“How Do I Say What I Really Think at Work?” With Rebecca Minkoff

Summary

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Podcast Summary: Help Wanted - “How Do I Say What I Really Think at Work?” With Rebecca Minkoff

Date: May 12, 2026
Hosts: Jason Feifer, Nicole Lapin
Guest: Rebecca Minkoff

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Episode Overview

This episode of Help Wanted centers around having honest, direct conversations at work—especially when it comes to giving feedback, setting boundaries, or navigating complicated relationships between bosses, employees, friends, and even family. Fashion designer and entrepreneur Rebecca Minkoff joins Nicole Lapin and Jason Feifer for an open, insightful discussion about communication strategies on the job, staying calm in crises, giving (and receiving) critical feedback, and raising resilient children.

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Key Discussion Points & Insights

1. Staying Calm in a Crisis

Timestamps: 06:14–09:46

• Rebecca Minkoff shares that her reputation in business is for being “really chill” during crises.
  • She recounts an early, stressful runway show where she lost three models last-minute and tried “not being calm” for once, but found that “the freakout didn’t matter.”
  • Quote: [07:22] “I really did. I got angry. And guess what happened? Nothing... the freakout didn’t matter. And it just taught me that in moments of stress… I just have to go into solution mode.”
• Insight: You can’t always change the external problem but you do control your response.
  • Quote, Nicole: [08:16] “But you can change how you react. There’s gonna be problemos no matter what you're doing… but how you react is totally within your control.”
• Rebecca admits she vents (to close friends or her husband) but tries to quickly move from emotion to action:
  • Quote: [09:19] “Sometimes you just need to get it out… sometimes scream.”

2. Balancing “Poker Face” with Honesty

Timestamps: 10:05–11:53

• Rebecca uses communication skills to show calm externally, but acknowledges she feels intense emotions internally.
  • She only lets those emotions show when it's strategic and necessary.
  • Quote: [10:28] “I definitely have the emotions of an angry person. But I know that like, screaming at someone… doesn’t do anything.”
• Exception: Sometimes intensity is necessary to get results (“He apologized. That was about it.” [11:54]).

3. Approaching Hard Conversations at Work

Timestamps: 12:36–19:13

• Feedback Role Play: Nicole and Rebecca simulate a feedback discussion about sloppy copywriting.
• Rebecca’s approach:
  • Be direct but empathetic—clearly state the problem, the expectation, and offer suggestions or help.
  • Quote: [13:19] “Hi—so I reviewed the copy. Thank you so much for sending. I noticed there was, like, a lot of spelling errors. So on the go forward, what I do expect when you come to me is that you’ve done spell check.”
• She prefers metrics over feelings (specific goals, deadlines, and signatures), separating personal feelings from clear business results.
  • Quote: [15:12] “Let’s make this very checklist oriented… Did you hit this goal… in this exact way that’s been written, signed by you and me?”

4. The Best Way to Receive Tough Feedback

Timestamps: 16:48–18:04

• Rebecca values employees who take responsibility and are proactive about problems:
  • Quote: [17:02] “I’d like to hear full responsibility… And here’s my solution. You gave me 12 articles. I can only really do 10, and I can do 10 at a good job.”
• She appreciates honesty and self-awareness over excuses.

5. Letting Employees Go With Dignity

Timestamps: 18:04–21:43

• Standard HR advice is to be brief (“I’m sorry, it’s not going to work out”), but Rebecca prefers transparency and recognition of the employee’s efforts.
  • Quote: [18:28] “No, there’s no burying. You’re sitting down, you’re like, I’m sorry, it’s not going to work out. Here’s your severance… But I cannot do that. I just feel like as the recipient, I would want to know why.”
• Even with underperforming or unfitting employees, she tries to support them post-exit: recommendations, connecting them to opportunities, and keeping in touch.

6. The Tension Between Being a Boss and a Friend

Timestamps: 21:43–24:41

• Rebecca acknowledges the blurred lines when close working relationships become friendships, and admits it’s challenging to balance being supportive with upholding performance standards.
  • Quote: [22:33] “It’s really hard, especially if they're your friend… but how do you have that not happen?”
• She tries not to hire friends, but inevitably some colleagues become close. This can mean more flexibility for direct reports (e.g., work-from-home leniency for social media staff).

7. Working with Family

Timestamps: 24:59–26:55

• Rebecca describes the complexities of 17 years working with her brother—mixing personal and professional dynamics led to communication issues they ultimately needed a business coach to resolve.
  • Quote: [25:59] “A professional, like, business coach… would sit us down and be like, we’re airing it all out.”

8. Setting Boundaries and Handling Contracts

Timestamps: 27:00–30:14

• Rebecca advocates structuring freelancer contracts as monthly payments (after deliverables are reviewed), and insists on documentation and clear expectations in writing.
  • Quote: [27:24] “No, I pay… at the end of every month once I see the work is done.”
• She’s direct when work doesn’t meet standards, regardless of someone’s assumptions about her financial standing:
  • Quote: [29:29] “Everything has a budget… If I’m saying in six months this person’s going to make my investment worth it, but I’m not getting the return, then I don’t have the money.”

9. Privilege, Scrappiness, and Team Selection

Timestamps: 32:41–36:17

• Both hosts discuss stereotypes about hiring “rich kids” versus “scrappy” team members.
• Rebecca says you can’t always know backgrounds, but looks for a willingness to work hard.
  • Quote: [33:17] “There’s no way for me to know if they’re rich or not… I really think it’s in their upbringing.”
• She shares a story about an entitled employee asking for a raise far above her experience, reflecting on differences in expectations.

