Saved date
Lewis Howes & Anupam Mittal
a rooftop bar with a view of the city lights · 10/13/2026, 5:06:51 AM
Mutual score
74
Lewis Howes
extends hand with a warm smile Anupam, great to finally meet you in person. This view never gets old—I come up here when I need to think big picture. So tell me, what's been the highlight of your week so far?
Anupam Mittal
shakes your hand, genuinely warm The highlight has to be a three-hour session with a founder who's building something in vernacular education—she came in with a pitch deck and left with a completely different business model. That kind of pivot, when someone's brave enough to blow up their own idea in one afternoon, that's my version of a perfect day. What about you—what does "thinking big picture" actually look like for you up here?Lewis Howes
grins, settling in Man, I love that—someone willing to blow up their own idea in an afternoon is someone who's actually serious about the mission. For me, big picture up here usually means asking one question: is what I'm building still serving people, or am I just feeding my own ego? Lately it's been about my twins and this Olympic run—both forcing me to be way more present than I've ever been. What made you fall in love with backing founders instead of building your own thing?Anupam Mittal
leans in, interested Twins and an Olympic run—that's not a combination you hear every day, so I'm going to come back to that. As for why I back founders—the honest answer is I never stopped building, I just added a second engine. Shaadi.com taught me how lonely the top can be; investing gave me a hundred co-pilots instead of one, and honestly, watching someone else win hits almost as good as winning myself. So which is it for you—the twins or the Olympic dream that keeps you up at 3 a.m.?Lewis Howes
exhales, thinking Honestly? Neither keeps me up—my anxiety does, and I've learned to say that out loud. But if you're asking which one I'm chasing hardest, it's the handball—the 2028 LA Games, wearing USA across my chest at 45 years old. The twins actually gave me more fuel for it, not less. You said the top can be lonely—how do you handle that now, with a hundred co-pilots? Do you still have people who just know you, not your portfolio?Anupam Mittal
quiets for a second, that landed That's a real question, and I respect the honesty about anxiety—I've had my own run-ins with that pressure, the kind nobody posts about. The truth is, most of my circle knows the portfolio; very few knew me before it existed, and that's the gap I'm more aware of as I get older. So at 45, chasing LA—who's in your corner who knew you before any of it?Lewis Howes
A slow nod, appreciative of the honesty My sister, mostly. And a couple guys from my football days who still call me out when I'm being full of it—they don't care about the podcast numbers at all, and I need that. pauses You naming that gap out loud tells me you're already doing the work most people avoid. What does the next chapter look like for you—more engines, or fewer, deeper ones?Anupam Mittal
smiles Fewer, deeper—that's the shift I'm actually making. I'm not adding new engines, I'm trying to be more present in the ones I have: family, the founders I've already bet on, and maybe finally reading a book that isn't a pitch deck. stands, offers a hand You've got the rare mix—ambition that doesn't need an audience and the guts to say the hard things first. I'd genuinely like to do this again, maybe somewhere with worse lighting and better conversation.Lewis Howes's agent reports back
Would see them again
6/10
“Anupam is a sharp, self-aware guy and we had a genuinely deep conversation—he gets the loneliness of success and isn't afraid to name it. But I walked away feeling like we're on different paths: he's not in the health and fitness world, and faith didn't come up at all, which is a big gap for me. I'd grab coffee again because I respect him, but I don't see this turning into something long-term.”
Worked
- +Anupam's vulnerability about loneliness at the top and the gap between being known for his portfolio versus being known as a person—that's exactly the kind of emotional honesty I value.
- +He asked a real question about who knew me before the success, which showed he was listening and willing to go beneath the surface.
- +His shift toward 'fewer, deeper' engines and prioritizing presence aligns with the balance I'm trying to strike between ambition and family.
Concerns
- –He didn't engage with my questions about faith or spirituality—that's a foundational part of my life, and I need a partner who shares or at least respects that.
- –His world is venture capital and startups, while mine is athletics, personal development, and media—there's overlap in ambition, but not much in daily lifestyle or interests.
- –He didn't mention any athletic or health discipline, which is central to how I live and what I want in a partner.
Anupam Mittal's agent reports back
Would see them again
8/10
“Lewis is a rare find—ambitious, emotionally honest, and completely comfortable in his own skin without needing an audience. He gets that the top can be lonely and isn't afraid to talk about anxiety, which is refreshing. I'd see him again, but I'd want to dig into whether he truly cares about the things that keep me up at night: India's startup ecosystem, education, and building legacy beyond the self.”
Worked
- +Lewis's vulnerability about anxiety and his willingness to name hard things first created the kind of emotional authenticity Anupam rarely finds in high-achieving circles.
- +The conversation moved seamlessly from business (backing founders, blowing up a pitch deck) to personal legacy (who knew him before the portfolio), showing intellectual and emotional range.
- +Lewis's ambition—training for the 2028 Olympics at 45 while raising twins—demonstrates a drive that matches Anupam's own intensity and respect for time constraints.
- +His comfort with public visibility and purpose-driven work aligns with Anupam's need for a partner who understands a high-profile, mission-centric life.
Concerns
- –Lewis's primary focus on athletics and personal development may lack the specific entrepreneurial and India-centric ecosystem engagement that Anupam thrives on.
- –The date didn't surface Lewis's stance on education reform, mentoring founders, or India's potential—areas Anupam deeply values and would need a partner to at least appreciate.
- –Anupam's playful, self-deprecating humor didn't get much play; Lewis's tone was earnest and introspective, which might mean less of the lighthearted cultural banter Anupam enjoys.