How to Build a Content Team That Actually Works | AOAB Episode 34 w/ Oren John

17:19I could do all these other things. And so look, I hired him all the time to be like, craft this message, present this thing. I'll execute it. But like, I need someone to do that. That's when you are a marketing leader, what do you hire out? What are you good at or bad at? But look, managing sales teams and doing part of round robin sales calls and stuff like that was probably the most useful part of my career, which again came from being entrepreneurial, right? I ended up in that scenario when I was, I was employee four at a startup and it was like, cool, now you manage sales. And it was like, okay, you know, and then same thing.

17:44We bought a company at one point and it was like, now I manage the sales team. And just being in a lot of those scenarios, sales is the most tactical one, right? You have to feedback, you have to talk to clients, you're interfacing. I cannot recommend enough anybody do a year or two in sales roles.

17:57Chris Cruz:Yeah. Cause the, in there you learn something so like overlooked and underrated in this because they can get growth fast in other places. And then you try to get them to, to work in these contexts and they don't. So I have a unique question for you because there's a, there's a, you have an ability to exude a confidence around your communication and the way that your ideas go. And that, that helps translate investment from people listening to you. There's a, there's a buy-in that you present that is easy to, to jump in. How are you honing that? How are you honing that communication skill. Content.

18:33If you meet me three years ago, before I started making videos, four years ago, and even as an executive, I was quieter, smart. I could still talk intellectually about stuff. People would listen. But I did not have, I didn't speak in the same cadence. I didn't have the same confidence around the speaking that came from I'm a thousand videos deep. So now I know if I want to present an idea, it's like you hook with the idea, you follow it up with a basis, and then you like, and you exert your confidence on it after because that's how people respond to media. And so that changed my career and the way I position things.

19:07And now, especially with social, I'm confident in it because like I'm, I've worked on all these projects, right? I am on all these campaigns. I'm working with all these brands and I'm doing it. And so I'm like, and it's, and with Cut30 and all the data from it, where it's like 2 ,500 creators were ever through it now. I am 100 % confident. We can fix this. We can hit it. Like it is done. I have, there is no doubt in my mind what I'm saying is correct. And I also have never had that level of like, even when you're working at a job, you're like, okay, well, I think now I'm like, no, I know. And that's when you have it, you got to hammer it.

19:37If you really know, let people know.

19:39Chris Cruz:Yeah. And for those even watching, like I've and listening, like I've a Cut30 alumni. I'm not the best content creator on the planet, but like I went through the course to learn so much of what you guys taught there. That was like spending my evenings, putting my kids to sleep. They're asleep and I'm putting my headphones on, getting on the live call. listening, putting my stuff in for feedback. And I think one thing about Cut30 that I loved that is so vulnerable for people that I think they avoid is, and I'd love for you to even speak into this because it's some of what you talked about, is putting your content for review before it goes live.

20:14Chris Cruz:Because you invest time, energy in doing it something and then someone comes in and goes, yeah, just not good enough. And you're like, you have to overcome this hurdle of like, oh my gosh, I just put myself out there and it's just not good enough. Talk about that. Yeah, so look, most people, this is one of the benefits of Cut30. Most people never hear something negative anymore. Like they'll hear it in the news, but we are so careful in work environments and whatever to be like, it's a compliment sandwich. It's positive reinforcement. And we've just had years of this, years and years. And that's not necessarily a horrible thing, but it is for the development of your content.

20:53And so one of the decisions we made on Cut30 was like, look, this is going to be one of the only times you're going to have 30 days where people are going to tell you, not in a mean way. We have no mean, mean, no malice. We are going to give you real critique. And if you just do the stuff, you will immediately see the changes of the results. That's the best part of content. You go make a video tomorrow and you do the changes, it's going to get more views. You're like, got it. This is why I do this feedback. And so, but yeah, look, that was a conscious decision because we're like, look, people don't like being told that their stuff is wrong.

