Morgan Friedman: Hello. Hello, everyone. Welcome to the latest episode of Client Horror Stories, and I’m very excited after a lot of anticipation to finally have the one and only Rich Wilmore with me. How are you doing today, Rich?

Richard Wilmore: I’m fantastic. How are you?

Morgan Friedman: Oh, I’m so excited for your story. I have my mug that has coffee with some whiskey in it.

Richard Wilmore: Perfect.

Morgan Friedman: And I hope there’s whiskey in yours also, but that is not a requirement.

Richard Wilmore: Straight gin.

Morgan Friedman: Straight gin at 10 a.m. Yeah.

Richard Wilmore: Even better. And with my Irish coffee in hand, let’s go.

Tell us about your craziest client experience.

Richard Wilmore: Well, I was fired five times in nine months.

Morgan Friedman: Yeah. You know, usually stories—I’ve done more than 100 episodes—they like build up to a climax. I love how you jump right into the excitement.

Richard Wilmore: Yeah. Well, and I feel like that’s almost like there’s so much more behind that, that that’s almost not even like the craziest part of the entire thing.

Morgan Friedman: Yeah. Let’s go. Tell us the story behind it.

Richard Wilmore: I had, looking back, probably one of the best jobs I ever had in my entire life, working for a university as a clothing buyer in the bookstore. So, I bought everything in that store but college textbooks. And it was a blast. You get to design clothes. You get to work with college kids who keep you young. It was so fun.

And I made the stupid decision that I would quit that job and go work at one of those clothing stores that they buy your clothes and then resell them. Not like consignment, but similar.

Morgan Friedman: Like a vintage clothing store.

Richard Wilmore: Yeah. Yeah. Yes. For less money, no benefits, and seven days a week, as opposed to—

Morgan Friedman: Like, none of that was smart.

Richard Wilmore: I was young and dumb and thought, well, I can run a store, so that was a big deal to me at the time.

The man who owned this small chain of stores in the Wisconsin-Milwaukee area was either in his late 80s or early 90s, and his daughter wanted a clothing store. So, he started a clothing store. She didn’t work there. She didn’t own any of it. He just had these stores and he was opening a new store.

And so, I was hired to literally start the store, design it, hire all of these things.

Morgan Friedman: Wait. So, just to be clear on the family dynamics: he did it because the daughter wanted it even though she wasn’t involved?

Richard Wilmore: She lived, I believe, in Arizona.

Morgan Friedman: Okay, I see. So, if we had like a red flag counter, we should have that on the bottom of this one because there were many things that I should have been like, just kidding. I don’t actually want this job.

Richard Wilmore: So, we opened day one without internet, without a register, without any way of actually bringing in and inventorying these clothes. And there was a line down the street of people every day while we were prepping to open because we needed inventory. And we had no way of tracking any of this.

And he was of no help. And it was every day. That’s how it was. It was just kind of chaos.

Morgan Friedman: Yeah. So, interesting. A few comments on it so far. Yes. I love the red flag counter and owner that lives far away, etc. I see the red flags coming.

The line down the street shows that there seems to have been market demand for it.

Richard Wilmore: Yes.

Morgan Friedman: So, and also in this tech startup world, where my career has been, they often say, “Launch before you’re ready.” So, there’s this conventional startup wisdom. But sometimes you launch too early. You don’t even have a cash register.

Richard Wilmore: We didn’t even have internet that I could go on my phone and look up the cost of a shirt to see what we should be buying it for. Like, we had nothing.

And this wasn’t his first store. So, he was actually just moving locations. He had a store already in a couple cities. He was moving this location to a different part of town and needed new staff for this location.

So, this wasn’t like, “Brand new. I don’t know how to run a business,” right?

I later found out because he would send me to different stores that were similar to ours or ones that he owned. And I found out that he—when I would go to a store that he owned to see how they ran it, do their inventory—he called me over to his house one day to fire me.

Morgan Friedman: So maybe this was six times I’ve been fired, actually, now that I’m telling the story out loud.

Richard Wilmore: He called me over to his house to yell at me because I didn’t do it correctly. And the reason why he knew I didn’t do it correctly was in his kitchen was a wall of TVs, and he would watch security cameras in all of his stores.

And what I later found out, he—

Morgan Friedman: Yeah. So he would just sit there and watch everybody?

Richard Wilmore: And so he watched me and then would call me and tell me if he saw someone in the store that he didn’t like, or if he thought an employee wasn’t doing, or if I wasn’t doing anything correctly.

So, he called me to his house to fire me because I didn’t go look at clothes correctly in his other stores or something.

And I—

Morgan Friedman: Another red flag was like—

Richard Wilmore: I started crying.

