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Ecommerce Therapy: 3 Nine-Figure Operators on Focus & Passion

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Ecommerce Therapy: 3 Nine-Figure Operators on Focus & Passion

The podcast explores how leaders in fast-evolving industries like AI and e-commerce maintain focus, passion, and effectiveness amid growing complexity. As companies scale, they risk drifting toward low-impact, safe tasks due to fear of failure, which undermines high-value innovation. A key insight is the need for dynamic, rolling planning—such as quarterly, 12- to 18-month rolling goals—instead of rigid annual plans, ensuring alignment with real-time market shifts. Daily stand-ups and short check-ins help teams stay on the same page, fostering accountability and shared clarity. The discussion emphasizes that AI boosts output but doesn’t replace judgment; companies must prioritize what actually drives revenue and growth. Smaller, hyper-focused teams are emerging as a more sustainable model, avoiding the inefficiencies of large, bureaucratic structures. Passion, the podcast suggests, comes not from loving a specific product, but from building value and enabling better lives. Finally, true success is measured by impact and effectiveness—not just hours worked or activity volume. The episode concludes with a call to reframe work as purpose-driven, where leaders use tools like AI not to expand output endlessly, but to focus on what truly matters, enabling smarter decisions, better results, and greater personal and organizational fulfillment.

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Welcome to the operator's podcast today. It's a therapy episode. We have Q4 right around the corner You can go to nine ops.com/blackfriday There's already been a webinar giving you tips tricks everything for it But today it's about passion and priority what makes us want to keep doing this How do we stay engaged in the world of AI and how can you run teams as teams change? Are they gonna get bigger smaller? There's excess work. What are you gonna do with it? There's good tips and tricks in here But a lot of it is us just spilling our guts out putting our heart and our sleeves listen to the therapy episode with Matt Mike Sean Let's get into it. I think right now the thing that I'm the focused on the most is How do I make sure that my organization is Focusing on the right things. How do I lead them in doing that? How do I teach that skill? And one of the tendencies I've noticed in myself is that as we're getting bigger I mean, we sell so many different things in so many different places that I do have this negative tendency whenever I feel like we're not Focusing the way that we should to just be like we should go back the way we did it, you know, six years ago seven years ago It's not realistic. It's just I Sometimes I really kind of long for the simplicity of the earlier days in the company and now it's much bigger or much more complex And so I'm just kind of wrestling with as a leader. How do I help people? To have good judgment about what it is. They need to be focused on it. They give them point in time How are you figuring out how to do that? Like what tips and tricks you have? Well, one of the things that we've run into Everybody probably has some kind of an annual planning cycle and we've been on an annual planning cycle for several years now And we're gonna change it. We're gonna change it to try annual And that that might not even be frequent enough because we started realizing we were setting these goals in December and by like March or April it was like those are the wrong goals and we're just we're in a trend industry that's moving and changing very quickly Plus, you know, like we don't control the market and our customers. So this year Kids has just been Awesome for us way better than expected. We thought it would be good. It was way better than expected Kids textiles has been way better than expected for us And so even if we had different plans about the things we were gonna focus on You know what point you just say hey guys stop everything the markets spoken This is what it wants us to be doing. This is what it wants us to be spoke to be focused on and I Think that the way I verbalized it in a meeting last week was If you think about everybody that works at your company, they probably have this array of things they can work on tasks projects and They range from exceptionally high impact but really really ambiguous hard to figure out what to do all the way down to Super easy to figure out, but are barely gonna move the needle at all and I think I've seen this observation made by others before and I think it's true that If you're not careful people in your organization will pick these middle of the road tasks where they feel reasonably confident that they can do them and do them well And we'll make some impact but aren't really the most impactful things and so you end up having your organization not necessarily Focusing all their attention on the most important things because those are always the most ambiguous Those are always the most challenging questions the ones where it's the easiest for you to look stupid the easiest for you to not be able to come up with an answer that actually You know works out and so there's there's this kind of like self-preservation like fear of looking bad that can Make our organizations and the people in our organizations drift away from doing like the the best work The best things to be working on at any given point in time. So like you guys have heard of EOS right like entrepreneur operating system Then there's like Rockefeller habits. So they've got this very prescribed, you know annual planning cycle and then you do quarterly Planning in between and there's a new wants thing that we did Mike that helped a lot Which was we just stuck we went to a quarterly Planning cycle, but it was always a 12 or 18 month rolling planning every quarter Because everything was changing so quickly. So like we no longer had like we set annual plans once a year And then we update as we go we literally Every three months we set new 12 month plans on a rolling basis Just because things would shift around too much the hardest part of that Was product because product cycles are just so damn long. Yeah, I mean and you don't know when they're gonna get done Is another thing? So when you're dealing with and all of us have to deal with tools But when you're dealing with tools and especially tools with plastic it it just You can think hey, this is gonna be a three or four month process and and then nine months later you finally get it So it's really difficult to say hey, we're gonna finish this product and launch it in this quarter When you're actually developing the the tooling or doing something fairly new for the first time Sean, how do you do this like you you said you guys always set your big priorities, right? Like you you deliver that at some cadence like here are my here the most important things in the business How often do you change them? You're talking about the patent did Sean Frank 12 things You know, we're not we're not doing EOS We're not doing the Rockefeller system. We're not talking about we do the Sean Frank 12 things and we've gotten I've personally gotten a lot from other people who run companies. I think 12 is too many Do I think it's perfect because like we try to hit like you know if eight of them get done We did a bunch of that year so like this year one of the 12 things it's done now with celebrity and sweeps so that is like The objective to the company and this is you know my CMO and my creative director is we're gonna do sweeps this year We do sweeps every single year the way we're gonna elevate it is we're going to get a celebrity in it I'm like, I don't care who the celebrity is Here's your budget you have to get this done and that this it's a deadline You have to shoot the content by May so it can go live in July or whatever right So that is like a concrete makes the company better if we get this done Another one of our goals probably more you know And big with it and big US there you go mailed it is I want to find an affiliate offer like we have you know Every year five million men come through a website make a purchase and I try to sell them other stuff Sometimes it works. I usually it doesn't so I'd like to find an affiliate offer to go with that first purchase or or upsell them later Like give them Netflix or HBR or whatever so I could make at least one dollar of incremental profit off all these customers That's not gonna get done. We have not found a good affiliate offer But like you know, I can explain the rationale of like why we're looking at this and