10. Parenting, Money, and Avoiding Entitlement

Timestamps: 36:17–42:12

• Rebecca is mindful not to raise entitled kids; she frequently asks them how they plan to earn money for things they want and encourages entrepreneurial thinking.
  • Quote: [36:22] “I am so conscious of it… I force myself to think about my mom, and I say no all the time. How you gonna earn it?”
• The hosts discuss generational wealth, responsible giving, and how to balance providing for children with teaching resilience.
  • Quote: [38:51] “It’s enough to keep you hungry.”
• Both guests reflect on spending to enjoy life now versus saving everything for their children, and the value of creating experiences and instilling independence.

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Notable Quotes & Memorable Moments

• “The freakout didn’t matter. And it just taught me that in moments of stress… I just have to go into solution mode.”
  —Rebecca Minkoff [07:22]
• “But you can change how you react… how you react is totally within your control.”
  —Nicole Lapin [08:16]
• “I’d actually like them to come to the meeting and be like, ‘I’m overwhelmed with the work and here’s why I’m messing up.’”
  —Rebecca Minkoff [17:14]
• “Their livelihood is making your dream come true, so like, that’s the least I could do.”
  —Rebecca Minkoff [21:34]
• “If I have a budget for a project… that is the budget. And if I’m not getting the return, then I don’t have the money.”
  —Rebecca Minkoff [29:29]
• “How you gonna earn it?”
  —Rebecca Minkoff [36:22]
• “I’m not ever gonna, from this point on… be working so hard for my children to have some nest egg. Like, I want it to be for our family to enjoy.”
  —Rebecca Minkoff [42:12]

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Timestamps for Important Segments

• Staying Calm, Venting, and Solution Mode: 06:14–09:46
• Giving Feedback—Role Play Example: 12:36–14:20
• Handling Underperformance/Performance Plans: 14:25–17:47
• Letting People Go—What to Say, How to Help: 18:04–21:43
• Friendship vs. Boss Boundaries: 21:43–24:41
• Working with Family: 24:59–26:55
• Freelance Contracts & Boundaries: 27:00–30:14
• Privilege, Scrappiness, and Job Expectations: 32:41–36:17
• Parenting and Money Values: 36:17–42:12

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Tone & Style Notes

The conversation is warm, candid, and practical, laced with humor and the unmistakable camaraderie between Nicole and Rebecca. Rebecca’s direct, relatable communication style shines through, especially in her role play scenarios and parenting philosophies, making her advice accessible and actionable for listeners at any stage of their careers or lives.

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This summary omits advertisements, intros, and outros, focusing solely on the heart of the conversation about workplace communication, leadership, and personal values.

Transcript

[Jason Pfeiffer]

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[Nicole Lapin]

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[Rebecca Minkoff]

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[Help Wanted Host/Producer]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of

[Nicole Lapin]

Entrepreneur Magazine, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[Help Wanted Host/Producer]

And on Thursdays, I give you one way to improve your work and build a career or company you love.

[Nicole Lapin]

And it starts now. Rebecca Minkoff welcome to Help Wanted. You know you were on the first iteration of this show actually and it was hush money.

[Rebecca Minkoff]

Oh wow. Back in the day, was this with Jason?

[Jason Pfeiffer]

Yeah.

[Rebecca Minkoff]

Oh, my God. That's where we met.

[Nicole Lapin]

Well, so we met, like, over the years at different panels and whatnot. But that was when we became homies.

[Rebecca Minkoff]

Yeah. We shared a cab ride.

[Nicole Lapin]

A cab ride? Yeah. That was seminal to, like, the rest of the stuff we did with books and podcasts and everything else.

[Rebecca Minkoff]

That's right. That's right. If it wasn't for you, I wouldn't have had my book.

[Nicole Lapin]

Oh, my gosh. I don't know about that.

[Rebecca Minkoff]

I 100% know about that. You reframed it for me. You got me the agent. You helped me figure it out. You sent me a list of people to call and sell my books to.

[Nicole Lapin]

You know, like, there's a lot of pie out there for everybody to have a piece of, and you deserve that piece of pie.

[Rebecca Minkoff]

Thank you.

[Nicole Lapin]

More than anyone. I just. Just love hanging out with you. I love talking with you. I, like, personally, professionally, I'm just so in awe of how. Also, the. The thing I've heard about you in business.

[Rebecca Minkoff]

Oh, I love the herd.

[Nicole Lapin]

Question is that in a crisis, you are really chill.

[Rebecca Minkoff]

I'm really chill.

[Nicole Lapin]

How the hell are you really chill?

[Rebecca Minkoff]

Because to me, my one and only experiment with not being chill didn't do anything like, you know, height of stress, Runway show. Like, all that stuff seems so small to me now, but when you're in it. And the way it worked with models is that you negotiated, you got a rate, they showed up, you fitted them, they did your show. But if they got cast by someone bigger and more powerful with more money, they could be like, no, we want her to have the exclusive. So in the morning of my show, three of my girls got booked exclusives. And so they couldn't. So I get the call from the agent. He's, like, very casual. You know, these girls won't be coming. They just got booked. Sorry. And I'm like, sorry. There's three looks that have been actually measured to their body, hips and bodies. And, like, I can't just replace anyone. He's like, well, I'm gonna send you some girls, and it's gonna be fine. And I was like. I got off the phone, I was like, here's where I'm gonna try not being calm. And I yell and I scream.

[Nicole Lapin]

I can't imagine you.

[Rebecca Minkoff]

I really did. I really got angry. And guess what happened? Nothing. He didn't give a.

[Nicole Lapin]

The same alternate girls came, huh?

