working with friends and family
 


In this episode, we’re talking about whether it’s smart to hire and/or work directly with friends and family in your professional life?

What are the pros and cons of doing this? What do you stand to lose or gain if you take this path? What are the most important things to think about before you take this leap?

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Episode 84 Transcription

Seth: Hey everybody, what’s up? This is Seth and Jaren from the REtipster podcast, and you’re listening to episode 84. In this episode, Jaren and I are talking about an issue that sort of had differing opinions on over the years, but it’s actually a really important thing to think about and consider as a business owner. And the question is, is it smart to hire and/or work directly with friends and family? What are the pros and cons to that? What are the risks to that? What do you stand to lose or gain if you decide to work with these people in your life who are the most important people there are?

So, we’re going to dive in that. I know we sort of have different philosophies on this in different ways we think about it. And hopefully when you hear a back and forth, you can kind of process this for yourself if you haven’t already. Are you ready to jump into a Jaren?

Jaren: Yeah, man. Let’s do it.

Seth: I’ll just start off by saying for the most part, I won’t do it unless I’ve somehow worked directly with this close friend or family member in the past, and I’m extremely confident about their competence and character. 99% of the time I’m not willing to roll the dice and find out if they’re going to be a good fit.

For me I think the bottom line is, the reason I don’t want to do it is that I need to be able to have a hard conversation with this person and even potentially fire them at some point if they’re not working out if they’re not delivering or performing. Because if I can’t have those hard conversations, if I can’t fire them if needed, my arms are tied behind my back and I can’t actually do what I need to do. Because the alternative is to possibly ruin that relationship permanently.

It doesn’t have to be that way. But a lot of times that’s just how it works when you fire somebody. It’s a difficult, offensive thing to go through. You can do that with somebody a lot easier when they’re not your friend or your family. You don’t have to either live with them for the rest of your life or cause a lot of hurt.

And I feel like if you just sort of draw the line where you say “no” to that, and just realize there’s a lot of capable, competent people in the world who aren’t your friends and family. And when I say friend as well, it sort of depends on how close I am with them and how much I value their friendship.

We all have people in our lives who are like acquaintances, like maybe you knew each other in high school and if the relationship ended, it’s not like your life is over kind of thing. So maybe that’s a little bit different. But I’ve done enough talking, Jaren, why don’t you jump in? What are you thinking so far with what I’ve said?

Jaren: Honestly, man, I think it just boils down to the nature of what you’re doing together work-wise and who the person is. I would never work with my sister ever just because we have different life philosophies and we have different work ethic and we have different ideas of what proper expectations are in a work environment.

I don’t know if I would work with some cousins that I have. I don’t know how I would work with any of my brothers, but working with my wife is totally fine. Working with my sister-in-law is totally fine because I have seen their work ethic and the dynamic of who they are as people are people I would hire anyway.

So, I feel like when you work with somebody, you have to look at it, kind of like in two different lenses. You have the relationship, the family relationship on one end, but then you have the business relationship on the other. And I know that the lines get blurred and the expectations get blurred. There’s no way they can’t.

But if it comes to you working with your spouse, well, are they competent as a partner in your business and actually get the job done? You need to have that emotions aside, logical, unbiased thought process and conversation to say, “Okay, are these guys able to perform? Are they a good fit for the program?” And if not, then they kind of let them go or not work with them.

Seth: I’m assuming you’ve never had to fire any people you’ve worked with.

Jaren: Yeah. I haven’t personally solely been the one responsible. I’ve been in the meetings with people who are let go, but I haven’t led to conversation.

Seth: Have you ever had to have like, really hard conversations? Like you’re doing terrible at this job right now? Maybe nicer words, but basically they’re not performing and they need to know about it. And how did that go?

