Sam Piliero, founder of The Moonlighters, joins Agency Alchemy to share how he’s shaking up media buying for challenger brands. From cutting wasted ad spend to building a lean, senior-only team, Sam reveals why founder-led content wins, how AI is reshaping growth, and what it takes to scale $1–$10M e-commerce brands without the bloat.
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Sam, welcome to the show. I’m so pleased to have you on today. Thank you, Richard. Happy to be here. So to kick things off, tell us a bit about the Moonlighters. I’ll give the quick background. Moonlighters is a performance marketing agency. We are focused on e-commerce brands, specifically in the $1 to $10 million revenue range. historically a very, very underserved market. And something we really focused on after I myself was moonlighting for about five or six years while I was working at VaynerMedia and then eventually BarkBox, doing stuff on the side for smaller businesses, quickly became a white space, blue ocean kind of situation for me. And that was the very, very, very start of the Moonlighters. Excellent. Well, how did your early experience as doing all of those things, you know, being in Vayner and scaling BarkBox, how did it shape the philosophy behind the middle layers? Basically, when I was at VaynerMedia, I was working on the e-commerce team there called VaynerCommerce at the time. And VaynerMedia, as most people know it, they know it through Gary and they know they work with these gigantic brands. But what they don’t know is that there’s an actual incubation for smaller brands and brands that I was working at the time were really, really cool. One of which was Liquid IV. They were part of the very early days of Vayner Commerce. And at the time, if you go back about 10 years ago now, you’d be like, who the heck is Liquid IV? And we got early hands in on a lot of these really cool high growth brands. And when I was there at Vayner, I learned a lot about the agency relationship and what that actually meant to the client, what they were looking for. And then I learned a lot at Bark on how to actually grow businesses. So at Bark, when I started there, we were making about $180 million. When I left, the business went public and they were worth at peak like $2.5 billion. And during that kind of transition, we’ll call it, or just growth period, I also worked with a ton of different agencies. So I got the experience on the agency side. I got the experience on the brand side. And then for us at the Moonlighters, what I tried to do is package it together. And what is the brand actually looking for? Where I was on the other side of that, I was the brand looking for something. And in packaging that in kind of a pretty package at a reasonable cost, hence the the Moonlighters as a whole, that’s what we are now, taking things to a very, very curated one-on-one experience as opposed to a typical agency model. This is no real knock to agencies, just what works for our ideal client profile. A typical agency profile would be you have this like massive team of people and you’re playing telephone and sometimes your media buyers are staffed overseas. Or if you’re a smaller brand, which are the brands that we deal with, a one to $10 million business, you’re oftentimes like bottom of the rung and you’re getting the least talented person in the crew or someone who always churns clients. You’re not cared about as much. You’re the little fish in the big pond. And we want to create, and we’ve been creating, thankfully, An experience that at least, at the very least, is always putting really talented people onto businesses, which means that most people should feel like they are the same size fish in the regular size pond, if that makes sense. Absolutely. You’ve said that media buying for $1 to $10 million DTC brands is broken. What are some of the biggest pain points you see in that segment? And how is your model at the Moonlighters built to solve them? How long do we have? Yeah, so there’s like a hundred things, honestly, that come to mind here. The thing I like to focus on the most is when you’re a tiny brand, you just have to get creative out, right? You just have to get your ads up, get some creative out, make sure the page is functional, just get the ball rolling. When you’re a huge brand, your scale… creates massive efficiency for you because you have massive word of mouth. You have a hundred other things going. You have influencers talking for you and mistakes actually are pressed down because a small mistake, a 1% mistake or a $10,000 mistake is actually not that big of a deal. But when you deal with a million-dollar business or a $2 million business, I consider this the ugliest part, right? This is the part where you’re scaling. It’s hard to do everything on your own now. You can’t do everything on your own if you’re doing $2 million. But you still need to do things aggressively and do them right or else you get sucked away by the brands that are doing it right. It’s a very competitive, very interesting space. And