Morgan Friedman: Hello, hello everyone. Welcome to the latest episode of Client Horror Stories. Very excited to have the long-awaited recording with the one and only Chris Simental. How are you doing, Chris?
Chris Simental: I’m good. Thanks for having me on the show.
Morgan Friedman: What are you drinking tonight? Drinks are mandatory in this part of the world.
Chris Simental: It’s a Belgian whip beer by Radiant Brewing Company. It’s called Blank Slate.
Morgan Friedman: You know, I think that’s a clever name for a beer.
Chris Simental: Or anything really. I like it. Like, you get drunk on the beer, you forget everything.
Morgan Friedman: Oh, I see. That’s a good angle. Start with a blank slate.
Chris Simental: Exactly. You’re starting over after you drink this beer. Well, it’s not a super strong one. I think it’s like 5%, but depending on how many you have, right?
Morgan Friedman: Yeah. Good point, Chris. I’m so excited we’re finally having this episode so I can hear about your craziest, most intense client horror story. Yeah, I have my drink in hand and all eager to hear. Tell us your story.
Chris Simental: What do you have in your bottle there?
Morgan Friedman: Oh, not nearly as exciting. A lemonade. I’m very boring, with some vodka in it.
Chris Simental: Oh, that’s a very refreshing drink.
Morgan Friedman: It’s refreshing. And I recently turned 50, so I’m trying to bring back what it was like when I was 20 and I would go out all night.
Chris Simental: Oh yeah, like vodka-infused juice drinks.
Morgan Friedman: Yeah, or a classic for the unsophisticated 20-year-olds. So I’m trying to recreate that.
Chris Simental: Well, it’s an easy-drinking drink, right? Easy drinking.
Morgan Friedman: And also, with a bottle like this, no one knows what you have on the inside. That’s right — could be water, it could be coffee. And with my coffees, I usually put in whiskey as well. No one knows what’s really in the coffee mug. In fact, one of my other water bottles — I’m not using that one today, unfortunately, my wife is cleaning it — says, “This might be whiskey” on the side.
Chris Simental: Well, at least you’re upfront about it. You’re warning people, right?
Morgan Friedman: Yes. And also, it’s sort of like subtle messaging. Like, now so much is moving to video calls and everything is digital — how do you differentiate yourself, how do you show your personality? So I think doing a recording with a bottle with a message is a fun way to let interesting information about you leak out.
Chris Simental: Yeah, and it’s a little bit of a conversation starter as well.
Morgan Friedman: Good point. It’s like the adult version of the t-shirts with funny phrases that I wore in high school as conversation starters.
Chris Simental: There you go. The first story that came to mind — and you know, we’ve been in business for over 20 years —
Morgan Friedman: Twenty years.
Chris Simental: — so we have a handful of such stories, right? But this one I thought was a good one to share just because it was quite unusual from any of the other stories. And I want to say this was about 20 years ago. And through a mutual acquaintance, we met this guy who ended up being a whole family. It was like a four-piece family behind this endeavor. And they came to our acquaintance, who was a marketing person at the time, and they wanted to build a web e-commerce website that was meant to be a hub for four important things, which is visual art, fashion, music, and film. So the idea was to get the world’s unknown artists all under one roof. And I think at the time Etsy was a thing — Etsy had been around for a couple of years. So there kind of was this model of unknown people sharing the things that they make, right? And I think that was kind of what inspired them about creating this website. But they wanted to take it many steps further — not just arts and crafts, but fashion designers, up-and-coming fashion designers, musicians, and filmmakers, and give them a place where they can actually reach new audiences and sell their stuff. But we quickly found out that these people had no idea what they were getting into, right? And so the demands were kind of wild from the beginning. There’s a lot of little stories within the story, I remember.
Morgan Friedman: By the way, I just want to interrupt with a parenthetical there, as we build up to the excitement. An interesting risk factor for me, that I see now at 50 years old that I didn’t see at all when I was in my 20s, is: I’m just a guy with an idea. And when I was 27 years old, cool, you have a guy with ideas — there are lots of guys with ideas, some money, maybe you’ll be the next Mark Zuckerberg, who knows, right? But now there are all these subtle risk factors — oh yeah, let’s have this hub for musicians, it’s a cool idea, and it might be useful for our audience to articulate some of — the one that stands out for me the most, and I can say this as someone with more than 25 years of experience in a comparable industry to yours, is something I look for now that I never looked for 25 years ago, is seriousness — like seriousness of purpose. I’m focused, I’m doing this thing, I’m going to approach it professionally, seriously. That’s the kind of person I want to work with. But what I didn’t appreciate 25 years ago was: if they’re not serious about it, then even if they have money, if they’re not serious about it, they’re just going to do weird, crazy things, make emotional decisions, and so on. And fundamentally, I’m just a guy with an idea — oh, and you mentioned the family, oh, and my family is going to help out too. Fundamentally, it’s just not a serious approach.
Chris Simental: Yeah. Right. And I think we were young, and had just started the business a few years ago, and so we didn’t know how to identify that, right? Like the level of seriousness, the level of professionalism.
Morgan Friedman: Yes.
Chris Simental: At the same time, we wanted to take it on because it was technologically of interest to us. Like, we knew we were going to learn a lot in terms of how to do video streaming, how to download audio, how to do audio streaming. And so that kind of experience really was worth the ride in some ways. But in terms of it being like — even since the beginning, like you’re saying, looking back on it now, we know that the pieces weren’t in place for it to be a success from the beginning, and a big part of that was their approach to it, which we’ll hear about as you go on.
Morgan Friedman: And tell us what happened.
Chris Simental: Yeah, absolutely. So I think from the beginning it was like they were very demanding. Like, they wanted to have this thing, and so they saw point A, which was “this doesn’t exist,” and then point B is “we’re going to create this amazing thing,” but they didn’t know anything about all the steps in between, in the middle.