Jaren: My wife’s family is from Kazakhstan. And so, I hired my brother and sister-in-law in Kazakhstan to help me in my land business for a number of years. Not currently right now, but for a number of years, they’ve worked with me. And there have been times where I said, “Hey, you need to have XYZ done by this time.” And they like, just flaked on me and they didn’t do it or had some excuse or some reason not to do it. And I had to have some pretty gnarly conversations where it’s like, “If you weren’t my family right now, I probably would be letting you go at this point. I’m pretty upset about this.”

Seth: But that right there. Like, should you have let them go but you didn’t? Like you made a bad business decision because you had hired family.

Jaren: I don’t think so. Because maybe it boils down to a leadership issue or something. But in those circumstances, I didn’t set the work culture to be very demanding. I was like, you’re expected to show up at this time and work these many hours. It’s kind of like, “Hey, I’m paying you this amount of money. If I need you for anything you need to do it.” So, it was very vague and it was not very good on my part on setting up an environment where they can thrive.

And the reality is there have been way more times where they’ve like, worked all night and got stuff done and pulled miracles off. Then there’ve been times where I’ve been upset at them. But there have been a few times where I have been upset at them, but that’s why it’s worth working with them because there are other family members that would flat out. Like I would just be a problem from day one. I can love them as a family member and support them as a family member.

At a high level, not operating out of performance is like a really big thing for a lot of people. Like people want to be loved for who they are and not what they do and that whole concept, right? Well, in work, the reality is it’s not nice, but it’s just true. Like the dynamic of the relationship is performance-based. If you can’t do the job, no matter how nice you are and no matter how well you connect and how much you’re part of the company culture, if you’re not able to do your job, you can’t be there because there’s a job to get done. And there’s an objective to get done. You know what I mean?

Seth: Yeah. Part of what I heard you saying earlier is all the people that you wouldn’t hire for this reason or that family and that kind of thing. But I guess this conversation is more about, let’s assume you would hire them and you are currently working with them and if they are your family or your friend, are you okay just destroying those relationships? What if you did have to fire them? What would they do? Maybe it wouldn’t destroy the relationship in your case. Maybe it depends on them too and how you communicate it.

Jaren: Yeah. I probably wouldn’t hire somebody that I would have to fire. Like I would vet them really strongly on the front end and yes there is…

Seth: It’s kind of a given though, right? I mean, if you thought you were going to have to fire them, why would you hire them in the first place? The assumption is that they’re going to work out.

Jaren: But in a traditional work environment, there’s like 90-day trial periods and there’s like, “Hey, let’s test the waters here and not fully commit.” But with family members, because there’s a full commitment already just by the nature of the relationship before I bring them that opportunity and even have that conversation, I’m watching them, watching their character and really saying, like if we work together in a moment of conflict, would I be able to work out that conflict and continue the working relationship? And if the answer is no, or probably not, or maybe, then probably shouldn’t do it just to keep the relationship intact and keep healthy boundaries.

But if you’re dealing with somebody who has extreme ownership. Somebody who’s willing to go the deeper sense and make mistakes that they make and take personal responsibility for their actions if they mess up, then I think you can work those things out.

It’s kind of like, it’s not to the same degree as getting married, but it is kind of like that where it’s like, I’m not going to marry somebody who has a high likelihood of me breaking up with, right? Like if I’m going to work with them, they have to be the right fit. It’s almost like you want to look at them as if they were not your family first and see if they would be a good fit and then go another layer deeper because they are family to make sure, “Hey, if we’re going to work together, this really needs to be a situation where it works out.”

And then have a lot of communication on the front end. Say, “Hey we’re family first and we have a working relationship second. So, if there’s conflict, what do we do if I need to let you go? What do we do if you start dropping the ball and what is that going to look like? Are you going to be offended at me if I have to pull the plug?”

Seth: I think that’s a good point. The stuff you were saying earlier about looking at them first, like they’re not your family member and then looking deeper because they are. I don’t know if I could really objectively do that. I feel like I have a bias just because they’re my family members.

