In this interview segment, Shawn Sheik discusses his approach to monetizing existing businesses within his portfolio. He emphasizes focusing on what the company does best—such as subscription and paid models—rather than trying to solve unrelated problems like cancer. Sheik explores opportunities to expand content-driven platforms, citing The Modest Man as a case where a clothing line could be launched leveraging an existing community. He also highlights the challenge of managing 18 companies, noting that no single venture receives enough attention. To address this, he suggests assigning dedicated leaders to specific sectors, adding high‑impact features, and building new businesses on top of current assets, like the mailbox money platform. The overall message is to prioritize data‑driven, incremental improvements that align with the firm’s core competencies.
Chapters
inherently that's what we're looking for. Like what exists that we can do slightly better or what exists, like for example, we bought a company that was monetized on display ads. Like I was saying, like we're really good at paid, so, or in subscription products. So like, let's just layer this in. Like, you know, it's all about looking at data, uh, making sure that we can actually monetize things.
And, and, and that's inherently it.
Like I am not at a point, at a place in my life where I wanna like go solve cancer or something like that. Like it's just not— Your problem. Not what we're good at, right?
Yeah. So not your experience. Is there anything right now you're like, okay, I would like to start this, I don't have time for it, or I'm getting to it eventually. You're like, what's on your mind?
Yeah, I think a lot of the content stuff is interesting. Like I think there's a lot of stuff that we can do with like The Modest Man, for example, that we don't really have time for. It's not necessarily our expertise. So as an example, like our head of growth was like, hey, I'm really into fashion and clothing. Like maybe we should start a clothing brand. I was like, Like everyone and their mother has done it, but it's not a bad idea because we have, you know, a pretty big community for The Modest Man. So maybe it makes sense to do it, right?
Yeah. Like where's your competitive advantage?
Yeah. Yeah. So I think like, you know, maybe we have a lot of platform businesses and there's a lot of stuff that we can expand on. Yeah. I actually think that's like kind of interesting. Like we have a lot of businesses that have been like, I was saying mailbox money that we could probably do a lot with if we just focus. So that's the other thing I've been thinking about a lot is like when you have 18 companies, like No child gets loved the most. So maybe we should be like putting people in charge of, you know, growing this like one sector or like adding features that like are actually pretty good. So, um, I think inherently that's like, how do we start businesses on top of what we already have?
Like, yeah, you know, it's a big foundation there already.
