12 Lessons These Ecommerce Founders Wish They’d Learned Sooner

27:38But, you know, I'm struggling now with, you know, like everyone is, like how to manage your business better, right? And there's a lot of, like a lot of conversations that happen that I feel like it's great that things are being recorded now and you can do stuff with it. But like writing stuff down, it just makes you more productive. You know, having a pre-read in a meeting, you know, someone had to take the time to write it down so that the meeting goes a lot faster and you just go in and you make decisions. And the good news is I do think that AI helps solve this problem. I'm seeing all kinds of people in my organization that like always seems to me to be very unproductive.

28:19and like, you know, they're using Claude and they're putting out good work products. I think it is enabling people. But yeah, organizing your thoughts and writing them down is a real skill and a real talent in so many ways, especially like just in general, like being a good communicator, you know, being a good writer, taking the time to do it. It's a little bit of a lost art, but it's incredibly valuable. I think, Mike, you and I share this, that we're external thinkers. So like we think by talking with people, right? And once I learned that about myself, that's when writing became super useful.

29:00And what Jason's hitting on, and I don't know if you share the same experience, Mike, where if you can build this culturally in your company, and that's why I like that Alex from PostScript said this, you can build this culturally, like communication does get easier. So as you add more people, and we know that adding more people creates more lines and it's more complex, that if you build this culture of like memos and just try to write very succinctly, that that will help you scale an organization up. What's your take on this one, Mike? I'm curious because you're strong. Yeah, I would start here in saying in general, writing is asymmetric.

29:38And we talk about asymmetric things are really valuable. and the idea is I write it once, but a million, a billion people could hypothetically read it. And so spending your time on asymmetric things is like really, really good, just in general. Like that's where you wanna be putting your time. And if you write something that really resonates on the internet, scores of people can read it, be influenced by it, be inspired to connect with you. So I think there's kind of a general, like for you as a person, whether that's in your business or just in general, there's all kinds of opportunities that come from writing.

30:15What I think writing does, and I think this is what you were saying, Matt, is that like I did debate in high school and the best thing about debate is that it'd give you kind of a topic and you'd argue one side and then you'd have - It explains a lot, Mike. This explains a lot. Yeah, I know. He's good at debating. Well, but it really, I think it was the frame for like how I came to learn a bunch of this stuff. But the thing I liked about debate is that it really made you externally process through both sides of an issue. And what writing does for me a lot of the times is I'll start to write something and I'll read it and I'll be like, I'm not quite satisfied or, oh, I don't actually have as much clarity of thought as I thought I had about this thing.

30:54And I have to kind of keep beating it up until I have internal quality of thought. And from that point on, it's very easy for me to speak about that thing because I have now done the work internally to be able to really know what I think about it. A lot of times people have thought 30 or 40 % of the way through an issue. And so when they try and write about it, it's not very good because the quality of thought is not very good and they haven't put in the work. The one other point I would make here, and I think that this is more important than ever before in an AI world, is that I think that AI can be a great tool to accentuate you if you already have a strong voice and you can only have a strong voice by going through and doing the work.

31:33So you have to do the work of beating yourself up and kind of like making sure that you have internally have clarity about the way that you see the world and what you want to say, then you can layer on technology on top of that to make the actual process of turning that thought into words easier. But the AI can't replace quality of thought and voice. And so that's been for me the best thing about X and all of the writing I've done is that it probably prepared me to be able to be the kind of speaker, the kind of podcast host that I am today. You know, what's really funny, just to add to that, you, you, Mike, you're, you're an excellent speaker, Matt, you're an excellent speaker.

32:17I find that for me, it doesn't come as naturally when it's like sort of like an important topic. It's just banter. Yeah, great. But what I find is I have to, this goes back to writing. You know, I have to write down a few things and even like when it comes to debate, I'm actually a terrible debater because I like I have really strong gut instincts that I think are generally always right. But like putting those out and we're expressing them in words like on the fly is actually challenging for me. And so but when I when I take a step back and I write down my thoughts and organize my thoughts, they're like incredibly effective.