Like I almost can’t see clearly because say if a family member or a friend, like they’re really in a bad financial spot, they need a job. And I know that they would be good at this particular job that I’m hiring for. It is a good fit, but because they’re a family or friend, there’s that sort of, “I don’t know if I want to risk that.”

I was actually in a Mastermind group earlier this year and we were talking about this specific thing where one guy was like “I want to work with this guy just to help a guy out.” And then another guy stepped in. He was like, “I don’t think that’s ever a good reason to hire anybody is to help a guy out. You hire him because of the right person and because they serve your business.”

It just gets weird. Like, I feel like my judgment gets clouded in many different ways when I’m dealing with a friend or family member. I’ll overlook stuff, I’ll hire for the wrong reasons. I’ll be the first to admit it’s a shame because there’s a lot of friends and family who would be great people to work with and we do a great job, but the only way to really know that is to work with them. And once you cross that line, it’s like, well, how do you go back without destroying something?

Jaren: Out of all of my friends, like real friends, like people that I would go to war with and be in a foxhole with, my true inner circle. I’ve all worked with them in some capacity except for one. And I want to work with him one day. And I’ve had a couple of times where relationships did have some hurt and some bad things go south work-wise.

But I always was intentional to seek reconciliation in the midst of those things. And I even have a guy who was like a mentor to me and somebody I really looked up to back in my door-knocking days in California, really do me dirty and just completely blow me off. Man, I didn’t work for pay for close to a year, just grinding it out with him and he just completely blew me off. That really, really, really hurt.

But last time I was in California, I sought him out. I sat him down and I said, “Hey, man, I want to make peace with you. I want us to be good.” And we’re good now, like we’re not like best buds, but we have peace between each other. We text each other and all that stuff. And I think maybe family is different from friends, but maybe it’s because it’s my personality and my work is my life. So inherently the people I’m going to hang out are the people I work with. I don’t know.

Seth: I do think your desire to seek a person out in a reconcile, that shows a lot of maturity on your part that many people do not have. People who are at the highest level of business should have that maturity don’t and you do. So, I feel like you’re more of the exception than the rule.

Jaren: What about you and me though? I feel like you’re my friend before you’re my boss. But if you and I needed to have a hard conversation where you were like, “Hey dude, your performance sucked. You need to step up your game.” I would appreciate that conversation. I’d be okay, thanks. I didn’t see it or, yeah, you’re right. Or now that you brought it to my attention, I can course-correct. And I would course-correct from there. And I know that that’s not everybody. I mean, if you had to fire me, if I’m honest with myself, you would have to fire me for a good reason.

Seth: And how do you define that? Because in your mind, there would never be a good reason.

Jaren: Well, no. If I morally did something stupid, like I stole money or I took the company credit card and I bought something that wasn’t good.

Seth: It’s usually not that cut and dry though. There’s a subjectivity to it. In the eyes of one person that might be okay but in some, I don’t know… I hear what you’re saying, but you and I both know, that’s never going to happen. That would never be a reason that I would fire you because you wouldn’t do it.

Jaren: Because this is where I think it gets interesting. Right? You and I are friends and what would be a reason you would fire me for?

Seth: Well, I do remember back when this first thing came up, where you could potentially work for me. It was actually really unique because you and I weren’t best buds or anything, it’s not like we hung out all the time. And at that point in time, if the relationship went south, like, that’d be unfortunate, but it’s Jaren and I weren’t like best friends in the first place. It’s not like I’m ever going to see him. That was kind of my mentality and where I was coming from. And I feel like it’s very different today. I feel like we were better friends today just by default because we spent so much time together.

But at the same time, I had seen enough of you and your thought process to just know like this guy’s got a good head on his shoulders. He’s teachable. He knows how to course correct. You’re a very obvious mixture of a lot of good things. I’m always very hesitant to say this, because I don’t want to put words in God’s mouth, but I kind of felt like it was a God thing in a way. It just felt like he was coming together so perfectly. I mean, that’s kind of how I made the decision in the first place. But in terms of like, what was your original question? How I would or why I would fire you?

