Jason Pfeiffer (4:27)

This is Help Wanted, the show that tackles all the big work questions you cannot ask anyone else. I'm Jason Pfeiffer, editor in chief of Entrepreneur magazine.

Nicole Lapin (4:35)

And I'm New York Times bestselling author and money expert Nicole Lapin.

Jason Pfeiffer (4:39)

The helpline is open.

Nicole Lapin (4:43)

The question of who pays at dinner can be such an awkward one. Birthday dinners, first dates, meeting the parents. This is the kind of weird money

Sponsor Representative (4:51)

situation I usually like, love.

Nicole Lapin (4:54)

But recently, our executive producer Morgan and I found ourselves at the center of

Sponsor Representative (4:59)

a very awkward money moment that had

Nicole Lapin (5:02)

Morgan pretty stumped and she wanted to call the helpline to get Jason's take.

Morgan Lavoy (5:08)

So who wants to welcome me to this show? Let me in.

Nicole Lapin (5:13)

You're welcome, Morgan.

Jason Pfeiffer (5:15)

Welcome to the show. You produce Help Wanted.

Morgan Lavoy (5:19)

It is so great to be here this time and every time.

Jason Pfeiffer (5:23)

It is always great to have you.

Nicole Lapin (5:24)

You're always here though. That's the thing.

Morgan Lavoy (5:26)

That is true. That is true. I'm always listening on the helpline. First time caller, longtime listener.

Jason Pfeiffer (5:33)

Apparently you have a problem.

Morgan Lavoy (5:34)

Yeah, so I have a problem. And I'm first going to direct it to you, Jason, because Nicole actually witnessed this and was a part of it. She wasn't a part of the problem.

Nicole Lapin (5:45)

Ah, I might have been.

Jason Pfeiffer (5:48)

Was she a part of the solution?

Morgan Lavoy (5:50)

We're hoping that you can be part of the Solution, Jason, which is to

Jason Pfeiffer (5:53)

say Nicole is not a solution. Ok? Nicole is not helpful in this problem. So I can't wait to hear it.

Morgan Lavoy (5:58)

I would not say that and I will tell you why through explaining what happened. So here's what happened.

Jason Pfeiffer (6:04)

Great.

Morgan Lavoy (6:04)

Nicole and I were at a conference in Miami and we were actually able to save some money while going to the conference. We were given passes to the conference because again we're savvy startup, we're bringing in ad dollars, but we also want to scale and grow. So we're putting so much of it back into the business. Slash, this was a couple of months ago when we had less of the money is coming in. More money's coming in now, but less at the time. And we met this really lovely guy who works at Google in a senior capacity and he was really helpful in sort of walking us through the ad agency world. And we were, you know, chatting in this very stuffy mixer. You know those terrible things where everybody's standing around with a name badge and. It's the worst.

Jason Pfeiffer (6:56)

Absolutely the worst.

Morgan Lavoy (6:57)

Absolutely the worst.

Jason Pfeiffer (6:58)

Why? Why do people submit themselves to this? It makes no sense.

Morgan Lavoy (7:00)

Exactly. So in the most like professional, like let's get out of here, but not in like the sexy kind of a way, but like the most like let's get out of this terrible setting and older brother vibes. Yes, exactly. So we, we went to dinner and because these things are at fancy hotels, the closest restaurant was a restaurant in the hotel which happened to be Nobu. Nobu. Very expensive.

Jason Pfeiffer (7:26)

Yeah.

Morgan Lavoy (7:26)

Very, very, very cuckoo bananas, like $70 entree that are also teeny tiny kind of a feeling. And so we had this great dinner, this great chat and it was very helpful to us. And then the bill came.

Jason Pfeiffer (7:45)

Yeah.

Morgan Lavoy (7:46)

And in my head I just had not even thought about the moment before it happened, but I had sort of thought that Mr. Google was going to pick up the dinner bill.

Jason Pfeiffer (8:00)

I hear Google has some money.

Morgan Lavoy (8:01)

I've heard that rumor as well. And Nicole and I both have company cards, so I have that accessible to me in the wallet. And as moments elapsed while no one was putting their credit card down, I thought I could put my corporate card down. But the thing about my corporate card and the Google guys corporate card is that Google guys corporate card goes to the Google bank account. My corporate card is connected to Nicole's personal bank account.

Jason Pfeiffer (8:36)

Right. This is, this is Startup Land.

Morgan Lavoy (8:39)

This is Startup Land. And so I should say it's not actually a personal account. She does have a business account and a personal Account, but everything. Funding the business account is Nicole's own money.

Jason Pfeiffer (8:49)

Yes.