[Rebecca Minkoff]

The same shitty girls came that didn't fit in the shoe size. And if you Go back to watch the footage. Like, her foot sliding out of the shoe the whole time. But, like, the freakout didn't matter. And it just taught me that in moments of stress, it's like, to me, my internal picture is like the Rolodex, the old school Rolodex, the one that only our generation knows remembers. Or you're just like, solution, solution, solution. You know, like, I was doing that on the plane this morning. I have. I'm throwing a family event for 80 people in a house that has no plumbing. And I was like, what am I gonna do? So I just. Rather than freak out, I'm like, you know, could I make box lunches and go to a playground? I don't know where I'm gonna go with these people. But it's just like, I just have to go into solution mode.

[Nicole Lapin]

Because you can't really change the base thing that happens.

[Rebecca Minkoff]

Right.

[Nicole Lapin]

But you can change how you react. So it's like the. The first. There's gonna be problemos no matter what you're doing, and especially when you're doing big things.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

So that you can't fix or you can't stop or you can't change. Like, it's inevitable, but how you react is totally within your control.

[Rebecca Minkoff]

100. And I think at the pace in which went wrong in my business, if I would have reacted every time, like, my cortisol levels would have been like, through the roof. You know what I mean? It just. Every day was something new.

[Nicole Lapin]

Yeah.

[Rebecca Minkoff]

And so, like, are you gonna just freak out every time? You'd never get anything done.

[Nicole Lapin]

I feel like my heart and my armpits sweat and like, you know, it's just.

[Rebecca Minkoff]

That happens. It's just not outward. Like, I might. Like yesterday something happened. I was so angry, and I, like, had my moment of venting, and then I was like, I gotta get on with my day.

[Nicole Lapin]

So what was that moment of venting? Like, who did you vent to? Or what did that look like? How did you get it out of your body? Because I think it is important to get that ick out.

[Rebecca Minkoff]

Yes. I was on the call with my. One of my best friends and colleagues, Mary, and I just yelled to her, not at her, about the situation. And then she was like, I hear you. I see you, and have a great rest of your day. Sometimes you just need to get it out. Like, sometimes scream.

[Nicole Lapin]

I love.

[Rebecca Minkoff]

Yeah. Or even like, my husband will come home, who's like, I just want to vent. I don't expect your advice or opinions or solutions. I just have to get it out.

[Nicole Lapin]

Well, I think a really important question in my almost two years of marriage, let me tell you, is asking, do you want comfort or advice?

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

And I think that for friends, for colleagues, anything. Because sometimes, like, you do want advice, and you want to figure out how to solve the problem, and sometimes you just need to, like.

[Rebecca Minkoff]

I know, but that really changed our marriage once I realized that, because he would. I would be, like, in solution mode, and he would say, no, no, no. And I was like, then why are you talking to me about this? And be like. So it wasn't until he very clearly was like, I just need you to listen, that I was like, oh, that's so much easier.

[Nicole Lapin]

Okay, so let me get this straight. So inside, you're still, like, fuming when crazy stuff happens?

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

Okay. But on the outside, your poker face. So how do you do that?

[Rebecca Minkoff]

That's a really good question. I've taken a lot of communication courses.

[Nicole Lapin]

You are a master class in communication.

[Rebecca Minkoff]

Well, I just think, like, again, I don't know that I let myself physically go nuts, but if I'm angry, like, I am definitely have the emotions of an angry person. But I know that, like, screaming at someone unless it's really warranted doesn't do anything, you know? And so I try to be just calm on the outside so that I can get to where I need to go or what I need to have accomplished. But I definitely get angry. Don't get me wrong.

[Nicole Lapin]

I just very contain it.

[Rebecca Minkoff]

I contain it, and then when I use it when I need to, I mean, we had a situation where it was like, I knew I was getting Covid for the first time. My business was under a lot of stress. Someone relating to the business was gonna call a loan that was gonna really mess us up, and they were relentless. And I went. And I was also with the kids, and Gavin was like, on two weeks a way of work, and I went outside on the phone, and I was like, do you know who you're messing with? I screamed so loud. I was like, all the neighbors can hear. But I just. I. That was like, a moment where I could not contain it because it was so. So many things were happening at once that it was just like, I lost it. And that did work.

[Nicole Lapin]

Oh, yeah.

[Rebecca Minkoff]

He apologized. That was about it. He apologized.

[Nicole Lapin]

Okay, so we're one and one. One time it didn't work. One time it did. But generally speaking, like, the word on the street, the word on the business street is that people come to you with crisis, and you are chill and it's like a nice environment to have hard conversations, I think. So that's what you foster. That's your rep. Yeah, that's a great one.

[Rebecca Minkoff]

I'm gl. I want to know who on the street you've been talking to, but. Okay.

[Nicole Lapin]

Like Aliza, for instance, or, you know, people that have worked with you. Like, everybody really loves working with you.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

For you, I've got good vibes.

[Rebecca Minkoff]

I try and keep the vibes good.

[Nicole Lapin]

But also, I mean, it's not just vibes. Like, you can't run the business operation that you do just on vibes, for sure. So when we've, in our work together have had hard conversations, it has been truly amazing to see how you approach it. Because let's say, let's do like a roleplay situation. Let's say you hire a copywriter and there are a ton of mistakes in that copy. And you need to write your newsletter, your social posts, whatever. They're not doing a good job.

[Rebecca Minkoff]

Right.

[Nicole Lapin]

How do you approach that situation?

[Rebecca Minkoff]

I think first I will call it out gently. Like, hey, you know, just.

[Nicole Lapin]

I'm the copy editor.

[Rebecca Minkoff]

Okay. Okay. We're really.