Jaren: Yeah. What would be like a realistic reason you would fire me that might potentially end our relationship?

Seth: Yeah. So that would be if the direction of REtipster went in a way that your talents aren’t best suited for the direction we’re trying to go kind of thing. That’s really all I could think of. As you well know, we have so much stuff on our plate all the time. There’s always somewhere where I can say, “Hey, Jaren, take care of this.” Say if we decided REtipster is just going to be a forum going forward. That’s all we’re doing. So, no podcast, forget YouTube, forget blog posts, forget courses. Just forget all that. We’re just a forum now. I don’t think I would really need what you’re doing anymore, honestly. And it’s one of those things where it’s a decision I’m making that is affecting you in a negative way.

Jaren: But if that was the reason, you’d have to be really delicate in the way that you delivered it to me, right? Again, maybe I’m an outlier and most people don’t think the way that I do, but I can speak only for myself. If you were to say, “Hey Jeren, I’ve been doing a lot of soul searching and thinking, and I feel like the direction of our REtipster should go this way for these reasons and I don’t really see a fit for you here.” It’s not you personally, but I just don’t know if I’m going to need what you do and I can save the money for paying you and put it somewhere else. And I’d be like, “Oh man, well, okay. I totally get it. Like we’ve had a great run. That’s awesome. Are we still going to be able to hang out?

My response would not be upset in that situation at all, because at the end of the day, you’re the vision cast there for REtipster and I’m here to support that vision, right? So, if the vision changes and I’m not able to support that vision, then that’s fine. I’ll go somewhere else. But I don’t think that that would be something that would hurt our relationship. And if you are healthy, if you have people in your family that have good self-esteem and then not dealing with major insecurities and all that stuff, if they are level-headed, they should be able to see that and respond that way I think.

Seth: It may not even necessarily have to do with being fired, but just having hard conversations or me stepping in and be like, “Nope, Jaren, I don’t like your work. I don’t like what you did here. Fix it, redo it.” I mean, obviously I would be as nice as I can, but I mean, that stuff happens where it’s like I have to pull the boss card and be like, “No, we’re not doing that.”

Understandably, I’ve been on the other end of that and it doesn’t feel good. It doesn’t make me feel warm, fuzzy thoughts about the person. I don’t know if it has to ruin a friendship, I wouldn’t go that far. But all the warm, bubbly stuff that you would normally have in just a pure friend where all you do is hang out and have fun together.

All of a sudden when you get work involved and there’s this hierarchy of “I’m over you now. I’m the boss and you’re not. Do what I say.” That’s effectively what’s happening. I think you’re actually very good at handling that and just dealing with it. Not that you’re always happy, but some people don’t do well at that. They almost feel like, because you’re my friend or family, you owe it to me to let me do what I want.

Jaren: If they have those expectations, you can’t work with them.

Seth: But that’s the thing. You may not know that until you do start working with them and you realize, “Oh, that’s what they’re going to be like.”

Jaren: Well, those are the kinds of things you have to look for in their character and in their personality.

Seth: That’s true.

Jaren: Do they operate out of these weird assumptions and expectations around work? Do they have a bad mentality around rich people and stuff? Тhe reality is if you’re working for a company and you’re doing a lot of stuff and making the company a bunch of money and you’re getting paid a certain amount and not making it what the company’s making, then you have to be okay with that kind of stuff.

You have to understand as the person that is the friend or the family member like, listen, this is Seth’s boat. This is his mission. This is his operation. And it’s an honor and a privilege that he’s giving you this opportunity. So, don’t come here with a handout thinking that he owes you something because he’s your friend and he’s fun to hang around and stuff.

But at the end of the day, this is your shot to prove yourself and to keep your worth. And so, I don’t know, I guess it just depends on the mentality. And again, I would never work with my brothers. I definitely wouldn’t work with my sister. I want to work with a lot of people that are in my family, but my wife? Yeah, my wife at the end of the day, she can grind. Sometimes it’s a little annoying because if expectations aren’t set where it’s just her and me, like in the land business, she might take longer than I would like for her to do stuff.

