The show’s guest in this episode Sean Castrina. He’s a best selling author. He’s a serial entrepreneur. And he’s the host of the 10 Minute Entrepreneur Podcast. And he started his first company at the age of 23. And he has not stopped since his book came out last April called Developing The Entrepreneur Within.

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Listen to the podcast here

Experimenting with conflict with Sean Castrina

Hey, it’s great to be here with you live on the experimental leader podcast today. I always want to give you a copy of my book. And I’m going to do that later. I’m hoping that somebody else Oh, here it is. If you go to digitalbook.experimentalleader.com , you can get a free copy of the digital book of The Experimental Leader. I would love for you to read it and look at it. There’s a chance to buy workbook if you want that sort of experience. I’m going to do it right at the top of the hour because I always forget to give it to you. And I don’t want to forget today.

Well, I have been thinking about relationships a lot. And I’ve been thinking a little bit about conflict. And, you know, like many things I talk about on the show, sometimes I talked about the things that are going well. And sometimes I talked about things that aren’t going well. And I had some conflict that didn’t go well, this week. And I’ve just been thinking about what that means and what it means in terms of leadership and what my role in it is in it. And whether or not I had, you know, some obligation because of my identities as a coach and an author and a human to get it right in some way. And it didn’t go well. And and now I’m left sort of just being curious about the idea of conflict, where I avoided where I have it, where it works, where it’s functional, and where it isn’t. And I’m sure you have these things that happen around conflict, either by avoiding it or by having it. And so I really want to challenge you this week. Just really think about it for yourself, where do you run toward it? Where do you walk away from it? Where does it serve you as a leader? Where does it not serve you as a leader. And I’d love to hear from you if you have any epiphanies or want to explore more deeply how conflict shows up in your life and how you grapple with it. Because I think this is a huge part of leadership because leaders have lots of big and important relationships and conflict shows up in relationships.

And I’m super excited about our guests today. My guest is Sean Castrina and he’s a best selling author. He’s a serial entrepreneur. And he’s the host of the 10 Minute entrepreneur podcast. And he started his first company at the age of 23. And he has not stopped since his book came out last April called Developing the entrepreneur within. And today, Shawn and I are going to talk about conflict too, because I want to make sure we get a chance to explore what he knows, in this arena, too.

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So Sean, I am so excited to welcome you to my show today.

Great. It’s great to be here. Melanie, let’s let’s talk about some conflict.

Let’s talk about conflict. Well, I asked you before we started today, and and you said I get paid to do three things. Can you tell us this three thing?

Yeah. I realized, you know, now 25 years into this, I get paid to deal with people and all the people dynamics employees, you know, customers, employees arguing among themselves, whatever the case may be partners arguing. So people problems, I get solved to solve problems. And I always say I solved the problems that nobody else can solve, I always get the biggest problems and the biggest consequences. And then to deal with profit. I have to manage money, you hope there you’re dealing with profit. But you know, my ability to manage money, you know, solidifies and you know, fortifies the company, but 75% of its people.

Yeah, I really loved when you were talking about that. And I was thinking, I wonder what I get paid to do and I think they’re very similar challenges actually. So when you think about conflict as a like, as a leader, like let’s you know, it is a leadership podcast. So like, if you think about it as a leader, what what do you think about in terms of a leaders obligation to conflict?

I’m at the point where I view I’m, I really feel like there’s always an opportunity for me to have conflict, because one of the companies I own is, is in construction, which is funny because I always joke I can’t put together a three piece birdhouse. I was talking to a client this morning and I literally was joking on how little I know. And she’s like, Why did I hire you all this kind of being funny? And I said because I’m the general. I know how to hire people and I’m the person who can, you know put things together and all that because as you as you deal with, you know, as you’re an entrepreneur and you’re you’re constantly Dealing with these opportunities to engage and create conflict. So in my business with construction, these guys have the shortest tempers in the world. I am, you know, white collar went to grad school, you know what I mean to get I drive a, you know, Mercedes AMG to job sites, I don’t have a pickup truck, I’m the antithesis of everything you could ever imagine. My clients love that because they know exactly what they’re getting when they hire us. But my guys, I’m constantly breaking up either their arguments, or are they just, they just get pissed off so fast, they just do. I don’t know how else to say it. And with that, and then I have clients who pay us a great deal of money. And they have expectations that are sometimes very unrealistic. And I found with COVID, where they’re home all day, I used to joke they used to, you know, we would make the soup and they come home from work. And they’d see it when they got home tasted, it looked fine. Now they watch you all day long. So it creates a new dynamic. So I’m constantly having these opportunities, where I’m saying to myself, every day I’m picking the battle or the battle I don’t want to get into, because there’s more of them now than ever. Customers are amped up more than ever. Thus, my workers are amped up more than ever. And it’s just I have to pick the battles, I have to say, you know, you know, I have rules of engagement I talk about there’s certain rules that I one rule is just one general rules I never get, I never get into the mud with a pig. I never fight with a pig because they’re far more comfortable. My point is, is that I’m not going to fight with somebody that knows not going to play by any what we would consider rules. There’s really interesting, yeah, there’s certain rules in arguing example, I could fight with you, I’m not going to bring if I know something that you and your spouse aren’t getting along, I’m not going to take a cheap shot. You know, I’m saying let’s say that you didn’t work out really well at your last job. And I know that because the interview process. So I’m going to get an argument with you. And I’m going to throw that and well, you didn’t get along your last buck. Now. I don’t take cheap shots. But they will. So if I know if I know, like a person’s like that, and I have people like that, and I know it like I know if I get into it with them. I know where could potentially go. So I try to avoid those conflicts.