[Nicole Lapin]

Hey, Rebecca.

[Rebecca Minkoff]

Hi. So I reviewed the copy. Thank you so much for sending. I noticed there was, like, a lot of spelling errors. So on the go forward, what I do expect when you come to me is that you've done spell check. You know, AI is also really good at it now. So you could just run the whole thing through AI and also fix grammatical errors. But let me know that you got that and we can do that on the go forward.

[Nicole Lapin]

Yeah. And I just feel like I've had so many deliverables for you that I can't keep up with it. And so I'm just doing the best I can.

[Rebecca Minkoff]

I totally hear you. But I think it's table stakes as a copywriter. You know, I think one of the things people look for as, like, just like being hired is grammar and spelling. So, like, I know you have a lot of deliverables if we need to relook at Scope or, like, what you're dealing with. Like, you could give me a list of everything and I can see where I can help you. But we have to fix the spelling in the grammar. I'm going to not be able to keep a straight face because I'd be like, you dumb bitch, get the fuck out of the room.

[Nicole Lapin]

Am I going to be fired? Do people ask you that?

[Rebecca Minkoff]

I had someone ask me that today.

[Nicole Lapin]

Wow.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

Because of a conversation that was similar to what we just

[Rebecca Minkoff]

this Conversation was trying to match talent with ambition. And this was a conversation and I'm going to keep it real general, where the person has such great talent for certain areas but has ambitions for more and that talent hasn't matched the ambition yet. And so you're trying to have a positive conversation of how incredible they are at certain things. The things they really want, they can't do yet. Mm.

[Nicole Lapin]

And so what's the way to approach somebody like that? Or do you believe in putting someone on a performance plan, which typically means, like, they're going to get fired.

[Rebecca Minkoff]

Right.

[Nicole Lapin]

But a positive one.

[Rebecca Minkoff]

I think what I tried to do, and I'm not directly in day to day working with them, but I. What I tried to do in the beginning was here's everything you're awesome at, let's build a role around that. And then these are the things that you need to have hit in a certain amount of time. And we're going to make this very checklist oriented. That would mean you get to go to the next level. And then let's look at it in six months and like, did you hit this metric? Did you hit this goal? And it's not touchy feely, it's not, I feel like you're doing a good job. Like, did this get done in this exact way that's been written, signed by you and me that we agreed was how it should be? And, and we've had many of those conversations and then in one of them, I was just very transparent. I'm like, what you want to do, you can't do yet. And what you're really good at is where I need you to be.

[Nicole Lapin]

I think that putting metrics on hard conversations is also really important. Like if you're doing OKRs, objectives and key results, which, you know, some people in business like, or just basic KPIs too.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

It takes a lot of that emotion out of it because you're like, these are numbers.

[Rebecca Minkoff]

Right? And someone can be like, but I'm working so hard and I'm stressed out and I'm doing so much. You're like, if it doesn't add up to the business expanding us, making more money, then guess what? Like, your effort is being. It's like when little kids run, there's so much energy not going forward, it's like going up and sideways.

[Nicole Lapin]

Oh, I, I know this firsthand.

[Rebecca Minkoff]

So you're like, if the worker's sweating because they're running up and sideways, it's like, good job. But you didn't get to the. You didn't get to the goal. That's right. But that's what I think about a lot.

[Nicole Lapin]

So what's the best way to do, you think, to respond to a hard conversation? So if I'm the copy editor and I'm hearing this hard feedback.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

What would you like to hear from that person?

[Rebecca Minkoff]

I'd like to hear full responsibility. I'd like to hear like, I totally hear you. And yeah, it is table stakes. And I'm sorry. You know, I'd actually like them to come to the meeting and be like, I'm overwhelmed with the work and here's

[Nicole Lapin]

why I'm messing up the self awareness that they're doing.

[Rebecca Minkoff]

Yeah. And here's my solution. You gave me 12 articles. I can only really do 10, you know, and I can do 10 at a good job. But I've had employees come to me. Like, my former social media would be like, I'm gonna give you crappy work if I have to do 14 posts a week. But we can do really good, thorough work with better results at 7. And here, let me show you. And I was like, I'm on the journey. Like, it wasn't to me about how much can we post as a company anymore. It was like, let's do great work.

[Nicole Lapin]

And if that doesn't happen. So you have sort of a hard conversation, you set up some deliverables, you set up some KPIs or whatever it is. And if that's not going on and you need to let somebody go.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

How do you approach that? I mean, sure, you've had that conversation many times. It's never easy.

[Rebecca Minkoff]

Here's the problem. Any lawyer, and I think even someone on the podcast, I want to say it was Emma Greed, but it might have been someone else, is like, you literally sit down, you're like, I'm sorry, it's not going to work out. Thank you so much. And then you just zip your lips. Because with like legal and HR and all the stuff, you're just supposed to like, say the minimum, but also say it up front.

[Nicole Lapin]

Don't bury it.

[Rebecca Minkoff]

No, there's no bearing. You're sitting down, you're like, I'm sorry, it's not going to work out. Here's your severance, here's your blah. Thank you so much. I cannot do that. I can't do it. I just feel like it's the. Like, as a recipient, I would want to know why and I'd want to know that, like, my hard work, if I did have hard work, didn't Go unnoticed. We had to let someone go. That just wasn't a fit. It was a fit for someone else, just not us, like, what was being done. And I wanted her to know it wasn't necessarily a bad performance. It just didn't. It wasn't what the brand needed at the time. And I really wanted her to know that so that she didn't walk away thinking she failed. And I was told, just sit down and say, it's not going to work out.