like what might be interesting The only people who wanted to affiliate offers with us are gambling apps and it's like okay Do we really want to make that that jump to try to give people into gambling right? Do they change it all Sean? So when you set the 12 things for the year Do you go back and replace any? And then how do you decide how who decides that yes, the 12 things Only come from me so that is like one of my jobs to see. I was just at those things up I've never changed one midway through the year We're the band in them, but I've never added one You know, it's maybe I'm not being as ambitious enough, but like What the symptom the symptom both you guys just described is that the year is Too long for a business changing fast, but the same time we wake up in the years over It's like crazy how fast these years just start sort of piloting up right like you know We're midway through the year and like sweeps is over at this point. We're getting into Q4 Like we already started planning for for 2027 and the product cycle for us is already in 2028. So Yeah, it's it's one of these weird things where like we've never been more change inside of a business with AI and everything else But the same time The years just go so fast, man Well, that's kind of the thing that Mike I don't know if you're dealing with this But the the promise of AI is you can do so much more because the nominal cost of doing everything is getting lower Now the problem is like should you do it all? Uh, how how do you decide what's a good choice like what's a good decision? What's a bad decision? Um, because I think that When you get to your scale mic with you have like team size that big The risk you're identifying is real, which is People aren't entrepreneurial by nature. So they're not going to have this like inherent. I need to choose this like the Uh, what is it that asymmetrical award thing that we do as founders people don't do that right they choose like that one looks safe and AI makes a lot of safe look great Uh That you can package it all up. So I don't know how you handle that. It's Well, I think I think you're you're saying exactly what people need to hear which is That the technology makes it easier than ever to do stuff and 90 95% of the stuff you can do probably won't move your business forward at all. I mean we were all You know impressed in the early days where it's like wow I can tell AI to write this thing and it just effortlessly like you know Spits out 10 pages of me But what we know today is nobody's going to read that nobody wants to read that you know like that's a It's kind of a useless skill that it can just generate you know crazy amounts of text output and And I think that in a similar way like you can say woman have really leveraged the technology to automate this or that But that doesn't even necessarily answer the question of whether you should be doing this or that You know what I mean like that's one of my favorite Elon quotes that the problem with engineers is they'll spend it a bunch of time optimizing a task that shouldn't exist in the first place And that I feel like it's my responsibility shana. I like your list Because it really makes it clear like hey here is how I'm evaluating our year and here's what successes And I think that the CEO has to do that ultimately the CEO or the you know the head shareholder somebody has to say Like this is the way that I'm going to grade the performance of the company this year. And you really have to shine a spotlight on those things. Or like people just they it's not that they don't work hard. And it's not that they don't want to do good work. It's just there's this organizational drift to things that don't actually move the needle sometimes. Dude, and our whole companies there's we all have one really special thing about us that is driving us forward. And then it's like not 95% of what we do is basically pointless. It is like it's it's feigning in support of the main important thing. It's depressingly true. How much that is the case that like most companies it's a singular product market fit product channel fit type thing and everything else orbits around that one thing. Black Friday cyber money are coming. Are you ready? Not in the normal marketing calendar and offers prep sense. I am talking measurement attribution. Are you even going to know what winning and losing looks like when the big Q4 season hits reality is the businesses that win set up their measurement solution when the times are slow not the night before the big weekend. There's a reason for this. You see with north beam you're getting a totally independent completely new set of ad performance numbers with infinite look back windows. That means that the longer that the data grows the more valuable it becomes. So when CPMs are spiking in November you will know precisely where every dollar is coming from while your competitors are guessing. This is important. Black Friday is one in the summer, not the day before. Book a demo with north beam today. The link is in the description. Go check it out. You end up building structure and you know like checks and balances and everything like to try to make them more secure. But it's kind of like you're building all this scaffolding around a building but it doesn't touch the building. The building is going to stand regardless. You're not actually supporting it. It just looks like it's supporting it. So then do you need to do that at all? And how do you identify what is waste wasted work? Is it worth identifying that it's waste to work? That's another question. It doesn't even matter. There's the perception of work is valuable to outside to like to outside investors or whatever. Like if you were just like, you know, let's say Mike's business really nails down to and you can try to be him wrong. It's like wholesale sales in Amazon sales and it's like we get rid of everything else. And that's probably 50% of all people, 90% of all work. We just get rid of that. Their business would be incredibly profitable but it would scare the out of banks and lenders and acquires. It's like, wait, you don't have an HR team? You don't have finance. You don't have an operator. Look now, we have one guy in the warehouse who does the wholesale orders and one guy who does the Amazon orders. And I'm sitting here collecting checks, right? But I do worry that a lot of that scaffolding work will be replaced with just AI over time, right? And then businesses get to just do the core thing. But that's when you talk about job displacement. What's it going to do? I don't know if you guys like, I'm sure you've looked at Apple ovens, uh, financials like their P&L. They're so profitable. The first time I saw that, I was like, well, that can't be right. Because like, I was just so used to these big tech companies, like Google and whatever, having a certain amount of EBITDA and then Apple oven shows up, it's like, well, no, if you just don't hire all the people and do all the other crap, this is the margin of a large software company. Uh, so it's a good point, Sean. I just don't see anybody doing it. We're the older dinosaurs, you know what I mean? Like we're, we've got to make sure we don't go stay, we gotta make sure we stay, you know, evolved. But like, there's some brands coming out. I won't name them, but they're $50 million a year brands and, you know, four people work there. And then the founder also has a software that's doing $5 million a year, right? Like, you have these entrepreneurs who are really leveraging their time network influence to do a bunch of different stuff. Uh, where, you know, I think we're we're all more of an older school CEO where it's like, oh, we got to be in the business, coaching these people, like, you know, driving up, but maybe you're coaching some coaching somebody or something that just doesn't actually move the needle. And that's like the scariest thing. Like inside of Ridge, I got to make new products and I got to put them on Facebook ads. It's like, and it's like, you know, our Amazon teams run by one person right now. Amazon will be eight figures this year and it's up eight figures this year. It's more, it's more than doubling, right? And it's one guy doing that work. But it's like, that work is coasting off of the work of our paid media team, that coastal work of our product team. But like, if you're not in those three funnels, it's like, what the hell are you like, are you actually making a meaningful difference? I think that's what Mike's, Mike's getting at. You know, you have support staff and then you have people that are in more kind of value creation roles. And I think every organization works that way. I, what I really want to do is get better as a leader teaching people