what I see the most when it comes to Facebook ads, Google ads, you know, what we focus on for D2C e-commerce brands, I see a ton of wasted ad spend. This is one of the primary things that I see basically on everyone that we work with. Every account I audit, we audit like 20 plus accounts a week. And almost every single time, I see overspending on engaged audiences, overspending on existing customers. I see a lack of exclusions, a lack of swim lanes in ad accounts. So that would be a very typical setup of you think you’re prospecting, you think you’re retargeting, but you always hit a wall. It’s so, so common. And that wall oftentimes comes from the fact that you’re not hitting net new customers all the time. Things like your frequencies are too high. You’re hitting branded search terms. You’re going… all broad when in reality you want a phrase and exact match mix. There’s a lot of easy mode ways that Facebook and Google have set us up to actually hinder what we’ve historically been so good at. And For most people, that comes in the way of advantage plus audiences, 100% broad audiences, not changing your budgets by the day of the week or the time of the day, right? Just running the same budget every single day. On the Google side, that looks like all broad match keywords, performance max only, not running individual demand gen breakouts. not even running exact match phrases anymore, not using target impression share. I mean, the list goes on and on and on. But the key is that these platforms have pushed in a way where they want it to be so easy. And as a result, as you’re scaling, you can’t use the same easy mode that you use when you’re spending $50 a day versus $5,000 a day. It’s interesting, you know, you mentioned Facebook ads, which I have to assume have evolved a lot over time because if marketers are still getting Facebook ads wrong in 2025, has it just been that much of a shift or has Facebook really just been that much of an enigma for people to unlock? Huge shift from my perspective, at least. So, you know, if we go back to, you know, there’s like the good old days of Facebook, which I’ll still say we’re in the good old days right now. But also, most people would probably look back at like 2012 to 2016 and be like, those were the good days of Facebook where felt like you can put a dollar in and get five out. Now, from my perspective, what’s happened, the shift that happened really occurred in 2020, not from COVID or anything around that, but from the iOS 14.5 change. So 2020 and 2021, iOS 14.5 was rolled out. That changed audience targeting completely. So Facebook went from a heavy detailed targeting system to a broad system. And the problem isn’t that it went too broad. The problem is that everyone was really, really forced into broad. So fundamentally, what changed was that interest targeting got worse. Facebook reps, really anyone who worked for Facebook, anyone that was in the know in the space was forcing broad down to everyone. So, hey, you just got to run broad. You just got to run broad. Now broad is fantastic. It is still the best tool to use, but if you use broad alone and you don’t have exclusion set up or you don’t have interest plus broad together to actually expand your broad, some of the tactical stuff that I like to talk about, you don’t get the best out of broad. And in many cases, as I mentioned before, you wind up not targeting all new customers. You wind up targeting a mix of new customers and existing customers. And then problems arise where you don’t actually know how much you’re spending on existing customers. Just think about that alone. Imagine you’re hitting your existing customers 10 or 15 times a week. So yeah, I think there was just a shift. And I think right now, Facebook’s working their way out of that shift. And I think they’re doing that with a combination of these AI enhancements and plus adding in a lot of… different breakdowns and segments that I personally love as a media buyer. And I think we’re seeing the shift in a good way for the advanced happen while still keeping some of the tools for the easy mode of things, as I’ll call it. Let’s jump from one platform to another and discuss your YouTube content, which is outperforming traditional agency marketing by quite a bit. Why do you think founder-led content resonates more this year than others? And what advice would you give to other founders looking to build trust and growth through their content? Yeah. YouTube has been fundamental, the most important thing for my business. And it’s because I just give away all the answers that I think I have, right? I’m definitely not always right about everything, but if I believe something pretty strongly, you better believe it’s in the queue for a YouTube video. And, you know, I come from the background, like I said, of VaynerMedia. And if there’s anyone in the world that was going to push to make YouTube videos and put out content, it’s Gary Vaynerchuk. And I think having that a little bit, that push of the background where I came from, that helps. But