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This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of
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Entrepreneur Magazine and I'm money expert Nicole Lapin. On Tuesdays Jason and I answer the helpline and help callers solve their work problems.
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And on Thursdays I give you one way to improve your work and build a career or company you love.
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And it starts now.
A
So Nicole, you are about to have a child and just telling you that in case you didn't know, I'm well aware. Yes, you're extremely pregnant right now and 87 months pregnant.
C
Yes.
A
So for a while, for many years, you will be doing everything for that kid and as you should because that kid is not gonna be able to move themselves or feed themselves. But of course at some point grows up, becomes a person who can actually do things for themselves.
C
Yeah, I've heard all about you wiping your kids asses.
A
Oh God, I've wiped too many asses. But at some point of course a parent needs to let the birdie fly off on its own and that is a really hard thing to do that what I am hearing, what people seem to be talking about culturally is that parents are having an increasingly hard time doing that and are more and more involved in their kids lives later and later. So for example, I was just talking to this person who runs a college advisory who was saying that parents are now very involved in their children's college academic experience. Like they'll text the kid and they'll be like, don't forget you have class on Tuesday at 10am or don't forget that test is due. Which sounds horrifying.
C
Yeah, I was told that it went from the latchkey kid generation to the helicopter parent generation to now the bulldozer parent generation. So that's like the parents who did all that crazy stuff to get their kids into school, like faking the rowing and the whole college scandal. And then it sounds like also reminding your kid about a test which is.
A
Yeah, the bulldozer being like the parent just paves the way for the child. That is a perfect tee up for what we're going to be talking about today. Because Nicole, you and I love examining bad emails, not well thought out dms and asking should this be very voyeuristic
C
but whatever that equivalent is for audio.
A
For audio, yeah. Yeah, you could still be voyeuristic. Audio. Audibly voyeuristic. Yeah. We want to know what are people saying and should they have said it. And in this case we are going to dig in not to your or my DMs but to a friend of mine and entrepreneurs DMs who got an email or got a DM from really one of these bulldozer parrots. And so we get to see what it actually sounds like for a bulldozer parent to bulldoze. And then my friend sent a response which he then asked me if he should have sent. So we're going to read this stuff and then we're going to bring him on and we're going to tell him if he was right. And also I think everyone's going to be able to judge for themselves whether or not he said the right thing. Are we ready for the DMs?
C
Yes. Let's do a dramatic reading.
A
I'll be the bulldozer parent and then you can be my friend.
C
Okay, so your friend is Jeff. Jeff is going to come on. I'll be Jeff. You be. Let's call him Bob.
A
Yeah, Bob. Okay, Bob. Not his real name, but here's Bob. Okay, so the context here is that Bob. Bob had been trying to get an internship for his son. So Bob, the bulldozer parent, is asking Jeff, my friend, the entrepreneur, if Jeff will hire his son for an internship. So now Bob is pushing a little harder, hasn't gotten the internship yet, really wants to get there, sees a couple trees left to bulldoze and is going for it. And here's what it sounds like. This is the dm. Jeff. Hi. Wanted to see if you filled the internship seats. My boy is finished with film school, successful with 3.77 GPA. He has experience and will be a plug and play teammate. He is a X D1 athlete and understands that sacrifice is mandatory. He just needs a door to open and a wing to get under. He comes with hunger. He would be an asset on day two of any team. Do you have any seats open? He has a part time job to pay the rent and doesn't eat much anymore. What? That is what it says. Doesn't eat much anymore. I don't understand that. But we're just gonna keep going.
C
God, like he won't eat your free snacks?
A
Yeah. Oh, I guess that's what it means, Bob. Jesus. You don't have to be a bulldozer, Karen, but you can buy the kid a hamburger. Okay. Can you fit him in or know if some leads? Surely. I don't want to overstep, but I know if someone with side work and contacts can develop this kid's amazing thing, it will happen. I see you nurture artists. Jeff owns a music company. We'll learn more about that in a moment. Would the same formula work for an aspiring film slash audio editing director? Work as well. Are you in town this week or next weekend? And that is it. Okay. So that's so much to say. Yeah, so much to say. We will say it all. That's what Bob sent to Jeff. You're going to be Jeff.
C
So Jeff says at 12:40pm hey Bob, I want to be honest with you. The fact that you are the one that continues to reach out on his behalf is not helping him. He needs to do this kind of thing on his own. Although we have a connection through business, that can't be the relationship that continues through the process. You are definitely driven to get him a position, but he is clearly not or he would be the one reaching out to me. If you are instructing him that you will handle it for him, you aren't doing him any favors. I have filled all of my internship positions and hope your son finds something that is a fit for him. Hopefully he develops the same drive and energy you have for his Future as he has for his own.
