WHAT CHARLIE SHEEN TAUGHT ME ABOUT B2B SALES AND SELLING
25 Sept 2025 · 30 min
In this conversational podcast episode, the hosts use the Charlie Sheen documentary as a case study to extract lessons for B2B sales professionals. They begin with a thought experiment about wishing to relive youth with present‑day wisdom, then pivot to the idea of learning from people who are 5‑10 years ahead in life. Charlie Sheen is presented as an "anti‑mentor"—someone whose destructive habits illustrate the dangers of unchecked homeostasis, emotional instinct, and short‑term gratification. The hosts discuss how salespeople often rely on contemporaries for advice, leading to confirmation bias, and argue for seeking mentors and anti‑mentors who have already navigated the next decade of a career. They introduce the biological concept of homeostasis as a metaphor for how people revert to a baseline after peaks or troughs, explaining why rapid change is resisted. The episode stresses that most sales performance issues stem from emotional instincts rather than pure intelligence or knowledge, and that incremental, consistent adjustments are more effective than dramatic resolutions. Practical take‑aways include: identify both positive and negative role models, listen to older professionals, recognize the emotional drivers behind sales actions, and adopt small, steady habit changes to overcome homeostatic resistance. The hosts close by encouraging listeners to watch the documentary, reflect on the discussed principles, and apply the “anti‑mentor” mindset to improve their sales careers.
Chapters
We've all had this thought experiment with our friends at one time or another where we say, wouldn't it be great if we could go back and be 20 again, 25, and relive that part of our life, uh, knowing what we know now, meaning having the wisdom of what we know now, but with that opportunity again? And then there's all kinds of variables. Well, is it going back in chronological time as well, so that we know what the stock market was like, the current events, uh, the life changes that happened in culture? Or are we just younger and today, starting right now? Now, This is something that I've thought about a lot, and it's like, what's the next best thing to that? We can't do that, obviously.
We can't time travel.
But we're at a certain age today, and we're gonna age a certain amount in 5 years and 10 years. What if we had some ideas, some heuristics, some examples? of what happens at that period of life to other people. And how could we leverage that wisdom, that experience, so that we could improve our life the way we want, readjust our values, maybe adjust our focus, our priorities? But then I said to myself, well, we can do that. And this epiphany—I don't know if it's an epiphany or just a crazy way of looking at life—is that I was watching the Charlie Sheen documentary on Netflix. So if you want to watch that and you don't want any type of spoiler alert, stop this right now and listen to it after you watch the show. I'm not going to reveal anything that is earth-shattering. because Charlie Sheen's been in the public eye for 30-plus years now, but you may not know it.
And I'm only going to focus on the second part of it.
So if you want to watch the first part, I'm not going to talk anything about his childhood or anything.
The second part of it is the most relevant to us as salespeople, because as salespeople, we're always wondering— You know, are we going at the right pace? Are we doing the right things? Are we listening to the right people? All good questions. Now, I was watching the Charlie Sheen documentary, and here the guy's 60 years old now, and it's pretty easy to diagnose what went wrong.
Okay.
He was a crack addict and, uh, had access to as much as he wanted because he was well-connected and wealthy and famous.
So people wanted to do whatever he asked.
So there was near zero resistance to partying, and it got Totally out of hand. And, you know, you could say it ruined his life, but certainly, you know, put it on a trajectory that I think today he would have rather not gone on. Easy to say. I mean, the guy was probably the number one movie star at one time, or up in the top 3 at least. Had made over $100 million in his career. Today they estimate he's worth 3, which is not a huge accomplishment for somebody with that, uh, not a great ROI, we would say. So what I bring up here is that we always look for mentors in sales. We look for people who can kind of show us the way or can kind of give us some feedback, some coaching, some guidance, someone who's been around the block who can kind of tell us what's on the other side of the block. We always look for that. And what I've always looked for as well is, well, that's great, and we usually pick people that, you know, like the Elon Musks or the Steve Jobs or the— which, you know, they're in the stratosphere, right? They're the The peak of the peak. Good luck. Okay, we may not have both the opportunity or the ability or both to get anywhere near that level, but we all can manage our lives better. We can be healthier, wealthier, more focused on things that matter to us the most. So I've always seen a lot of value in anti- Mentors, meaning people who have made mistakes that we can learn from, because a genius learns from other people's mistakes.