21:19but if we're those people and we just do it without again any ill intention you're not being mean not being whatever uh it goes a long way and look i i want that around everything that's even the hardest part now is like i want people more experienced than me who are like that ads bad that hooks bad i don't know any of them anymore right do you do you do like what do you

21:37Chris Cruz:what do you do what do you do with that internally when someone says that's not like how do you handle that that moment like what do you go through in your head do you have a moment of like oh man that sucks and i'm or are you like quick i'm gonna go not take it personally like it's always that okay does this person know what they're doing and if i change that will be is it going to make a real result and then how much of the work to change it versus to the result reward of the result that's always like my look at like very quickly run through that right and uh and if they know what they're doing and there is enough reward from the like the time put into making the change yeah you make the change um and and i think what you end up in look if you ever have ever been in like a really high-performing team of like creating a product, launching an agency, whatever it is, you know that like that critique and the willingness to cut stuff off as early as possible and be like, let's fix this is crucial.

22:24A lot of people just haven't been in those scenarios. So I almost welcome that. Like the hardest part of my life is I don't have like, like my manager will say some stuff, but I don't have a lot of people being like, this could be better. And also there's not a lot of people that know when you operate at like a really high level of content. Even like my buddies who are other huge creators, like we're all like, okay, hopefully. Yeah, you're like, well, this works.

22:43Chris Cruz:Hopefully you've gotten to a level that you're like, hey, it's hard to actually find those peers that can speak to the level I'm at to help me with this. The other question I have in this is like, when you get an executive or someone from a brand that's, they look at content and they say, my customer isn't on social media. Like, I know that's like - And I encourage them to look at it. So basically the first to come is everyone's on social media. you know and i look at this and i and look i am a uh i am obsessive about consumer habits my almost all my content now is about a consumer habit or a consumer insight okay and i encourage uh anyone who's in those scenarios to kind of think like that and to be like okay like are are they like what does my consumer do so one of my favorites is like when people like oh these decision makers aren't on instagram for instance or tiktok yes like word for word and uh but it's like, okay, you know what a habit is?

23:42A habit that I see all the time from millennial and Gen X leaders is that they are on Instagram. They have 150 followers and they follow their kids. And they're also following stuff in the niche of their business. And that usually ends up being a lot of my content, Ashwin's content, stuff like that. And they are forwarding it. They are taking links and they are sending it to their team in a Slack or a group chat. And they're saying, why aren't we doing this? And, or did you see this news? And when you start to notice that, you'd be like, oh yeah, guess what? 75 % of all fucking executives in that age bracket, male and female do that.

24:14And so all of a sudden you're like, okay, cool. Basically our entire model is. And people used to say that on YouTube. YouTube's Gen Z, Gen Alpha. My number one source of bookings for like workshops from execs and stuff is from YouTube. But guess what? They're a second order effect. They're the opposite of that. I'm always trying to trace it down. But basically I had three workshop bookings off this one video I did. It was like the worst marketing of 2025, I think, or 2024. Okay. Okay. And, um, and they all have the same habit. A junior person on the team who watches a lot of YouTube, put the video in their marketing team group Slack or group teams.

24:48And the executive was like, I fucking love this video. I don't watch a lot of YouTube, but I watched this 20 minute video. Get me this guy. And so then you're like, oh, well think about the second order effect. If your, if your guy isn't on social media, do they have a chat with their team where people post social media links because every single team does, right? And so then you start to be like, oh, this is the way people consume. And so I think that's a useful one. The other, the real tactical one is there's a piece of software called Outer Signal, not highly recommend, that does personas. So basically you put in your customer list or your Klaviyo list, whatever, like your email list, and it will basically do the personas of your customers and your leads.

25:30And it works same thing for B2B. and it will give you like five profiles. It'll be like, you know, the personas you've seen in marketing. Hey, Jenny, she's a 30 to 38 year old Latina living in Riverside where these areas and she consumes these things. And you'll get four or five of those, but it will tell you things like social media consumption habits. And you can be like, look, these are data-based personas from a cutting edge company in this game telling us how our people consume.

25:56Chris Cruz:And you can use that as a real proof point to convince leadership based on data. I've not heard about that one. What was that one called again? Outer Signal. And that's a, it's one, that's a funny one. That's a newer one that we had used. A brand of mine, we're relentlessly focused on influencers in our customer base. We send mailers to influencers in our customer base and you can use them for that too. But then I kept seeing every time I logged in, like their logo wall was getting like more aggressive. And I was like, oh, like Estee Lauder, you know? Like, and you're like, oh, but you probably pay a lot of attention to these guys.