how to look at the array of things they could work on and sharpen their judgment about what would be the thing that would drive us forward the most. Because ultimately, everybody wants to earn more, everybody wants to be able to have more potential in their career. So whether or not they own shares in the company, like it's in their best interest. And sometimes I think that we've done a pretty good job of that. And sometimes I'm like, I don't know that we have, I mean, another thing that I've suggested to our group is I think we need to get back to having some kind of like either a very short weekly stand up or a very short weekly like, Hey, this is our definition of success for this week, which we had gotten kind of all the way into the other ditch where it was all like, Hey, here's success for this year. And sometimes I think it's hard maybe to boil that down into, okay, but what am I supposed to be working on today in order to make sure that we're successful as we want to be. And this isn't a bandage of small teams is it's very easy for everybody to be on the same page about what matters right at this instant. Oh, dude, yeah, it's incredible. Like working with Cody right now on Winks is just so fun. There's two of us doing like on all the like stand-up of the brand because we're recording this and we were launching literally today while we're recording this episode. So by the time this comes out, it'll be live. But it's just a lot of fun when you only have to really talk to like one or two people. This is like Curtis Cody and I are just like, what do you want to do? Okay, do that. That's the most important thing today. Next. And it's multiple times a day, which I actually find really refreshing. It's like it's very the work, like it's blue collar work for sure. But it feels great. Like we're just checking stuff off lists. Like you're just making things happen, you're making ads, you're loading them into accounts, you're writing copy, you're getting emails approved. Like so that feeling is great. It just doesn't scale that way as you had people. It's interesting. I think I've said this before. But if you get on elevators, a lot of elevators, the door shut button isn't actually tight end anything. I mean, it's there, but it just doesn't do anything. And they also do this at crosswalks. I've been told that a lot of crosswalks, the button doesn't actually do anything, but it's the button's still there. And the reason is that like we like to feel kind of agency and control that when I, you know, I get to control when this thing closes or when this crosswalk changes. And man, more and more, I feel like e-commerce is just littered with those types of buttons. It's like, oh, there's this little convig. This number I can change. I should, I should play with that. I should change that. That maybe that is the doorway to future riches. Who knows? And it's like, it's not. It's just like there's a, there's a million little things that you can end up, you know, wasting time and attention and capacity on that don't move the needle, but they sure look interesting. On the stand-up point, and then I'll talk about Mike. We got to play it on this depression dog. But on the stand-up point, do I sound depressed? Maybe, I mean, maybe it's that I have a freshman now. Maybe that's more my problem. You know, my kids are car insurance and have my, have somebody, but my son driving, that's scary enough. That is depressing. All right. There you go, real depression. My son got a tooth last night. So he has his first, he has his first tooth. So I'm right there behind you, bud. Yeah, we're in a little bit different worlds. But dude, on the stand-up piece, I would not be able to run my company if we did not touch base every single day, right? And if I was on the same coast because we have people over the world, I would do it twice a day. I do it at the beginning of the day and the end of the day. And like, like, I know people think it's bad or crazy. The first, the first one to be an hour, the second one to be 15 minutes, and it would just be, okay, teams, tell everyone else what you did today. And like, I know the sound of the sound is micro-manager or whatever. But it's the only way to hold these people accountable, it's accountable to each other. Like, we're all trying to work off the same, the same playbook here. But like, one way I've been able to make sure teams focus on what's important is on those daily stand-ups. On Tuesdays, we tell you sales for last week. So you'll see growth rates by products, by geography, by channel, the whole thing. Growth rates, what's happening in this business. And if something's broken, I say, hey, that's bad. We need to focus on that. Or, hey, this is the most important thing in the business right now. I think like it's, I've never found a way to scale that up past literally being the one telling everyone the entire company on a weekly basis what's important. So yeah, Mike, you got to bring back the weekly stand-ups. I think daily stand-ups. You're paying these people for eight hours a day, dude. You can use it however you want. I think it's a good point, Sean. And maybe this is one of the questions that we're talking about, is like, how much do you talk about doing the thing versus doing the thing? And it's easy to be like, well, we want to spend the maximum amount of time doing the thing. But it's like, well, but if you're not on the same page about what you should be doing, then no, you shouldn't, no, you used to spend more time communicating about the thing. And so like, you don't want to fill your people schedules with meetings because you know that's a path to not where you want to go. I don't know what's down that path, but bankruptcy, you know, boldness, anger, hypertension. But it's also like, if you're not spending time really making sure everybody's on the same page and focused on the same things, then they're off working in disparate directions and that's not going to work either and so I'm trying to figure out, hey, in this world that we're living in, especially as the technology's getting better, how do you kind of balance those two things? But I definitely am leaning more towards what you're saying, Sean, where it's just like, and I don't even know if it has to be a stand up as maybe it's an asynchronous thing that happens at the beginning of every morning where it's just like, via written form, people are able to understand, okay, what is everybody doing and what's being worked on? Dude, I think everyone doesn't actually just break the bone. Why can't I talk to my employees every day? It's like, it's like, what's so important, just make a 30-minute talk. If you're a founder using AI for analytics, you know the trap. Claude plus BigQuery gets your answers that are fast and wrong or slow and right, never both. The problem isn't your analyst, your data, your tools, it's your business context gap. Sarah's IQ fixes that, Connor, who runs my marketing, kind of is reporting time from ten days to 45 minutes. IQ answers in plain English, built on your business logic, consistent, deterministic, and fully transparent with the assumptions and SQL behind every answer. Same answer whether you ask, your CFL ask, or your board asks. And if you're a Claude user, the IQ MCP is ready to plug in today. Claude plus BigQuery isn't enough. It needs your context. Get it at the link in show notes or go to saracentaletics.com to learn more. I was just going to say, meetings are bad. You should try to avoid as many meetings as possible. And I think our version of standup, when everyone gets together and everyone talks, that removes meetings from the calendar because I've been Jason's on the pod, but I've been trying to hack cloud meetings, and people spend all week putting together reports to then present to other teams on, and it's like, you're actually narrowing the band of communication. You think you're doing this thing to help make clarity, but you're actually making it you, doesn't need a time to talk, so problems wait until then, and you end up putting way too much time into the report. You should just show them, "Hey, this is a problem. Let's fix it right now." And that's what a daily communication lets you do. When you theme your stand-ups, right, Sean, like every day is a different focus. Monday, Tuesday, Wednesday, Thursday, Friday, yeah. I know stand-up is in the solution to everything, and Sean's version of the 12 things is in the solution to everything. I'm sorry. I'm crying with those everybody's throats, but. I'm a huge fan of the stand-up, like a huge fan. And I know really large companies that still do it. Daly's, whole team, like hundreds of employees. So I know it's Gales. I was talking to a chief of