But at the end of the day, I know she’s not going to drop the ball that’s going to cost us. And everyone that I hire that is a friend or family or that I work with I know at the end of the day, I can count on them. If you can’t realistically count on them, they’re lazy. There are some really fun people that don’t like to work hard. And if you need to have people that work hard in your business, then don’t hire people that don’t work hard.

Seth: Yeah. It’s a similar but different vein. I know my dad has led some pretty big organizations for most of his career. And one time I was talking to him about this and he was telling me that his advice is that when you do work with people, whether you’re their boss or they’re your boss, or you’re just co-workers, be really careful about how close you get with them as a friend. Like almost don’t become best friends with your co-workers.

And the first one I heard that I was like, man, that’s rigid. That seems cold and harsh and unnecessary. Why can’t you be friends with people that you work with? But his rationale was, you never know where a working relationship is going to go. You never know if they’re going to be your boss someday or vice versa or you leave places and they have something good or bad to say about you.

Maybe they have a very loud mouthpiece and can say something good or bad about you. Maybe they can open doors or inflict damage on you. There’s just lots of things where it’s like, just be careful, keep it professional. Obviously don’t give them reason to hate you, don’t be a bad person.

But even when you develop a genuine friendship with somebody, a lot of expectations come out of the table then. Like, “Oh, okay. So, if you’re my good friend, that means you’re going to do this for me. When you go over there, you’re going to look out for my best interest and stuff.” I mean maybe if that’s what you’re the best for, but maybe not, if you’re not the right person for the job.

When you’re a good friend with somebody, and again, this depends on the person. I think some people are much more mature about this and don’t have these expectations, but it can just get weird when you weave the professional and personal thing together.

Jaren: Yeah. I think you just have to ask me for the right fit. But I feel like a dream of mine is to have a group of best buds that go and build some large company or something that I miss from the Simple Wholesaling days is the synergy of the team. And having the team dynamic. Obviously, you and I are a team, but I think we talked to each other this week on Monday and then today. So, it’s a different dynamic. You got to do your stuff, I got to do my stuff and then we slack in between when we need something from each other.

But my wife worked at Simple Wholesaling. My sister-in-law worked at Simple Wholesaling. And my other sister-in-law in Kazakhstan did some like VA work for us at Simple Wholesaling. And they were all on the disposition side.

So, I was the head of disposition. And then I ran my family like a crew and it really worked for us. I feel like even though you do open the door for getting hurt, I would rather have my friends be people that I can go and build amazing things with and rely on them to actually get stuff done and to be mature enough if I need to have a hard conversation, because you’re dropping the ball, have that hard conversation.

I would rather somebody have that hard conversation with me because at the end of the day, I want to be able to perform well and add value. And if I’m not, then I want help to make sure I can do that.

Seth: It probably does come down to not only the individual, but also the business owner, the boss in terms of how good are you at communicating problems and how tactful are you? And how far do you let things go versus stepping in and correcting things.

Now there can just be a lot of implied expectations when you start treating each other like family when you’re not or treating each other like best friends when you’re not. And if you just don’t do that, I feel like it’s not as much of a wound if something does happen. Or if there is a wound it’s like, it doesn’t feel so inappropriate because you never treated them like family or friend to begin with.

Jaren: Yeah. But I think it ultimately boils down to who you are and who they are and how you can navigate their relationships. Because if I have a big wound, I think in my life philosophy and the way that I view the world at the end of the day, that’s my fault. It’s not their fault that I’m offended. It’s my fault that I’m offended. And it’s my responsibility to go and figure out why I’m offended and get unoffended, forgive them and make peace. I feel like that’s my responsibility as a human being.