A
That is a shank at the end. Okay, so Jeff then sent me screenshots of that, and he asked me if he should have sent that, and I said, why don't you come on my podcast and we'll answer that question together. So, Jeff Peterson, welcome to Help Wanted.
D
I am so happy to be here. I think. I didn't think a screenshot message with a response was going to turn into a podcast of me really finding out what the world might think of my answer.
A
That is the danger now, you know, of asking a question of someone who has a podcast. Jeff, before we answer that question and more, why don't you explain who the hell you are and therefore why someone wants an internship with you.
D
I own a couple of companies. One of them is Geneva Supply, which we handle a bunch of manufacturers to the world of Amazon. Been doing that for, I don't know, 15, 18 years. Within the last three years, acquired a company by the name of Interstate Music, which we sell music gear, but we developed into, I'll call it a service based music company where we actually now have a location right on Music Row in Nashville. And we're offering services of video content production, recording studios, writers rooms. We also handle artist management. So this was a situation where the person that sent this DM when I was building out the space that we had and finding the decor, he was actually somebody that I reached out to through Facebook Marketplace to just buy something from. And he made the delivery to the building, saw it, and just thought his son was absolutely the perfect fit for the future growth of our company. And then the second time I bought something from him because I needed more of what he was selling, he brought his son with him to go for a tour and started to actually film for a class that he had his experience at our company, Interstate Music. And so it really just was this huge ordeal of the process of just getting to know him by buying something and being appreciative. And then all of a sudden, it started to just turn into the future for his son and everything else that wrapped into it.
C
So you saying that you guys have a business relationship was very generous on your part?
D
Yeah, I'm a Facebook Marketplace guru when it comes to finding stuff for decor. And it just turned into this, oh, my gosh, you're the perfect fit for my son's future. And it just grew from there. The message that you just read, this is the fourth message that I had gotten to some level of degree. The previous ones were a little bit softer. The first One was really introducing him as far as all of his skills, what he's doing, and he's going to be graduating and all of this. And then it kept on saying, hey, I just wanted to make sure that you got the information that was sent. And like, all of the little things that just kept on going. And. And then this one, honestly, it just pushed me to the end where I'm just like, I could just say, sorry, filled the positions, or I could say, if you're doing this for him with all of his other job opportunities, this is going to be a tough road for him. And I'm not sure any other companies are going to want to hear any of your messages as much as I really don't want to hear you pitching your kid for a job either.
C
So you were concerned when you reached out to Jason as to whether you should have responded at all, or were you the asshole in this? That's what your question was?
D
Yeah, it was probably a little bit more of the was I the asshole in this? I meant everybody word. I said every single word. I felt it got to a point where I'm just like, I cannot believe that you're not being self aware enough that your son should be the one that's doing all of this. Coach him into how to handle it. Write out your response, write out the email and tweak it for him and help him out and then have your son send it. And then I'm working, going back and forth with his son on this entire process. And it just hit me because I've done a lot of mentorship with high school students and college students and all this kind of thing, and I just felt that I had. I could not, not say something. And it just hit me and I sent it all off. And then I'm like, oh, Jason kind of knows me personally. Was this over the top or did I hit it?
A
And Jeff, I would just important context so people know where you're coming from. Yeah. You had built an entire career development program for high school students, correct? Yeah. So you care about this and you've seen what it looks like.
D
I do. And I think that's really the reason why it hit me is because I started this program for high school juniors and seniors, and I know what a high school junior and senior is capable of doing and the way that they communicate, how they can interview and how they can represent themselves. So somebody that graduated college, I'm all about it. Like, my first job out of college was because of connections that my dad had in the liquor industry. And I'm all about the opportunities and the connections to get you that interview and get you in front of somebody. But from that point on, it's hands off, make the connection, introduce, and then hands off.
C
If he says that his son has hunger, I find it so funny that he says he comes with hunger, but he doesn't eat.
D
What is he doing to himself? That is an internal struggle. You've got to eat. If you want a pizza, just eat the damn pizza.
A
Yeah, that's true. He's not hungry for a job, but he. Get him some food.
D
And there's a couple other things that I. It's when you start hitting the D1 athlete and the 3.77 GPA, these are things that I don't even get on a resume. Like, very few people put their grade point average. If you put your grade point average on, you just don't have that much else on your resume for experience. And you're trying to waive the I'm really smart card, which I get it. But I just don't even see that many GPAs on a resume, let alone I was a D1 athlete to lead the story.
A
Yeah.