Morgan Friedman: Wait, so wait. Before you crying, getting emotional, he just want to comment on: he has like a wall of security camera TVs and watching everyone. Like, that is creepy.

Like, we all expect security cameras, and we expect there to be like a security guy in a back room that watches it. But for like the CEO to be watching it all the time to like manage our behavior, I’ve never heard of anything like that.

Richard Wilmore: I was petrified from that moment, knowing that he was literally just sitting in his kitchen watching our every move. And I was like, how do you make a comfortable situation for your employees—an uncomfortable environment for your employees—when you know that someone is breathing down your neck? Like, that is ridiculous.

Morgan Friedman: By the way, I’ve known companies that do versions of this digitally, that like watch everything that you type and you see on your screen.

Richard Wilmore: Yes.

Morgan Friedman: So, and a lot of people don’t even know. It’s like when they kind of like sign a contract to work for the company. It’s like on page 40, footnote: “Oh, yeah, by the way, we can—by the way, every—”

Richard Wilmore: We’re even watching your facial expressions during meetings.

Morgan Friedman: Yeah, like they know everything.

Richard Wilmore: Yes.

Morgan Friedman: Yeah.

Richard Wilmore: So when we finally opened the store and got it running, he would come in every day, every single day for nine months, and he would yell at me about something, whether it was employees, what I was doing—we had a backlog of clothes in the basement because we had no system.

He—there was no system to do this.

And then he would fire me.

And he would fire me and then ask if I can stay until he found my replacement.

Now, what I later realized, I think he was suffering from a little bit of dementia because he would forget that he fired me. So he would tell me, “Do this today.” Like, he’d come in and he’d yell about something and, “Do this today,” and then he’d come in the next day and then yell that I did that thing.

And then it was like, this was the cycle.

I literally, every day I was there, seven days a week for nine months. I ended up getting—I would get ill every morning. I would throw up. I would have diarrhea. I would have—because there was so much stress. I felt like I didn’t—it was awful.

Morgan Friedman: By the way, most red flags that we usually talk about are external, like your boss secretly watching me on a video camera, but they’re also internal red flags. And you throwing up before you go to work every day is as big of a red flag as it gets.

Richard Wilmore: I know. But I felt like I can’t just leave, you know? I can’t just quit. I don’t have a job.

Morgan Friedman: By the way, I want to make a quick comment. This reminds me of the classic Larry David story of when he was a writer for Saturday Night Live. Do you know that one?

Richard Wilmore: No.

Morgan Friedman: So, do you know Larry David, the creator of Seinfeld and Curb Your Enthusiasm?

Richard Wilmore: I’m a fanboy. I think he’s probably the funniest human being in the 21st century.

Morgan Friedman: Yeah. And in the ’90s, pre-Seinfeld, he was a writer for Saturday Night Live. And there’s a classic story where, like, one Friday afternoon he got into a huge fight with his boss. So, it was like Lorne Michaels, the head of Saturday Night Live, and he was so angry he just quit the job Friday after the weekend.

Then over the weekend, he kind of repented and he just decided to go back on Monday. And he went back Monday morning and didn’t say anything. No one ever said anything, and he just continued the job as though it never happened, because the paperwork and he had been fired. But they never discussed it and he secretly went back.

And it reminds me of this, like, being fired but kind of pretending or forgetting and then the cycle repeating itself.

Richard Wilmore: That’s what happened. He fired me five times and then would leave and then never found a replacement.

Morgan Friedman: So, was the question: was it that he forgot that he fired you, or would he just be so slow and backwards in trying to find a replacement?

Richard Wilmore: He never actually—and he, like, he didn’t even really look for one. I don’t think he remembered to look. I think it was like in the moment, and then he would go and he would forget.

And then, I don’t know, weeks, a month later, he would fire me again.

It was—and it got to be like, “Oh, I know this is going to happen and we just have to like—okay, I know I’m going to get fired, and that’s fine.”

Morgan Friedman: Yeah. And at the end of the nine—

Morgan Friedman: Were you the only one that he did this to, or was this how you treated everyone in the store?

Richard Wilmore: No. No. No. He would tell me that I had to fire people because he was watching everybody, and he wasn’t—sometimes he wasn’t wrong. And, you know, like, you’re not paying people a lot, so you’re not getting—you’re getting young people. This is probably some of their first jobs, you know? Like, it was all of that.

So, but no, he would only fire me. He would only yell at me, and he would only fire me.

Morgan Friedman: Special treatment just for Rich Wilmore.

Richard Wilmore: I felt very special. Yes. Every day.

Morgan Friedman: Yeah.

Richard Wilmore: It was even—like, he would yell at me about the type of paper towels I would buy for the restaurants. Like, nothing I could do would satisfy.

Morgan Friedman: This is classic micromanager. Like, the video recording takes it to another level. Were there microphones in addition to the video?

