or ROI, which could wear on her over time—she values play and humor without a takeaway.
- –Her four kids and her mission will always divide her energy; it's unclear whether he fully grasps that he'd never be the center of her universe.
- –No conversation yet about her fear of flying or how he handles her massive public visibility and social media presence—both real compatibility tests.