for me, founder-led content, it’s the most important thing, especially when you’re in like medium high ticket like I am. Having that trust built that, you know what, Sam’s not just showing this result that he got for one client one time. And even if you don’t see any of our results, even if you don’t look at one of our case studies, you’ve probably watched hours of my content. And seeing the way that I think about things, seeing the way that I’m walking through something, That does two things for me. A, it attracts clients, no doubt. And then B, it attracts talent to my team. People want to work with people who are giving. People want to work with winners. People want momentum. And if I could put out the most valuable content, even though I’m giving away the answers, as my mom would say, why do you give it all away? Um, I still think very firmly that giving as much possible out and having someone pay for the execution is by far the best model that you could possibly have in medium high ticket. You just have to be excellent. Um, because if you’re not excellent, you get lost in the noise and you’re exposed really, really quickly when you’re, when you’re public like so. It’s a really interesting take on that because we’re in a society that for some reason or another along the way has decided that knowledge is power, and you’re never supposed to give away knowledge because why wouldn’t you want to hold the power when really, per your approach here, you’re talking more about, no, the execution is the part that everybody needs, but it’s helpful for them to know along the way what it is you’re doing and have that knowledge. For sure. Clicking buttons is really easy, right? If it’s just the setup, anyone could… Click the buttons and set up. And we’ve had dozens and dozens of clients that come to us for an account audit. And I’m like, cool, your setup’s great because you literally copied it the way that I said to do it or similar, right? Not every business is the same, but similar. But then strategy is really challenging. And strategy has such like a, it’s like a bad taste in my mouth when I say it out loud. Strategy when it comes to growth marketing is very complex, right? Because it does not just involve, hey, set your ads and maybe make a special ad set or something like that. That doesn’t exist anymore. There’s no hacks to this. But what is the hack, so to speak, is making sure the right products are being served to the right customer and spending the most amount of money when you’re most likely to make money back. That could be time of day adjustments, platform placement, landing page adjustments. It could be just literally narrowing down your product sets Um, there’s so many levers that we can pull that until you’re in it, actually managing it, you don’t think to pull. And what I like to think about is, you know, at the Moonlighters, we have, of course, like pretty robust training, um, where we, I like to think about it’s like, we’re just equipping tools in everyone’s toolkit, but you’re already coming to us with minimum seven years experience. So you have your own set of tools that you like that have worked for you in the past. So. I think about it like you have someone with a lot of tools in their toolbox or toolkit. And once they get their hands on the account, they’re actually understanding the business. They’re thinking about things like margins, growth, scale, what is actually the goal of the business, et cetera. And then they pull out that tool that someone’s never seen before. And they say, if we do this thing, I think this will impact X metric or Y metric. I think this will increase new customer acquisition by X. That kind of formula is what we try to curate to. And I think that’s a lot of the gap that people see right now. And I think I got a little bit off track there on how that leads to content from a founder perspective, but to truly tie it all together, that’s why I’m so okay with giving as much as possible because the execution is in fact the most challenging part. Where to apply is the challenging part. No, I love this. This is a, you know, an approach that you don’t often see. So I’m excited to hear you talk about it. Let’s transition over a bit now to the team at Moonlighters. You know, you’ve scaled very quickly without outside funding or having a bloated team. What are the biggest lessons in growing to a high performance agency with so many, you have nearly a hundred clients, as I understand, active clients. What are the lessons in growing as far as you’re concerned thus far? One of the things that I’ve tried to do so well, and it’s hard, is giving as much freedom to talented people on the team, which has allowed that kind of lightning in a bottle effect to occur. It’s what’s allowed some brands have scaled with us legitimately 10X in 100 days or 180 days, right? And from a management perspective of team, we’ve gotten the approach of, I’m not going to hire overseas media buyers. We are not going to have a game of telephone. I’m not going to try to skimp on my margin or beat