26:26Chris Cruz:Yes, yes. You're like, this is, that's fascinating. Okay. Okay, inside of this, you've been a creative director, all these kinds of different positions. What makes a good creative director and what is a bad creative director? Yeah, so look, there used to be this era where you could be an idea person. And there was a lot of people who were creative directors who were like, I'm the idea person. That role is like extremely tactical now. So what makes a good person is that if you need to put together a campaign or a shoot or you have a, like some initiative for your company, a person that can pull in within the constraints, timing, budget, whatever it is, you give them 10 grand, you give them a million dollars, you give them two weeks, you give them three months, they are able to pull in a group of creatives, whether it's internal or internal and external to execute on that problem.

27:17And whatever the holes are, someone can't do something, you know, the designer fell out, whatever, they can, they'll just do it. Like those are the best creative directors. The ones are like, yeah, I have a person for that. okay, I know I'd be a cheap person or versus, oh, I got the best person. They'll drop something to work with me because they respect me. And all right, okay, you know what? No one's good at the messaging. I'll do the messaging. That's who the killers are.

27:39Chris Cruz:Yeah, we had a conversation as our team the other day. We're going, hey, if this is the deliverables this designer can do, anything that doesn't fall into that category, I'm doing. And that's the kind of difference between that previous gen of like, well, I'm just the idea person to the people that like, the creative directors now, Now the ones that are like pulling the whole shit across the finish line, right? Like, look, it's on their back. But that's like such an amazing opportunity. Whenever anyone like responds negatively to that idea, I'm like, you have the basically the most ideal job in the universe.

28:08You get to pull a complete creative concept, like with a budget to life to change your brand's entire trajectory. And if you don't want to be all in on making that amazing, like this isn't the job for you.

28:17Chris Cruz:Bro. Right there. Like, oh my gosh. Like if people would just reverse back five seconds there and just listen, you're like, That's not the job for you if you don't want to do that. That attitude, that kind of tenacity with it. Okay, that answered my question that I had there that I loved. So here's something I wanted to ask you because I've watched your content for a long time. You have this ongoing thing. I don't know how long it's been going or if it's even continuing, but brand versus product. And you kind of highlight whether you're buying the brand or you're buying the product. What's not only, what is, why did, I don't want to ask why does that hit?

28:50Chris Cruz:I want to ask what's the ethos behind that? What is the frame of mind that you have that you're evaluating that and why that matters. Yeah, and so this was, one of the biggest inspirations for this was the recommendations engines that we've grown up with, right? Like Wirecutter, for instance. I bought several bad things on Wirecutter, right? I just didn't like their recommended choice. And so I started thinking like, why, right? Why don't I like this? Why are they recommending something kind of arbitrarily wrong for most people? And then I started to kind of have this idea like, oh, guess what?

29:23Like there's people buy things for different reasons. And when someone looks at something purely as a function of price to value versus then you start adding on taste or you start adding on like the level of connoisseur that person is inside the category, it becomes very nuanced. And then when you have a marketing knowledge on top of that, my thought as a marketer, every time I see anything, I'm jaded. I'm like, okay, well, why are they charging free times the price? Oh, it's made of aerospace grade aluminum, like sick. Right?

29:48Chris Cruz:So you see all these things. Yeah, it's like your recent video about truffle. You're like, you've never tasted real truffle. Yeah, exactly. So we are constantly being sold stuff. And you get jaded, right? The more time you spend in marketing because you know everything's being sold to you. And then you see your friends, right? Or you see people who are just buying in, right? And the biggest one, one of the biggest impetuses on the product versus brand one was like the Our Place pans, where my wife was so excited about the Our Place pans and she bought them and they sucked and then they wouldn't let them return them.

30:12And then I realized when we looked online, that was like a shared millennial experience. Like thousands of people had the same thing where they wouldn't accept the return. and I was like, oh, that's like a, a lot of great videos are born from a shared insight or like a shared thing. Everyone's like, yeah, that happened to me. That's funny. Like I had another one where I was trashing on Sonos. If you've had a Sonos, you're like, Sonos sucks. Like at least once in the arc, you were like, this thing is whack. And so like that's a shared experience. And you're like, why is it so whack if I spend all this money and everyone has it?