staff over at Robinhood, and she asked me if I had ambition to ever run a 5,000-person organization, and I'm like, "No." Who says yes to that? I'm like, "I don't even know how you would do that." I have this logical profile of that person, and I bet you it's really close to might also be serial killer, right, and some other negative trait. Like that person. The entire managerial class or serial killer sociopaths, I love it. My ambition in life is to run 5,000-person organization. What is wrong with you? Like, no way. I think that it's true that it's a totally different skillset. And I think this is the hard thing about entrepreneurship. The more entrepreneurial you are, the less you're excited about just managing big groups of people. Yeah. I had that. I don't think Zoom has a limit to get 5,000 people on a call. I don't know what I would do. We have to get back there every day. It'd be 12,000 things, not 12 things. Totally. All right, Matt, what's your piece of therapy you need support on? You know what? I feel like I have whiplash. So, going from most of my day being what Mike's talking about, running larger teams, and a bigger company with rhythms and just stuff on the go to now being in the weeds building the winks, it feels like it's like a total different animal, right? It's like I'm back to hands-on keyboard, lots and lots of button pushing. Cody and I talk a weird amount, just standing everything up right now. And I suspect that it will settle into more rhythms as we get going and it becomes more about like just straight up marketing. But right now, it's just like launch mode is such a slog of like, like yesterday I spent all day, literally all day, just reviewing copy in every email flow, making sure that the links weren't broken. Using AI to do a lot of this, too, it's still like the work has to get done, you know, generating like any missing assets, like we've got to get those made. It's onboarding vendors, you know, setting up whatever those weekly rhythms are. Like it's just a lot, it feels like blue collar digital work. It really does. Like I know we joke about it, but man, when you're launching and you're small, yeah, this is a lesson. Yeah, dude. It's a lot of fun. I love it. But it's holy. It's a lot of work. It's true zero to one nature, man, you know, a lot of a lot of people celebrate that zero to one. But when you're doing it, boring, it's so boring, man, like, yeah, last week I was, I focused on like landing pages and I just every, every so often, I would just slap Cody. I'm like, all right, this one's done. Let it rip. Cause we're just trying to take our best shot on goal at a good launch, right? And like we, I mean, we've been in this game long enough. We know what the game is, like it's a marketing game. It's like we've got to find product market fit right now. And so it's like what are all the best ways that we think we can do that? Like the minimum effective dose to find product market fit is the name of the game. And to do that work is just boring work. Like I just don't know how else to put it like it's, I just sit down on a right copy. Like that's it. It's hard because all of the growth happens so much slower early on. It's just like revenue, but like, okay, so you write some new copy. How quickly can you get a feel for whether or not that's working? The way that everything progresses is slower. And I've seen this with people that have run companies that are whatever doing 50, 100, 100 plus million that you get really romantic about the early days of like, I love to do zero to one again. And then you do it and you realize like, oh man, it's like I've been running at 10 miles per hour on a treadmill and now I have to jog on a treadmill going one mile per hour. You know, it's just like, it's very frustrating. Like you want it to be going faster than it is because you have the muscles and the capabilities to be running that thing at a much bigger scale, but it just can't, you can't just kind of hit a button and something be at that pace. You know what else Mike? Honestly, like I had this thought yesterday. I don't think you can do startup mode, zero to one while you're also running something that's at large scale. Like the modality and the mindset and how you're spending it is so freaking different. Like if I had to switch from hand running like day to day at simple modern to now I've got to go and like dig into the weeds for hours on end, that is massive whiplash. Like you are, that's a serious amount of context switch. I think that would be very hard. I don't think I can do it. I've definitely done it. That's been my last year. So I, and I think that going back to that point I made earlier, like the one of the risky things of doing that is that it's just very easy if I'm frustrated about something in simple modern to be like, I'm going to go work on Trevi, or I'm going to go work on our new projects. And if you know Trevi is going slower than I want to, then I'll just kind of be like, I'm going to context switch over to this thing over there, but that doesn't mean I'm necessarily working on the best thing or the highest leverage thing. So, and you're right, it's a huge, I do a huge amount of context switching. And I'm probably less effective as a result of it, you know, I think I can do it. But the research says you're probably not very, you know, like multitasking, you're probably not as good as you think you are. Most AI tools in software don't give you direct ROI every month, but PostScript does. I run two PostScript AI products at Ridge, both show up on our PNL. Infinity testing runs continuous AB tests on our SMS automations completely in the background. It's driven $446,000 in incremental revenue, not just attributed incremental. That's a 32X incremental row as with click the rates up 43%. Then there's shopper and AI sales agent that answers every inbound text in under 40 seconds. We're running 23X ROI on messaging cost of loan. If you want SMS software that gives a proven ROI, go to PostScript.io and book a free demo. Do either of you have a strong take on that on with AI now? Because like, I don't know if I'm actually more productive. I've got like six frickin terminal windows open. They're all doing different, I feel it, I feel like a badass, but it's like, am I actually more productive? Or should I just shut it all down? Like I did that yesterday, the yesterday was copy day, email. I shut everything else off, didn't do anything else, and all I did was work on, you know. Got a lot done. I'm sure zero to one teaches you guys lots of empathy because you know, like you have David Herman freaking out about Facebook bugs or whatever. And I'm like, whatever, David, I don't care. But you actually have to do it, you have to look deal with or crashing as a window. So, you know what else? I'm what I'm really appreciating, like one of the pieces of feedback that we always, that we get frequently for this show is like, make more content for the smaller brand. Like the zero to one, the one to five, the five to 10, it's like, oh, yeah, this is going to be really easy. I'm just standing this up now because that's all we're doing is in the weeds, don't have all the accoutrements of a company, like which sounds great, I mean, but you hear Mike, it's not that great sometimes. Well, it's like I've I've said as we were getting ready for it that like there's like three or four episodes early on and us building something new that'll be like super easy. It's like oh yeah, we got to set this up. We got to stand that up. We got to do this, whatever. But if you don't find some kind of traction product market fit pretty quickly, it's going to be a pretty boring show pretty quick because it's like, yeah, this is episode 18 still hitting $300 pack have no idea going to throw some more stuff at the wall. See you next week. You know, don't you know the art depressing today? That's world season two, dude. That's season two. That's right. Huge cliffhanger at the end of season one where we go from 300 to 200 pack. You'll have to tune back in to find out what happens next. Well, look, I think at the very least it'll give us a great post-mortem about like the realities of launching a modern day brand. And I think it's going to be so fun to listen to that. Matt, on your thing about are you more productive with AI? For sure, but I do think there's this degree where you get you end up having so much productivity and so much free time. But then you're like, okay, well, what else can I do with it? And that is that is the danger zone. Me and Connor talk about this. I do think AI is going to let people work four days a week because at a certain point, all projects worth doing at rage are going to get done. Like we're getting to