[Nicole Lapin]

And what did you do instead?

[Rebecca Minkoff]

I just said, it's. It sounded like a breakup. It's not you, it's me. This isn't right. And it was hard, and the outcome was still shitty. She was still upset. I felt terrible. It, like, never, you know, the only time you feel good is if, like, they sucked from the beginning, you know, or they were evil or stole from you. But even a guy that stole from us, he had a whole scheme with, like, getting customers to get refunds, but the refunds would go into his PayPal account. Yeah. Then our someone in the finance department at the time was about to catch on to it. So this guy accused this guy of sexual harassment. So we let go of this guy being like, we. We don't want to be part of this. Let go of the guy that was about to discover the thief, okay? Then we find out that he's a thief. We let him go. And I see him on the street, and I'm in a car, and I was like, you stole from me. I can't believe you did this to me. Like, how dare you? And you should pay us back. He's like, go yourself. So I was like, well, that doesn't work either. What?

[Nicole Lapin]

Gangster. Gangster moves.

[Rebecca Minkoff]

This was a long time ago, by the way. This is like. So today I probably wouldn't be in a car yelling at someone who, like, stole from me, but you never know.

[Nicole Lapin]

Well, I hope that doesn't happen again. But those are the egregious examples, right? Where you're not giving somebody a reference. Like in the example of the woman who, you know was good but just not good for you, do you say, I'll give you a reference or a helper.

[Rebecca Minkoff]

I personally helped her. I don't think she wanted me to be in touch with her, but I personally probably reached out to, like, 15 people with her resume. And I text her every time I did that. And then I said to her, like, this person's interested. They're gonna reach out. Like, I had three to five people reach out to her. And then I tried to hire freelance her for other things. And I could see how she's like, please, woman, stop contacting me. But I wanted her to know that I'm like, I really want to help you. And I do that anytime I have to let go of someone. If it is like, again, they are well intended people, not the PayPal thief. I will write them a letter. I'll be their, you know, I'll go on their LinkedIn, like, whatever it is I can do. And you know, we had to do layoffs last year and that was horrible. Like five people and I, every single one of them, I was like, what do you need? You know, and also in six months, if you need that, I'm still here. Because I just feel it's like they're people, you know, that their livelihood is making your dream come true. So like, that's the least I could do.

[Nicole Lapin]

Where do you draw the line though, between being too friendly and still being a boss? Because if you're staying in touch with them for months and months and you're like up in there LinkedIn and trying to help them and, and maybe they are so, so appreciative. But maybe they're also like, this is. I don't even need that.

[Rebecca Minkoff]

I'm not upping them. I'm just like, I'm here. Like, here's your letter of recommendation and I'll be your letter of reference. If you need, like, let me know. Like, I'm not like sitting on their LinkedIn every day. Like, hey, you're doing great, star. Like, I'm not like, weird, creepy lady,

[Nicole Lapin]

but where do you think the boundary is between being overly friendly and holding a line? Well, at the end of the day, you know, this was a job and you're tied to revenue and performance and

[Rebecca Minkoff]

you didn't do that job. Yeah, I think it's really hard, especially if they're your friend. And again, they're really tough conversations I've had to have because I'm learning not to make as good of friends as people I work with. But it does, it's. How do you have that not happen? Like, I work so closely with the girl that oversees our social media. Like, how is she not my friend? You know? And so it also is hard when you do have those tough conversations. Like I have, like with Mary. We work together, we love each other, and then we have hard conversations and then I'm also, huh, no, we cannot. No, we cannot. But like, I'm going to her wedding. Like, like she's part of my life and sometimes she And I have very strong, differing opinions. And it's just. It's tough.

[Nicole Lapin]

So you do hire friends and you become friends with people you hire?

[Rebecca Minkoff]

I do not hire my friends. No, no.

[Nicole Lapin]

So they just become your friends?

[Rebecca Minkoff]

Some of them have become my friends.

[Nicole Lapin]

Closely.

[Rebecca Minkoff]

Yeah. Together, yeah. Usually people are like, rebecca has favorites. No, it's the people I'm working closely with. They're not my favorites. I just happen to talk to them every day. So it's usually someone in PR and someone in Social.

[Nicole Lapin]

And so do you. When you're more friendly, do you give them more of a pass? Like, are those conversations different or do you. Are you harsher on them? Because, you know, sometimes you let your real self show to people who know you the best?

[Rebecca Minkoff]

I think it's a bit of both. I think. I think if I, like, I guess a pass is if there's rules in the office, let's just say, that are like, you have to be here between this and this time. And like, if you're working, if you're sick, but you say you're working from home, you're sick. These are not my rules. These are just the company's rules. I don't care if you work from home when you're sick, work from home when you're sick. But that's a pass to people that are my direct reports than other people who might not have that luxury. If that's an example.

[Nicole Lapin]

Okay.

[Rebecca Minkoff]

Or I know you're working nights and weekends because Social doesn't sleep. So, like, if you're gonna come in late because you wanted to, like, I don't know, sleep in one morning, I don't care, you know, because I know that at nine o' clock at night, the last thing you want to be doing is responding to comments on dms.

[Nicole Lapin]

All right, what if. Let's do a different roleplay situation then, because you passed on conversations with Mary. Suggestion. Not just Mary, but anybody who is a friend of yours that you work with or, you know, people that are working with family members or friends find those conversations to be trickier.

