How to Handle Difficult Wedding Vendors | Wedding Planning Q&A
6 May 2026 · 28 min
In this Union Podcast episode, host Jamie Wolfer shares personal stories and practical advice for wedding planners. He reflects on early career lessons, recounts a tense encounter with a difficult videographer at a dream venue, and explains how he shifted from paper binders to the digital platform HoneyBook for contracts and client management. Jamie promotes industry‑specific contract service LegallySet and recommends Brightco event insurance. He answers a listener’s backyard‑wedding logistics question, covering space measurement, layout tools (AllSeated), ground‑level concerns, restroom and parking solutions, power and noise considerations, and the importance of a "flip" plan. The episode also features a conversation with planner Justine about note‑taking habits, hybrid paper‑digital systems, and confidence‑building for new planners. Throughout, Jamie mixes storytelling, instructional tone, and occasional humor while promoting sponsors.
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Hi and welcome to Union Podcast.
My name is Jamie Wolfer and I'm a wedding planner who absolutely loves to share how I got started and scaled my business to above 6 figures in this amazing and occasionally extremely competitive industry. In this podcast, I share the tech, tactics, mindset, and mistakes that got me to where I am today. No gatekeeping, no cloak and dagger, just full disclosure and a little humor along the way. So whether you're a planner or a solopreneur, my goal is for you to be a better business person than I ever could have been and support you on this journey. Let's dive into this week's episode. Today's episode is one of my favorite things in the entire world, and that is a live Q&A from one of our Union Mastermind calls.
I know you're gonna love it. Take a listen. Uh, what's the best advice you got as a new planner that still sticks with you today? A big learning point for me was the first wedding I worked. I worked it, uh, under a different planner. She was begrudgingly let me work for free, and I was like, no, listen, it's fine. I'm not gonna steal your clients. I just like, I just want to try it. Um, and I learned a lot of what I did not want to do from that event. Uh, I thought I was wearing comfortable shoes. I was not. I had blisters a couple hours in. Um, we took like a full hour break during dinner. Hated that. Hated everything about that. Their emergency kit was an over-the-shoulder, like a crossbody bag. It was so heavy that my shoulder was cramping. Uh, like my trap was cramping. From holding it, but I wasn't supposed to put it down. And we had clipboards and I'd keep it on me at all times and I kept setting it down. So there was a couple of things that when I was like, okay, not a clipboard girly. Cool. Uh, also I'm getting a rolly bag for my emergency kit. Cool. Also during dinnertime, I'm not going to go disappear for an hour. Cool. Just so many things like that where I went, okay, that's, that's going to take some adjustments. One of the most poignant pieces of advice I've heard though, and I feel like I just talked about this recently, it might've been in a call. Um, was it that? I'm not sure. There was an event where the bride was someone I grew up with. Like, we used to have a lemonade stand together. I had an entrepreneurial spirit really early on, folks.
I knew—
I mean, I didn't know, but, uh, yeah, we— our parents are dear friends. Our mom sang on the worship team, like, my mom, her dad sang on the worship team together. Our moms were best friends. Um, and so when they hired me to do her wedding, I was like, I am so honored. And also, I cannot script this. I can't. I can't do it. Okay, this is really important. And lo and behold, they picked literally my dream venue. My dream venue. I about pooped myself when I figured out that they picked this venue. It's Big Daddy's Antiques in Los Angeles. Google it. Google it right now. It's so good. Cause before I did wedding planning, I actually used to work in antiques with a company, much like Big Daddy's Antiques, just smaller. And they sold wholesale. So you go look this up, like that's what I used to do. So I'd always wanted to do an event there. A lot's riding on this event in my opinion. And a lot had already started to go wrong where they got ready. There was an Uber surge at the time, so we couldn't even get the bride to where we needed her to be on time. So that set off the clock to have things go very, uh, start running late. Well, the videographer in this particular scenario was such a butthead. He was mean. He was mean. He was snippy. He made the professional photographer who'd been doing this for over a decade cry, and she was like angry crying. She's like— so I come up to them, and we're— this is during cocktail hour. It's supposed to be the end of cocktail hour. The bride's mom, again, remember, like, I grew up with this woman.
She comes up to me, she's like, hey, can we get this moving?