the point where, you know, where we call it a hundred percent organization, but we're probably doing the work of 300 people. And then how much more work could there be? It's like we're launching thousands of ads. You know what I mean? We're working with tons of partners. Like we have all the product stuff going on. And I do think like the real, the real curveball and AI is that productivity will just all the works done. Okay, where everyone could take Friday off. Like that's what I think we're going towards. What do you guys think about that? Well, quantity doesn't make up for judgment. I think is the big takeaway from AI that, yeah, you can fire out 10x the code. You can, you know, write 100x the output, but that doesn't replace the judgment of what should you be working on? What should you be talking about? What are the things that matter the most? So yeah, Ridge can launch 100 products. I'm sure if you wanted to, but that doesn't mean like your top five percent are still going to be your top five percent. You know, it's not like there's that many ideas out there in the universe of things that Ridge should even think about launching. And so I think that what you're saying is a really good insight, Sean, which is just because you have the capacity doesn't necessarily mean that's a good thing, especially if that capacity takes you out of judgment mode of like what is important to work on right now? And what is likely to drive the bottom line? And don't confuse, you know, like we talk about this sometimes when it comes to like the people that work with us that it's important for them to understand and not confuse like showing up and working a certain number of hour of weeks or being, you know, productive and doing something, that's not actually success in your job. Success in your job is actually being able to drive output and successful, you know, sales and profit and stuff like that. And so I think there is definitely where in this era where we're we're very in danger of confusing productivity with being effective. It's the activity versus accomplishment thing. Totally. And it's like, look, we're hitting the point where you every company has 200 additional digital workers in AI, right? And it's like, great, put them to work. But at a certain point, how many more digital workers do you need? And maybe I'm just not thinking clearly enough about the future, maybe I'm not being ambitious enough. But at a certain point, if I have a thousand free digital workers, I'm only going to send an email every day. So I totally, I totally have a take on this, Sean. My take is, and I think the data already is proving that this is where the market's going, is that organizations are going to get smaller and there's just going to be a lot more of them. But if you think about like the thematically what I've been talking about today, like that's exactly what you would expect to happen, that you would expect that as our tools get better, organizations will get more and more focused on doing like a thing super awesome, right? Like, Ridge can sell toothpaste, I guess. But like, are you ever going to do that at a world class level? Probably not. And why would you? Why not just start a separate company that sells toothpaste? And like, I think about that even with simple modern. And this is one of the reasons why we've gone the brands route where we're just exploding things out, very small teams, very focused. So my guess is that that's going to be one of the ways it's not going to be like, oh, this team now does 10x as much. It's just like, no, there's just teams are smaller and there's a lot more teams that are hyper focused on a thing. If you're scaling any commerce brand today, ads alone aren't enough. After self-focuses on the one moment that every brand already owns, after checkout and turns the post-purchase moment into more profit, monetize every order with post-purchase offers and thank you page experiences without disrupting checkout or hurting conversion. Enterprise grade tech used by Gap, Ticketmaster, Macy's and Target, now driving results for brands like True Classic, Hexclad, Ridge, and Jones Road. I would know. This is the reason I ended up buying three pants from Hexclad instead of two. Aftersell has already generated over one billion in additional revenue for e-commerce brands, revenue that doesn't require more traffic or higher cack. Check out Aftersell and tell them that the operator sent you. To take that a step further, Mike, you do just get lots of time back and you decide to do something else with it. I think that's the question, Sean. It's more a question of goals. Why stop at a four day work week? Have you ever seen the graph of hours worked in the United States over the last 150 years? What do you think the average number of hours that was worked by person in the United States at the end of the 1800s? 120? It was like 95 because most people were farmers. You know? It's like, you just have a ton of farmers and it's like, yeah, when the sun's up, I'm working. And so like, it's crazy when we talk about work life balance of like, yeah, man, you know, 40-hour a week job. I don't know if I've got work life balance. And you know, previous generations are just rolling over in their graves. So, but yeah, I mean, that's the trend. It's been the trend. And I don't see any reason why that trend is likely to stop, which is all this like, doomer mentality about the technology. I push back on because I'm like, what if the technology means that we are much more connected relationally with other people and that work takes up less and less of our mind share? And, you know, there's less and less disease. And like one of my my theories is that we're at peak screen peak mouse click that from this point on, you know, the technology starts to become less and less intrusive in our lives. And so anyway, like, yeah, it's like, how can you not be excited about a future that makes that possible where more and more of my week is not spent trying to figure out, you know, how much this type of P.P. plastic is going to shrink and what that means for a mold and like actually, like, spending time with my son or like getting to know my neighbors or whatever else. People will spend less hours working on one job or one thing just because there'll be more, there's I, when I'm trying to realize I think there's a finite amount of work and organization can actually absorb, right? And then outside of that is actually a detriment. You end up doing more process for the sake of process to fill up hours. Yeah, I agree. I think the what Mike is sitting on is important. I think the other thing I would add is that most people don't actually like to work. Like work is not something that a lot of people want to do. You could argue that like, a lot of people like to create and maybe they just don't have jobs that allow them to create. But if you said to somebody like, you can make the same amount of money and work half the time, they would have like very happily do that. And they probably would not go get another job to make more money. They would probably just take the time. You know, I think entrepreneurs are just weird. Yeah, like all of us are trying to be like, yeah, maybe we'll have multiple companies and the average person's going to be like, I'm going to go to the movies twice this week, right? Yes. Yeah. Yeah. I watch football all day on like whatever the night is. Yeah. Yeah. It's I had a friend once we were talking about this. Like, what do you think? What what happens when people have AI do all the work for them? What are they going to do? He's like, whatever they do on the weekend. That's the answer. It's like, whatever you do on Sunday, you're going to do that every day. Yeah. Look, and do humans normalize? Like we're we're talking about how everyone's like, how this is the worst time ever and capitalism is stealing money from her, whatever. And then you just heard Mike say that three generations ago, everyone you know worked till they died on a farm, right? And it's like and and now you have self-driving cars and iPhones and you can order of, you know, private burrito taxis or whatever, right? It's like, ma'am, it's a life's great. You're ever needs to shut up. So Sean, what about you, man? What's going on in your world? Yeah. So I originally come into this pod. I was like, therapy episode. My life's an awesome dog. I'm killing it. But you know, I started thinking about what are what are challenges that I face? And it really is how do you say passion about something you've done for so long, right? I did not found Ridge wallet. I'm not passionate about wallets. Like, this is a passion about e-commerce and system building. So like, that's what I that's why I