Morgan Friedman: Yeah.
Chris Simental: And they put in, I think, a decent amount of money for an MVP — what we would call an MVP, right? But what they wanted was an Etsy-type experience, that had been around already for a few years and that had millions of dollars of investment, you know what I mean — not a few tens of thousands of dollars.
Morgan Friedman: They spent tens of millions of dollars building it. You can do the same in three months and $20,000, right?
Chris Simental: Exactly. And we never let on that, “Oh, it was going to be this amazing thing.” We were very realistic about it, but they didn’t want to hear the realism of it, right? They wanted to hear that we could do it all, and that it wasn’t going to have any kind of impact on scope, it wasn’t going to have any delays whatsoever, right?
Morgan Friedman: It’s surprisingly hard to keep clients’ expectations realistic because, during the sales phase, you always have an instinct to sell the moon to them. But then when you actually need to build the moon, it’s hard to reconcile that. On top of that, I’m a guy with an idea, and entrepreneurs in general tend to be optimists, and people who are optimists tend to have this instinct — oh yeah, of course you can do it.
Chris Simental: Right, right. So that’s the thing — when we come across people who have an entrepreneurial spirit, whether they know all the ins and outs or not, for me particularly that resonates with me because I have a similar spirit. My partner is a little bit different — we’re kind of yin and yang in that case, whereas I’m the optimistic one, she’s the more skeptical one. So that’s part of the initial excitement — I know that something like what they’re asking for can be built, but whether or not they have the patience for it, they have the budget for it — that’s a whole different story. Right? But what drives me is that I know this can be done with the technology that we have, and I know that we can design something great, but whether we can do it in the timeframe and the budget is a whole other thing, and that’s where we kind of run up against things. And since we were new to building web apps — like, we had done web design, we had done for many years online training, multimedia stuff, really cool stuff with Flash and even HTML and hardcore JavaScript, but we had not done this sort of e-commerce thing before. But I didn’t want to let — and I’m not the kind of person, and we’re not really the kind of business that would let that get in the way of trying to do this, because we know that we have a lot of experience and can pull it off. But there’s always the unknowns that happen, right? And these are things that we did not know because we had not done this before. So you learn those along the way, right?
Morgan Friedman: But 100%. So this family comes in with this idea for bringing artists, designers, and filmmakers together. And then what happens?
Chris Simental: It’s a family of four, and the dad was sort of the initiator of the thing. But I think the ideas came from the kids — mainly their eldest son, who was kind of a musician in the LA area.
Morgan Friedman: Okay.
Chris Simental: Of sorts.
Morgan Friedman: A musician of sorts. And I know what that means — wannabe musician.
Chris Simental: Yeah. And one of the other ones, either the mom or the youngest son, had an interest in fine arts and visual arts. So they’re pursuing their passion, which is all to be applauded, right?
Morgan Friedman: Yes.
Chris Simental: But the way they approached it — and it taps into what you were saying about seriousness and professionalism and just being a decent person in the world — those sorts of things were what we started to discover were kind of missing along the way. And one of the disconnects for sure was that they were from the UK. They’re a UK family, all of them British.
Morgan Friedman: Okay.
Chris Simental: I’m not sure when they came to the United States, if they were here temporarily or what. And they were also pretty well off in terms of wealth and such, or at least that’s what — who really knows the story when people come in and they own a mansion and a house in the UK and one in the States.
Morgan Friedman: You really don’t know where they got the money from?
Chris Simental: Yeah, exactly. You don’t know where they’ve got the money from. You don’t know how much of it is even still left, right? Or if they’re thinking that this thing they’re going to build for $50,000 is going to be the thing that’s going to catapult them into the next level of wealth and notoriety.
Chris Simental: If only it were that easy.
Morgan Friedman: Yeah.
Chris Simental: So there was that disconnect. They were coming from different places — they would be hanging out in wealthy circles, and we’re more like working-class, upper-middle class, whatever. So in some ways we weren’t even speaking the same language, right? Because we’re talking about the nuts and bolts, and they’re talking about the flashy veneer and how it looks, and what the perception is. They don’t really care about how it all works.
Morgan Friedman: By the way, this goes right to a pet peeve of mine — people who call themselves visionaries. In my experience, there are so many people — “No, I just need a big picture, I have this vision for the future, I’m such a genius” — no, you figure out the little details. When really the little details are 99.9999% of everything.
Chris Simental: And I remember — I forget who the quote was from — but it was something about how ideas are meaningless and without value; it’s the execution that matters, because ideas can come from anywhere, they can come from anyone. But if you don’t have the means, and the leadership, really, to execute it, then the idea is nothing, right?
Morgan Friedman: One of my favorite definitions of an entrepreneur — and it’s not a famous one, it’s just like the crazy things my mind thinks — is someone who does things wildly below them. And what I mean when I say that is, in a bureaucracy, in a normal hierarchy of the universe — no, I’m the big boss, I tell you what to do, I don’t need to lift my finger, I give orders. But what happens to entrepreneurs is, because there’s no one to get it done other than you, the good entrepreneur, the successful one, is the one who says, “The toilets need to be cleaned — I’m cleaning it.” There you go. But the powerful thing that happens is when your huge brain and energy goes to do things far below you, that’s when you realize, “Wait a minute, this could be done more efficiently like this,” or “Oh wait, the best way to do that” — you only have the key insights, you need to unlock the success by doing the things far below you.
Chris Simental: Yeah. To understand all the pieces that go into it, that it’s more than one thing. You need to understand — if you don’t, no one will care about your company the way you, the founder, does, and if you just outsource it to someone, then no one’s going to be thinking about it in the shower.