Because the cocktail hour is going really long. Like, yes, I know, I'm so sorry. I'm trying to get photo and video to wrap up. I will come and check in with you in just a few minutes. She goes, oh my gosh, thank you so much. Um, go and check in with them. And I'm like, hey, how you guys doing?
We're running a little bit low on time here.
Like, we really need to get things moving. And so I asked the photographer, I was like, hey Jenny, how you doing? Did you get all your shots? And she's like crying. She's like, no, I can't get all my shots. He keeps stepping in front of my camera. Like, usually photo and video communicate, they dance, right? They do these back and forth things. But in this particular scenario, like, he just kept stepping in front of her and he was like, well, I'm sorry, I have to prioritize my craft.
Like, just what?
No, you don't. You could both do this at the same time. Everybody else does this. So I told him, hey, we're gonna have to let, uh, guests in for our reception soon, so I just need— I need an ETA from you. He said, I don't know, I'll be done when I'm done, but don't let them in because I promised the couple to get a shot inside of the reception space before people go in. And at this point I was like, oh gosh, I need a minute, I need a minute. I'm done when I'm done. Oh, because I don't— I'm not confrontational. I just get my job done. I don't get spicy in argument, at least unless you're my husband, right? With those that are closer to us, yes, obviously we fight different. But in situations like this, I'm like, I had never had someone be so blatantly rude So I took a step back, walked away, and I was like seething. And my assistant planner comes up to me and she goes, hey, what's going on? I was like, that videographer is a piece of work. He is something else. She goes, Jamie, you're a mom. I have watched you explain things to your children in ways that are perfectly understandable and let them know the boundaries and the rules of the situation. And they get it. And then you move on. She said, so he's acting like a child, so treat him like one. I went, that's really interesting. Not be patronizing, but just go, hey, here's the deal, here's what we got going on. So I go back over, I said, hey, uh, listen, I understand that you promised them the shot. I have 150 guests that are late to dinner, so while I would love to prioritize your art, I need to make sure I'm taking care of all of the other vendors that we got going on here. Catering wants to make sure their food is hot when it's served, the photographer needs to make sure she's getting her shots, and I need to make sure that everything else happens as on time as possible. So unfortunately normally at this time you have about 5 more minutes, and that will not include a photo shoot time inside the reception space. Hopefully you can get that later. And at this point, the bride's crying too. It's my friend, and I'm like, oh my gosh, I'm so sorry, but like, I, I'm not sure what to do. And I spoke with him privately. I said, we'll make space to do it afterwards. He should not have promised this to you, especially if he was going to take so long during photos or videos. And she's like, I totally understand. So for me, it was a, uh, almost setting aside my ego because I was really offended. That was really mad. I was super, super mad. So it made me realize that, you know, obviously you're going to deal with stinkers in every single job you work. You know, we've had stinker employees. We have like employees like, um, on the same level as us. We've obviously had stinker bosses or teachers that were difficult. We've had people in our life that we've had these interactions with, except for now you're at the helm. Like, now you're in charge. Now it's someone's day that you're being paid to run. So now you have to have a response to someone like that. So my encouragement is to, you know, make it not about your ego, not about yourself, make it about the overall benefit of the event. I also once had a videographer tell me, Dave from Amari Productions, we did an interview about this, or it was in the interview. He said that, you know, obviously he's very keen to pay attention to the timeline to make sure his stuff gets done and his videographers do their stuff. I said, yeah, well, I have to think it from the perspective of not just you, but also the photographer and the chef, because the chef needs to make sure the food comes out at the proper temperature. And this guy has been— at that point had been doing wedding videography for over a decade, and he was like, I have literally never thought about the temperature of the food. I was like, yeah, well, that's why I do what I do and you do what you do. So that perspective is really important. Um, don't get pigeonholed, don't get offended unless obviously they do something super offensive, you know, obviously react in kind. But in a scenario like this, you gotta rise above and go, okay, while I appreciate and respect your craft, I have more things to tend to than just to carve out this one opportunity for you to get this shot inside. So I, I hate to inform you that you've got about 5 minutes left, um, and then, and then I'm letting guests inside. And we did, and I got the shot later, and the bride looked great, and she loved it, and it was romantic, and it was wonderful. It was everything she wanted it to be. So as far as advice treat people like children if they're acting like them. No, just kidding. I mean, well, that's probably a good synopsis of it. Um, we have a bigger goal, we have a bigger vision, and when someone's being a stinker, that ain't it. That ain't it. We don't have time for this. I don't, I don't have time, respectfully. So I'm not gonna talk down to you, but I'm gonna lay it down and be like, okay, well, you have 5 minutes. So, uh, it's not our fault the surge happened. It's not our fault that hair and makeup ran late. It's not our fault that you're taking forever. For video. Uh, none of this is our fault, but it's our responsibility to make sure it goes as smoothly as possible.