[Rebecca Minkoff]

But the conversations with family is really hard. I can't role play that with you, but I can tell you that me and my brother working together for 17 years was, like, great and hard at the same time because I think he held his feelings in more. And I would feel like sometimes his frustrations would come out in ways that I didn't, like, imagine. Or he would. He would assume certain things about me, and then I wouldn't realize that he thought maybe I was out Lollygagging when I was meeting with an editor or whatever it was and, and vice versa. Like when he would make a financial mistake and like I got pissed. I didn't have the tools to even communicate about what that was. So I think on both of our ends we, we had to have like a business coach truly help us communicate to each other. And until we learned that from an outside person supporting us to do that, it was really hard.

[Nicole Lapin]

Like a professional therapist.

[Rebecca Minkoff]

A professional like business coach. Yeah. Who would sit us down and be like, we're airing it all out. And when you guys say this incorrectly and start the other person going crazy, I'm going to translate what they really mean in a nice way.

[Nicole Lapin]

Obama translator. We don't need that. Okay, so gun to your head, would you work with family member again or would you tell other people to work with a family member?

[Rebecca Minkoff]

Oh my gosh, it's so different. I know so many successful founders that have worked with their family. If I were to ever get into business with my family again, there'd be like a, like floor to ceiling list of rules, you know, and expectations and there would probably be instead of quarterly business coaching, there would be like monthly business coaching. Like I would just make sure. But it would only be if the two of us came together because we had some great idea or whatever. I think now we're just enjoying just being brother and sister.

[Nicole Lapin]

What if you are trying to get a refund from somebody who did from att?

[Rebecca Minkoff]

Sure, let's go there.

[Nicole Lapin]

They did. If you hired them on a contract and the work wasn't up to par and you want a refund.

[Rebecca Minkoff]

Did I pay them up front?

[Nicole Lapin]

Well, that's a good question. Should you for those types of terms. So let's say you have, you know, a six month contract with a freelancer and ideally would you pay up front?

[Rebecca Minkoff]

No, not. No, I pay. If it's a six month contract, I'd be like, I pay you at the end of every month once I see the work is done. And then by all means, if I'm seeing red flags on the work, there's going to be conversations that are documented. Because I think then if it isn't good work or it's not written in the contract, the expectation level of the work, you can be like, you didn't meet this expectation, therefore the contract is null and void. Like you don't just get to have a contract with someone and have them do shitty work. It would be like, I would make sure of that because I think I've been in that situation before. Okay.

[Nicole Lapin]

Hi, Rebecca.

[Rebecca Minkoff]

Hi. Are you my six month freelancer?

[Nicole Lapin]

Yes.

[Rebecca Minkoff]

Okay, well, what month of the contract are we in?

[Nicole Lapin]

We're on month three.

[Rebecca Minkoff]

Okay.

[Nicole Lapin]

And I've been, you know, doing the best I can to deliver all the material that you need. And how do you think it's going?

[Rebecca Minkoff]

Have, have we had any touch bases? Have I given you any warnings?

[Nicole Lapin]

Yeah, I saw a couple of your emails and you flagged some errors that the team promptly fixed.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

How are you feeling now? Are you happy with the services?

[Rebecca Minkoff]

So we're halfway through and I think that the things that I'm flagging, I shouldn't have to based on the scope of work and like why I h hired you. So in the next month, I do have to see a complete change and no errors. And you know, I came to you because you clearly stated that you could do A, B, C and D for me. I took a risk. It was a big investment, more than I was ever used to. I need to see it turn around or otherwise I'm going to have to cancel the contract because I can't afford it. Like, I came on thinking this was going to be the solution to our E Commerce traffic, you know, and if our E. Com isn't growing the way it should and the way you talked about, then it doesn't matter how hard you're trying.

[Nicole Lapin]

So you use an interesting phrase there. I can't afford it. Yeah, but if somebody looks at you and they're like, oh, you're Rebecca Minkoff, of course you can afford it. What do you mean you can afford it?

[Rebecca Minkoff]

Right.

[Nicole Lapin]

You still explain to me how you use that term.

[Rebecca Minkoff]

Well, everything has a budget, Right. Just because someone says they can't afford something. Listen, you have no idea financially what's going on in someone's life, a, B, it's not a faucet. Right. So if I have a budget for a project, let's just say an overhaul of our E. Commerce site, that is the budget. And if I'm saying in six months this person's going to make my investment of X or Y worth it, but I'm not getting the return, then I don't have the money. And I think people, they could say who they think I am or how much I have or what the Internet estimates my net worth to be, but no one knows what's going on behind the scenes. It's not a matter of like, oh, let me look at your bank account and decide if you could afford it or not. It's truly like, no, we're all running a business.

[Nicole Lapin]

Yeah.

[Rebecca Minkoff]

And so the business has metrics and goals and it has budgets attached to it. And that's what you should be judging on. Not like, oh, Rebecca Minkoff has so much money.

[Nicole Lapin]

So when you say you can't afford it, it's not in budget. We experience this a lot because, hello, we're Money News Network and there's a faucet there.

[Rebecca Minkoff]

Just endless.

[Nicole Lapin]

Yeah, it's just, of course, it's, look at the money roll that we have. We might as well just use that.

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

Or, you know, like I wrote a book called Rich Bitch. And so people just assume that there's endless money and that what I can afford is not along the same lines as what, you know, you would have in mind for other people.

[Rebecca Minkoff]

Right.

[Nicole Lapin]

And so how. So I'm really glad to hear you use the phrase I can't afford that. Even when you're having conversations with people who are convinced that you can.

[Rebecca Minkoff]

Right. I think that there are probably people that you could say that to that definitely could afford it. You know, like there's other, there's other people that probably you see what they're investing into an area and you're like, oh, they can afford that because. But that's when you're in the industry and you know how things are monetized and you know that, like, you can't make that investment because you know, that wasn't monetized yet. But I think in, in my case, there's a budget and it has to be held to because I'm running a business.