Richard Wilmore: No, I don’t—I don’t. No, not that I know of. I don’t think so. I think it was all video.

And he eventually sold the business and came in one day and said, “I sold it and you’re fired.”

And then asked if I would still work again, like, another week while they transitioned this new owner. But then I was fired. And then I had to leave.

And then he wanted me to come back to bring the keys to this new owner. And I remember him saying, “We’re going to give you a severance.”

And I was probably in my early 30s, like maybe late 20s, and I was like, “Oh, a severance. Like, I’ve never had a—I’ve never been fired before. So a severance, this—I like this. How many months am I going to be able to not work?”

It was $1,000 is what his severance was.

And I thought at that time, I was like, it was almost like relief of like, “Oh, thank God I don’t have to do this anymore.”

And the next week, after I officially got fired, my old job called and said, “We never—we couldn’t—like, can you come back? What do we have to give you to come back? Because we’ve—we can’t have anybody replace you.”

And so we negotiated that, and I went back to work in a job I loved, which I never should have left.

Morgan Friedman: Something interesting is, often in jobs it’s hard to get a raise. So, I’ve known people that have—but they pay people more when they come from somewhere else.

So, I’ve known people that have purposely taken jobs elsewhere just so they could be hired back at a better salary at the original company.

Kind of sounds like, without planning it, that’s what you ended up doing.

Richard Wilmore: Yeah. Yes. Without absolutely not planning any of that. Like, I just assumed that bridge was burned.

Morgan Friedman: But I’ve known people that have done this because there’s this very common pattern. If you’re an employee in the US, you get, okay, you get a raise of 3% a year or 4% a year forevermore. That’s it.

But often, like, salary changes are much higher than that. So they need to hire someone new. They’ll pay much more than that.

So the only—or like, let’s say the most classic way to get out of that trap is to go somewhere else and then come back, and then you’re in like the bucket of someone new.

Richard Wilmore: I never thought about that. I would not trust myself to get to leave and be guaranteed to be—I would—that would make me way too nervous. Way too nervous.

Morgan Friedman: Yeah.

Okay, so let’s summarize the lessons that we’ve learned and then see if we can extract a couple of other new surprising ones from here.

So, lesson number one: if you’re being video recorded, that is a huge—that is like as big a big red flag as it gets.

Another interesting lesson from here is connecting your story to the Larry David story I said a few minutes ago. I feel like when I was young, people would say these big things to me like, “You’re fired,” and I would be like, “Oh my God, the world is ending.”

But it’s really surprising the degree to which people just say shit and then, like, five minutes later, for whatever reason, they forget it.

Sometimes they forget, oh, they’re getting old and having Alzheimer’s. Also, there are a lot of people that just blow up and get really obnoxious and say, “You’re fired,” and then guess what? They’re just the sort of person that gets really angry and blows up.

But they know they need you.

So, for multiple different types of reasons, when people say things, including things that threaten your job and your livelihood, it’s often not as serious as it seems. And often you can just go back in on Monday and act like nothing happened.

Richard Wilmore: Yeah. I think if I would have—once I figured out that this was a pattern that wasn’t really going anywhere, because at first I was like, “Oh my gosh, what am I going to do? I just got this job, you know? Like, what’s going to happen to me?”

But part of me was like, once I settled into like, “Oh, this is—this is what happens, whatever,” then it was kind of okay.

But he would still like yell at me every day. Like, every day was a different problem.

Morgan Friedman: But another huge red flag: you’re yelled at every day. It’s the most obvious one, but it’s worth saying.

I actually have a question. The first time that happened—or maybe it was like that second time after the first one—how did you, like, come back in the next day?

Oh, I guess actually you did answer that. You said because he said to stay around until you find a replacement and then he would just forget to find a replacement.

So, ignore that question.

Okay, so we found a couple of interesting red flags and useful insight that sometimes you want to leave a job on purpose, and also when people say you’re fired and say these really bad things, often they don’t mean it.

Can we find any other, or less obvious, lessons from this experience? Do you have any other learnings to share before I riff on it?

Richard Wilmore: It was definitely a lesson in listening to your gut instincts. That’s a good one.

Like, my guts were literally telling me, “Get out.”

Morgan Friedman: Yeah.

Richard Wilmore: That was huge because it always—and since then I have walked away from jobs. I’ve quit jobs without another job in place, like that, “Oh my God, what am I going to do without this?”

And everything worked out.

And so it was definitely like, okay, like, we know your limits of what a job should be and when it goes over into abuse territory.

Morgan Friedman: So, yeah, I like that. Here I’m quickly trying to brainstorm for—I was trying to come up with less obvious lessons. Here is one interesting: that the run by an old guy because his daughter had the idea, who lived in Arizona.