Morgan Lavoy (8:49)

And so I didn't know what to do because it seemed, as these moments elapsed, that he was not planning on just putting down his card. What do we do?

Nicole Lapin (8:59)

But also that I think there was a moment where the check came and I always offer, can I contribute to this? Especially when I'm trying to draw a boundary between, like, this is not a date.

Morgan Lavoy (9:15)

This is a business thing.

Nicole Lapin (9:17)

But I really didn't expect him to take me up on it. It was a faux reach.

Jason Pfeiffer (9:25)

Yes, the faux reach. A classic move of dates. Do people foe. Reach and dates?

Morgan Lavoy (9:30)

Oh, yeah. I faux reached.

Nicole Lapin (9:32)

Yeah.

Jason Pfeiffer (9:32)

All right.

Sponsor Representative (9:33)

This was.

Nicole Lapin (9:33)

This was, like, very clear. There have been other times where I've done it to create a boundary. This was very clear, like, very professional vibes. I didn't do it to create the boundary. I did it to be nice and considerate. But it was also very clear that there was, like, an imbalance in business resources. There was one behemoth in the room, and it wasn't me.

Jason Pfeiffer (9:59)

Just to be clear, because I don't feel like I have a picture of the. The moment he is not. Not paying, he is reaching for his car. He is making a gesture towards contributing something for dinner, at which point you said, your stock line, can I contribute to this? And he said, yes.

Morgan Lavoy (10:23)

So it was a little. It was a little bit of a fumble.

Jason Pfeiffer (10:26)

Yeah, take me play by play.

Morgan Lavoy (10:28)

Nicole was like, can I contribute? And I think what would have been easier in the moment probably was if he would have just said yes or no. But instead he was like, oh, well, we just talked about how you guys really need to bring in more advertising dollars. So I don't know. And so then I was like, do I? So I'll just fast forward the videotape and present the question to you in another way, which is that Nicole ended up putting her card down, and the Neil was split 50, 50. And it was a big. It was a big bill, but not for Google, but definitely for us. And so our question after that moment was sort of like, should that have mattered? Because the. The awkward dance was like, you know, if you ask to contribute to a bill and someone doesn't say no or yes, then you're almost in a position where you have to convince them that you can pay. Like, no, really, it's fine. Like, I feel like it's. It's harder to then retreat behind the line and say, you know what? Yeah, we were just talking about how we need more advertising money. Really good point. I'm gonna take my card back. You have to sort of talk them into it again. And it was just weird because hearing Nicole be like, no, it's fine. I just really genuinely in that moment wasn't sure if there was any other path for us. And. And also wasn't sure if it was even right for me to be thinking that way. Like, does it really matter? You know, if I'm going to a lunch with a friend, for example, and the friend has more money than me? I still don't expect my friends to pay for me wherever I go. But it feels different in a business setting if it's not the person you're having dinner with, if it's not their money, and it is your money. But the question is, is there any other way? Am I thinking about this in the wrong way? And what can. Because, you know, we're having business lunches and dinners all the time and how should we handle these conversations moving forward?

Jason Pfeiffer (12:47)

Okay, one other piece of information I need. Was there any expectation of future business with this Google person?

Nicole Lapin (12:57)

Yeah, I think we've continued the conversation. We really hit it off. He believes in our mission. Ultimately, we split the bill. It was, I think, $800.

Jason Pfeiffer (13:11)

It's not nothing. For dinner.

Nicole Lapin (13:13)

It was not nothing. It was definitely a little bit of a sticker shock, you know. And yeah, I think the dance of like, are you sure? Are you sure? Was a very uncomfortable dance for me to partake in.

Jason Pfeiffer (13:28)

Yeah, it does sound very awkward. The reason why I asked that question was because, you know, if in a way, sometimes I think what you do in this situation has to be factored into what is the long term nature of the relationship. Because sometimes it's just worth investing in something because maybe you'll get some return on it later. Versus this was a perfectly fine dinner with a person from Google who I will never see again. And therefore we can just be really awkward about it and who cares? I am going to float a hypothesis by you guys, which is that I think that, Nicole, you talked him into you paying for this in a way in which had you either stayed quiet or taken him up on his kind of awkward, but I think perfectly reasonable out that he would have just picked up the bill, but you talked him into letting you pay. Do you think that's true?

Nicole Lapin (14:33)

Um, I definitely, in hindsight, could have made like a joke about it. Yeah, I guess there was a balance between the offer and the lack of expectation, to Morgan's point of like, I don't expect anyone to buy me Something, ever. I never order something as a rule that I can't afford myself. And so there's that sort of pleasantry. But I also could have said, like, oh, yeah, like, papa Google, like, they have far more zeros in their bank account. Like, you got this, no problem. You're at a conference.