[Nicole Lapin]

That's right. Yeah. I mean, I remember having a conversation for a book event with Walmart and they were like, oh, we don't have a budget.

[Jason Pfeiffer]

Walmart.

[Nicole Lapin]

What do you mean you don't have a budget?

[Rebecca Minkoff]

Yeah.

[Nicole Lapin]

And so sure, they don't have a budget for that specific thing. I respect that, you know, as similar sized businesses. Absolutely respect that. But you know, some people that you've, I'm sure worked with that come from really rich families that say, I can't afford that. Or I remember like a big family office reached out to do a speaking thing with a bank and I was like, great, what's the budget? And they're like, oh, it's not, we don't have a budget. And I'm like, this is like, actually kind of offensive.

[Rebecca Minkoff]

Yeah, it's really offensive when people say that and you know that there's funds behind it. And I think that is annoying. But I don't know, like, or even I questioned, I was Asked to speak an event with two other people. And I was just like, I'm wondering if we all got paid the same. And I have a big suspicion that we didn't.

[Nicole Lapin]

Do you ask?

[Rebecca Minkoff]

No, because I didn't. I didn't wanna. It was like a new relationship. And I didn't want to be like, are you paying us all equally? Like, I just didn't want to be that person at that moment.

[Nicole Lapin]

Well, I love the content that you've been putting out. Hard. Stop. But also just talking about your scrappy upbringing and what you had to do and where you slept to make happen in your life, and I feel so similar to that in a lot of ways. And I wonder when you're hiring people and you probably get recommendations from friends who want you to hire their kids or whatever, and you know that they have a lot of money, do you hire rich kids?

[Rebecca Minkoff]

There's no way for me to know if they're rich or not. You're looking at me like there's a way I would know. I've hired rich and scrappy, and I really think it's in their upbringing. Like, if, if, if, if we have hired a rich kid, usually the ones that I gravitate towards are still the ones that are really willing to work hard. And I think you can see that in how they shake their hand, how they look at you and straight across the board or just like, what are your boundaries? You know, there's certain questions I think you can ask in an interview, scrappy or not, or, like, brought up with money or not, that really just tell you, like, are they going to get their skin in the game and, like, do this, or are they just, like, leaving at 4 every day? And I think I look for those signals not. Not how much money they have because you just. It's so different. It, like, you know, I had a girl, this was again, so long ago, she had a great deep Long island accent, and she was like, rebecca, I need a raise. And I was like, okay, but you haven't been here for very long. Like, what are you looking to get your rate, like, from where you're at to watch? Like, well, the apartment I want is like $5,000 and like, I just need a raise so I can pay that. And I was like, I won't say her name. I was like, my rent is $5,000 and I've been doing this for like a decade. And I'm also like 15 years older than you. So, like, you got to adjust your expectations around this because of what you think you want to, like, you just are like, six months into the gig, she was like, right, right. But, like, could I get a raise, like, later? And she. She ended up working really hard, but she was also brought up with money. And so her level of comfort that she was trying to attain for herself and her personal life was just outsized to the fashion week job or the fashion industry job.

[Nicole Lapin]

I had no idea that you also had such sweet skills with the accent

[Rebecca Minkoff]

and dialect,

[Nicole Lapin]

ladies and gentlemen. What can she not do?

[Rebecca Minkoff]

Well, I can't do all accents. I think I could do a really good Scottish accent. And my husband is like, you fucking suck. O. It's not Irish. It's like, somewhere in the middle, I

[Nicole Lapin]

will see our next role play. Must just be a Scottish role play. I don't know why, but that feels right. Yeah, I think it can cut both ways. I think, you know, people who are brought up with a lot of privilege, the. The default answer, and I hate cliches, is that they're not going to work hard because they have, you know, this backup plan, which, you know, I didn't have. And so, like, there was no option but to succeed. Like, there was no couch to go back to. There was no plan B. And so I think. Think that the default when you have somebody from a really rich family is that they're not going to work, but sometimes they just have such a chip on their shoulder to make it on their own, too, that the fire is there. And so you don't really know.

[Rebecca Minkoff]

You don't know. And I think it's like, how. How much of what they taught and saw was like, if I work hard, I get this or just handed to you. And I think it's the ones that just. Everything is handed to them that are the ones that just. It just doesn't quite work out.

[Nicole Lapin]

How do you think about not raising bratty kids?

[Rebecca Minkoff]

I am so conscious of it, and I force myself to think about my mom, and I say no all the time. How you gonna earn it? Like, the. Like, when I say yes, they're shocked, you know, to like, mommy, will you just buy me this thing? And I'll. Sometimes I say yes. And they're. And they're like, she didn't say how you can earn it, because that's my thing. How you can earn it. Or my daughter's like, can we go to the mall? I'm like, you have how much money in your wallet right now? How much? $5. No, that's not enough to go to the mall with. You know, I'm like, do you want to. And then I'm like, do you want to do some things around the house? Do you want to have a business? And she gets the bug. Like, she has a. A stand at a little market. And we, like, this weekend it's going to be flowers, but last weekend it was cookies. So, like, she's getting that. If she wants things, she has to. Or with my sons, you know, we're Jewish, so over the holidays, there was a need to, like, light up the neighborhood with lanterns. I was like, you guys want to make some money? People are paying a lot, and I'll help you. And they're like, yeah, let's do this. And so we lit the whole neighborhood up, and that was their money. And so I just. I say no so often because they already have a level above what I had just by the fact that my husband and I want to enjoy, like, nice things and vacations. But then it stops there, and then it's. It's about like, well, what are you going to earn and how you going to pay for it?