my margin by 5% or 10% by hiring cheaper. We’ve taken the exact opposite approach. So we hire senior level, director levels is what we call all of our titles. They’re all called growth directors. And a growth director is the same person that’s responsible for the client management, the actual ad setup, and the reporting and communication. So it’s one person all in. And it puts a whole lot of responsibility on an individual, but it doesn’t let them work on, say, 19 accounts like some agencies do. And again, no slight to other agencies. It’s just what works for us. What I saw in the market as this needs to happen in regards to like growing and like how we’ve tried to, you know, facilitate our own growth. It comes from a few different places, right? I mentioned it comes from YouTube pretty heavily. Just educate. the best we possibly can. And as a result of educating as much as possible, we’ve had one of the fastest growing. I think it’s actually the fastest growing e-commerce channel on YouTube right now. That doesn’t just happen, though, from like me making up a random topic and just someone else talking about it, right? It’s not the topic necessarily. I think that comes from me being in the space for like 12 years now and having a lot of weird, nuanced experiences and little things that I’ve seen along the way that I’m able to share. And then also, when you think about growth, it can always come from two different places. You’re either forcing growth in or you’re leveraging what you already have. So when we have around 100 active clients and we’re getting people good results, people talk about us. And whether they’re talking about us for the first time and saying, hey, you should check out this guy’s content, which happens a lot, We also have a lot of internal referrals come our way. So clients that just, hey, I got this friend, entrepreneurs, no entrepreneurs. And for us, that’s been a tremendous growth driver as well. Yeah, it’s funny. What has feedback been like from those clients? Because to me, personally speaking, I like to work with the same person from the word go to, you know, the end of execution, whenever that should happen. Has the feedback from your clients been positive that they’re working with that same person on everything across the board? I have to imagine that’s a pretty fresh thing for them to experience. Have they remarked about that along the way to you? That’s been the number one thing. I think it’s, it’s the reason that we have low churn. It’s the reason that, um, we build like real long-term relationships. People are people, people like, like we like relationships as, as a species. And when we have that person that we trust to do the thing and we allow them to continue to do the thing, plus we’re getting results. that takes so much pressure off a founder, right? I myself, like as a founder growing my own business, right? When I hire someone to do something outside of my normal scope, I’m like, hey, I got to make my Instagram look better or something, right? Like if I hire someone for that, knowing that it’s handled and I build that relationship for maybe a few weeks, maybe a few months, maybe a few years, it gets to a stage where you know it’s taken care of. You know that X person on my team or X person on that team, they’re going to take care of it. And from a client perspective, we’ve gotten feedback in a couple of different paths for this. And one of the paths that we get the most feedback is, this person’s great and we want to integrate them with more things. And that to me is like, the biggest green flag ever. We want to also get this person’s feedback on how we should grow this part of our business too. And that tells me that the team is expanding beyond just the media buying, just the clicking the buttons, but they’re also thinking about the growth of the business from a strategic perspective. Yeah, there’s probably no better compliment right out of the gate than that, is there? It’s a nice one. I would be remiss not to pick your brain a little bit about AI. AI has been a huge topic in this industry for a variety of reasons, both extremely negative from the word go and now these days quite a bit more positive, at least as I’ve been discussing it with people. What are your feelings from the perspective of both yourself as a founder and from the Moonlighters in general, When it comes to AI, is it presenting opportunities that you are astounded by? Is it kind of, I don’t know, it’s the latest thing everybody’s talking about, but nobody really knows why. Are you using it? And if so, how? Yeah. So I think there’s in the media buying space, in just like the e-commerce space in general, there’s visible opportunity and there’s invisible opportunity. The visible opportunity is very clear. There’s AI creative, whether it’s video, imagery, enhancements of AI creative, right? That’s very obvious. It’s in our face and it’s actually happening. I’m not like overly bullish on AI creative for certain businesses while other businesses I’m very, very bullish on. So I think