You know, the knuckleheads have to make the mistakes themselves a couple times before they get it. And a lot of us fall into the knucklehead category quite often. And Charlie Sheen is definitely An anti-mentor for certainly for any guy in their 20s or 30s who thinks that partying every night, all night is a lifestyle that's sustainable. Everyone thinks it is because it's fun, right? And a little of it is okay, but a lot of it is not okay.
And where's the tipping point?
And we all have to face these values and balances in our lives. And having an anti-mentor where we say, that's what I don't want, is just as important as finding people who say, that is what I want.
And I think we get into a lot of traps.
And the point of this particular episode is to get you to think differently. Because you can't go back in time and redo it with all the wisdom. You can't. But you can find people who have been through the next 5 years, 10 years, 20 years of your life, their life, and they learned stuff.
They did stuff. They had consequences. Of stuff, and you can choose to learn from that. You don't have to.
And some of it you might think is obvious. Well, was it obvious to Charlie? Was it?
Well, watch, watch the show, because here's a person who had it all.
And here's the other thing you got to learn about.
Homeostasis. Homeostasis is an innate characteristic of us mammals that keeps us regulated. It's our baseline. It's our thermostat. Keeps things from getting too hot or too cold. Now, it's real. Go check it out. I'm not making this crap up. It's not a New Age thing. It's a science thing. Homeostasis. And it's critical because when Charlie's life got too successful, homeostasis kicked in and goes, well, why don't you party a little and bring it back to the baseline? Now, was that consciously going on or it was just an instinct? And we all have it. You know that feeling? You ever gone on vacation and like the The first day you come back, you almost missed work, or you had to work harder just to get yourself back there. Or the inverse, at the end of the quarter where you scrambled and you crammed and you got that deal in, and then you need 2 or 3 days off. That's homeostasis. That's bringing yourself back. Or you train too hard and then you get a little fever and you need a day or two off. It's a regulation and we all have it and we can change it slowly.
That's the key.
You can't change it fast because fast has an equal and opposite reaction. And, and this is critical because What was Charlie's instincts when he was in his 30s? It was like, I've got money, I'm popular, I've got a lot of free time on my hands, and I like to have fun. All good things in balance.
That's a good Friday or Saturday night. It's not a good November or a good 1999.
It's a good night, right? If we take it too far, then what ends up happening is it becomes our new baseline. And how do we leverage this?
Let's first talk about what we do wrong.
Most of us, we hang out, we listen to, we consume information content from our contemporaries, people our own generation, people who are going through what we're going through now. And there's value in that. I'm not saying don't do that. I'm saying we may want to broaden that, meaning that if we only listen to our contemporaries, Are we learning or are we confirming? Are we confirming what we already know, what we already want to know, meaning our instincts? Because Charlie's instincts were to party, and that went on for 20-plus years. And he had people around him who cared about him and We're trying to get him clean. We're trying to intervene in his self-destruction, his downward spiral. But he didn't listen to them because his instincts said, I got this. And we all have that exceptionalism, meaning that this happens to other people but not to us. And once in a while that's true, but more often than not, it It happens to us too. And we don't want to recognize it or accept it until it's already happened. So the problem with listening solely to your contemporaries and only wanting to listen to your contemporaries is that you're not seeing where you're going. You're seeing where you are. But you're not going to be there much longer. You're not going to be 30 for more than a year. Then you're going to be 31, and things start changing. And your contemporaries, all of a sudden, you go along with them, but you're not anticipating that 5 or 10-year difference. What you want to do is listen to people In their 40s. Why? Because they went through the 10 years that you're gonna go through. Is it identical? No, it's not identical. Culture changes a little bit. Technology changes a lot. Um, the economy changes a little bit. And that's okay. But a lot of those life choices that they made had consequences. They all had different values and personalities. Some you align with, some you, you don't, but you can learn from that. Now, if you— let's say you take— who's the 30-year-old Charlie Sheen today? I don't know. Pick whoever you want. If they looked at Charlie and they said, Ah, that won't happen to me, but I'm gonna still have that lifestyle. Eh, that's pretty risky, right? But what if they said, well, instead of investing in crack, I'm going to invest in a sober coach. Somebody's going to live with me to make sure that that doesn't happen to me. Which one would be better? I think we know that. So as salespeople, and I see this all the time because the people who listen to the show, they want guests that are identical to them. They want— every woman who sends me a note, have more women on the show. I go, do you have a recommendation? Now, is it different for a woman to be in sales than for a man?