32:57And that comes from writing. So that's just that's just something that I. Within a company, Jason, if you think about it, like you really have to codify things. You have to get them down in words. Like even if you get everybody in your company in a room and you talk about a subject and everybody gets on the same page, if nobody writes it down, you know, there's actually this has been a thing on Twitter, like being the guy that writes it down is like in and of itself just an incredibly powerful skill because it has to be documented. It has to be documented so that everybody has the same remembrance of what we agreed upon.

33:31So that the person that was on vacation knows about it. So that the new hire three months from now is aware of the decision we made so that we can strip the emotion of the moment out of things. Like, I think you mentioned that, Jason, that's true. Like writing gives you, it gives you the kind of the time and the space to breathe. Whereas in a back and forth conversation, sometimes emotions are higher and, you know, or a point that you really, it was kind of like just at the tip of your tongue, but you didn't know exactly how you wanted to say it or what you wanted to say. But then when you have the two hours to write, you're able to really clearly lay it out.

34:06So I think there's a huge part of it for it in companies. And I think that that'll continue to be incredibly important in the world ahead. Most AI tools and 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 P &L. Infinity Testing runs continuous A-B 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 ROAS with click-through rates up 43%. Then there's Shopper, an AI sales agent that answers every inbound text in under 40 seconds.

34:45We're running 23X ROI on messaging costs alone. If you want SMS software that gives a proven ROI, go to postscript.io and book a free demo. All right, Mike, number seven, take it away. Number seven, the market does not care. It doesn't care about your feelings. It doesn't care about you only having$15 in your checking account. It doesn't care that you haven't slept this week because you've been grinding away. It doesn't care about any of that. It cares about one thing. It cares about what it wants. It cares about the value that you can deliver to it. And it is ready and willing to reward you when you do that.

35:20but it's only going to reward you when you give it what it wants and no amount of hard work sacrifice want to drive grinding is going to substitute you giving it what it wants and so learning to be very market focused is the name of the game and this is a delivery output game this is a performance game there's a netflix culture doc that i've referenced several times I really love it. But one of my favorite things they say in there is that in their company, it is strictly based on output. They do not care how many hours you work every week. They only care about the output. And the market is the exact same way.

36:00It doesn't care. It doesn't care how many hours or how much effort or how much capital it took for you to get the solution it likes. It just cares. Did you give me what I wanted? And this goes back to several of the other points. Like when the market is telling you it wants something, you should lean in, you should double down. You should go faster. And when the market is not, when the market's throwing up a yield sign or a stop sign, you have to listen to it. And often we get this idea that persistence means that even when the market's telling me stop, I need to just floor it. And that's exactly how you go bankrupt.

36:32That's exactly how you waste five years of your life on a project the market doesn't want you to solve. One simple way I'm putting this to my team, guys, is that the extent to which the market wants a problem solved is the margin for error that you have in your business. The extent that the market wants a problem solved is the margin for error you have in a business. So you've got to learn to listen to the market and really respond to what it's asking you to do when you grow your business. I think this is another thing that Jason, you guys do so well. Well, this is the biggest problem in life right now.

37:07This is the biggest problem in society right now is that we're trying to solve things without understanding how markets work right um doing doing like government controlled grocery stores in new york city are you me yeah yeah not you not perfect example soviet russia like there are so many people out there that just don't understand and they just don't buy in to the fact that like this is just the way it works since the beginning of time, right? Markets have been there since the beginning of time. And understanding how markets work are going to make you a lot of money and save you a lot of headache.

37:49I love this one. Jason, why don't you take us to number eight? Because I think this is... I mean, the higher slow, fire fasting has been, um, like a very difficult lesson for me. Um, and, and fortunately it hasn't like really, it hasn't done any major damage, but, but boy, you know, could we have done so many things better by, by like, just like really being careful with, with who we're hiring, really vetting them, you know, really like really discussing people versus, you know, oh, we need someone in that seat. You know, we got to get someone in that seat ASAP because there's so much work to be done.