I'm only mildly embarrassed to admit that in the beginning I printed out every single piece of paper, every single contract. I took handwritten notes and created a binder for every single one of my wedding planning clients. Now, in theory, that sounds really cool, uh, and I thought I would look really cool showing up to these meetings with these binders that are full of all of these contracts with handwritten notes. But let let me tell you the chaos that ensued when I tried to stay organized on my own and got over 5 events at a time.
It was a nightmare. Enter HoneyBook.
I am telling you guys, HoneyBook was literally exactly how my brain was processing wedding planning, but just in digital form. It's so easy to go in there and make any sort of customizations that you want, from adjusting your contracts to adjusting your packages, maintaining conversations back and forth that not only pop up in in the app, on the website, but also in your inbox as well. It's a great way to stay organized. So get out of the paper and get onto the digital. Head to wolferandco.com/hb and use code UNION at checkout to get the best deal. We interrupt this podcast because there is something extremely special that I want to share with you guys. I don't know about you, but for the last who knows how many years, I have been using a Frankenstein Googled, copied and pasted contract. And while that is extremely embarrassing to admit to all of our listeners, I know that there are people out there who feel the same as I do. And there were a couple things that kept me from actually getting an attorney-drafted contract. Actually, no, there was one thing. It was so expensive and it seemed so out of reach. That's when I learned about LegallySet. You see, Kunbi with LegallySet has created industry-specific contracts for people like you and me working in the wedding industry. They're easy to customize. They're drafted by an actual attorney and not Googled. Can you imagine that? And last but not least, they are so extremely affordable. So if you were like me and maybe using a less than appropriate and/or legal contract, it's time to step up your game. You have no more excuses. Head on over to theunionpodcast.com/legallyset to check them out. Use code UNION for 20% off your contracts.
Ashley says, I'm a new wedding planner and my first big wedding I'm planning is in a backyard overlooking a gorgeous lake. However, it is a skinny rectangle and they're wanting to fit up to 160 guests. As the planner, how do I configure the floor plans for the ceremony and rehearsal, which will be in the same space? I'm assuming you mean reception. There will be a teardown/setup situation. The cocktail hour will be in the front yard while we do the swap. How can I make sure a DJ, tables, drinks, dance floor, etc. can all fit? I'm just so stressed about making sure it all comes together and I don't know where to start, essentially. Okay, Ashley, Oh, I feel this so hard for you. We've done so many backyard weddings. In fact, that was like our shtick for a while, especially out in like Temecula. There'd be all these really cute little properties. People just want to have their events there, and I'm like, okay, there's a lot you have to figure out, which I'm sure you're currently feeling, feeling a lot of. There are a couple ways that you could figure out how to do this. One, you got to figure out the spacing, right? If it's basically a skinny rectangle Can you get the measurements of it? We need to get the measurements to see how many tables and chairs can logically fit back there. That's, that's priority number one. You can either do that by getting the measurements and using the website called AllSeated, and you could put in the measurements, and then, um, the, the tables and chairs are set at scale, so you can drag and drop different table sizes. Um, and then there's also a ruler that you can use to measure the distance between tables This gets a little nerdy, gets a little techie, but this is a great way to make sure things will actually fit. Cause we get a lot of, yeah, yeah, no, it's okay. I think they'll fit. I think, I think it's going to be fine. And you're like, well, great. I can't bank this entire wedding day on what you think, especially if you don't, you don't do this. You hope. You don't think, you hope. So if we can get all seated and then do a setup that way, that's a great way to see if things will actually fit. Another thing that you can do is get a rental company out there. And tell you what they think, um, how many could fit based on their guesstimation. I need a measurement. I need you to put it into all seated, maybe bring out someone from a rental company to kind of give you a ballpark. Another issue we run into into backyard spaces is uneven ground. So what looks flat to the naked eye and what kind of feels flat as you're walking on does not feel flat to, you know, uh, a round— an 80-inch round table like that. That's not that doesn't feel flat. It feels completely lopsided or wobbly. So you're going to want to be really, really attentive as you're walking around. Are there any— like, is it as smooth as they think it is, or is it going to kind of be like a little bumpy, a little all over the place? Take a chair around with you and set it down in different spaces. I know this sounds really extra, but the reason that I'm saying all these things is because we've run into these issues, um, where people are like in their chair but like sideways because the ground's not even, right? So that's important. Getting people— or getting tables in and out, is that feasible? How easy is that? Of course, there's a whole lot of other things when it comes to restrooms. 