C
So what would a winning email have been from this hungry child?
D
A winning email is not child. Yeah. So I think really what it comes down to is if it just came from him. It's one of those things where if that exact message came from the voice of this young man. Like, I was a D1 athlete, so I know what it's like for commitment and drive and energy and passion, and I really put my effort into my school, and I got myself a 3.77 GPA. And I'm really proud of that. And I'm really hungry, but I don't have enough money to eat because. Explain the reason why you're not eating and all the rest. And it can be that simple. But it just hit send from your damn email. It's like from your. From yours. And. And it's one of those things where after I sent it, I didn't feel bad that I sent it. I just wondered if it was right for me to put as much detail into it or if I should have just said, oh, man, I'm really sorry. All the spots are filled and just left it alone.
C
It was generous. We talk about this on the show a lot. What's nice versus kind. It's very kind of you to take the time to educate him as to what would be a better process for success. That took more time than you saying, hey, sorry, I failed.
D
I'VE always been a person that has been a straight shooter and always wants somebody to be a straight shooter with me. And I think it just cuts through a lot of wasted time to figure out whether or not something's going to work as far as a partnership, a friendship, a relationship, any type of situation between two entities. Now I. I get it. You don't want to be like Nicole, you mentioned earlier about being the. Was I the asshole? You don't want to be that in the straight shooting. You want to be compassionate, you want to be kind, you want to be professional, you want to be all of those things. But you can still hit the. The facts of the details, what you're looking for, what your expectations are, and go back and forth and just cut to it. Instead of having this long, drawn out process of, of fluff and building up something that you think you are or what you're trying to do is. And how it's such a perfect fit. It almost came across to me like you're a fool if you don't hire my son. You know, the fool.
C
As a matter of fact, yeah.
A
Did you.
C
Did you get a response from him?
D
I did and it was really brief.
A
Yeah, that doesn't surprise me at all, but.
D
Didn't surprise me at all. I was one of those. Thanks. I don't know how you didn't mean it like that. You literally spelled out everything. You meant it exactly.
A
You definitely meant it exactly.
D
You meant it exactly like that.
A
Stick around. Help Wanted. We'll be right back. Welcome back to Help Wanted. Let's get to it. We haven't, I guess, officially rendered a verdict on this. We set it up as if we were going to tell you whether or not you should have sent this. I'll tell you how I feel. I feel sympathetic to literally everything that you have said. I think that this guy is doing his son absolutely no favors. It is very weird and something we haven't said here, but that is built into this is also, Jeff, if you had said yes to this internship, it would almost be with the understanding that you're going to have to deal with two interns, the son and the dad, who's just going to continue to reach out to you, always going to be involved. Nobody wants that. So, yeah, so I'm sympathetic to everything here. I don't know if I would have made the same decision only because I have written out many versions of responses like this to people where they sent me something and it was inappropriate and it wasn't going to achieve their goals. And I can see how this thing that they're doing with me, they're doing with other people too. Surely, like, this is not the only person that this guy is like, harassing for his son. And. And I know that if I send this note explaining this, I am going to. I'm going to be this sacrificial deliverer of wisdom, which is to say I'm going to tell them something really hard and they're going to hate me for it. And it's going to feel weird and. But it's going to. It's going to make them better because it'll make them think twice before sending out something like this. And I have sent emails like that. And I always just feel like I know I did the right thing in that I shared the right information, but I also feel like a jerk that I did. And then they are going to respond in some way that like, clearly shows that they were wounded. And I just don't want to think about that. And so I have stopped sending notes like that. But that's just me. I say I salute you for saving this guy from future embarrassment. And also, hopefully he just pulls the bulldozer back a little, a lot and just lets his son find his own damn way. So I say the message was great. I don't know that I would have sent it, but I'm glad that you did. That's my verdict. Nicole?
C
I think so. You have what I think is maybe four options. So three options for one path and one option for another path. So two paths, one saying yes. Come on aboard.
A
We have snacks.
D
Eat our snacks. Yeah, it's a perk.
C
Come on down. Option 2 or door 2 is no, but with like three different possibilities there. One is ghost and ignore. Two is lie and say it's filled or some innocuous thing. And three is what you did, which was explain why it's a no. I applaud you for the path you took. It's a very generous one. You took the time to write a thoughtful note back. I'm not sure if I would have done that. I definitely would have chosen one of the three no options. So that's we're in the right sort of bucket or we're in the right path. I think we all agree that giving this kid an internship was a bad idea. I think it was really kind move for you. And whether or not he takes it in the way you intended is not your thing. That's up to him, not you.