38:42And I look back to 2021 and 2022 when we didn't hire fast, frankly, because we didn't have the time. I didn't have the time to interview anyone, you know. and it was like, oh, we're leaving so much money on the table because we don't have people to do stuff. But then you go and hire bad people and it doesn't get better, right? And don't get me wrong, we hired a lot of great people. We've got a great team. But like the few bad apples, it's like, wow. And there's like, they cause drama, right? Which is the other category. Like you're hiring someone to fit a role and they either cause drama or they're not very good.

39:18And it's like, what a mess you've created. So like just you got to really, really, really take the time as much as it's like as you're dying to hire people in a role, you got to be just like incredibly diligent and methodical about it. And then you got to fire people fast, right? Like if someone is a drama person, like you just you just know it and you just got to figure it, figure out a way. You just got to figure out a way to get rid of them fast. I have a friend right now who runs a very successful company, but they've had a lot of churn in the last month, like a lot of churn. Some of it, they, you know, action some people out and some of it, a lot of it is just people leaving.

40:00And the misdiagnosis was like, oh, it's a cultural problem. And I actually think that when you see this in companies, it's really a hiring problem. is that like you're letting people through the front door that shouldn't even be let in and that it's very much worth, I think Jason, what you're saying, in investing in a proper hiring process. So like something that is consistent, it is repeatable, it is measurable, it's more objective than subjective. I think that is so valuable. If you're gonna build a team, you should take your damn time and do that part of the building as good as you possibly can and refine that.

40:39it'll make the back end of this much easier it'll make it easier to fire people quickly right people will stick around because you're doing a better job of bringing in the right people um i think it just compounds mike what do you say on this one i think that there was a period in time when to scale your brand you just absolutely had to get more hours and more hands and i also think think that I've been at a lot of events for business owners where one of the first questions they ask is, how many people work for you? And that's kind of like a badge of honor. And I think that used to be the way that the world worked, that success was, yeah, it's somewhat your top line, but it's like, how many people really, you know, do you kind of report to you or whatever?

41:24And I don't think that's the way that the world is going to work in the future. My advice now to people would be that the smaller your team, like it's a inherent advantage to have a smaller team because communication loops are quicker, decision loops are quicker, actions get taken quicker and less things get dropped. And that, um, you should expand basically as a last resort, the number of people in the room. And that when you have a problem that you're like, man, and I really need to put more towards X, you should first and foremost say, can I answer this problem through better system design, technology, whatever.

42:05And then when you really have convinced yourself that you cannot solve the problem at the quality level you need to, then you hire. And I'm not against adding great team members, but I would have a bias towards being very, very slow to add, which that's the first part of what you said, Jason. like the let's let's be honest when we fire it's two two different reasons why you can fire one is that you've got the wrong person they don't have the qualities you need or whatever else they've changed in a way where they they're not demonstrating the qualities you need but at least 50 percent of the time maybe more it's because actually the organization doesn't need that person to do what you've been paying them to do and that's on the organization right How many times is it like, man, we need to actually reorg.

42:52We need to let this person go because we overhired, because we thought we needed X and we didn't really need it. And those are really painful. It's not fun to disrupt somebody's life that way. So I would just be very slow to hire. And I would challenge yourself to do as much as you can with as few people and as much system building as you possibly can. And this is the overarching theme of everything I'm saying inside of Simple Modern is that everybody should become a system builder. And as they are, I think what we're seeing is that we're just able to do way more with a tight group of people. Yeah, I love that one.