So let me ask, why do you try to avoid those conflicts?

Because I always say what am I gaining? Yeah, can’t you can always say you can’t fix stupid. You can’t, you cannot fix some people that are 40 years old and just pissed off at everything. They’re just some people, they’re just that’s their DNA. They’re there. They’re always there’s always they’re always a victim. And they’re always mad at somebody. You know, I’m not saying that’s everybody but in my business there’s that’s probably much more common. So I just go Alright, do I is this fight really worth having it? There are some Listen, I love knockdown drag out as much as anybody. And my staff says Shawn is the only person I know that could literally eviscerate you without ever using a four letter word like you will have wished he cursed you out the way he does it. Because he’ll intellectually just dismantle your argument. And you’ll stand there feeling like you just got you know, slapped around. I can do that. It’s it’s in my wiring, but I got to pick that like, what do I gain by like in this situation, if I do that every day, that’s an exhausting week.

I’m curious what’s worth fighting for?

Okay, fighting is if you find someone that it’s going to continue their bait behavior has to change. Like they’re, they’re becoming a cancer within your organization. And all you’re doing is allowing them to get worse. You’re the Met, the monster is growing. So if you don’t have and now again, there’s styles in every fight. So typically, the first way I’ll get into that with him is I’ll use humor. Hey, listen, John, I love having you here. But listen, we all got to play in the sandbox, and you’ve got really sharp elbows and you know that I always said you know that probably by now and I know that I’ve got you you’re more valuable to us if I can put other people if you can work better with other people. I always say because if not, you have a mercenary that’s what they are. They’re mercenaries they’re great by them. So you want to send get somebody shot you know, you know, you know in war, you want to take out someone you hire a mercenary because they have no conscience. They’ll they’ll perform the task, but they’ll just as if somebody pays an extra dollar they’ll just as easily come back and take care of you. And you have employees like this. And so you got to kind of look at the you know, look at the playing field and why I have somebody like that where I know they can go down that They I sense, there’s very little trust, very little loyalty. You know, I’ve got to have that conversation early because I got to see what road they’re gonna take next. And if it’s the bad, you know, where I realize I just have a concept, I get rid of, no matter how talented they are, I don’t care. If there is no talent level. And I want to say this, there is no talent, there is no amount of money that’s worth having a cultural cancer. When you have that person on your team, that is constant tension, and all that there. I thought, you know, I used to say, I used to have a phrase, you know, I could you know, Better the devil, you know, than the devil you don’t know. But there’s a point when the devil is just too damn bad. And it’s worth it. It’s worth it.

No assholes policy like people.

I love that. I didn’t know I could say that. But we have that that exact phrase we have. It’s like they’re in a hole. And it’s just exhausting.

Yeah, absolutely. You can say whatever you want on my show.

I don’t dare you. There you go. I joke that I would have Tourette. I’m very quick with my mouth. And my staff knows that if Shawn cursed regularly, he would have Tourette Syndrome. It’d be like you mother effer in use. So I just I took the road years ago, like, Okay, I’m never going to try to curse because I know, I would have no self control. I would literally be dropping F bombs every five seconds.

I have. I knew, I knew I had a bad mouth. I’ve worked in tech too long. But I knew that when my three year olds were swearing at my mother, you see the effort? Sign? Oh, that it’s the nanny, like, I’m sure it’s happy.