D
So I've got to be honest. Both of you said, good job. Glad you sent it. I wouldn't have. I don't know what this means. Like, in my future next situation, should I continue to. To respond in these situations, or should I be like, jeff, you did your one good deed. I would tail off on all the future ones because of just rubbing people the wrong way, I guess, in my thoughts, okay, I sent it. It's done. What do I do now? And hearing both of you say, but I don't do this anymore. I would have just gone a no route. But I'm, like, wondering, how do I handle myself moving forward? Because I'm a straight shooter.
A
Yeah.
D
Should I rein it back a little bit in the future? Or if I've got the time and I actually do find myself in the situation, should I continue to be that person that does explain things out?
C
I think if you have the time and you have the energy and you have the brain space to deal with it. Because it's not just this email. It's like you going back and forth. Or it's not just this dm, it's you going back and forth. Should you have sent it and then thinking about it more? Like, it took a lot of space in your brain, right?
A
Yeah.
D
It takes more than you actually think. When you're writing it out and the whole process of it, it does tend to just hover and hang around, and
A
then you have to anticipate the response. And then every time you open Instagram, you're like, oh, did they respond yet? That's the reason why I don't send these things. This is an interesting philosophical question because what we all agree on, and I would be shocked if anyone listening to this does not agree with here. Like, everybody, Everybody agrees this guy is doing no favors for his son. It's competing. The complete wrong. And I would say everybody agrees that the advice that you gave was good. The thing that's interesting to ponder here is what do we do when we see people make mistakes who we don't know well enough to really have the license to step in and intervene. Right. Like, if Nicole or you, Jeff, were like, we're doing something that I just knew was a terrible mistake. I feel like I know both of you well enough to step in and be, like, gently, you know, like, hey, look, I see what you're trying to do, but I don't think that's the right way to do it. And here's why. Like, we have the relationship that enables that. But then you see people making mistakes in public all the time, and you're like, good luck. To them, you know?
D
Right.
A
And in a way, we would all be better if all of us were catching each other's mistakes. But also, that creates an incredible amount of noise and risk and complicated dynamics in the world. And so we have to make these lines about when do we tell someone else that they're wrong?
C
With my girlfriends, we call it like fixing each other's crowns. We're just like, oh, your crown is a little bit off. We'll have to just fix it for you. And I think that's a loving way to think about it, because it is a loving gesture because you are going to out of your way. You are taking the time you do it out of love and care for this person. So I think, yeah, Jason, reserve it for the people that are your people. And this guy that was the Facebook marketplace, dude, I think no response is a response in that case.
D
Very fair. And that's. It was one of those things where it was just, I. I felt like I was already back and forth invested because I. I had responded to these other things and this and that, and it just dragged me into it, honestly. And I wanted to put an end to it because it didn't seem like there was an end to him.
C
I might change my mind because in this situation, this guy knows where you live or work. Right. So I might have actually tried to troubleshoot that. I'm pretty cautious. It's weird when you have these types of inquiries from people that come to your house for whatever reason and they feel like they want to overstep and have a more personal relationship with you when they know stuff about you. I think responding is probably the right move because you just never know. People are cuckoo crazy.
D
And I think the big thing for me was I was okay. A lot of people say that's something that you could have a conversation if you're face to face with that person, but you don't want to put that in writing. I actually put it in writing because I wanted it very specific to what I meant, what I was saying. I would put that out on social media and let anybody read it type of a thing. I didn't say anything, like, wrong necessarily. It was direct. But I wouldn't be ashamed of somebody reading that. Somebody could say, oh my gosh, Peterson, you should see hear what he said. When I was. I just simply went to him and suggested my son would be a good fit for his company. And oh my gosh, you should have heard what he said. This. I put it in writing. It's. This is what I said. This is what I meant and this is why I said it.
C
Yeah, there's a litmus test within business community or writing sort of work emails of, would I be okay if this was published in the Wall Street Journal? And I would be fine with that if I had written that DM response back.
A
Yeah.
C
I am just particularly sensitive to you about people knowing your personal space and your address and, and stuff like that. So that might add a layer of complexity. But if this was a random person who just reached out to you because they found you on LinkedIn or something like that, which Jason gets a lot, I think that. No responses, a response.
D
Yeah, absolutely.
A
I have started to draft versions of the kind of note that you sent on different subjects. And then I always stop myself and just delete it because I'm like, ah, you know what? It's not worth it. This is a random person in the world. Jeff, I love that you're a straight shooter. I think maybe the way to think about it here is like your straight shooting is a gift. Like, it is a gift to people in that you're willing to tell them difficult things. Right. Like this is Nicole's nice versus kind thing. Right. To be nice is to just say whatever gets you out of the situation
C
or makes they're all filled, exclamation point.