Morgan Friedman: Right, that’s right.
Chris Simental: So one of the examples of how their disconnection from what it takes to build this was kind of a hindrance — we were in a user experience meeting, showing wireframes and explaining how the thing was going to work. And I think that they were a little bit frustrated with that whole process anyway, because they wanted to see it working, right? But this is the way we get from them how they actually want it to work. You can’t really jump from idea to finished product without those conversations and talking through the details.
Morgan Friedman: Totally. It’s shockingly hard for so many clients to realize or understand that no matter how good of a professional you are, you’re not endowed with the magic power to read their minds.
Chris Simental: Right, exactly. So we have to have those conversations. So we’re in there talking about how people are going to upload their stuff — if you’re a visual artist, you’re going to have to upload photos of your art, set a price, and all of these things. Musicians will have to upload MP3s, or they could upload a WAV file or whatever — we can convert it behind the scenes. Likewise with up-and-coming filmmakers, they’re going to have to upload video to be able to sell the thing. And so the dad came into the conversation, and he was like, “Wait a minute, I don’t want people” — because he wanted this to be an international success too, not just in the United States, it had to be all over the world — he said, “I don’t want people in Africa to have to have a computer in order to put their artwork up for sale.”
Morgan Friedman: I’m a little bit confused.”
Chris Simental: And he’s like, “And I don’t want them to have to have a camera to take pictures of their thing to put up.” And so we’re like, “How are they going to — are they going to mail their art to someplace and then you guys are going to scan it? It needs to become a digital file at some point, it needs to be uploaded at some point.” But he just — his thinking was, “I don’t want them to have to do it,” but didn’t see that they can’t sell it without doing that — it’s a whole catch-22 thing.
Morgan Friedman: So when you clearly responded to him to be like, at some point the analog needs to be digitized — right — do you have anything in mind, do you have a plan for that?
Chris Simental: Oh, we did not have a plan. No.
Morgan Friedman: Did he at least understand when you explained that to him?
Chris Simental: I think eventually he did, but he was not happy about it. I think he saw it as a limitation of our team to not be able to figure this out.
Morgan Friedman: Okay. There’s an important lesson here, which is some people are just stupid. There are a few important lessons. One, some people are just stupid — if you cannot understand that for someone to sell art online, in which the image is displayed, then you need to somehow digitize the physical art — that’s a severely low level of IQ. And I think I grew up thinking everyone is smart — everyone, I grew up in a bit of a bubble of smart people. So because of that, I just go over this and think, “Oh yeah, everyone’s smart,” but some people just aren’t — IQ differences are real. There’s a second, subtle lesson here, which I think is good for our viewers, which is the following: most people kind of think that rich people are smarter — but no, no, dude, this guy has some huge mansion and extra money to throw out to invest in this crazy idea, like no, he clearly knows what he’s doing — but all the time, really rich people, it’s just the same IQ distribution as everyone else. I always say wealth is effectively distributed randomly. The fact that he has a lot of money doesn’t mean he’s smart. This ties back to a joke I was about to make five minutes ago, but now is an even better opportunity, where we’re talking about how if someone’s rich, you never really know how they got their money. And it ties directly to the IQ point, which is an old joke that I like, which is the following: how — what’s the easiest way to make a million dollars? Answer: start with two million dollars.
Chris Simental: Yeah.
Morgan Friedman: And I think it’s a stupid, classic joke, but what I like about that joke is it actually makes a deep and subtle point, which is: if someone has this luxury lifestyle and luxury mansion, you truly don’t know how good of a businessman they are — maybe they inherited ten times as much, but they lost it all, and this mansion and this $50,000 is all they’re left with, right?
Chris Simental: Yeah, that’s exactly right. We don’t know anything about the story. And I believe, thinking through how people develop when they come from money — if it’s old money, the money’s been around for a while, there’s a tendency for this idea of people failing upwards in a way, right? They get handed things and they don’t have to work as hard — we’re speculating, right — but we know, we’ve seen examples where this is true, like people getting into colleges without having the academic prowess to actually do it, and then we know that a family member went to that college before, and so they get to go to that college because of their relationship to whoever was there before, or they donated a building, you know.
Morgan Friedman: Yeah, 100%, 100%. But it’s over the top that he couldn’t understand that art needs to be digitized to be shown on a digital property. It’s like that.
Chris Simental: Well, yeah. And his tendency to jump to blame us initially was also part of the socioeconomic differences, I think too — we were always considered subordinate, it wasn’t like a true collaboration. We were hired to do this thing, and we were going to do it however he wanted, and if at any point we said, “Oh, this is going to be more difficult,” or “this particular thing can’t be done,” then he would take on this mentality that, well, we just weren’t smart enough. And he even went as far as to say at some point that he was blaming some of the features that we said couldn’t be in scope, or even further down the line in the project when there were delays — he was blaming that on this idea that American workers are lazy compared to workers in other countries, and he was thinking that we’re just sitting around killing time eight hours a day and then working one or two hours a day, and that’s because we’re American, right? And I don’t know if we told them this, but at some point we had non-Americans working on the project, because we’ve always been really keen on finding the right people for the job, whether they’re sitting in the room or they’re thousands of miles away. We’re really adept at finding people who can get the work done, and not just take up space — we work very efficiently. So that’s offensive on several levels. But just his idea of thinking that, “Oh, the reason why this can’t be done must be because you guys are somehow deficient,” or don’t have the right attitude, or don’t have the right work ethic — so there’s that too.
Morgan Friedman: So, okay. So there’s some interesting stuff worth teasing out from that. As you know, you’re American, I’m American too — where in the US are you from, by the way?
Chris Simental: Los Angeles, in California.