30:40And so you start to like lean into that. But yeah, so it was really about, you know, why it hits is because it gets people to think about why they buy. And people get tribal. if you say that yes i said you made a bad purchase they're like well da da da and then you'll start to realize like you'll see they'll either achieve self-actualization and they'll be like oh i got got yeah or they'll be like i've developed enough conviction in my purchase that like you know like or they'll like become even more entrenched in the brand and i think it's just a really interesting dynamic to bring up and and i do that that series less now uh because it's like very copied which is fine and that's going to copy stuff uh but i'm still hunting after the same thing, which is like, what is the consumer insight?

31:18And how do you get people to think about why they buy and present theses on it that they can then debate, whether it's with themselves, with others in the chat or like in the comments?

31:27Chris Cruz:Yeah. Okay. I want to, I didn't plan to ask this question, but you said something there that makes me think about this. Two industries I'd love to get your, like you to rapid fire about, cause I'm seeing so many different likeness in the fitness, hydration the golf like you're seeing so much of the same that i'm like i actually want to hear your take on these these spaces and go what's working what do you think about them the future of it yeah look it's there's so many brands in so many spaces i look at it two ways one is that like i do think that whenever anyone says anything saturated even golf gear even electrolytes yep look at the look at the tam the total available market look at like how big is it really and i always look at it like okay does unilever or like you know uh any these huge conglomerates do they own still some ridiculous market share 65 of the category and that all moves through cosco or through c or wherever i was like cool you know what there's probably a lot there like even with golf i was like how much golf is just like kind of whack older brands being sold in dick's sporting goods like if that's still above 40 there's still room i basically look at it like every single one of those poor experiences.

32:36It's just getting eroded. And 1 % of that market share for a new brand is enough to make those people rich and have a fully successful company. And so I do think that there is just a lot of room. That's a great perspective.

32:49Chris Cruz:That's a great perspective. But the problem is, while that might exist, if your brand is not unique enough in both its product mechanism and its distribution mechanism, it's not going to reach that opportunity. And that's where I think a lot of the issues. It's like, all right, you start that other brand and it has to be a better product in some way. You have to be able to articulate a value proposition somewhere. Even if it's just like, this is a better product for you because you have this particular fashion sense or proclivity or allergy or whatever, you have to have something. And then you also then have to have, how are we getting attention at a way that is cheaper or better than what we're replacing?

33:24And if you don't have both of those, really, it's like, it's kind of a matter of time before you're washed out in the great electrolyte or protein bar wars, you know?

33:31Chris Cruz:Okay. So, okay, I'm going to stay here for a second because when you're looking at helping a brand distinguish that thing, that differentiator, that, hey, like, are you, like, what's some of the things you think about or that you ask maybe when you're like, is it just what makes you different? Is it just purely that? Yeah, and also it doesn't really matter, right? The protein bar one's a great one where like David is destroying the protein bar category versus the competition because they have a distinct product advantage. They have, they bought technology that means that their macros will be better than anyone else can do.

34:02And then they excluded the competition from also having that technology. And so they are, they have a value prop that every other brand has to compete with. So if you want to succeed in that niche, it's like, okay, what is something that a consumer will choose on the shelf better than a better macro? And so then you have a couple options there. It's like, all right, everyone cares about what goes in their body. So you can 100 % be like 100 % natural, but then 100 % natural, it's kind of taste whack. So it's like, okay, can you make it taste good? Okay, does not have too much sugar. You just start to find your way to that customer.

34:29Like, all right, people were allergic to a specific ingredient. Lifestyle, I was like, counterculture is always one. You can always go liquid death, black rifle coffee, death wish coffee. You can always say, I'm going to make it black. I'm going to put zombies on it. There's an, you may not dominate the market, but there's an angle, right?