Yeah, I know that I could be. So I try to do the best I can to, to keep it as clean as I can. But no matter when you have staff like that, and then there’s certain conflicts that you just see, you know, there, there are people that are intertwined in your life. And I’m also finding this I don’t know if you’re there, but I’m realized that some people are in our life for a reason, a season and a lifetime. And I used to think everybody was in there a lot longer than I thought. And I’m concluding that sometimes they’re in our life first a lot shorter period. And that’s okay.

I think that’s really lovely. A reason a season or a lifetime. A lot of people in my life for a lifetime, and like clients stay forever. Like, there’s some interesting things. But I think it’s interesting to think of that, especially when we talk about conflict, like, it’s okay to not choose to stay in perpetual conflict with someone. And to allow that it’s been good. And now it’s not and to move on. I want to ask you about anger. Yeah. Um, and I think sometimes, especially that sort of white color culture is that we’re not allowed to be scrappy or angry as we express how we feel. How do you think about that?

I mean, I my rule is, I try not to say anything that I wish I wouldn’t have said. And even if I think you’re in a hole, if I do say that I will come back, even if no matter what, and I’ll apologize for that. I’ll go, I completely disagree with you. But if I could, I wish I wouldn’t have said that. I do that for my peace of mind as nothing. I don’t care what they think. I just, that’s just for me, that’s just for me to go to bed feeling you know what I because there are certain conflicts you can’t fix. That’s the other thing we have to come there are certain conflicts that are over. And it could be you could have said one sentence. And you will go back oh, I should have said it this way. It doesn’t make a difference. I always say if if one conversation is enough to ruin a business relationship. It was meant to go if it was that fragile? I mean, I don’t want any relationship. That’s one one conversation wrong away from being done. You know, that, to me, that doesn’t interest me because I I think you’re allowed to argue but I think as a general rule, you have to have you know, even in war, there’s called rules of engagement. You know, what I’m saying? Like, you don’t take women and children, you don’t shoot an unarmed person. There are just certain rules, you know, the Geneva Convention, and I think in business and in life. D you know, you have to have certain, you know, places where, where the fights not worth the fight, or you’re not going to lower yourself to that person’s level. You know, I always like firing people a great example. I remember firing someone taking them in my conference room and firing it. And I always bring a second person in there. Yes, it’s a rule of mind. You know, it just it’s not it So, this practice, so I’ll do that. And then the person got up and Kurt, you know, called me every name in the book conceivable and I’m like, basically just assuring them that a front door making sure they have their last paycheck. And and and my secretaries like why did you ever let that person bother? I go, what was I going to change? I just let them go, like what was I going to say that they really wanted to hear? I had one goal, get them to the door, what they called me from the conference room to the door was completely irrelevant to me. So there’s just certain battles that you know, just aren’t worth you don’t have to win them. They’re not worth winning.

Yeah. Um, where do you think I always like to talk about gender and race around these kinds of topics? Because I think, you know, and I, you know, you and I are both white people. But yeah, I think I mean, at least, that’s how you hear. Um, but but I don’t want to leave those conversations out, because I think the stakes are higher around race and gender sometimes. What do you see from your vantage point, when you think about those topics?

I mean, there’s no, anybody who, who’s thinks that you don’t have to talk differently. I don’t think I talk differently. But I think over the last five years, I would definitely view every conversation through a different lens of you know, could it in any way be interpreted? In such a way? Like, so I would, you know, my there’s no question now. Like, I like to think I’m a funny person, by nature, I’ve done stand up comedy, so I could be very funny. But there, I, I don’t know certain subjects matters. I don’t wouldn’t touch anymore. And even dealing with, you know, you know, certain, you know, different, you know, people that are different than me, I don’t even try to man, you definitely have to look and consider what you’re going to say. I just think that’s reality.

And if we think about even reversing it, and you think about what the challenges might be for someone who has an is of a different race. Yeah, it isn’t white. Or some are women, for example. As leaders, how do you think they should? Like what what can we shed light on? What can you shed light on by what you see in your experience about what they should think of when it comes to conflict?