43:30It's we're all – AI is sort of forcing us all to be workflow people. Like much more deliberate, much more intentional workflow people. I think it's turning us all into software designers in a way. Yes. Yeah, yeah, totally. which is what software is. It's kind of like what we do can't be turned into software. And we did that whole episode where we ranked them. And there are a couple of areas. Product dev is one where it's like it's very difficult to turn all of this into software. But man, most of what we do, it really, it's a lot like software. The reason why it hasn't been software in the past is because it was prohibitively expensive to internally develop a software for your unique use case or your unique workflow.

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44:47After Sell has already generated over$1 billion in additional revenue for e-commerce brands, revenue that doesn't require more traffic or higher cap. So check out After Sell and tell them that the operator sent you. All right, number nine. And this one might piss some people off. Let's find out. All marketing should make money. All marketing. So I don't care if you're a brand marketing person, a performance marketing person. If you are doing marketing that does not make money, that is a freaking art project. That is not marketing. Okay. The only difference between brand and performance is the time to return.

45:26But all marketing should make you money. Period. full stop. Fight me on it if you want. I'll be on Twitter or X, whatever the hell we're calling it these days. But that is I hold the line there. I'm willing to die on that hill, boys. I don't think that's controversial. Like, why would you ever spend money that you thought you wouldn't get back? You got to meet some brand people. Well, I mean, it's like we're not running nonprofits here. Like everybody. I don't know why anybody would spend any dollar on marketing that they didn't think in some way was going to come back. I think that the issue is a lot of the more brand marketing, it can be kind of hand wavy with how it's going to come back.

46:03It's just kind of like, well, you know, we do this crazy thing where we, we give our top hundred customers a horse and somehow, you know, it's going to go viral and like, we're going to like make all this money. And, you know, and you're like, well, how, and they're like, nobody knows, but it will. And that's probably the part of like, I think the big thing here for me, Matt, is that on a spectrum of like, I know I'm getting a return to like, I have no idea. I'm kind of firing this, you know, campaign out into the ether and just kind of my strategy is hope that it comes back to us. You want to live more on the side of the spectrum of like, you can really verify that this is actually leading to the outcome that you want.

46:42Well, verify that's, that's the term, right? Like the term that I would use is measurement that you, it's very hard to measure some of this brand spend, right? So that's, but that's the problem here. But clearly, like you can let, you can let people who aren't data oriented or people who just aren't like really numbers focused. Yeah, I mean, they can figure out ways. Like there's a lot of creative people out there. It doesn't mean that they can make money, right? So you got to have the right people in the room. You have to have, you want the creatives on your team. And hopefully you can get them to think commercially too.

47:20Like we have a great head of content here at HexCloud and more and more he's become more commercial, even though he's an artist, right? And so that's the key. And I think that's absolutely the truth. It's just all about measurement. All right, Mike, take us away, man. Number 10. Before we do, I just want to say this is probably the spiciest thing I could say about this subject. It's a way to take it. Here's my spiciest take on this. Everybody in your organization is going to have things that they want to do that are not to your organization's benefit. They're to that person's benefit. That they think, oh, it would be so cool to do this type of creative.

47:59I don't know if it would actually back out, but I've always wanted to do X. I've always wanted to meet Y celebrity. We should do a collab with them. You know, you could go on and on. Oh, I like, I really want to design a product that has this kind of feature. I don't know if the customers really want it. It might be really expensive, but I just, I want to see if we can do it. There is so much of that out there. we all have interests that are our own and don't necessarily align with our companies. And you really have to lead your company where you deeply incentivize them to do the things that are in the company and the company's profitability's best interest.

48:32And all of those hobbies, those go outside of work. And you got to shut those down. And you got to prevent people from doing things that aren't really serving the company, but are serving them. I see this with myself, even, you know, you'll see, you'll see CEOs do this all the time where they do stuff for vanity reasons and not because it's what's best for the company. And like be on a podcast, for example. And just kidding, kind of, maybe, I don't know. But the point being like, that's actually one of the biggest things you've got to manage. And I think that that's actually what you're getting to here, Matt, is that sometimes you get people in marketing that have ideas where they're really excited about the idea for creative reasons and not necessarily for business reasons.