160 guests is a lot, and that's a lot of booties on house toilets. That's a lot. So you're probably gonna need to bring in trailers or some sort of porta-potty situation. Now let's talk about the shuffle or the flip. So that's when you take one space and you flip it in from like one activity and flip into the next. That's a lot of bodies moving very fast in a very short amount of time. So you have chairs already there, you got tables probably still collapsed somewhere off to the side because there's probably not enough room to have them preset up, which means you're rolling out tables, you're throwing tablecloths on them, centerpieces, putting chairs around them, etc. Flips happen really well when there are people who have done them before, um, but they can happen pretty well when there's someone who is completely prepared at the helm of this. So this is going to be you in this scenario, Ashley. You need to have that all— take that all seated layout that you, uh, developed earlier, and this is going to be literally your legend for this. Have Post-its ready, have a pen ready, and then what you're going to do is you're going to tell where to place out those tables, and then walk around after tablecloths are put on, or maybe before, and put Post-its with a number of how many seats, how many chairs belong at each table, because you're gonna have differing numbers. So that way you can keep it pretty simple, or not simple, you keep it less people asking you questions, more people just look at table, go, okay, 7 chairs, cool, got it. Okay, 8 chairs, cool, got it. I said 80-inch round earlier, didn't I?
I don't think that exists.
I'm really good at my job. Maybe there's an 80-inch round. I highly doubt it though. As I'm saying this, I'm like, wait, I said 80? No, I like 72 would be more logical. Um, and then you're going to want to keep everything that's on the table very minimal. So if it's a single centerpiece and 6 votive candles, hallelujah, bless it. Oh, and a table number, great. Love that. Now when we're talking about— sure, a DJ, drinks, dance floor, etc. can all fit. That would be where I go back to the all-seated situation. The DJ is probably ideally not gonna move from the ceremony place to the reception place, like just keep the equipment in the same spot. Drinks you can have pre-set up, just don't have a bartender there, and maybe don't have anything out so people don't swipe stuff before the service starts, before the ceremony starts. Dance floor, I Um, dance floor is something that's gonna have to be pre-installed, which is kind of obnoxious. Some people don't want it there until after the ceremony is done. It takes too long to set up, so you might have your ceremony on top of the dance floor or forego it altogether. Now, I don't know if you're in this call— yeah, um, okay, so you're not. If there are follow-up questions, like, this is— backyard events are a lot. I've done a few YouTube videos on them, but if you— a lot of scenarios, especially when you're coming from a planning side, um, get pretty specific. So if you need to talk about this further, please let me know, because that's like— that's a lot for sure. It's totally manageable. It's managing expectations and also, um, managing the, uh, when, when a family is convinced that something is going to be great and convinced that it's a good idea, that you're like, oh, uh-huh, I understand it's your property, but that doesn't make this work. And Rebecca Bradwick, great point, consider power outlet locations. You're also going to want to consider, um, noise, amplified sound. A lot of places have a quiet time where it's just like at a certain point there can be no amplified sound outside. Um, typically most places it's 10 PM in residential areas, but you might run into issues with, uh, disgruntled neighbors regardless. We have had the cops called at two different backyard weddings, so I highly recommend that you highly recommend to your client to go around pass out some brownies, some cupcakes, some something, go door to door, uh, pass out a little flyer, give them your phone number, say, hey, we're having an event from this time to this time, we plan on ending on time, um, and here's our phone number, or here's the phone number of my dad if you need to talk to anybody should you have any issues with the noise. We love this property, this means a lot to us. I mean, I grew up here, so I can't wait to celebrate my big day here, you know, kind of get them with the feels. Um, but basically make sure neighbors know. And parking, that is another issue that can be— that can get legal pretty quickly, is if there's a bunch of cars and they're parking in front of you. I've seen people— I don't know what it is about the second someone hears