got into this. And the longer you do a business, the bigger it gets, you know, it does start to lose some of the luster, right? The actual shyness of being in because I see the reality of it. I'm sure everybody businesses like this. And the other thing is we are five years into a stagnation cycle. Like, interest rates have not come down. The signals from Wells Fargo point to the interest rates are actually going to go up, right? And that just makes it really difficult to be running a discretionary consumer brand. Like the market at all time highs. Like people I know we're getting fabulously wealthy. And I'm like, yeah, no, I'm still selling the wall. That's all the internet. And it just seems very unvalued in today's market, right? Where I'm, you know, I'm a 1% outcome. I am so happy and blessed to be doing this and have a great job and rich is growing. It's all great. But Bayes is a great brand. They got the 230 million in revenue. Then they had a couple down years, they're at like 200 ish, whatever, 210. And they just sold for one ex revenue. And it's like, all right, everybody, that is the reality of the e-commerce market. They got about 10x EBITDA, right? And that's a really good outcome to a strategic. That's basically all you could pray for. And I'm like, you're looking around. It's like, oh, god damn, I just spent 10 years of my life. And I, you missed that one window. Timing is everything, you know what I mean? You know, in real estate, people say location, location, location. If you're in any sort of business, it's timing, timing, timing. Like if you're too late or too early, it just, it could take, it could take a decade of your life. Most AI tools right now are all promise and no delivery. You know exactly what I am talking about. Super fancy launch videos. This is why I'm in loving what Rich panel is doing. They have AI and support smashed together, made it practical, made it useful, made it valuable to brands today, not on some future promise. And instead of asking you to spend weeks writing prompts and uploading help docs and babysitting, they flipped the whole script. There AI builds your support team for you and everything it needs. I've watched it. It works. It's freaking amazing. Rich panel even guarantees 50% of your support volume will be automated by AI within 30 days or your money back. I call that a no brainer offer. The pricing is also kind of wild, about 20 cents per conversation instead of most other vendors being like a dollar to $3, which is low nuts. If you are interested, go to richpanel.com/demo not for some generic demo, but do actually book a call and watch them build your actual support team. Do you guys actually believe that you can be passionate about the thing that you do? Like or like the products, the category. I just feel I sometimes wonder if that's actually just like not the right frame. Like I've never been passionate about any product I've sold. But I love building companies. Like I like the active creation. I like creative. I like writing and all that stuff. So there's like an element of it I like, but like the product I don't give. I'll sell anything. I will sell toothpaste happily. Yeah, my Michael's talking about rich sound toothpaste. I'm like, I write that down toothpaste. I had a power bank that could just shoot toothpaste into my mouth. I love products like that so much. But I actually think you can be passionate about whatever you do trying to do it at a standard. And I think that that's probably the way that a lot of the people that think about the world the way that we do the way that they approach it is. And so like if I'm going to sell water bottles and I want to do it well, you know, and like I think you're right, I'm kind of more agnostic like about product. It's not like oh, I could only work on that or sell that. And I get kind of annoyed, you know, especially in the consumable world. There's there was a little bit of a Twitter kerfluffle about this of like people like kind of running down other people's products. Well, well, you use, you know, you use fruit, you use sucralose like, oh, well, you, you know, you're not really serious about making a good product where yeah, and it's like I just think I think it's an honorable thing. So I'll give it, I'll give a story that illustrates the way I feel about this. Took my son with me on a trip to Utah. We work with a partner there for all of our trevvy production and we're going to do some other things with them. And I'd never taken him on a factory visit with me. Like I said, he's 14, he's about to turn 15. And the guy that's the CEO of the factory was real gracious. And at one point he took my son around him, it's just showing him all these things in the factory and the line was running and like how they worked and what they did and whatever. And so it was cool. It's cool for Carter to be exposed to that. And then I pulled him aside right in front of one of the lines and I said, this is what it takes for all the people in the world to be able to have the kind of lives that they want to live and the kind of standard of living that we're all used to. And it is an honorable thing that we get to do, that we get to work hard so that people are able to experience life that way. And that is what it's all about. And I think that I think you can get excited about that. Like I am adding value to the world by doing this thing and doing it with excellence. And that's the lives that we all get to enjoy today are just a result of countless, you know, people, businessmen in the past that took that mindset and did it with excellence. And so I don't, that's kind of more the framing I'm using for him as I'm giving him vision. He wants to be an entrepreneur. And I think that that's the framing I try and take to my day today when especially when I'm doing stuff that I'm doing it for the 800th time, you know. Both was you guys said I think kind of sums up the like passion is just like any other skill. It's like you either have a lot of it or a little bit and you can kind of train it over time. And then once you have a lot of passion, you could be passionate about whatever, you know what I mean? If you're going to sell rocks, you're going to be the most passionate rock guy on earth, right? I think there is rare entrepreneurs who are able to exclusively work on something that's very meaningful to them, you know what I mean? Like maybe it's epic gardening and Kevin over there. Maybe he really loves gardening like this is like his life's work or whatever, right? But it's not wallets for me. Yeah, anyway, so it's like the thing that I challenge with every single day right now is like look, our industry used to be way cooler, okay? Used to be way more prestige working in e-commerce. Now that's gone entirely to AI. I think if you're in SaaS, you're probably like people who make it funny, like you're like a rapper or stripper or whatever, you know what I mean? Like it's like a low value work, right? I feel like E-commerce SaaS stripper, my goodness. We've got everybody who is a manager, is a sociopath, and we got the SaaS strippers. Let's tune in next week for her. Yeah, anyway, so it's like it's like it is hard to manage that, right? Like things are going well, but at the end of the day, it's like it's a major work out of public company and your stock's down 80%. That's that's what a private e-commerce business is or whatever. So anyway, so that's that's one of the challenges. I do think the point that was made earlier is that people work for money and they should work first and foremost for money because that's, you know, they're providing for themselves and their families and those people that matter to them. And like I feel like sometimes I've kind of forgotten that because I'm kind of more intrinsically excited about the work, but that's why 99% of people work is because they need to drive an income and we should always, if you're not thinking about the world that way, you should always keep that in mind and you should respect that, you know, that's why people are doing it. They're trading time that they'd rather not trade to work. They'd rather spend it with their kids or go fishing or whatever. And so there's a responsibility to help them be really effective in that. Dude, money is a great motivator. I hate people who say that you shouldn't be motivated by money. And I'm like the only people who say that are people with lots of it and they should just shut up and go back to their corner. You know, like it's, it's fine motivator, especially at the beginning when you were like new, go for it, like chase the money, you know, get to get to the, whatever financial freedom number you need right away. That's like great motivator. Yeah. Okay. So