No.
I can't really speak to it. I've worked for and with women, and there's better parts and harder parts that I've noticed. They all tell me it's harder. I have no reason other than to believe them, but is that only because they want to confirm? I don't know.
But I certainly remember being in sales when I was in my 20s.
And here's a secret. I thought I knew it all. After that first crushing year, I thought I had this thing nailed until I got my next job. And then I found out I didn't. And then I got good at that job, and then I thought I had it nailed until I got my next job. And my point here is we tend to depend and feed upon our instincts and our feelings and see the things that we want to and ignore the things we don't want to see.
Now, I did have some luck in one of the jobs working with people who were 20 years older than me, and I listened to them. Why? Because they were rich, they were successful, and I wanted to understand how they got there. And I didn't believe much of what they said because it didn't align with me and my contemporaries. We wanted things fast and easy and flashy.
Why?
Because we felt that that was the right way. And this thing about relation— I remember a guy talking about relationships and I was like, you know, I like the top-down, You know, really get to the core of the business and close it. And they would say, well, how do you get there? Ah, different. So today what you want to do is ask yourself, where do I want to be 5 or 10 years from now? Who's there, or who are people that I can observe, both positive and negative, because today it's very different. I mean, there's podcasts, there's YouTube channels, there's— everyone's freaking sharing their knowledge. Now, if you listen to your contemporaries, it's pretty much what you're doing already, but you think that they've got this little tweak, that subject line, that call to action, that's going to make all the difference in the world. Maybe they do, or maybe they just want your email address to be on their newsletter. Or you could listen to people who have been through it. The reason I interview the people I interview for this show is they've been through it. They're probably 5 or 10 years ahead of you in chronological age. And they probably know something. Now, you're probably wondering, well, I, I got this. Well, think back 5 or 10 years ago in your life, and I bet you would have wanted to do things a little different. Hence the original thought experiment that I opened this episode with. If you could go back and know what you know now. You can do that. You can't go back in time, but you can now look forward and learn from other people's mistakes. But you can't have the exceptionalism, and it's not gospel either. It doesn't mean you're gonna make those mistakes. It means you're going in with your eyes open, that you're going to want to learn from other people's mistakes. And teaching sales, you know, I think I had this epiphany last year. It's like, it's not IQ, and it's not really even motivation directly. Indirectly it is, but everybody in the courses wants to become better. What gets in their way is that better does it feels different than they currently feel today, meaning that they have to change their instincts because if you've been cold calling or cold emailing for a year or so, the way it's taught online on LinkedIn by your contemporaries, and you try and do something that successful salespeople do, it feels different. Different feels wrong. So you don't feel authentic doing it. You don't feel like you want to do it. It's different. It's new. Doesn't mean it's wrong. It might mean that it's right. It is right, but people won't change. And this is the kind of thing about sales that traps people. You know, I've got this one guy who's been selling for 25 years, a know-it-all, and I've had to work with him, and there's no getting through. He has a platitude for everything. He's done everything, knows everything, but yet he's not succeeding.
Is it knowledge?
Is it IQ? No, it's 100% emotion. He doesn't want to get out of his comfort zone, doesn't want to consider that it's a little off. And that's the thing about sales. It's not always 90 degrees off. A lot of times it's 10 or 20 degrees off, just a tiny bit. But that tiny bit is a lot from the customer's perspective. It's a lot from a deal perspective, and they're missing little skills. But they had a good year back in 2014, so they remember that. They have the plaque. It's up on the wall. They got this. But as Babe Ruth once said, yesterday's home runs Don't win today's games. Sales is a very different game. You know, we don't get a credential. You can go to President's Club one year and be on a pip the next year. That's the nature of the beast. So if you want to become great at sales, have mentors, have anti-mentors. And find groups, find people. Now, it doesn't have to be anything official. It can be listening to someone's podcast, YouTube channel, reading their newsletter, but preferably somebody who's 5, 10 years ahead of you chronologically, older.