Because I operate that way, I feel like I can navigate conflict really well because I know a lot of people are out there and they get offended and it’s always the other person’s fault that made them offended. And they hold grudges for years and all that stuff. But I just feel like that stuff, it’s a poison, man. Unforgiveness is a thing that keeps you in prison. They’re out there living their life, doing whatever they do.

Seth: I hundred percent agree with everything you’re saying. But what you’re saying, you’re taking responsibility and you’re being mature about it. As a business owner who is trying to deal with an employee or co-worker or business partner who may not have the maturity that you have right now. They don’t get that “Oh, it’s on me. I need to forgive.” They may think, “Oh, it is the other person’s fault and I’m going to do as much damage to them as I can.” I hear what you’re saying, but many people don’t think the way you do.

Jaren: Yeah, okay. If that’s the context, again, it comes back to that particular person’s character. If I know my family member is going to have a high likelihood to get offended and hold grudges, I’m not going to hire them. And I’m probably not going to hire any friend or family at a lower level position. I’m not going to have them come and be my VA.

Seth: Is not what you’re doing with your…?

Jaren: Yeah, I guess. But I don’t treat them like subservient, if that makes sense. I don’t treat anybody that way anyway. But if there was a dynamic where I was like some high-level executive, I don’t know if I would hire my family member, my best friend to be my shoe shiner or to be the guy that works in the mail room. I think I’d have to give them a level of “Hey, you’re somebody of importance in the company or you’re somebody who I value your input and your advice and your thoughts.”

Seth: That’s what I’m talking about though, man. Because what if they don’t belong there?

Jaren: Then I won’t want to hire them. I want to give them the opportunity.

Seth: There is a case then when you would say no.

Jaren: Heck yeah.

Seth: Even if they’re great for the shoe-shining job, they’d be perfect for that. But because they’re down at that level by policy, you wouldn’t hire them?

Jaren: I don’t know about that.

Seth: So, it changes, I see.

Jaren: Yeah. No, but it’s good because it’s like, I’m an external processor. So, it’s good to ask these probing questions and figure it out on the spot. But here’s what it is. Perfect example. My mother-in-law, she lives with us. She’s like in her 60s, she’s from Uzbekistan. She grew up in villages in central Asia. And she’s not the most skilled person. She’s an extremely hard worker. She’s amazing at what she does. She’s Mary Poppins on steroids. So, I have lots of respect and honor for her.

I was paying at my other house $60 a mow tool to a lawn care person. I don’t want to mow my lawn. My mother-in-law was mowing my lawn the other day. So, I said, “Hey, I’ll pay you $60 to mow the lawn instead of the other person,” right? Technically she’s being hired for a shoe shining kind of thing, like a mowing the lawn kind of thing. It works within her skillset.

I’m not going to put her in a position where she’s going to fail and we’re going to have problems. I would never have her answer my emails for me. She doesn’t speak English. That would just create a lot of conflict. It wouldn’t work. But to the degree that I’m working within my friend or family member shrinks, and I have the opportunity where I know if they were to come on board, it wouldn’t ever come to a point where I’d have to fire them. Unless it was something like immoral, or something super majorly weird, then I would bring them on.

But I’m going to work with their personality, their skillset, just who they are and watch them and really get to know them before I start working with them to make sure like, “Hey, are they able to handle me telling them off?” Because if they’re not, I can’t work with them.

Especially me. I get really impatient when it comes to work. It’s actually a leadership flaw in me that I have to be constantly aware of. It’s really easy for me to be snappish and kind of mean. Like, “Hey, why don’t you do that? What are you doing?” And so, if we work together, we have to have that understanding that, “Hey, if I’m like that, I’m not trying to be that way. I’m just trying to get the work done and I’m frustrated, I’m acting out of emotions. My heart’s not to be a jerk.”

All of those things have to be talked through and worked through and the expectations have to be there. And if they don’t work out, then don’t hire them because you’ll ruin the relationship and Christmas dinner.