49:14And, but I would just make the point that happens everywhere. happens in every different way. Yeah, I think that's a great point, Mike. I tend to be a marketing first everything, but you are right. It works. This as a principle sort of works across the whole organization. All right, Mike, take us to number 10. Yeah, absolutely. So strong positions loosely held. The idea is as a leader, you have to have a strong point of view and really your job is to end the ambiguity in the times that you really need direction to be able to set that. And that requires, I think, having strong values, strong mission, strong vision and certain things that you're like, I have them in an iron fist and I will never you will have to pry them out of my dead hands.

49:58Like we in my company, we are going to be committed to generosity and I will fight you over that. You know, that is my hill to die on. But tactics, the execution of strategy, trends, those can't be things that you hold in the iron fist because those things change. And like, so as a leader, I think what I've learned is that you have to have a few things that you're like, no matter what happens, no matter what AI does, no matter who's in the White House, no matter what our competitors are doing, these things are going to be true. These principles are going to guide the way that we run the business.

50:35But then everything else we're going to hold with open hands because we know that it will change and it needs to be flexible. Another way that I've said the same point is that as a CEO, I think one of the ditches you can fall into is this hubris of it's always my way or the highway. And so being a good CEO is about being able to listen to the feedback of the market and your team or whatever, and to be flexible and to go with the suggestions of others 95 % of the time. And then 5 % of the time to be like, I don't care what anybody's saying. We are not doing that. I will not listen to you. I'm putting my fingers in my ears.

51:12And knowing what that 5 % of the time is that you're like, no, under no circumstances will I compromise on this point. But that's actually what makes great leaders. 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 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.

51:48Their AI builds your support team for you and everything it needs. I've watched it. It works. It's freaking amazing. RichPenal 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$1 to$3, which is a little nuts. If you are interested, go to richpanel.com slash demo, not for some generic demo, but to actually book a call and watch them build your actual support team. Can't argue with that, Mike. So Jason, take us to number 11.

52:22What do you got, dude? Yeah, this is a good one. This is consistency beats genius. You know, some of the most successful people I know they're definitely not the smartest people I know. Moreover, there's a lot of smart people that aren't super successful, right? And it's like, there is a level of like, you can call it consistency. You can call it like just grinding. And look, you can't just grind your way out of anything, right? But grinding really, really helps. and that's to me consistency and grinding are almost synonymous. When I started my career as an M &A lawyer, I worked at a really big firm and there were 60 people in my entering class and we didn't even email documents back then.

53:13That's how old I am. We literally would fax documents and hand deliver documents and doing those little things right but really consistently got you to move up really, really fast in the organization and you could be a first-year associate running deal or you can be a first year associate making copies. The issue there or the differentiator there was like being really consistent at doing things right. And I think that kind of, that just transcends everything you do, right? Just being really consistent, really grinding at it, adding that to like all these other principles, know when to give up, right?

53:49But just like being really, if you look at the HexClap journey, the journey of the co-founders of HexClap, man, You know, everybody told him it wasn't going to work. You know, nobody wanted to give him money. You know, they just kept after it and kept after it. And I think from the time that they decided, hey, we've got this great cookware, there were many reasons to quit. You know, there are many reasons to not do it, but they consistently grinded at it, ground it out. And that's how it became what it is today. You know, I can expand on this a little bit. I think e-commerce, consumer, DTC, whatever we're calling it, is blue-collar internet work.

54:34I like this framing. And if you think of all blue-collar work, to do that work well means that you're doing a lot of seemingly mundane and boring things. But the reality is that in this game that we play, most success, most winning is found in just showing up every day and doing a lot of boring things consistently. And that over time, that those things do actually add up to what we've talked about. Your brand mark and your equity matters. And that you can actually generate the margin. All of it just comes down to just consistency. So I completely agree with this one. I just think that in consumer, it matters a lot.