if you’re selling something that’s a little bit more high ticket, something that is luxury in any sort of way, even if it’s $100 plus, I think you really need to question whether using AI fairly is fair, if it’s ethical. And then on the flip side, if you’re selling a lower ticket product, if you’re selling an info product, if you’re uncomfortable behind the camera, then AI is going to be fantastic from a creative perspective. And that’s just the visible part of it. The invisible part of it is going to come and is happening already thanks to a plethora of tools, but they’re all kind of a mixed bag right now. So easy way to think about this is, remember when like the first AI note takers came out and it was like, whoa, this thing’s crazy. And now all of a sudden you can just like find like any of them for like nine bucks a month and they’re like all astounding. That will happen with this as well. And what I’ll say here is that We’re already seeing companies try to build AI agents that can apply unique ad strategy. The company that builds it the best is going to take a huge portion of the market share, but then likely others will catch up very quickly. leveraging a large language model in conjunction with massive amounts of data points that are unique to a business and are not just from one individual place, right? You can’t just take what did Facebook ads do or what did Google ads do? You need to see what did Facebook do? What did Google do? What did Shopify do? How much inventory do I have? What are my margins, et cetera? There’s so many different parts of the equation. And if that could be fed in properly, and pushed into a large language model and executed on, then yes, we’re gonna see some disruption for sure. On our side, we’re paying attention. We play with it all day. There’s just like a chunk of my day that I just have pretty much dedicated to just like clicking buttons over here. And I think that’s all you can do until it’s ready. We’re never going to like impose something on our clients too early. But at the same time, we definitely will not be late. And I think any founder probably feels the same way. Everyone’s playing right now. For my last question, I like to ask something of a crystal ball question. And for this one, for you, I mean, you’re already doing a lot of things, I think, very originally and very differently than we would typically see, you know, with the regular agency model. What does the future look like for you and for the Moonlighters, say five years down the road? Is it just a steady growth? Do you see something radically different happening? What’s your forecast? Right now, grow like mad, just foot on the gas, grow, grow, grow is the name for us right now. The next stage of that though is going to be using the resources that we are growing from. So using the resources that we acquire from this period of growth to then just build the best possible experience for all of our active clients. And that could be anything from some of the AI stuff we talked about. It could be different product lines on our side. We strictly do media buying. We strictly do strategy on the media buying side. And there’s very few people doing affordable email SMS marketing for the $1 to $10 million business as well. So there’s a lot that could happen. But I think most people get to this position and they say, we should monetize every single client right now because we’re leaving tons of money on the table. I’m taking this a little bit different. I just want us to be super, super good at this one thing for a long period of time. I want to make my mark here as an agency, not just as an employee as I was for years. And then once the trust is unbelievably high and we have the resources to hire super, super, super high level talent to build something that I am not an ASAT, then we make a transition. I think if you do it too early, you could really hurt yourself and really hurt the client relationship, which is the last thing that we are going to do. I love that. All too often, I think we hear people who have very broad goals when it comes to this sort of thing. And you kind of go, yeah, best of luck to you. I don’t see that working out, but, you know, I’ll keep my mouth shut at the moment. Sam, this has been great. I really love your sort of ethos to this entire thing and, you know, just the fresh perspectives you’re bringing to all of it. I mean, you know, going back all the way to what we were first talking about with kind of giving away the secret sauce, but, you know, somebody still has to cook, right? Yes. If one wanted to find out more about the Moonlighters, where should they go? Yeah, go to themoonlighters.com. Doors are open until Q4 right now. So hopefully everyone sees this pretty early. I’m also on all socials. I mean, best social to grab me on is YouTube. You could also pop me a DM on Instagram too before I get too many followers there. Still active and that’s about it. Excellent. Well, thanks so much for taking part today. This has been fantastic. Appreciate it, Richard. Thank you.