it's a wedding, they'll just like park wherever they want. And I'm like, you just block someone's driveway, dude. Like, you can't— did you forget that that's a rule? Did you forget that that's a law that you can't do that? So, um, kind of preparing for some of those things, I would recommend watching the backyard wedding videos because I know I did one for— an updated one recently. So there's, there's a few of them, but those would be, those would be a really good resource for you. So then you can go into it with the knowledge I'm sharing in that video, and then you'll look like a boss. Yeah, so power outlet locations, lighting, are they cooking on-site? If so, are they drawing power? There are— because cooking power is a lot. Is there lighting where people are parking? Is there clear lighting walking from place to place? We don't want people tripping in the dark. We don't want any of that happening. But sometimes people are like, oh, it's fine, they'll see, there's moonlight. Nope, you need to make sure that pathways are lit, that if there's like an empty lot where people are parking that they can see, etc. And then I highly recommend insurance. Highly, highly, highly recommend insurance. Um, in a situation like this. I think Brightco has become my favorite recently because they cover things that literally nobody else covers. If there's someone that gets COVID, they will cover the wedding. Like, if either a mem— like, the bride or the groom gets COVID, they'll cover the wedding. Um, if the grandmother gets COVID and she's important and integral to the wedding and they won't— they want to postpone it until Grandma can be there, they'll cover the wedding. They also have cancellation insurance. Literally cancel for any reason, that's part of their cancellation insurance. They'll cover it. If the florist no-shows, they'll cover it. It's insane. And I think my favorite part about it is because it wasn't made by someone who's in insurance. It's made by someone who is in the jewelry industry, and they kept running into issues with jewelry insurance, and so he made his own. Then he decided to branch out to the event space, and they decided to interview hundreds of wedding planners and venues before even starting this. And so it's my favorite. They're my absolute favorite. I highly recommend checking them out. So, and that's a good place that you can get coverage for yourself if you want to. But in backyard scenarios, like, it's not the same thing to go through renter's insurance or homeowner's insurance. Sometimes people are like, oh, I'll just get it through them. It's not the same thing. They're not going to cover the same things. This one, the packages start— oh, did I knock it out? I didn't. Ha! Stinking microphone. Their packages start at $120. So for peace of mind, especially if it's on your own property. I can't— I cannot recommend that enough.
So I have— I just started 2024, late 2024-ish, maybe. Okay, maybe mid-2024. And now I'm at a place where, you know, I started, I was super nervous, and, you know, I've watched the videos, I've done the things, just decided not gonna take a class, not gonna train, just gonna start. And with a friend. So now I'm at a place where I have 15 couples and I'm kind of going crazy. Oh, it's all about— I think— and fun and awesome, but I am now feeling a sense of disorganization.
Yes.
Um, and the writing notes down during the calls, and you know, I've got HoneyBook and I'm trying to work with them, and I actually like schedule meetings with them to help me out.
Okay.
But I am still going crazy. So I am now at a place where I'm like, do I hit pause or do I implement a new system or try new things to just like, you know, get some stability going?
Yeah. What part feels crazy? What part feels chaotic? Is the notes? Is it the, the details are kind of swirling in your head? What part is that?
Yeah, I would say like, because I was handwriting notes for a while.
Yeah.
Now I'm like, dang, now I have a system. So I need time just to put the notes in the system while I'm still taking inquiries.
Okay. So I would say probably need a new system of sorts. I'm a pen to paper kind of gal too. So while I love tech, I'm a hand note person that I'm surrounded by handwritten notes. So, um, what I would do is I would have one main notepad that I would take my notes on. And after a meeting, I would tear it out, hole punch it, and stick it in the binder behind their name. So I would still have my paper trail there ready and available, but those were more for like, uh, hey, don't forget this detail. Hey, here's what I asked them to do next time. Um, so that's kind of how I handled the whole note-taking thing, because if I had to pull myself away from writing notes, I would have a hard— you know, I'll type it if I have to. But for me, writing it down, that's, that's, that's where my brain processes better. So if, if that's an option for you to have a big mega binder where you have all your couples in it, and then you put your notes in there, um, after every call. So that's, that's something that I consistently did that helped instead of importing the notes into the system or learning to take them in the system. But that's just extra work, right?