there's a scene in the wedding singer that old Adam Taylor movie. Yeah. He goes, he goes to like the bank trying to get a job. He's like, I like money. I have some of it. I would like more. Yeah. That's one of my favorite. I have a jar. There's a little money in it. I'd like to put more money in it. That's where you come in. The, if you ever hear me say, Billy, I don't get to it. Why doesn't she? I'm referencing a wedding singer, which is an all-timer. But yeah, like for sure. And I think what it is, Matt, is that when people say like, oh, you know, it's, it's bad when people are motivated by money. I think that probably the implication is that people, those people love money. But it's like everybody is motivated by resources and what they can, how they can impact the world around them. Like you'd kind of be stupid if you weren't. Like I would kind of question somebody who was like, yeah, I don't, I don't get excited at all about being able to earn resources to, to be able to provide better for my kids or to be able to make the lives of people around me better. Like, okay, are you, you're the sociopath? You know, so like it totally makes sense. And I think that this is one of the reasons why I was talking about the effectiveness thing and the focus thing is at this point, I've got enough money. You know, so like to tie all these themes in here, I've got enough money. So why do I keep going to work every day? Why am I adding extra brands? And like because there's a lot of nonsense that comes with running any one company, much less many companies. And I do think it starts to be more motivating like the story I was telling with my son of like, hey, when I go to work, I can make the lives of many people better. And so like, okay, that is motivating, which isn't to say money doesn't play any role, but it's maybe just not as strong a role or the dominant role or whatever. But okay, if I'm going to do that, if I'm going to go to work because I want to make people's lives better than, you know, regardless of whether I'm feeling super passionate about water bottles today, I need to make the best water bottle that I can. And I need to be thinking about the way that I lead people to help them accomplish their goals and that they're able to earn what they want to earn. So I do think like in one way, like all these different things we're talking about, do tie together. Fulfill is the ERP built specifically for D to see any commerce brands. Inventory, purchasing, warehousing, financials, all-in-one system built for the way your operation actually runs. There is not an ERP on this planet, not one that has more direct 3PL integrations and Fulfill. They integrate with over 403PL locations globally, and most you listen to this right now, either running your own 3PL relationship or you're about to, and the second you're 3PL and your ERP aren't talking to each other on real time, you're flying blind. You don't know your true landed costs, you don't know your real margin, you're reconciling spreadsheet to the 11pm, trying to figure out what $40k is what. I know, because I am on Fulfill. The visibility we have now versus what we had before, it's not a marginal improvement, it's a different game. Fulfill is the only ERP I've seen that was actually built from the ground up, 4D to see, and it's not some bivocated piece of crap. Believe me, those exist, Fulfill isn't one of them. Go check out Fulfill, tell him Sean's saying. You know, going back towards your thing, how do you make sure people stay locked in focused on things that matter? I'll give you just one example inside of Ridge. You know, Ridge has a multi-million dollar pen business, okay? We sell pens to people. I hate it. I've always hated it. I think the margins are horrible. I don't think people buy pens, I don't think it's ever going to get bigger. So this year, I made the decision to shut it down in front of everybody. It's like on standard explaining, yeah, you know how we sell pens, we're not doing that anymore. We're going to sell this other stuff. It's way working. I think it sells pencils. Yeah. Racers. That's what we're going to do. Make all the jokes, guys. But why did I delete this? It's millions of dollars revenue is going to come off the top line, and it's because the same amount of work that goes into to launch a new wallet or a luggage piece or whatever goes into the pen. You have to make a skew. You have to make a render. You have to do product dev. You have to place PLs. You have to store it. All this into the stuff. Now, it's harder. It's easier than luggage. It's not as big, but it's like all those same steps go into it for a business that is never going to be bigger meaningful and has horrible margins. So I'm like, we just need to shut this down, right? And then you have a bunch of people screeching being like, no, but we're going to lose the revenue or what are we going to do with the kits or X, Y or Z because we have web infrastructure built for it. We have all this stuff built for it. And as an executive, you have to just be like, I don't care. It's deleted now, right? And that just shows, I think, the whole organization what's actually important, right? It's like, I never want to hear about pens again. Pens are dead to me. They are not important anymore. And the people get, they just move on. They're like, okay, we're doing something else now. So that's a tip for everybody. Do something drastic in your organization. Delete something. Add something new. It's easier to do on standups. Sean, I think this is really, you know, like, I don't even know what I would title this episode. By the way, if you're still listening, but I actually think this is a great discussion that deletion and editing is actually a superpower. And in a world where AI and just the sprawl of doing things is going to be, you know, I mean, it's like, do I even go on social media anymore? Like what percentage of this was even human generated, right? And so like, I really think the ability to edit is probably how you're successful in the world ahead. It's not by doing more, but it's about having more focus. And that's, and editing is just another way of saying focus, right? There's a great line into Ocean's 11 memories. It says something like, never use seven words when two will do. You know, and it's like that, that same kind of idea of like, in our businesses, like, never sell seven products when two will do, because you'll just do those two better. And it'll be more enjoyable and you'll make more money. You know, like you said earlier, AI can spit you out 10 pages, but like, brevity's a skill, you know what I mean? It's like, I want to know that like, it doesn't help me to read the 10 pages of random AI notes that like have way too many adjectives in there, right? It's like, just tell me the four bullet points, oh, I need to see to make a decision in my life. Then I'll feed that into my AI and talk to my AI about it. So by the way, you, I don't know, this is a pro tip on AI. You can control, and people should do this. You can control the output of your favorite tool, like cloud code, cloud codex, whatever it is. Like, you should absolutely, if you're an entrepreneur, tell it to be brief, right? Like, give it instruction. There was actually a really good post on AI, if I could find out. Yeah, about directors. Is that the one you're talking about, Matt? Yeah, it's like, you, I don't want, like, because they've actually gotten more verbose in their responses. I don't know guys, this has like been a thing with, uh, fable or opus. It's like, why the, are you writing four paragraphs? Like, I just want an answer. And you actually have to, you can do this. You can actually go give it instruction to say like, no, just give me point form. I don't need all the crap. Mike, you feel better about this because throughout the episode, you look like you've kind of worse and worse, dude. Wow. I, I don't know what vibe I'm giving off, but it must be, this is you have with the app. Oh, yeah. Guys, I just, I just needed to give me a wellness check, uh, call tonight. And, uh, no, I'm good. I'm good. Early morning, but I, I do think the stuff we're talking about, like, is just challenging. Maybe that's some of what you're picking up on is like, this stuff is just hard. I don't know the right answers to this. And you know, a lot of times when you run a company for a while, you start to get to where you like, you feel like you know how you want to handle the thing or you, you have a pretty clear kind of set of principles. And I, I do feel more and more like we're in this kind of uncharted world where we've got to re-learn the way that we think about some of these things. And so helpful therapy session. Thank you both.