Morgan Friedman: I’m from New York. Americans don’t like to talk about class. So Americans kind of pretend it doesn’t exist, right? But what happens is class does exist, and class differences are real. So you get these — and working with people from a different class kind of just is hard, it’s hard to understand. So there are lots of things people say and do that, in one class or social context, message, “I’m working hard,” but to people from a different class or social context, message that you’re lazy. I will actually share a fun story, because it’s just an interesting example, and it happened a week ago. I met a famous film director — I will not name him — and we were introduced through a friend of mine from college, and I went to a pretentious Ivy League university — no, my parents did not donate a library, and my grandparents did not go there. I was just a very, very nerdy Jewish kid from New York with crazy good grades.
Chris Simental: There you go.
Morgan Friedman: Yeah. So I went to Penn. So I told this director, we’re talking about our common friend, I said, “No, I met her freshman year at college.” And he’s like, “Oh, where’d you go to school?” And I said, “Oh, college in West Philadelphia.” And then he burst out laughing, and he was like, “Morgan, that’s the most humble way I’ve ever heard it described.” And he’s like, “Wait, I went to the University of Pennsylvania, a very pretentious school.” But instead of being, “Oh no, I went to the famous University of Pennsylvania,” I was like, “No, just a local college in West Philly, in the middle of a slum.” So I happen to describe him that way — it’s my weird sense of humor. But the funny thing is, he caught it because it turned out he — I didn’t know he went to the same university, but he did, a few years older, ten years older. So he caught on because he went there, and he thought it was funny. But I’ve used that same line to people who don’t know the good universities and don’t know this sort of subtle humor, and many times I’ve left conversations where the other person thinks that I just went to some stupid community college in the middle of a slum in West Philly.
Chris Simental: Someplace they’ve never even heard of. Right?
Morgan Friedman: Yeah, yeah, exactly. So many people — I might be aging myself here — know West Philly from, oh my god, what was that Will Smith show when he was like 20 years old? The Fresh Prince.
Chris Simental: Oh, Yeah.
Morgan Friedman: The Fresh Prince of Bel-Air. The opening song in the opening sequence — “West Philadelphia, born and raised” — like from the slums of West Philly. But so many people are like, “Yeah, no, he just went to some stupid school in a slum.” And this is just a humorous, funny example of a deeper point we’re making, that when someone’s inherited wealth from daddy, but is really stupid, and you’re just working with a working-class team, there’s so many things you can say and do, on both sides, in both directions, that just — like my West Philly joke — get wildly misinterpreted to mean very different things.
Of course my whole story is giving him far too much benefit of the doubt, because just based on the way you describe him, and not knowing that you need to digitize analog art to get it onto a screen — it sounds like he’s fully up there.
Chris Simental: Next level.
Morgan Friedman: Yeah, Next level.
Chris Simental: Another example of that disconnect — so when we finally got the thing launched, and this was not without a whole lot of trouble in between, but we finally launched it, and he’s like, “We’re going to take you guys out to dinner to celebrate.” And so he took the whole team to Spago in Beverly Hills. I don’t know if you know about Spago, but it’s a Wolfgang Puck restaurant.
Morgan Friedman: Yes, I’ve heard of Wolfgang Puck.
Chris Simental: Yeah, and real expensive, in the most expensive part of LA. And so we’re there, it’s very awkward — the whole family’s there, a few of our top people are there, not the whole team, but a few people. And we’re there having dinner, and the owner of the restaurant, Wolfgang Puck, is there kind of walking around. And then the dad — so Pops calls over Wolfgang Puck at some point to the table.
Morgan Friedman: I’m so scared.
Chris Simental: And he starts to tell him about this website that we just launched. And I don’t know if he was trying to get —
Morgan Friedman: Oh my god.
Chris Simental: — Wolfgang to be an investor or something, like he didn’t have that kind of relationship with them, as far as I know — they weren’t buddies. But I think it was like him trying to show that he’s on the same level. Here’s Wolfgang, who has this multinational culinary empire, and then you got Pops, who just launched a website that’s going to change the world, but has zero users so far, no marketing plan, no traction. But that was wild — just the gall to be able to think that you could call over this celebrity chef and that he’s going to care about something that you just launched.
Morgan Friedman: Yeah, you know, that is another subtle clue that they’re like next-level incompetence. I think we could call that the cheap show-off — like, “I got a first-class plane ticket, wow, look at me,” or “I’m a customer at the same expensive restaurant, with a famous chef walking right by, that I talked to” — these sort of things that are cheap, not in the financial sense, like, really easy, that stupid and incompetent people tend to think though it tends to be like, “Wow, he can talk to” — but I kind of feel like almost all humans just see through it very easily.
Chris Simental: Well, you know what’s interesting too about that — I was thinking that the person who introduced us to this family, they were a marketing professional. And at that time in our career, we were executors — we didn’t do marketing. We were like, “Give us your spark of an idea, we’ll walk you through this process and build this thing out.” But what happens after that was off the table for us, it wasn’t in our domain. But this other party, who was the marketing person, he was always a huge advocate for the family. And I don’t know if it was because they were paying him hourly or whatever — whatever he did, they paid for. I know that he was getting paid, I don’t know what their arrangement was, but he had the kind of attitude about them that really rubbed us the wrong way, which is that anything that the family wants, we’re going to do, or we’re going to try to do, we’re going to break our backs trying to make this happen. And our approach has always been: if it’s impossible, not only can we not do it, nobody can do it, right? And you touched on something about this a little earlier, and it made me remember that what we learned, sort of early in our career, and this was one of those stories, is that there are certain people who you cannot help, right? Like, they have a need — you see the need and you’re like, “Oh my god, if we could just get this and this done, it would be perfect for them.” But then, either because of their incompetence, like you’re saying, or they get in their own way, or their ego becomes a problem, they become someone that you are unable to help. Like 100%. You can’t bridge the gap between what you know they need and what you can do for them, and getting them out of their own way to make it actually happen.