Because my one rule is this is that I don’t ever want to assume a role of somebody that I can’t assume the role of. So I don’t know how an African American would feel. And I don’t know how a woman would feel I am allegedly, and there’s good reason to say, a white male. So I’ve had all the privileges, you know, and all the benefits of the doubt. So for me to, you know, get in, you know, to assume I don’t even, you know, want to try? I mean, do I think it’s climbing the ladder is harder, you know, and has been probably for different people. Yeah, I think it’d be you’d be ignorant not to just look at the, you know, the numbers of that. Yeah, but but we’re, I always say it’s getting better every day. Is it where we should be, but it’s getting better every day. And where I say to that is that, you know, if people want to go down I go, we do have a female vice president. And we did have a two term black president who got majority of the votes, and was highly liked. Regardless, so we’re further than we’ve ever been. It’s it constantly improving. Is it perfect on? Yeah, golly, de no, nobody. Nobody says that. But it’s moving in the right direction. And so but so with that being said, I think that we’ve gone back further in the last few years, we’ve repressed, felt like there was a time we’re maybe moving in a better direction. It’s, I think, you know, I think it’s worse than it’s been in my lifetime.

Well, and I’m quite aware that, you know, different cultures do conflict differently. Yeah. And I think you know, you you sort of alluded to it from your white collar perspective. I think that that one of the leadership awareness can be that we don’t make the way that I don’t make the way that I’m comfortable with conflict be the way that conflict should be that people can approach these things differently. They can approach challenges differently. They can communicate differently, they can, they can play differently.

My wife would avoid conflict, like her approach would be pretend it’s never there. If you never have I always joke with her. So the way that you do it’s like the five year old. If you cover their eyes, they don’t see it. You’re not there and then you can be they can hear your voice but where’s Mommy you because you put the hand right in front of their eyes. That would be her approach avoided.

Impact is of avoiding conflict. I know, I do a lot of personality profiling. And there’s definitely personality profiles that are more likely to avoid conflict.

I think that’s all like, in my wife situation. It’s like kind of all she saw growing up, you know, they never talked about anything. And there was always an elephant in the room. And nobody ever talks about it. And if I stereotype myself on the Italian, Italians just argue, we’re at the dinner table, my my wife will be like, You got I go, but it was over in five minutes. You know, we banter and it’s out and five minutes later, you’re hugging at CES, the way that we do it. It’s not the end of the world. We don’t take it personal. And you know, I’m used to seeing that where you kind of let let it fly. And I like my friend when time talked about in his house, he said, we we are how do we fight? He said, we fight loud. We fight vulgar. And then we make up. We’re loud. We’re vulgar, and we make up you know, you guys, but you know, if you saw it taking place, you’d never think we were gonna make up?

Well, Faith Fuller, who’s one of the founders of CRR global, it’s a coaching company. She always said that the only way to increase trust is through resolve conflict. And I really love that. I think I think it’s true, like however we resolve it, we do create deeper relationships through.

Well, there’s no doubt I, some people you can never resolve it with. Again, it’s the one intent. There are certain people though, that you can’t because they don’t. They’re not it’s like playing Monopoly. And, and, and, and every time you go by go, you get $200. Every time they go by go, they take 2000. How do you if they roll the dice, and they move to whatever spot that’s open? They don’t follow what’s on the dice? How can you ever compete with that person in Monopoly? They’re playing by a totally different set of rules. We, there are certain people we have conflict with that goes, but they go by such a set of rules that if you’re just normally decent, you can’t you can’t You don’t stand a chance.

Well, I’ve, since I had this go badly. I’ve been thinking about times that I’ve had conflict that it went really well.

And instant time it does, when most most people are noticed, right? Well, most people are normal. And most people have an inner date sensors tension. Yeah, most people want to resolve it and, and they’re glad you brought it up. And we’re glad to, you know, clear the air. You know, that’s a, you know, phrase that we use, most people like that.

I think that it’s also like, at the heart of it, what I’ve realized, is one of the key indicators of whether or not it’s gonna go well, if you have to talk about a problem is like, do you literally care what the person feels? Do they care what you feel like?

There’s what I’m talking about the certain? Yeah, you have certain people that do not care.

It’s really hard. It’s like, and, and, you know, there’s people that want to extract value out of other people, as if they’re, you know, a factory or a machine. And, and it’s all in there.

Some people are takers, as we would say, they take into, there’s nothing left to take. And then the relationship blows up, because they you catch on. So you kind of slow down on the taking or modify the what you’re willing to give. And then the relationship reaches an end. Because you’ve chosen I’m not going to continue to give it that level or be taken advantage of at that level. They realize you’ve caught on to them, or they view it as you don’t like them as much anymore. However, they interpret it and then it runs its course.

And then they fight the way they fight. Oh, yeah. I I want to give you a chance to talk about some of the things that you’re up to, in your leadership in your work. Like what’s exciting that’s going on in your world.