Podcast Summary

Key Points:

  1. Leaders must focus on clear, evolving priorities rather than clinging to past simplicity as companies grow.
  2. Annual planning is too slow in fast-moving industries; a rolling quarterly planning cycle keeps teams aligned with real-time market shifts.
  3. Organizations often drift into low-impact, safe tasks due to fear of failure, undermining high-value, ambiguous work.
  4. Daily stand-ups and short, focused check-ins help teams stay aligned on what truly drives performance and success.
  5. AI increases output but doesn’t replace judgment—organizations must prioritize what actually moves the business forward.
  6. Scaling requires more focused, smaller teams rather than larger, bloated structures, especially as AI automates routine tasks.
  7. Passion in entrepreneurship stems from purpose and impact, not product-specific love—driven by value creation and enabling better lives.
  8. Productivity should not be equated with work hours; true success lies in effectiveness, not activity, especially in AI-driven environments.

Summary:

The podcast explores how leaders in fast-evolving industries like AI and e-commerce maintain focus, passion, and effectiveness amid growing complexity. As companies scale, they risk drifting toward low-impact, safe tasks due to fear of failure, which undermines high-value innovation. A key insight is the need for dynamic, rolling planning—such as quarterly, 12- to 18-month rolling goals—instead of rigid annual plans, ensuring alignment with real-time market shifts.

Daily stand-ups and short check-ins help teams stay on the same page, fostering accountability and shared clarity. The discussion emphasizes that AI boosts output but doesn’t replace judgment; companies must prioritize what actually drives revenue and growth. Smaller, hyper-focused teams are emerging as a more sustainable model, avoiding the inefficiencies of large, bureaucratic structures.

Passion, the podcast suggests, comes not from loving a specific product, but from building value and enabling better lives. Finally, true success is measured by impact and effectiveness—not just hours worked or activity volume. The episode concludes with a call to reframe work as purpose-driven, where leaders use tools like AI not to expand output endlessly, but to focus on what truly matters, enabling smarter decisions, better results, and greater personal and organizational fulfillment.

FAQs

Leaders should adopt a rolling quarterly planning cycle instead of annual plans to adapt to rapid market shifts. This helps teams stay agile and focused on what’s truly driving growth, rather than sticking to outdated goals.

Teams often default to middle-of-the-road tasks that feel safe and familiar, avoiding the ambiguous but high-impact work that could drive real growth—leading to organizational drift and missed opportunities.

AI enables rapid output and automation, but 90% of generated work may not move the business forward. The key challenge is not just using AI, but choosing what to do—focusing on decisions that align with core business objectives.

Daily stand-ups keep teams focused on immediate priorities, ensure accountability, and prevent misalignment. They help everyone stay on the same page about what matters today, especially in fast-moving environments.

Yes—many businesses spend a large portion of their time on low-impact activities. Streamlining operations, eliminating redundant processes, and focusing on core product-market fit can dramatically improve efficiency and profitability.

Companies should evaluate based on market fit, revenue potential, and alignment with core brand identity. Shutting down underperforming lines (like pens) frees up resources to focus on higher-growth, higher-margin offerings.

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