Morgan Friedman: Yes, that is a great point. Two quick thoughts on that. First, it’s a very useful skill to identify when you cannot help someone, right? And often that just comes with time — now, decades later, you realize, “Yeah, this guy was beyond help,” but you probably didn’t realize that at the time, right? Another hopefully useful observation for our listeners, on the butt-kissing marketing guy that wanted to do whatever they wanted — first I just want to point out, it’s so hard for people to fight against the person paying their salary. The person giving you money — you just, there’s this human instinct to say yes, yes, yes, you give me money, so I understand why I was doing it. However, I actually think people like that fail at their professional obligations, because I think, as a professional being hired by someone, one of your most important obligations as a professional is to tell the person paying you the bad news, right? They don’t want to hear it, of course, but it’s the best thing, it’s the most important thing. Imagine a doctor that wouldn’t want to tell the bad news to the patient — I wouldn’t want to go to that doctor, right? Let’s say you have a terminal illness, and you tell them, “I want to live for another ten years,” and they’re like, “Okay, let’s make you live for another ten years,” but realistically they know you’ve got another couple of months, right, but they won’t tell you that — I mean, come on, what kind of professional is that? A key part of your professional obligation is to tell bad news. I just had a realization in real time, right now — this is a new thought I’ve never had before, but it’s a slight tangent, I think you’ll find it interesting — our audience might not, but I think you will. I’ve been thinking a lot and playing a lot lately with AI.
Chris Simental: Oh, the new buzzy thing. We do.
Morgan Friedman: Yeah. And a lot of people are like, “Oh my god, everyone’s going to be replaced by AI.” I actually don’t think so at all, and I think the formula is professionals working with AI, because no matter how good AI will get, it can’t be a mind reader, it can’t read between the lines, it can’t understand what’s really happening — there’ll always be endless context, things that can never be written or digitized, that it could never know. And also, the experts are the ones who know where to guide it, how to figure it out. So it’s like that old story of having enough rope to hang yourself — if you get into the wrong pathways with it, you could really end up in a real jam, you know. So this has been my approach since AI started, or became big, and I say this as someone who really enjoys playing with it. However, here’s the new thing that I just realized in real time: there’s an aspect of how AI works that contributes to my argument that I never realized before, that reinforces it, which is — AI will never tell you bad news. Like, anytime you use any of these chatbots, by definition, “Oh, I have an idea for this,” or “will you help me with a business plan?”
Chris Simental: “That’s a great idea.”
Morgan Friedman: Yeah, exactly, I’m writing a book on the subject” — “Oh my god, this is the most original, newest genius book.”
Chris Simental: I know, I’ve seen that too.
Morgan Friedman: And then when you get a second opinion, or do some other research, and come back and say, “You know what, actually this solution seems better,” and then AI is like, “You’re right, that’s an even better idea.”
Chris Simental: Exactly.
Morgan Friedman: And not just is current AI like this — by its very nature, it always has to be like this, because you’re paying money to the big companies that are providing this service, and like marketing 101, you want to make your customers happy and optimistic and positive. There’s literally — of everyone that pays to use AI now, it’s like 0.001% of them would pay for the bad news AI. No one would, humans aren’t wired like that. So I didn’t realize, until right now, contributing to my skepticism of AI without professional oversight, is this unbounded optimism.
Chris Simental: Yeah, so like in that example, our marketing liaison is like the AI, because he was always saying yes to whatever idea the family had, and at the same time also didn’t know all the ins and outs of what it took to make this thing happen. We were the ones who knew, like, “Oh, this is going to be x amount of work, this is going to be x amount of dollars, it’s not in scope, I don’t think you want to pay — it’s not worth it to pay to have this feature in version one of the thing.” But the marketing guy would be like, “Why not?” And then the family would be like, “We really want this.” So it’s hard, and I think another lesson is that, as a younger company, it’s difficult to have that position, with confidence, to say, “This is not right for you, and you will be making a mistake if you pursue all of this in version one, rather than having an MVP and adding these features later.” It took some experience to be able to say that with confidence, to be like a consultant that they would respect, whose opinion they would respect. And I know we couldn’t do that in those early days, because we were just starting out. And also, in some ways, we didn’t want to, because we wanted to see how far we could take this, and we were willing to have a lesser margin to have more experience under our belt after this thing was done.
Morgan Friedman: Totally, totally. But I think that young companies and young professionals kind of have to do that on some level — like, if you start out in your 20s at your first job, and you’re just contradictory all over the place, you’re not going to get very far, you know what I mean? But once you have years of experience, you can say, from a position of experience, “Here are some examples of how this didn’t work in the past, and this is why you shouldn’t do this right now,” you know?
Chris Simental: Yeah.
Morgan Friedman: I think confidence only comes from two places — I think deep belief, or having other options. And a challenge that small agencies and small companies have is they don’t yet have either of those. You’re a small company, you really need the work, so you kind of have to take it, as opposed to, “No, I’m making bazillions of dollars, we’re doing great — no, you guys aren’t serious, ciao.”
Chris Simental: Yeah.
Morgan Friedman: And then it’s also similar with deep beliefs — we’ve been doing this 25 years, this is the process that works, it starts with discovery, and we do a wireframe, and at that point we get your feedback — whatever your process is, you’ve developed your process over decades, and you’ve realized, no, when you do it like this it works well, when you do it like that, it does not. And having done it for 25 years, you can confidently say, because you deeply believe in your process. But when you’re 25 years old, even if you’re handed the process, you get a 25-year-old getting a job at a company, and they say, “Here’s the process” — because you’re brand new and you started yesterday, and you didn’t develop the process, you don’t yet have that confidence in the process as well. So you need time to develop the deep belief.