55:16because it is blue collar work that we do mike what do you think i think the earlier when we were talking about brand building and why it's such a long uh process it's because you it's you're building a house brick by brick and you're doing the right thing over and over again for a really long time and uh every day that you do it you had a few more people that know who you are and care about uh your brand and and you can look up after a really long period of time and realize that you've built something pretty special. And I really think that we have a culture where on the kind of D2CX and other platforms, it's like what is hot, what is new, what is working right now.

55:56And there is something to be said for that. But I really don't know any company that their playbook and their success that is really built off of constantly riding the next newest wave. I think the really great companies, you just see an engine of predictable growth being churned out by doing the right thing over and over and over again. And one thing I would say here is that this also ties in with some of the hiring things we've talked about. If you want consistency in your organization's performance, you're going to need consistency in your internal team and processes. And so having a really solid, predictable team that's getting after it.

56:33I mean, for us, we had all these people that I, this group of people that I hired at the very beginning. And almost all of them are still at the company. And we've just been getting after it 11 years now. And every year we get a little bit smarter and a little bit better. You know, I'll finish off this episode. I'll give you guys number 12, but I think it actually follows this whole consistency thing really well. And number 12 is you have to talk to your customers until it hurts. It weirds people out, guys. It weirds them out when I tell people that I read every review and every comment. And then I have a stream of customer feedback, thank you AI, where I can just dashboard, here's everything that is being said about us at all times.

57:17And I spend a weird amount of time doing that. Early on, I would literally call customers. We would send out thank you videos one by one. There is so much value in this seemingly boring work of talking to your customers. and for some reason we don't i think as you get bigger we we lose this but the very best operators i know in consumer are obsessive about what their customers are saying it's where all your best marketing comes from it's where all your product improvement is going to come from it is just listening to your damn customers and how they speak about your product and about your brand naturally yeah i love that i mean that's something that we we surprisingly i think could be way better at here.

57:59And we have so much information. We have so many reviews that there's just so much gold there. It's worth being someone's full-time job, honestly. Dude, I think if the CEO is in charge of growth, which I think that that's true, I don't know how you grow a consumer brand if the CEO doesn't know what the consumer is thinking and saying about the brand. And that might be a more controversial take that like i think this is one of those things is very hard to 100 outsource you can have somebody who is accountable to it internally like there should be like a head of customer in the business of whatever that role is called but you the the founder you the ceo should have a pretty good pulse on this at all times as a great illustration of this one of simple modern's huge advantages is our spouses because the target market that we serve and the person that's had the best insights about strategy and simple modern doesn't work for the company.

59:03It's been my wife. It's been my wife. And like, it's amazing. Don't kiss Mike. She's not listening. Listen, it's funny. It's like there was a point when we made the decision to get into kids where she was like, you should do this and you should do it exactly like this. And she was completely right. And a couple of years ago, she gave me another very controversial piece of advice about the company that I kind of sat on. And the last two years have completely validated that she had the right insight. But the reason why she was right actually is, I mean, she's very smart, but it's less about intelligence and it's more that she's the customer.

59:40She's inside the mind of the customer. And so her insight and feel for the brand is actually even better than mine. And that's kind of what you're saying, Matt. I mean, really what it gets back to is like, what do you think you get paid the money for? You're getting paid the money to serve the needs and the problems of your customers. So the idea that anything else would be more important than knowing what the needs and the problems your customers want solved is, is kind of insane in and of itself. Like that's what the money's for. And so you've got to find ways to be in touch with that. I always love that line.

1:00:14You guys ever watch Mad Men? Oh, well, that's what I was. Or if she's asking for, what is she's like, you don't appreciate me. He's like, that's what the money's for. You never tell me how much you like me. All right. I think that's a wrap, guys. That's 12 solid lessons on how to win an e-commerce. I would actually say it's also 12 areas that a lot of mistakes are made. So this is good. I learned a lot. I think that's the pod.

1:00:45One