Jason Pfeiffer (15:09)

All right, first of all, I think that this guy missed the opportunity to take advantage of one of the great joys of having a corporate card for a company that's not yours, which is being able to treat people on that corporate card. When I have traveled and expensed stuff to either entrepreneur or if I'm traveling for a speaking gig and I'm going to file my expenses, if I go out to dinner with somebody, I. I put as much of, if not all of their dinner on the card as I think whoever's paying it is going to accept. And I delight in that because, you know, I'm in, like, a nice little temporary free bubble. And isn't it nice to walk around the world in a little temporary free bubble where you're just like, the next thing that happens isn't on me. And that's a delight. And to be able to grab people and be like, you're in my free bubble right now is just so wonderful. And so that is too bad for that guy, though. For what it's worth, Google did just go through a bunch of layoffs. It's very possible that they've also told people you have less discretionary spending when you're traveling. And so possibly this guy actually can't put $800 on his card. We don't know. Just because Google is very large. So let's give him some credit. Maybe he couldn't do that. But because he said to you, oh, you sure? Because you're in startup land, I think that you could have very easily said something like, yeah, yeah, you know, I mean, money's tight, but we can get it. Unless Google doesn't mind picking it up. Because at that point, you're not talking about him, you're talking about Google. And Google and him are separate things. And he understands that. And so the question that you're really asking is, like, what kind of policy are you operating under here? Because you don't. You don't know the answer to that. Right. I feel like this is a fundamentally missing thing that we have from this conversation, which is that we don't know how much money someone from Google can spend when they're traveling.

Morgan Lavoy (17:20)

There's another layer to this that I was thinking about in the Moment too, which is that what are the optics and how significant are they when you are with a potential business contact, and the implication is that they don't have as big of a budget as you? And then also, I want to know the reverse. So let's go back to the example that you were giving, like, the delight that it is to pay for somebody else in this free bubble, in your free bubble, Totally. Are you at all impressed if that person is like, no, I'm a business owner and I can split this with you? Are you thinking, huh, savvy? Or are you thinking, huh? We just had a conversation about how you really want to bring in some more ad dollars. Weird that you're picking up the bill. Are your budgets really tight right now? Are you inferring anything about how that person is running their business depending on what they do in this moment?

Jason Pfeiffer (18:28)

This is a very interesting question. I am not, but I always, in this situation, always just think of the bill as the annoying thing that just has to be taken care of. And whoever can take care of it with the least amount of fuss is the person who should do it. And so when I am out with somebody else and like, let's say they have the ability to put it on their corporate card, I just let them do that. Because to me, this has nothing to do with who has more money or who's in a position or whatever. It's none of that. To me, this is just a matter of, we had a nice business meeting and now this is the annoying part at the end that just has to get taken care of quickly. And so whoever can do that fastest and best should do that. I don't read anything more into it, and I don't know that you need to. I think that there's a world in which this becomes a kind of gamesmanship where you're expected to pay for someone or expected to let somebody else pay for you based on whatever the hell the superseding relationship is that you as business entities have, right? So, for example, if the entrepreneur sales team takes a client out for dinner, entrepreneur is going to pay for it, right? Because they're the sales team and they're pitching this client. And so dinner's on them. And everybody understands that. And so that's very clear. And it would be weird if entrepreneur was like, hey, actually, can you pick this one up? Right? Because then entrepreneur is signaling that there's some kind of financial problem, which is not what you want to be signaling when you want to be a great partner with somebody. And so in Those situations, I think that the business relationship, and this is the reason why I asked earlier whether or not there was going to be any kind of longer term relationship relationship with this person from Google. The business relationship sometimes dictates how somebody should pay. But I don't think that that was the case here because in this case there isn't like one partner who is offering something specific to another or looking for something specific. Instead, what it sounds like is that you've made a good professional personal relationship and maybe something useful can come from that. And I think in that case it's open season. I don't think that this guy would care one way or the other who paid or how. Unless it turns out that a lot of this money has to come out of his own pocket, which is possibly what's happening here, because if he can only pay a certain amount from Google, then the rest of it's coming out of his own pocket. And he was probably thinking about that when it was time to pay.