A
Right. That's like a nice thing to protect that person's feelings. The kind thing is to tell people something that is maybe harder to hear. And this is much easier to do in the right friendship circumstances. Nicole and I have talked about, like, ways in which we've done that. Nicole has given me some very direct feedback, for example, on like, my speaking presentation style years ago, which really helped me think through how to evolve that. And that is a. It's a harder thing to do. It takes more time and work and you're taking a risk that someone might take it the wrong way and so on. And so in a way, it's a question of who do you want to invest in? That is a investment of time and energy and is it worth investing in this person who you don't know all that well? And it's just annoying. There's one final thing, Jeff, which we have not covered, which is lingering, which is you have met the son because he came in, what was he like? And does he actually look like a go getter?
D
I was lucky enough to actually not be there that day, but my team in Nashville was there and they called me afterwards. They're like, yeah, that was awkward. So this is why this lingered on and why it draw me to that response. And I think the biggest thing for me is I hope he doesn't think I was trying to tell him how to raise his son. I was more really focused on how he was handling a situation about his son. I'm not trying to change how he raised his son. Clearly he did a great job. He's did great in school.
A
3.77 GPA.
D
Yeah, 3.77. Let's go. And I think the big thing for me is just I hope that he truly, at some point will digest this the right way, and that is okay. Maybe as a parent, it's hard to let the reins go a little bit because you just really want what's best. And if they think they know what's best for their child, they go for it. Nothing's going to stop them. And I feel like I was the one that stopped him. So I hope he takes it for me not telling him how to be a parent, but more how to be a person that's handling totally.
C
But you are not responsible for that. What we care about is you in this. Jeff. And I think Jason's analogy to investment is a really good one. If you think about investing your money in different companies, would you just give him money if he was like, hey, kid has a thing, just be like, fine, take my money. Goodbye. Get out of here. If you think of your time as money, who are you giving it out to? And that investment in somebody else with your time, if that's more valuable than money, would you give them actual money or can you think of it that way? Does that change the equation?
D
That helps a lot. It really does. It's just, can I retrain myself to be that way? Because I've always been very accessible, very approachable, and I think that's sometimes why I run into these situations that kind of end up being more elongated than where I could have cut this shorter, like earlier in the back and forths. But I was trying to be open and maybe, hey, maybe, maybe that's something that if I've got something and he happens to be a fit, I was setting it up more for the son to actually be the one that I started communicating with. Because I still don't to this day really truly know if he would be a perfect fit because I haven't gone back and forth with him. It's all been through his dad.
A
Jeff, thank you for coming and bringing this to us. I feel like we've helped a lot of different kinds of people through this bulldozer, parents who should be less bulldozer straight shooters who should maybe decide when they want to shoot and hold fire. And hopefully this boy who throughout all of this, if his dad can bulldoze something, he needs to bulldoze his way through the side of a Burger King so that this boy can eat something.
D
If this kid. I feel like I should send some, like, gift cards.
A
Yeah.
D
Like the different restaurants. Maybe that's the best way out of it.
A
Right. Just, like, five bucks to Starbucks. Sounds fine.
D
Something.
A
All right, then you will have done your real full duty.
C
And I think what anyone says, I don't want to overstep. They're overstepping.
D
Oh, if you lead with that. Yes. I don't mean to offend you.
C
Yeah.
D
Be ready.
C
You're about ready for the offensive.
D
Yep. Exactly.
A
Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason
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Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our helpline at HelpWantedOneNewsNetwork for the chance to have some of your questions answered on the show. And follow us on Instagram at Money News and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?
A
Oh, I didn't sign up for that.
C
All right, well, talk to you soon.
A
Sam.
In this episode, Jason Feifer (Entrepreneur Editor-in-Chief) and Nicole Lapin (money expert), explore the tricky territory of parental over-involvement in young adults’ careers—specifically, when feedback and support cross the line into “bulldozer” territory. They discuss a real-world case with guest Jeff Peterson, a business owner who confronted an overly persistent parent trying to secure an internship for his son. The episode dives into generational shifts in parenting, professional boundaries, and the challenges of giving hard feedback.
The episode is candid, humorous, and reflective—full of real talk and lighthearted jabs (“he doesn’t eat much anymore!”). The hosts maintain empathy throughout and ground their advice in personal experience. The story serves as a cautionary tale about parental overreach and the value of direct, situationally-appropriate feedback.
Deliver kindness, not just niceness; but make sure you’re investing your energies where they’ll truly make an impact.