Chris Simental: Yeah, experience.
Morgan Friedman: Yeah, that’s right.
Chris Simental: Exactly, exactly. Okay, so this marketing guy —
Morgan Friedman: He wasn’t super helpful.
Chris Simental: Yeah, yeah, but we got through it. And then we went to the dinner at Spago, the celebratory dinner —
Morgan Friedman: And wait, this was for the launch, was it?
Chris Simental: Yeah, the launch. And I think we had been saying, leading up to the launch, that — I don’t know if we said the term, but it’s a soft launch in a way, right — we’re going to invite some people, we’re going to test it out, there’s going to be bugs, we’re going to fix things along the way. But if you don’t want to hear that, then you don’t actually hear it, right? And I think that’s what happened in their case, because over the next week after the launch dinner, we were getting reports of some things that weren’t working — there were a couple of bugs, as we were expecting.
Morgan Friedman: Yes.
Chris Simental: But he sent out this email that was like — I don’t know if it was in all caps, but it felt like it was all caps, right?
Morgan Friedman: Oh my god, what are those?
Chris Simental: He was like, “We’ve completely lost all momentum of the entire project” — like, in a way, saying it’s all for nothing, because we have these bugs on the launch, and that people are struggling — some people, not even all the people, a majority of the people are having these issues. And we’re like, “Wow, man, this is—” and I wonder if, in some ways, when you have that kind of “I’m the boss, you’re my subordinate” relationship with everybody, I think in some ways you’re expecting it to fail, because you want to blame the people that you’ve hired.
Morgan Friedman: Oh, that’s — I hadn’t thought about it in that way before. That’s an interesting—
Chris Simental: It’s like, we know some people we’ve gone dining out with, and the way they treat the staff at the restaurant is just wildly inappropriate, and it’s like they’re very demanding, and by the end of the experience there’s basically nothing that they enjoyed about it. And I feel like they went into it expecting that, because they have some sort of mentality that, like, when I go to a place and I’m getting service from someone else, there’s always a problem — but I think they don’t get that, in some ways, they’re creating the problems. It’s like a self-fulfilling prophecy kind of thing.
Morgan Friedman: I hadn’t thought about it that way before, but I like that. If we’re being charitable, I would say some people are afraid of success, but actually with these guys, it sounds like — I’m not going to be charitable.
Chris Simental: Right.
Morgan Friedman: I think it’s hard to know the real reason why people are doing things.
Chris Simental: Yeah. And like, if they’re starting the business, are they really starting this because they’re betting the farm on this to make lots of money, or whatever?
Morgan Friedman: Oh, yeah, okay.
Chris Simental: Or is there maybe some alternative motive?
Morgan Friedman: I’m glad you said that, because—
Chris Simental: What we found out later is that it appeared that the dad wanted to start this company so that he could put his eldest son in charge of it as president, CEO, or whatever, and that that was somehow going to get him a visa to the United States, because he was the owner or leader of this company. So I think there was a rush to create a company that had some revenue — maybe they needed a certain benchmark of revenue, I don’t know — but that seemed to be their ulterior motive, versus really wanting to start a business.
Morgan Friedman: So super interesting. So, an excellent twist in the story. So a few thoughts on that — first, knowing that that is what was happening, that could explain why, right after launch, you get the all-caps email, because of the tiny little bug, everything is collapsing — it’s not working, because they weren’t serious, they never actually cared about it working, and now they just needed an excuse — a public, not a public, but a way to kind of close it, calm it down, because they got what they needed — there’s this company with his LLC, where the son has a job that justifies it. So now, rather than actually trying to build it, then they need to go into blame mode. So that’s kind of the point I want to make on that.
Chris Simental: Yeah, I hadn’t considered that — I always thought that maybe they didn’t — they never got to a point where they needed what they needed, or what they got, what they needed. But you’re right, it could have been that, as long as it was up and running, and that they had the LLC form.
Morgan Friedman: an LLC like if you have a company with at least X dollars in the bank, like a company with a million dollars, and you get the job, a salary job as a CEO — that company, that has a million dollars, can hire, and get the visa application for the son. The government doesn’t care where the million dollars came from, as long as it’s legal. Maybe daddy put a million dollars into the company bank account, shows it to the government, and then withdraws the money, or whatever is left after the salary, and then closes the company when it’s no longer needed.
Chris Simental: Wow. And so in that case, they really just needed something up and running.
Morgan Friedman: Exactly, something to show the world that it’s a legitimate, real company, and they weren’t actually trying to make money. My bet would be that it was the scam they were doing.
Chris Simental: Yeah.
Morgan Friedman: What I’ll also add is, I’ve seen so many companies that — the reason why they exist has nothing to do with what you think it would be, and nothing to do with making money. But I had never really thought of what we could call the “visa farm” before, which this was — just like a method for a visa. Of course, this is like — I’ve seen so many companies that are like, husbands just supporting the bored housewife to keep the wife distracted. I’ve seen companies where the CEO really just wants to be famous, and publicity, and everything else in the company is just the justification for that. I’ve seen people, having done bad things in the past, and they just wanted lots of publicity about what they’re doing, and lots of SEO things online—
Chris Simental: To hide, to counter.
Morgan Friedman: Yeah, to counter, yeah. So all the bad things would be completely buried and nearly unfindable. I knew one person — now is marketing a book, “I want my book to be a top-10 bestseller in the New York Times.” Okay, let’s mail lots of copies to the key people, dude — he didn’t care about the cost. Guess what? You got a top-10 bestseller. And I think a naive person, such as me 25 years ago, hopefully less today, but me 25 years ago, like, “No, of course a company exists to make a profit, that’s the definition of a company — we’re going to build this product and sell it to—-
Chris Simental: Why else put all that effort into it? Right?