Seth: Yeah. I think maybe something that I’m learning through this conversation is that maybe it’s not great to have just a militant policy of ‘no friends and family.’” Because I say this all the time, “never say never” or “never say always.” So maybe I shouldn’t say never always about this particular issue. Maybe there are situations when, if you’re very, very careful and communicate very well and it’s the perfect person and all the right reasons are there and they understand, and they have the maturity and yada, yada, yada, maybe there can be a time when friends and family can make sense.

So, I hope what people are taking away from this talk is just the things to think through. If you are going to go down that road or even if you have a policy like I did before we started talking where it’s like, “No, I’m not going to do it.” There’s just a lot to think about. And I just can’t imagine if I had never hired you Jaren, where would I be? Where would REtipster be? It would just be a totally different life and everything.

Jaren: Thanks, man.

Seth: You can throw a lot away by sticking to a policy or a thing like that, that you haven’t really thought through all that well. And you don’t want to get lazy in your thinking when these opportunities come up. You want to sort of look at every variable for what it is and there could be gold waiting there.

Jaren: And communication, I think, is essential. Have the hard conversations in the beginning, run scenarios, ask until you’re blue in the face everything that you could think could possibly go wrong. You can really ruin your relationship if you don’t steer it this well.

And a prime example, when you brought up firing me, if you came to me and you were “Jaren, you are kind of useless around here. I know you’ve been here and it’s been good, but I just got to be honest. I’m tired of paying you. You’re kind of deadweight. So, I’m just going to cut you off and send you on your way.” I would be really hurt. Like if that was sincerely coming from you, I would be like, “What the heck happened Seth? What did I do? Why didn’t I have an opportunity to course-correct? What’s going on?”

But if you came to me in the right way and you were like, “Hey this is a directional change. It’s nothing personal. I just don’t think that you’re going to be a fit here anymore, man. It just doesn’t make sense for the future.” I’m like, “Yeah, man, I get it. That’s totally cool. Can you write a really amazing recommendation letter for me?” That’s exactly what I would ask.

Seth: So, are you saying I should stop using the word useless in our weekly meetings when I talk about you?

Jaren: No man, you can do that. I’ll keep finding tissues to cry in in my car.

Seth: It’s a big thing. I know I’ve always looked at family businesses in awe. I remember I used to work for a car dealership as an internship when I was in college and it was a BMW. Land Rover and Jaguar dealership. And it was run by a father and his two sons. And I think there was a sister in there too. But it was interesting. The sons didn’t call their dad, “dad.” They called him by his first name. They just kept it very business and I’m positive they knew how to have hard conversations with each other and they sort of have that boundary and they had the maturity to deal with the hard things that just come up in the day-to-day course of business.

Jaren: That would be weird for me. If my son called me by my first name, I would probably slap him on the side of his head.

Seth: Yeah, I know. It would be kind of weird. But if your co-workers were standing around and you called your boss “dad,” wouldn’t that be weird? Wouldn’t that just automatically make you look better than everybody else because it’s your dad?

Jaren: Maybe. But if I’m going to bring my son on to my working relationship, like if he’s younger, then sure, have him do groundwork. But if he’s like stepping into the age where he’s starting his career, the only reason he’s working with me is to be my right hand and to run the business with me.

The expectation is going to be there. And if he’s not pulling his weight, I’m going to probably be even more hard on him because I don’t want people to think that he gets favors or whatever. So, he’s going to have a big demand on his shoulders. But as long as he is there, he’s being groomed to work alongside me more on my level. Because otherwise that would be a weird dynamic. If he was like 12 or 15, sure. Like help me do the filing cabinets or whatever, but I’m not going to have my son be working for me unless he’s a part of the leadership team for sure.

Seth: I think the thing is we’re talking about communication is really a huge deal though, because if you’re doing it right, if you do give a person ample time and a very clear understanding of what they need to change, like what is the problem exactly. Repeat it a few times and if it doesn’t change, it’s almost to the point where they could fire themselves. Because they know what they are doing is wrong. It’s not like they’re caught off-guard. It’s like, “Oh, I didn’t know. You didn’t tell me. Like, I thought it was fine.”