Morgan Lavoy (21:26)

It's interesting, I didn't even consider that

Jason Pfeiffer (21:28)

I learned this doing all this work for these large companies where somebody once reached out to me from Amazon and they were like, hey, I love your work and I think that you would be a perfect speaker for this group that I have. I've read your book and I've told everyone to read your book and it would be great. And now so when I hear this, I think number one, Amazon has all the money in the world. And number two is that what I have found is that when people have read my book and reach out to me about speaking, I can get a higher fee because if they've read my book, it means that they're looking to book me versus if they haven't read my book, they're looking to fill a role with someone like me. And there are different budgets for that, right? Like if the more specifically somebody wants you, the more they will were willing to pay for that. So I thought, oh, this is great. And I, they, it was a virtual thing and I, and I was like, I was like, sure, my rate is $10,000 for, for like a virtual event, right? Because I just figured Amazon's got all the money, they'll just throw it at me. And she wrote back and she was like, oh, you are totally worth that. And I wish I could pay you that. But actually my budget for this is $600. And so I shouldn't say this aloud, but I just did it for $600 because it's just be sitting in front of my computer and she was so nice. But anyway, the lesson here is that just because someone's at a big company doesn't mean that they have a big budget, because that's not how big companies work. And so I think that in a way, it's almost like this guy is going to be able to expense a little bit of it to Google. And now it kind of comes down to, what is this relationship? And what would you do if there weren't corporate cards involved? It's just something that you have to think about if he doesn't immediately grab it and say, it's on Papa Google. Which he didn't.

Nicole Lapin (23:31)

Yeah, that's really interesting. And I also felt like a little ugh when you said, oh, it's free. Like, corporate card free. As somebody who has a business or like, that feels like my biggest nightmare. If somebody's like, I got a corporate card party. It's like a bubble of freedom. Like Nobu. Breakfast, lunch and dinner.

Jason Pfeiffer (23:56)

Right, Nobu? Yes. Boo. Stick around. Help wanted.

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Jason Pfeiffer (25:23)

Welcome back to Help Wanted. Let's get to it.

Nicole Lapin (25:26)

Rich people stay rich by acting like they're poor, but poor people stay poor by acting like they're rich. And I guess big companies become big companies by staying on budget. And small companies probably should stay on budget. Like it shouldn't be a free for all. You became a big company, not because you just like, yes, Booed all day long, right?

Jason Pfeiffer (25:47)

Yes, that's right. And some of the largest companies are also the stingiest. I mean, that was when that woman responded and she was like, my budget is 600. She literally said, Amazon is a very cost conscious company and Walmart is another one famously incredibly cost conscious. And I mean, when I have traveled for Entrepreneur, people don't always know this, but is actually just a small family owned company. So we operate like one. But I've worked for larger brands that were owned by larger media conglomerates like Men's Health, and I would travel for Men's Health. And there was a very specific policy for breakfast and for lunch and for dinner. And it was not a lot of money and it sometimes wouldn't even cover the meal if you were staying at a fancier place. I remember traveling once for a story. I had to stay at this like, fancy hotel because it was where the photo shoot was or something, I don't know. And the budget that I had for breakfast did not cover breakfast at the hotel. And that is just not a thing that you would expect for someone who's traveling for Ben's Health, which seems like this fancy thing. But that was the case. And so that meant that that extra money had to come out of my pocket unless I wanted to walk down the street and find a McDonald's. And that's how people are operating a lot of the times. And so I think what you're ultimately facing here is just a lot more complex, complicated than either, oh, what does who pays have to say about whose business is stronger or what kind of business statement I'm making or whatever. No, because I think a lot of it is just coming down to human beings who are managing their own budgets and are mixing personal and professional experiences in ways that are hard to navigate. And I bet everybody is navigating it. And after talking through this, I am willing to bet that that guy was making a decision in the moment that he obviously wasn't able to calculate in his head fast enough to like, decide what he wanted to do. But I will offer the alternate reality of the bill comes.

Advertisement Voice (28:05)

It's $800.

Jason Pfeiffer (28:07)

He's thinking to himself immediately, I can expense whatever fraction of this on Google. You know, these wonderful dinner companions of mine are at a startup, and so their finances are maybe a little less predictable than mine because I have a nice Google salary.

Nicole Lapin (28:27)

So pre Google, you know, we're just pre Google.

Jason Pfeiffer (28:29)

You're just pre Google. Exactly. That's a good way to think of it. Everybody's. Everybody's Everybody's either Google or pre Google. So he's thinking, I'll cover them. But also, that's pretty expensive. I have a family, things that I do with my money. And for what it's worth, I have friends. I have many friends at Google, some of whom have told me their salaries. They are large salaries. They are large salaries. But also, these people do not spend like they have large salaries because they're thinking about their family and their future and their, you know, they're helping their parents out who don't have a lot of money. Whatever. There's, like, all sorts of reasons why they're not living large, even though they have large Google salaries. And so they're cost conscious. And maybe he's cost conscious and he's thinking, well, I'll cover them if need be, but I'd rather not, frankly. And so then you say, hey, can I contribute to this? And he kind of, like, tries to feel you out, and he's like, yeah, unless you are tight on money. To which, Nicole, your instant, like, reaction is like, nope, we can do it. You know, it's fine with me. You know, money's in the name. And now you're in a situation where he doesn't really know what the hell is going on, but you keep insisting on paying. And frankly, he doesn't want to pay this whole damn thing himself. And so you just ended up where you ended up. And it was messy and complicated, but also fine, except that it was a lot of money that none of you really wanted to spend. The only winner here is Nobu. Basically. The only winner is Nobu.