Yeah, exciting. It’s funny, I text Bradley Brad’s really big on Instagram, I don’t know, maybe seven or 8000 followers or something like that real to the point kind of guy. And I remember on a Sunday, about four months ago, maybe six months ago, I text him about if I was going to join a mastermind group. Now I’m an upper level entrepreneur, I like which one would I join? You know, it’s just like, Where would I go? You know, I don’t need the beginning level. And I don’t have a billion dollar company. So you know, I’m a realist, like, Okay, that’s great. Tony, you know, Tony Robbins, you can go work with Ray Dalio in that group. That’s fine. It’s not me. I have an extraordinary life great living, but I my company cannot scale to that level. It’s not possible. So I’m somewhere that floods The middle and I remember texting him and he goes, we should do something, we should create it. And I started thinking about it, then I flew up to Vegas to talk to him. And we decided, you know, we need to do an event. It’s called The Weekend MBA. Where because most business owners don’t know what they don’t know. And we said, why don’t we create a two day event that says, We’re gonna let the people forget all the hype, the cotton candy, we’re going to teach people what they really need to know, we’re gonna find people that have been on our podcasts and actually know what they’re doing, you know, taking a product to market have taken a product and it’s sitting in Walmart sitting in Target, or you know what I mean, or whatever it is, they’ve mastered that niche. And we’re going to get speakers that can actually where you go now, okay, I want to sell it ecommerce, that person can only I want my product to be in target that person’s done. Well, I need to raise venture capital, wow, she’s done. I need to sell my company. Oh, that person’s done. I said, What if we put together an event like that, and we you know, in our it’s brainstorming, and it’s conference room, we came up with the Weekend MBA. And we’re doing it since April, 29, and 30th. So if you go to www dot, the Weekend MBA, you can get it set my beautiful hilt, Miami, 29th and 20/29 and 30. But I think it’s a unique event. I’ve been to so many things where it’s nothing but hype. You know, it’s high pipe, pipe pipe pipe. And I always say it’s cotton candy. You got to tell me what to do and how to do it. You’ve identified the problem, okay, well tell me what I need to do and how I need to do it. And don’t make it a course I have to buy while I’m there. You know, where they give you just enough of it to let you know, they’re an expert. And for another $2,000 they’ll solve the problem for you. No, we’re gonna do everything we can to help you while you’re there. So yeah, so yeah, we feel like it we feel like it’s, it’s unique. It’s like he and I were both sitting there going, Hey, listen, you don’t need the money, and I don’t need the money. And that makes us a unique opportunity.

Who should come to your event?

I think anybody who’s you know, not doing $50 million in your business. I you know, I always say let somebody help him with the billions back. It’s not me, I haven’t done a business like that. But you if you know, your business is not growing at the level, you know, you’re missing something you don’t know quite what it is. But you’re This is amazing. The 91% of all businesses don’t hit a million dollars. So I’m like, what is the 9%? No, that the 91%. So that’s a real good start, why my business doesn’t even do a million or my business doesn’t do 10 million. Okay. They’re kind of the benchmark for I feel like, we could be a tremendous help to that. You need help over 100 million. Okay, we’re, we’ll pass on that. But that is only like 1% of 1% of all the businesses left. So we feel like there’s a tremendous amount that are, you know, sub 50 million in revenue. We feel like that’s the person we could really help.

Thank you so much for being on the show. It’s been fabulous to have you what a what an interesting conversation about conflict.

It was good because we came up with it right before we started this, this is genuine a conversation as you could possibly have the one her and I had.

Yeah, this was fantastic. Thank you for being here.

Great. Well, thank you.

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Well, it’s  been great talking with Sean Castrina. I am so grateful for the thoughts that we explored on here. I think, as leaders, we have to be thinking about who we are, we have to be thinking about who someone else is. We have to be thinking of what fight we pick, what we are invested in what we’re not invested in. And I really challenge you to experiment with the conversations you need to have, and also with who you are in those conversations, so that you can have the most positive, productive conflict possible, so that you’re taking it somewhere so that you’re developing skills, and then experimenting differently with the way you approach it, to see what works for you and what doesn’t. It’s been great having you here today. And being with you. Go experiment

Important Links: 

• 10 Minute Entrepreneur Podcast
• Developing the Entrepreneur Within
• SeanCastrina.com
• Sean Castrina –  LinkedIn

Sean Castrina

Sean Castrina is a serial entrepreneur, having started more than 20 companies over the last 20 years, and still seeks to launch a new venture annually. He is an investor, teacher and highly-sought-after speaker who communicates with humor and a bluntness that engages and captures his audience.

He is the author of 8 Unbreakable Rules for Business Startup Success, The Greatest Entrepreneur in the World, and World’s Greatest Business Plan.

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