See what they're saying.
Find that— the older guy in the office. And ask yourself, just observe his life or her life. Is that the life I want? I'll give you an example of kind of an epiphany I had. I remember I was in the Ontario airport and there was a sales guy at the bar. I think I've told this story a couple times.
He was disheveled, you know, kind of pants that didn't really match his socks that didn't match his shoes.
Clearly a sales guy, you know, had the bag that all sales guys seem to have to want to carry, the suitcase and the briefcase. And he was burnt, you know, just kind of beat up. He was out of the bar. And my sales engineer looks at me and goes, hey, in 20 years, that's going to be you. And I remember telling myself, I go, no way, no way am I gonna be, you know, 20 years from now hating sales, sitting at a bar, not putting enough attention into what I wear, and hating my life. And I saw a lot of salespeople that that happened to. They get in an economic trap where they don't like being in sales, but they have to be in sales because they built a lifestyle that requires the sales income. Not a good place to be. And I've met a lot of salespeople that stopped learning after that one good year.
That 2014 year where you made club, or you might have been number one.
And it might have been 80% because of you. And did it transfer to your new job? Sometimes it does. And I met the salespeople, met one this week. He thought product knowledge was 95% of sales job, his sales job. And I go, well, Really? Is it either that competitive, or is that knowledge so hard to get, or is it that you just want to believe that? Because product knowledge is like a— it's a crutch.
We feel good about it.
We think it's an asset, and it's important. I'm not saying it doesn't matter. How much does it matter is the question. How about getting the next meeting? What do you mean? Of course they're going to want to talk to me. I go, aren't we talking about you being ghosted? Well, that's rare. Okay, here we go.
Now, is that intelligence or is that emotion?
Doesn't want to face that he doesn't either know how to get the next meeting Or doesn't want to put the effort into it, or doesn't feel comfortable asking for it a couple times. See the difference? We think it's always intelligence. I'd say 80% of the time it's emotional instinct-based. We don't feel comfortable pushing back. We don't feel comfortable asking hard questions. Oh, I don't want to offend anybody. Okay. See, the 10 years is going to pass whether you listen solely to your contemporaries or you take this little podcast and go, you know, Brian, he's got an idea. Maybe I should check this out. Have somebody that's that milestone, both for what you want And for what you don't want, because what gets in our way in life is usually we pursue or spend too much time on something that gets us what we don't want. We eat too much. We get negative too much. We we do a lot of things too much, and. Like with Charlie, he didn't, you know, go from, you know, smoking crack once a month to once or 5 times a night all at once. It took a little bit of time. And here's the other thing I learned from it. How did he get off of crack? I'll leave that up to the documentary to share with you. But the same way he got addicted to it, the same way we all make big changes, permanent changes, we manage our homeostasis a little bit at a time. And none of us want to believe that because we, we like the New Year's resolution idea. December 31st, we're gluttons. January 1st, we're Puritans until noon. And that's human nature. What we got to understand is how do we get around human nature? It's a little bit at a time, both good and bad. Nobody gains 10 pounds at one meal. Maybe Thanksgiving. How's it happen? It's a meal at a time. How do we get in shape? Slow. But the open secret to success is consistency. And none of us want to do it because it's consistent. We like new. We're addicted to new and change and confirmation. We want to hear our contemporaries. They're cool. They're hip. They're like us. We're different. We do it our way. Do you? Uh, one of the gifts of getting older is you see the patterns because you've seen the movie over and over again. The characters change, but the plot is almost identical. All the characters think they're unique and special and Exceptional. One percent are. The other ninety-nine percent kind of fall into all the traps that everyone else fell into. Now you can do that, but then you're going to be like, wouldn't it be cool if we could go back and not fall into those traps? Here's the hack. Give it a shot. Let me know what you think about this episode. Check out the documentary. It was quite enjoyable. Part two was a whole lot better than part one. A lot of both funny, you know, kind of the tragedy and humor are very close. And I'll see you next time.