[Nicole Lapin]

I think a lot of people who have made their own success think about that. And like, okay, well, we struggled. And so how do they struggle responsibly?

[Rebecca Minkoff]

I have friends, though, that don't struggle responsibly. Like, they. They scrappy. Made their business really successful. And I watch them just like, here, have it all. And I. It, like, it gives me, like, a visceral reaction. Like, I'm just like, I don't think that's right. I don't think you should do that. It's a conversation I've been having with my family of, like, how much do you want to give someone at a certain age? And even my mom and I were talking and, you know, if they're. If they decide to give our kids anything, she's like, I think 45 seems like a good age to give them more than at 18. And I was like, I fully agree. Because the money that I got from my grandmother at 25, which was not a lot, like, thank God. No, I think I got it at 30. Thank God I got it at 30 and not at 18, because it would have been gone. Whereas at 30, I was like, let me just put this in the stock market and just keep it there and see what happens. So I think that she and I have been like, how do we want these kids to. Like, we want you to work really hard and know that at 45, you get something that's helpful, but it's not the solution. It's not Like I retire often in the sunset, so it's enough to keep you hungry.

[Nicole Lapin]

And when do you have that conversation with them? So like tying this whole beautiful conversation up in a perfect bow, having hard conversations happen in, in different areas obviously of your life, I'm thinking how do I tell my daughter or when do I tell my daughter or do I tell my daughter that there's like a magical pot of money for her?

[Rebecca Minkoff]

Right.

[Nicole Lapin]

How do you message that?

[Rebecca Minkoff]

Well, I don't know that $3 million is a magical pot of money for them. Especially if you fast forward, let's say I die, let's hope I die at like 95. So like in 50 more years, $3 million. Because it'd be like a hundred grand. So I think that when they're like 21, I'll be like, when I die you'll each have like 4 cents each. Good luck. But I think on the larger conversation, when you add, you know, the estate and whatever, whatever it is, you know, that my husband and I have amassed, I think I'm going to tell them an age that they can be responsible and not know, like I can just coast till I'm 30 and then, you know, and I don't even, frankly I don't even think it's enough because I'm planning on spending as much money while I'm alive to enjoy it as I can. Are you? Yeah. I mean, how do you think about that? I had this thought the other day because I've had a lot, I was having, when I say a lot of anxiety. It's not that much but like, just like I got to prepare for their future. I got to prepare for their future. Like I got it and I'm like, I'm working so hard and I love what I do.

[Nicole Lapin]

You are, I co sign on that

[Rebecca Minkoff]

and I love it. I'm having fun. But I'm also like, am I working this hard so that they can feel like not stressed out about money when I die or should I just make sure that my husband and I are having as many enjoyable experiences as possible? So like, okay, fine, go on the five to ten thousand dollar vacation and just enjoy it. So for me, I've just been lately having a really different look at like, okay, so we're gonna spend more money now, you know, and then, and then also like I'm seeing the beginnings of my 14 year old, like he's going to be gone in four years and so how do I also spend as much money as I can now on adventures and experiences for us together. Because once he's out, it just. I feel like it'll change. And so to me, I'm like, you know, if they have nothing, when I go, like, hopefully I've raised them to be successful people.

[Nicole Lapin]

Yeah. I think about it, like, setting up different accounts that will take care of her, but she has to have the. Her own wherewithal to do the right things to make those last. And then lately, you know, I've been thinking, like, I haven't prioritized thinking about how I'm gonna enjoy my life and my money that I earned.

[Rebecca Minkoff]

Same.

[Nicole Lapin]

So, like, I talked to an executive recently who's gay and about to retire, and he has no kids and his partner has no kids, and they're like, how do we just spend literally every dollar, our accounts?

[Rebecca Minkoff]

I know. It's really wild when you put it in that perspective. Or I have a friend who's single, and, like, she's getting married, and she is spending all her money on the wedding. I'm like, don't do that.

[Nicole Lapin]

Save for a house.

[Rebecca Minkoff]

She's like, why? This is gonna be fun, you know? And I'm just like, you know what? There's. There's an aspect of that that's really great.

[Nicole Lapin]

Yeah. There's a balance, Right. Between thinking you're gonna live forever and thinking you're gonna die tomorrow. Know, the sweet spot is somewhere in between. We just don't. We all have a different interpretation of that.

[Rebecca Minkoff]

We definitely do. But I. But I do. See, like, I'm definitely not work. I'm not ever gonna. From this point on, or I would say the last six months on, I'm not gonna be working so hard for my children to have some nest egg. Like, I want it to be for our family to enjoy. And whatever's left. It's like whatever's left over. Great.

[Nicole Lapin]

Okay, so I'll see you at 95. Like, you, me, Gavin, Jared will be partying it up. We're gonna be partying it up in

[Rebecca Minkoff]

my next business venture, which I'll share with you after. Oh, yeah, I'm not starting it yet. It's. It's been. It's been going.

[Nicole Lapin]

But does it have to do?

[Rebecca Minkoff]

It has to do with getting old.

[Nicole Lapin]

Sexy. Retirement. I'm in. Sign me up, sister.

[Help Wanted Host/Producer]

Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason

[Jason Pfeiffer]

Pfeiffer, and me, Nicole Lapin.

[Nicole Lapin]

Our executive producer is Morgan Lavoy. Do you want some help? Email our [e-mail] for the chance to have some of your questions answered on the show and follow us on Instagramoney News and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

[Help Wanted Host/Producer]

Oh, I didn't sign up for that.

[Nicole Lapin]

All right, well, talk to you soon. It.