34:45Chris Cruz:And so you start to look like, what are these pieces? So, okay, in that, is that not, like, are we saying in that conversation at that point, even bringing back to brand versus product, are we essentially going, hey, the product is just as good, but you won't win here without brand? is that what you're saying? So basically your options are, do you have a differentiator in terms of like an actual product feature? And if not, if you're not, if you're just Liquid Death, okay, do you have a brand advantage that is good enough to make up for that? That is good enough to just sell water the same as every other water?

35:15Then your brand has to be incredible. And an incredible brand isn't like sick logos, isn't whatever. It's like Liquid Death is a good example. It's a true, it's true insanity at this point, right? And there's very other few examples that aren't picking a, oh, I'm going to pick, I'm going to target the right, you know, or I'm going to target, I'm going to get some entrenched lifestyle ideology and like nail it down. And so you don't have a lot of options in that space. Like honestly, you start rolling through that. It's really like ingredient, natural, hippie, and like beach doesn't work anymore.

35:44You know, it's like, okay, so you kind of get like extreme, like you only have a few angles to go on. And I think it obviously like product still heals all wounds. I think this morning, Grooms got acquired by Unilever. Oh, wow.

35:55Chris Cruz:I didn't see that. Yeah, and so, and like, look, they had a product differential. They said there's an entrenched category. AG1 has taken the greens category. AG1 is a bad product experience. You have to mix disgusting-tasting greens in a fucking water cup. That's a crazy, that's a crazy product, right? Like, but people want it bad enough. They want their greens bad enough. They are willing to do this insane user experience. And they're like, we're cool. We're just going to make it American. It has sugar now. Here you go. And now it's a gummy. And like, and just dominate. That is a product advantage, you know?

36:24Chris Cruz:and yes you're like i love that because like the the reality of what you're saying is so it's just so real real there um when you're when we're when we're i want to go back a couple steps here and then we'll begin to land this plane because when we're when we're seeing these brands developing their media companies i want to go back to this media company play here because i thought about liquid death you said liquid death and i remember seeing the the outlandishness of the media they created, the things like that. But I also have this question, like we, we even eternally try to do content like where we're doing this thing.

36:56Chris Cruz:We do the show called Field Trip where it's nothing specific brand. It's like Anthony Bourdain style, like going to Nashville and we go to experiences in Nashville, but it lives on our social. When, but the question I get from people when they start engaging with content that doesn't deliberately mention their product, doesn't deliberately mention these things is where's the ROI on this and how are we going to actually make a difference with this for our business? Yeah. And so I talk about this every day. Um, topic I'm passionate about. And I look at like content is a funnel. So if you're like, cool, we only make videos about our products and they all do.

37:32Okay. And you're like, okay, if you make viral content, even if it's not about your product, even if it's just about your category, my whole goal on like top of funnel content, viral content, is to reach your target demographic. That is your number one goal. That content's job is to reach your target consumer. It does not matter what it's about, whether your product's included or not. There's plenty of ways to do it with your product. But even if you were just doing, again, you're a company and you're doing tour guide about whatever, you know, and like, and your product's not even mentioned, does it hit your consumer, like a large chunk of that viewership is your consumer?

38:01What's going to happen there is it's going to raise the floor of the rest of your content. Your middle of funnel content is more educational about your product and your bottom of funnel content where you have a CTA. More people are coming in at the top that are in your target demo. There's going to be a fall off like any funnel between them and who watches your actual product informational. But because of the way the algorithms work, they're at least going to get shown it. Your next video is going to get shown to the people that watched your viral video in a small chunk. And if it goes well, it's going to get shown to more of them.

38:26If it goes mediocre, it will stop. But you still got that demographic you didn't get before. You weren't even going to get a view from them if you only did middle of funnel. And so that's like a conversation I have all the time with brands where like, it's just going to raise the floor on your views for all your other content. And that's why you attack it. And, um, and like the more that you do with that, the more you find a synergy of like, oh, our product is in our top of funnel content, the better it goes. But even if it's not, you have to raise that floor. If your floor is still, oh, we only get 10 ,000 views or we only get 40 ,000 views of video.

38:54It's because you're not doing enough top of funnel.