And I actually think this is a relevant point to the craziness, which is roughly speaking, I would divide companies into very broadly speaking into kind of two categories: companies that exist to make money and companies that exist for vanity purposes.

And, like, the vanity-purpose company is some guy has too much money and his daughter says, “Oh, it’d be cool to have a clothing shop.”

And there are a lot of versions of vanity companies.

I’ve had clients hire me to really promote their course and their product, etc., all over the media, and I was like, “Oh, wow, they were like selling e-courses, they want to be an influencer. This is a great project.”

But it actually turns out they’re just people with too much money that kind of just wanted media attention, and they’re doing everything else for that.

So, they really didn’t care about making or losing money, but they did care about getting lots of media attention.

So, for these vanity companies, because I feel like there’s a much higher risk of them being crazy and horrible, because I feel like if the company is a standard profit-driven company and we have all the complaints about that, you know, sometimes a profit incentive incentivizes people to do crazy stuff.

But, dude, I need to make money. I know I need my key employees. I know I need to treat my employees well so they don’t quit.

There’s like this minimum human thing you need to do to keep a business running, right?

But on the other hand, if it’s just vanity, vanity, vanity, then you’re just letting the worst side of you out. So, I feel like it’s much more likely to result in this terrible behavior.

Richard Wilmore: When he told me when I was interviewing for it that he didn’t know anything about running it, he didn’t want to. He didn’t know—like, his—I don’t remember what he did, but he had made a ton of money in his life, and he didn’t want to do any of that, and he didn’t know how to do any of that, and that’s why I was brought.

But then it was like there was no trust there. Like, he didn’t trust me enough to just do the job, and so because of that, he just—I don’t know. He just rolled over everything that happened in that story.

Morgan Friedman: I often teach executives I hire, or directors I hire, to delegate with oversight.

And by that I mean, like, there’s this dichotomy where, on the one hand, you hire someone. You’re kind of not going to trust them by definition. I met you yesterday and I’m going to trust the future of my company with you. How do you balance that?

And they’re kind of often two extremes. There’s delegation: “Okay, you go do it. Good luck. Let me know if you have a question.”

And then the other extreme is micromanaging, like this: “The towels—there. I saw on the camera that there isn’t enough toilet paper on the toilet rolls,” whatever it is.

And most managers tend to go to one extreme or the other.

And I advocate sort of “delegate with oversight,” where, hey, you’re in charge of the store. Also, let’s have a weekly meeting where you can ask me questions. Let’s set these numbers that you need to do. Here’s the checklist of the minimum requirements that you need to report on weekly.

There are a whole bunch of things you can do so that you get enough insight into what you want so you can problem-solve and help with the big things, while also giving them space to make decisions and grow.

Richard Wilmore: Yeah. It felt very—building the plane while we’re in the air often times, and we were also getting bombed down every single day as well.

Morgan Friedman: Another red flag.

So, some other red flags worth pointing out: the daughter living far away. You mentioned it as a joke in the beginning if you live in Arizona.

But it’s actually an important point, which is when the people running it aren’t nearby, it’s the sort of—it goes to this dichotomy we were just talking about, where it’s either too much micromanagement or they’re just far away, not paying attention and literally being in another state is such a risk factor.

And also, I find it fascinating that despite all these problems, everyone wanted it. And this goes to like, there’s a line around the block.

This goes to show a few things. One, even when there’s market demand and people want it, that doesn’t mean it’s actually being well run.

And also, and also on top of that, while I like building things fast, there’s this is also a good reminder: no internet, no cash register, can’t even look up, as I love your example, can’t even look up what it should cost on the phone if someone wants to buy it.

That sometimes you just like—it’s good to build the plane fast. Well, I actually like building the plane while you’re flying it, but sometimes you need a minimum base. You need—

Richard Wilmore: Right.

Morgan Friedman: Yeah.

Richard Wilmore: Right. You at least need something to put it in.

Morgan Friedman: Yeah. Exactly. If the plane doesn’t have wing, fuselage, or an engine, like, good luck trying to build the plane while you’re in the air. It will never even get off the runway.

Richard Wilmore: Yeah. Seriously.

Morgan Friedman: Okay. This is an incredible story. We got a bunch of lessons from it, and we actually got a few new lessons.

I’ve done more than 100 episodes and I was trying to get a new lesson each time, and a few of these ones that we just said—the leadership living out, living in another state, etc.—were brand new.

This is great. Very, very useful.

Rich, this was an awesome short and sweet story and episode. Thank you for coming on and sharing it.

Richard Wilmore: Well, thanks for having me, and everyone who’s watched it until here, we hope you’ve laughed as much as we had and enjoyed the crazy story.

And we hope you’re not fired six times in nine months.

Until next time.