Yeah. It feels like extra work and then I'm not focused on the couples.
Yes. Yeah. So if you find that you're a pen-to-paper person, set yourself up for success with that. In fact, the binder I have right next to me used to be the binder that I put all my couples in because we don't have any couples at the moment, or at least I don't. And I've got like their names. Let me see if I can lift it up without knocking too many things over my desk. Like their names on different tabs. And any time I'd write a note, I'd put their notes behind their name.
Okay.
So that would be my literal, like my wedding planning Bible where I would just keep all the information. And then if there's anything I needed to transcribe over or have written up, I could do that at a later time. I'm sure there's some sort of AI that could help with that too, but my chicken scratch is probably— yeah, ain't gonna cut it. Yeah.
Okay. Thank you.
Yeah. How does that feel? Does that feel like that would be a good tool for you? Or are you looking for a little bit more guidance on how to be less scattered?
No, honestly, I, I like pen and paper and I feel confident about it. And there are certain ways that I do talk to my, you know, brides or whatever. They'll be like, Justine, I'm going crazy right now. Can we jump on a quick call? And if I can, sure, you know. And so that helps me. Like, I always have my notepad or I take out my phone. Yeah, I'll just take a quick note. I need us to bump up to the next service because I can't do this. No problem. Make a note, boom, boom, boom, bump them up, send this and that. But then I was getting overwhelmed with the thought of, okay, now I need to import it into another system.
No.
Yeah.
No. Yeah. If you, if you find that it's still working for you, don't feel like you have to go full tech.
Okay.
Um, in fact, I still like printing up, um, contracts sometimes and reading over them or like redlining things if I need to bring it to a client's attention, especially if something's a little dodgy looking, cause you'll find, you'll find some dodgy looking contracts. Probably somewhere in your career. Um, so no, I'm still definitely a paper girly even though there's so many tech options. I did— I even tried doing an iPad with an, uh, Apple Pencil to like write my notes there. Not the same.
Nope, nope. Yeah, I have one too. It's, it's not the same.
So yeah, are you a pen girly too where you have like specific pens that you like?
I am, and I only write with black pens, so it's like, that's another thing. It's, it's weird, but whatever. That's me.
So yeah, I'm not a gel pen girly. I love a good ballpoint, but it's got to glide well. Yes, if it's, if it's at all like choppy or anything, it's in the trash. I will not give it a second chance.
Yes, yes, for sure. So that's, that's also one of the things. And I know it's super like these minute details, but for the expo this weekend, I'm doing it at, it's at a Poughkeepsie mall. Okay, it's kind of in the neighborhood I grew up in. It's a small mall, so I thought that's a really good place to start. Um, and anytime I go there, I see someone I know. So it's like, that felt like home. Sorry for your background. And I'm still almost like, I feel like if I was around strangers, I would be panicking less. But because I'm going to be around people that I knew and grew up with, and then, oh, Justine, it's like, oh no, oh no, oh, oh Lord. Yeah, yeah, yeah, yeah.
I think that, I think that this is a scenario where I would use a fake it till you make it approach where it's just like, they don't know that I don't know what I'm doing. Okay. This is all mindset though, because you already have 15 couples, Justine. You, you are a wedding planner. You're doing it.
Okay.
You're already there. You're already planning weddings. There is no sort of like state of enlightenment that you have to achieve to be considered a wedding planner. You're already doing it. So you being there at the expo, it's just adding more people to your resume of wedding planning. It's not like you were trying to achieve it any further or any harder because it's already done.
Yeah.
Okay.
Okay.
Thank you. Thank you. Yeah, of course.
That's all we have for this week's episode, guys. If you enjoyed it, do me a favor, screenshot that episode and share it on socials.
Tag me in it.
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You can also let me know if you didn't enjoy it, but I'm probably not going to reshare that one. I hope you guys enjoy this week's episode, and we'll see you in the next one.
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