Morgan Friedman: Yeah, exactly. Another very common reason I see for companies that’s not profit-making, that’s actually losing money, especially in the restaurant industry, is for money laundering — like, if you think about it this way, restaurants traditionally are all cash, and if I get dirty money and I need to somehow get clean, kosher money from it, I could — if I put my money into a cash business, and I fund it, where I put the money in the bank, and then I get random dollars, which are by definition clean, that I can then legally deposit into the company bank account — boom, I’ve made my money legal. And guess what — if you ask yourself, wow, everyone always says restaurants make no money, except for the famous chains, restaurants make zero money — why are there so many restaurants that lose 5% a year? Who would pay for restaurants to stay open for decades when it’s losing 5% a year? Oh, if you happen to view that as a 5% tax on money laundering, dude—
Chris Simental: A fair fee for what you’re getting.
Morgan Friedman: Yeah, exactly. So it justifies this. So the naive professional, or employee, might be working in a restaurant thinking, “I want to get the whole city, my whole town, talking about the restaurant, and everyone going,” or “I want to make the boss happy by doing this great thing, by making sure the food is even more delicious” — I don’t know — when the reality is the boss doesn’t give a damn, truly doesn’t, because it exists for these very unexpected reasons. Something I often advise consultants and agency owners is that one of your most important duties — no, not one of, the most important duty you have — is to understand reality, because once you can understand the reality of the situation, what the company exists for, what your boss wants, what’s happening, where it’s going, the reality of the people — these are the people that are doing good things, these are the people doing bad things, and the way things get done here is like this, even if they say the opposite — once you understand the reality, then you can navigate in it, and it’s freaking hard.
Chris Simental: Yeah, And I think, like, much like you were saying, 20 years ago, we never considered any of this would be the case.
Morgan Friedman: Oh yeah, me neither. Like, 25 years ago, you take everything much more, or entirely, at face value.
Chris Simental: Yeah, yeah. But yeah, all these pieces of what we came to understand about the dynamics of the family, and this whole thing about the visa — it all kind of trickled in over the course of, I don’t know, six months or so that we were working on this thing. Of course, you’re not going to have all that information at the beginning of the project, right?
Morgan Friedman: Of course.
Chris Simental: Like, they say, when we set project schedules and the budget, that’s the point in the project where we know the least about any of it. because you learn the most of it when actually doing it.
Morgan Friedman: I actually had never heard that phrase before, but I love it. You define the whole project plan when you know the least about it. It makes no sense, but that’s how it’s done.
Chris Simental: That was an argument I heard at a conference in favor of agile development, which hasn’t really panned out the way that anybody had hoped. But if you can get someone to pay for that, to say, “Look, let’s just settle on a retainer basis, we think it’s going to go for this long, but let’s build the plane as we go,” right, instead of trying to pretend that we know everything about it before we even start.
Morgan Friedman: Totally.
Chris Simental: Which you can do if it’s a cookie-cutter, boilerplate, something you’ve already done before, just putting someone else’s logo on it. But nobody wants that, right? Everybody wants their own thing, they want a custom thing.
Morgan Friedman: 100%. So tell us about the unraveling and the conclusion. So the dad sent this angry, possibly all-caps email. I bet it’s something like, “It’s all your fault that we launched and we don’t have a million users yet.”
Chris Simental: Yeah. So I think the project went on for a few weeks more after that, because we had built into the project plan that there was going to be some period of bug-fixing — of course, anything that was deficient, that we built, that needed to be fixed, we were on the hook for fixing that, and we were happy to do that. So that continued for a few weeks, but there never was a phase two, right — there was never, “Okay, now we’re going to add all these features that they wanted but couldn’t afford, or weren’t in scope.” And so I think that plays to your suspicion that they had gotten everything they needed for whatever they were trying to get out of it, which was not to make a viable, money-making, profitable business, because they never really pursued it beyond that. But that reminds me, speaking of email — he, the dad, would send us odd emails from time to time, and we came to understand that he had been searching our names online to find out other things that we were involved in.
Morgan Friedman: Yeah, what?
Chris Simental: So, really creepy kind of stuff. So, well before starting the company, or a little bit during the beginning of the company, I was a hobbyist home brewer — a beer brewer, right?
Morgan Friedman: So dude, when you were telling me about the beer you’re drinking at the start, I had Blank Slate — I had no idea you were a bear specialist.
Chris Simental: And I had gotten a second-place ribbon at the national home brew competition — that was my highest achievement as a home brewer. And so I was on a bunch of websites about competition entries, and I had some comments here and there on other websites.
Morgan Friedman: Wow.
Chris Simental: And so when he was talking, in those moments, about thinking that he could continue to think that all of us were lazy Americans, and if we could only do this everything would work out — at one point he was like, “Maybe you’re spending too much time on your beer-brewing hobby and not enough time on our project.” And I was like, “What? Talk about unprofessional and inappropriate.” Now he’s snooping on personal — that’s just wild. Yeah. Okay.
Morgan Friedman: Rule number one of stalking people is never let on that you stalk them — just use it to your advantage.
Chris Simental: Right, no, he came right out with it.
Morgan Friedman: Someone smarter — someone with an IQ high enough to understand if you want to sell art online and you need some method to digitize it — someone smarter than that might have realized that, instead of making comments like, “I’ve been stalking you,” instead things like — for the launch party, you know — go to a brewery, or there’s just so many ways to use that sort of information to your advantage.
Chris Simental: Yeah. Well, they did a lot of things wrong, as you can hear. And I think part of it is privilege, right — I think when you come from certain circles, you feel like you can get away with anything, and we’ve met other business owners like this — it’s unfortunate, where they feel that even if they pay you even $1.