38:58Chris Cruz:That's good. That's good right there. Uh, all right, we're going to begin to land this plane here. I want to ask you, you said, when we asked you about brand versus product, you said something, you said, I'm no longer doing this as much. Why are you, what's the metrics you're deciding to not do certain things? Is it just because other people are doing it? Yeah, I literally run the same pillar system. So I just look, I just look at views. And I've also noticed there's like series. I have a bunch of series. I have the series status of hot. I have before product versus brand. I had a similar series called status.

39:25I had a red flag, green flag. Like I've always Is it like versus content? And you'll start to notice like dwindling efficacy where it's like cool. When I'm looking at the pillars, it's like cool, if I do that, it was product reviews in general. I thought because that's what's the pillar. It's like product versus brand. I'd also just do like a buying guide. And I kind of know it's like, yeah, I guess January, February, March, those just fall off. The views aren't there. Some of it's seasonal. I'm sure back next November, December, I'll be ripping it again because people are in the mood to buy. Christmas, yeah.

39:53But then I just look at that data where I'm like, cool, I tried some more in January. it was all down, even though the content was pretty good. I was like, cool, that's just like that pillar's gone, new pillars in. So now like I'm doing more travel content, I'm doing more like psychology of purchase content where I'm still like hitting my base in a different way. And I'm gonna test back into it, right? I may try in April, May, or like I may not. It all really depends on if you have enough good ideas where your content goes. I am, I also think like content styles in general get saturated. People used to really want buying recommendations two years ago, even last year.

40:25I think a lot now we're overwhelmed with buying recommendations. People are way more interested in why they buy and what's going on in culture and being educated. And I love making content like that. And so I'm attacking that angle. In a year, it's probably going to be different. People are probably going to be like, please stop teaching me shit. Okay, then what's the content going to be?

40:42Chris Cruz:Yeah, because I noticed the psychology of buying stuff that you're doing, like watching you unpack golf, unpack some of the, you've never actually eaten real wasabi or never actually eaten real truffle. like it tied me back to a con uh a statement you made a long time ago this is just kind of like how deep i've been in your content before is like you wanted to be this kind of like the generation seth godin like thinking going i want to bring ideas refresh to this thing now if you're if you're going hey right now something i'm chewing on that i'm wondering like hey is this gonna make is this gonna make progress or is this gonna die like what's something that you're like man it's on the cusp of my thinking right now?

41:22Oh man, I have a look. So I'm always, my life for content is like, I workshop bits basically. Like, almost like a comedian. And I learned this from a friend of mine who's a popular YouTuber where we hung out and he was like workshopping a bit. I don't know if he used it else. I don't want to say it. It's actually hilarious. But he had this whole thing. I'm like, oh, he, I was like, I hadn't thought like that before, but I have a bunch of these bits. I always have bits in my videos. And so I'm always like workshopping a concept. So for instance, that golf video is anchored by this bit that like there's so many golf brands just with this letter M.

41:54Like Malvin, Manners, Mizuno, McCod, Bavar, Matthews, Mellon. Like you can just keep going. And I was like, oh, that's funny. Like I can anchor a video just in that idea. And so I'm always thinking in bits and I'm working on one right now about tech introspection. Like I don't know if you saw the Marc Andreessen had the like, and I was like, so I'm like, how do I connect that to like some other trend in culture like I can like make a connection. So I was like, oh, like there's also of that trend, single till series B, where like guys are saying, cool, I'm not going to date until we get series B.

42:23And so I was like, okay, look, the lack of introspection in tech comes from the lack of sex in tech. Like that's a, that's a bit, right? And it's like, you know, like, and so I'm like workshopping this idea to see if it has legs. And what I'll literally do is like, I was like, I'll do have comments like this. Okay. He laughed. That's a good sign. I'll probably like talking to people being like, yo, is this like a thing? You know? And like, okay, how do you feel about this? and like my wife's opinion or like her friend's opinion. And you start to be like, you piece together a picture of, is this a real scenario?

42:50And then it's like, how do you expound around that? And so I have like a hundred of those bits at all times.

42:56Chris Cruz:Wow, bro. I love that. I love that. Well, man, I think there's a treasure trove here. And there's so much that you dive into, even on your YouTube, where people can get so much more in depth on some of these topics we discussed. I'm really grateful for the time, man. Thank you for spending some time with us. Of course, happy to do it. And yeah, thanks for having me.