Nicole Lapin (30:05)

That's right. I mean, I think that I left that feeling like it was the right outcome. I remember him saying, I really appreciate that. Which I interpreted to mean, like, oh, I don't know, like, maybe job security. Weird. Like, he doesn't want to answer a question about this. Like, he doesn't want, like, any red flags. And so, yeah, maybe he was at an executive level, but not like, at. In the C suite, where you don't have to explain, you know, big bills and things like that. And so I took it as like, oh, that just, like, takes off another problem or potential problem that I could have and de risks it. I'm sure he's not ever thought about this ever since then. But I guess the other layer to this is the gendered layer, right? Like, would it have been. Would we have felt different if it wasn't an older brother figure and it was truly, like, another woman our age? Like, does age and Gender factor into it.

Jason Pfeiffer (31:12)

It factors into it for me sometimes in this very specific situation, which I'll tell you, and I'll be curious what you think that specific situation is. When I go out for a businessy lunch or dinner with a single individual, not unmarried, one person who is a woman. And then I don't want her to think that I am picking up the tab because it's some kind of move or gesture or something. So if I have the ability to expense it, I will make a show of how it is not my money. Incredibly clear. Right? Like, I could, oh, I got this because they give me X amount of money, you know, dollars, and I'd be happy to take care of it. Right? Or, like, so I, like, I make it as. As, like, business clear as possible because I don't want her to think that I'm trying to pick up the tab. Because sometimes picking up the tab is some sort of sign of something. And. And I don't make that same show with a man because I don't worry that he thinks I'm making a sign or something. Should I be doing that? Should I be thinking about that?

Nicole Lapin (32:30)

I do it on the reverse. So I do. I default to wanting to pay. You know, in general, like, we've talked about this on our previous iteration of this show, but I also use it as a tool to hold boundaries. I actually did it the very next day, I think, at that same hotel. Like, I went to the lobby part of Nobu with this guy who we also met. But I did feel like, weird, maybe romantic Y vibes. And I was very clear, like, I got this. Like, I didn't even say company. Not company. I was like, I'm getting the whole thing. You. You and your tuna crispy rolls. Like, all of it. I want all of it on my card. And that was like a very clear, like, this is business buddy move.

Jason Pfeiffer (33:21)

Did that seem to be received?

Nicole Lapin (33:23)

Yeah, I mean, we didn't make out

Jason Pfeiffer (33:25)

well, but I mean, like. I mean, like, if you were getting weird vibes from him. Him. Did those weird vibes, like, change at all when you were like, I got this. We are not having a personal interaction right now.

Nicole Lapin (33:36)

Yeah, it did.

Advertisement Voice (33:37)

Huh.

Jason Pfeiffer (33:38)

Interesting. I don't know. I think that what we just described here is fairly similar in nature to what we've been discussing already, which is that in both cases, what's being taken into account is some kind of personal dynamic that is happening on top of or underneath the professional dynamic. And they're just not possible to totally separate because we're not a bunch of numbers sitting down with a whole bunch of other numbers to talk about numbers. We're people. And business is about relationships as much as it is about anything else, which means that.

Nicole Lapin (34:21)

And relationships are complicated as fuck.

Jason Pfeiffer (34:24)

That's right. And. And so I think what we just need to be mindful of is what do we need? And what does that other person expect? And how do those two things weigh against each other? And maybe the next time you just don't fucking go to Nobu, because that's an expensive dinner.

Nicole Lapin (34:47)

We're going to McDonald's down the street.

Jason Pfeiffer (34:49)

There you go. That feels right to me. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason

Nicole Lapin (34:58)

Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoy. If you want some help, email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagram at MoneyNews and TikTokoneyNewsNetwork. Work for exclusive content and to see our beautiful faces.

Morgan Lavoy (35:18)

Maybe a little dance?

Jason Pfeiffer (35:19)

Oh, I didn't sign up for that.

Nicole Lapin (35:20)

All right, well, talk to you soon.

Advertisement Voice (35:40)

Sa.