If you’re communicating it right and if you’re doing it tactfully, in a way it almost seems like it would work itself out. If you do have to pull the plug, there’s no shock here. It’s not like you’re yanking the rug out from underneath them. They know and they’ve known for a while. And if they’re smart, maybe they’ve already found another job.

Jaren: I feel like good businesses operate that way anyway. And it should be the next level with friends and family. I mean, I don’t know. Maybe I’m just different, man. I don’t know, but I just want to do my absolute best in everything that I do. And if I’m like dropping the ball, I just don’t want to drop the ball. So, help me not drop balls please. A lot of your feedback on my writing skills and video stuff. I think there have been some videos where I’ve had to redo like four times or sections at least four or five times.

Seth: That’s hard, man. That is a hard, hard thing to do.

Jaren: But it makes me better. At the end of the day, if I can trust that you are for me. Like you’re my friend and you’re my family. And I know that confidently that you’re not out to get me. You’re out to make me the best version of myself and have my work be the best standard it can be. Why would I be upset at good constructive feedback? If your heart’s in the right place. If your heart’s not in the right place and you’re a jerk, then that’s a different story. But if your heart is in a right place, I would want your feedback. I would want to become better.

Seth: My friend was telling me about this the other day. I think this came from Dr. Henry Cloud. I think it was who came up with this. He basically was talking about when you give feedback to people, there’s the wise, there’s the foolish, and there’s the evil. So, wise people will accept the criticism and adjust and become better. Fools will deflect and point fingers, and the evil, they’re just out to hurt you. There is no reasoning. They’re just out to cause you pain and misery.

I think you can usually figure out pretty quickly who you’re dealing with when you do offer this kind of criticism in a helpful, constructive way, kind of helped me to just hear that breakdown. It seems to make sense.

Jaren: And there are horrible people out there, man. Watch out for them. They’re out there. Few in numbers, but boy do they, they exist. I’ve had to learn that the hard way.

Seth: That’s for sure. Cool. Well, that was a good talk, man. I’m glad that we passed through that. I feel like I learned a few things from your take on that.

So, people out there, if you have any comments or thoughts on this, maybe you have a unique experience. In fact, you most likely have a unique experience that we don’t know about and didn’t account for.

And by all means, feel free to leave a comment on the site, retipster.com/84 because this is episode 84. You just scroll down beneath the show notes and transcripts, get to the comments section. Feel free to leave us a comment. I’d love to hear any other thoughts out there about this.

If you guys haven’t already, and if you’re listening to this on your phone, take out your phone and text the word “FREE.” That’s F-R-E-E to the number 33777. And you can stay up to date on all the stuff we got going on, the new stuff that’s coming out. And some things you won’t normally find on the blog or here on the podcast.

But again, thanks everybody for sticking with us. Hope you got something out of this talk and we’ll talk to you again in the next episode.

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About the author

Seth Williams is a land investor with hundreds of closed transactions and nearly a decade of experience in the commercial real estate banking industry. He is also the Founder of REtipster.com - a real estate investing blog that offers real-world guidance for part-time real estate investors.

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  1. Carlos says:

    Bad idea, I would stay away unless absolutely necessary and detail all responsibilities and boundaries in writing since day one. Did a partnership once with my wifes uncle, halfway down the road turns out he decides to place his son as managing partner, which I agreed to since we were close. I found he was stealing from the company, something I never thought possible since he would have to steal from both his dad & me, which is what he did. All hell broke loose and ended up selling my part of the company and family relationship will never be the same

    1. Oh man, I’m really sorry to hear about that. Sounds like a nightmare. I think those kinds of horror stories are what I always think of when I consider this kind of scenario. It’s too bad the world has to be so full of potential downsides like this, even within one’s circle of family and friends.

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