Morgan Friedman: Yes.
Chris Simental: All of a sudden—— they own you, to some extent, and that you have to go out of your way and jump through hoops, anything that they want, anything they say, anytime they call. I don’t know if you ever saw the show Mad Men, but there’s a scene—
Morgan Friedman: Yeah.
Chris Simental: — there’s a story arc with Connie Hilton, where he invites Don Draper to the hotel, and he’s like, “I want a new ad campaign.” And so they end up working together, but Connie, as the owner of Hilton, would just call him at all hours of the night and expect him to come talk to him, whether it was 2 in the morning, or 4 in the morning, or on a weekend, or whatever. And I feel like, on this particular project, the family was kind of like that — the dad was kind of like that, where it’s like, “I’m paying you, and therefore you must be available at all times, you must only work on my project, you must give it 125% every day, even on the weekends.” And that’s just unfair — it’s not, especially when you’re only paying $50,000 over the course of six months. That’s not enough to employ a whole team of people to be at your beck and call 24/7, you know.
Morgan Friedman: So interesting. So there’s a way in which I view this similarly, and a way in which I view this differently — and this is a good way to wrap up a super interesting episode. Here’s how I view it similarly: one of my pet peeves of work life, agency life, software development, having clients, is people pay you a dollar and they think they own you. And that is the worst. And so many of my strategies on how to work like a professional are all about counteracting that, to find boundaries early, to find policies that you share proactively beforehand — they’re just so painful, and I can’t stand it. So this problem you’re mentioning, I think, is the big problem of client services.
Chris Simental: Yeah.
Morgan Friedman: And yeah, they pay you ten cents and then they want you to be their slave forever more. So in that sense, in line with that analysis. Here’s where my view is a little bit different — it’s unclear to me the connection of that to privilege, because I’ve known lots of unprivileged people — for example, unprivileged people who are diagnosed narcissists, who would then — it’s also a very narcissistic characteristic as well, “I gave you $1, so—” so to me, what is the commonality? I would say it’s not narcissism, and it’s not privilege. It’s what I would call — have you ever been humbled in your life? So, to me, people like these grew up with a bazillion dollars, elitist, they’ve just never been humble, they’ve always been — so because of that, they’ve never had to work in a restaurant. Working in a restaurant is a fundamentally humbling experience — you just see all the crazy, difficult people. And guess what, many working-class people have worked in restaurants and low-end service jobs, so they see how humans are, as opposed to these sort of people in a bubble. And while I’ve also known lots of people who are not rich and don’t have resources, but have never been humble — I’ve just known the hot girl that was always hot, that married the football player in school, all solidly middle class, but just being like the hot girl that everyone loved, that never had a problem — “Oh, I’m so much better than everyone else.” Even though they have no money, they’re the exact same type.
Chris Simental: Oh, you’re right.
Morgan Friedman: There’s another type that plays into this. The famous stereotype of the Karen. And the Karen also pays you $1 and says, “Oh yeah, you’re going to repair my home, and it’s a $500 job.” The parents don’t have any money, they’re like middle class, but they pay $500 for the home repair, whatever it is, and then give you a thousand phone calls about every little thing, and then when there’s a tiny issue with it, six years later, still calling you for those lousy $500. And like, what? Why are parents like that? Parents are like that because they never had this deeply humbling experience.
Chris Simental: That’s a good point, because then they don’t have the compassion, or the correct connection to humanity, you know.
Morgan Friedman: Yeah, because I think there are a lot of people, too many, who just grow up with an ego, thinking they’re better than others. And I think part of the arc of life is — the universe gives you experiences to bring you to reality, to humble you, to say, “Hey, you’re just a person like everyone else.” And there’s just a subset of people, unfortunately a large subset of people, who just never had those experiences.
Chris Simental: Yeah, I suppose if you have safety nets everywhere, and people shield you from that experience.
Morgan Friedman: Yeah. And often it’s not even intentional — parents shield their children from bad experiences because they don’t want their children to get hurt, and they want to protect them. So often it’s coming from a good place. But no matter how good the place is, it ends up with people living in their own bubble, divorced from reality.
Chris Simental: Right.
Morgan Friedman: Causes problems down the line.
Chris Simental: Yeah, completely living in a bubble, in their own reality — I think that’s exactly where this family was coming from. And I suspect that they’re still out there doing this very same thing somewhere else in the world, or here — maybe they’re still in the United States, I have no idea.
Morgan Friedman: Right after this episode, you can go to Google and stalk them.
Chris Simental: Oh yeah, I could do that. Send them weird emails about their hobby things.
Morgan Friedman: Yeah, “You’re spending too much time on whatever, golf, or whatever.
Chris Simental: I see you started another fashion website, how’s that going?”
Morgan Friedman: Chris, this has been a super interesting episode — philosophical, interesting, fun. I hope you’ve enjoyed our time together.
Chris Simental: Yeah, this was great. I’m glad we got to do it. I knew from our first meeting that we would have a good conversation, and there’s, as you heard, a lot of layers to this story that tell a lot of tales in various directions, about what to look out for. We learned a lot from this, and I think that others can too, from hearing these similar stories.
Morgan Friedman: 100%. Lots of learning and lots of fun and beer — what more could we ask for?
Chris Simental: Right. Beer and vodka lemonade.
Morgan Friedman: Yeah, exactly. This is a good episode — so I think I need to do more alcohol-infused episodes. That’s a learning for me.
Chris Simental: Nice.
Morgan Friedman: So, Chris, thank you for your time, and everyone who’s watched this — thank you for watching it until the very end to see this point.
Chris Simental: Thanks for having me.
Morgan Friedman: And until next time, everyone.
