#10: How Dink and Dine Is Rethinking Eatertainment | Monica Challingsworth, Eustress and Demeter

Daniel Tsentsiper (00:00) All right, we're live. Monica, welcome to the show. How are you doing today? Monica Challingsworth (00:03) Thank you. Thanks for having me. I'm great. Daniel Tsentsiper (00:06) Super stoked to talk to you. It sounds like you have a lot of exciting things that you're working on recently, a lot of big projects, but we dive into what you're working on today and all these amazing grand releases, let's first learn more about you. We talked last week and I got a chance to just get the highlight reel of your career and your background in hospitality. But for some of my guests who don't know who you are, would you mind telling us a little about yourself and how you got to where you are today. Monica Challingsworth (00:33) Absolutely. Yes, though, my name is Monica Challingsworth and I own Eustress and Demeter, which is a restaurant consulting group. And we are also getting ready to open Dink and Dine Pickle Park in Mesa, Arizona. are on the, think we're 75 days out. So really exciting. Yeah, we've been working on that project for three and a half years now. So to be close to the finish line is really, really exciting. Daniel Tsentsiper (00:50) Nice. Wow. I'll definitely we'll talk more about the that three year process. I want to hear how did you so you didn't actually start with this is this is your first concept that you ran yourself right but before that correct me if I'm wrong you were working at ⁓ a ton of different brands you got being on the operations catering side of things you mind telling us a little bit about some of the earliest brands that you worked on and perhaps maybe how they were pivotal and in your trajectory. Monica Challingsworth (01:24) Absolutely. Yes. So my degree is in hospitality and ⁓ I went to college in Ohio and I moved out to California, I think like two days after I graduated and I was very excited to get into the hospitality space. But I, I, you know, was just out of college and wanted to have some fun. I, my, probably my favorite job was selling wine for summer. So a girlfriend of mine, her and I, she had this little convertible. we drove around selling some actually pretty terrible wine. We had to like take the bottle, dump it into an empty bottle, take out all the sediment and put it back. you know, it just kind of got me into, you know, going into restaurants and meeting the managers, meeting the owners. And I just continue to fall in love with the industry. And my first kind of real job outside of that was Season 52, which is owned by Darden restaurants. And Daniel Tsentsiper (02:02) Bye. Yeah. Monica Challingsworth (02:17) So I remember when I was interviewing with them, gosh, I think I was probably one of like 300 candidates, they said. And I really had no experience. I was right out of college and they were like, oh, I don't know, I don't know. Like we're really taking a risk on this girl. But our president at the time, was like, she was like a barnacle. Like she was so like claws in to this job. And I had never wanted something so. that I was so excited about the industry, so excited about working for Darden and I was doing like private event sales at the time. you know, growing up in Ohio and Pennsylvania, I didn't know that was a job. And I'm like, wait, this is perfect. So I plan parties for a living. I can network for a living and like still be in operations and the sales side. And that was what made me really, really love kind of this whole piece of it. And it was Daniel Tsentsiper (02:52) Okay. Monica Challingsworth (03:11) driving incremental revenue, ⁓ putting programs together, still in sales, still in leadership. And from there, I went to Bottega Louie, which was really cool. I'm not sure if you're familiar with that. Yeah, very much. I loved it. Loved it. same thing, it was all building these incremental revenue programs. So we started doing wedding cakes, our e-commerce program, catering. We were... Daniel Tsentsiper (03:21) Okay. Well, you worked, of course, yeah. You worked at some fun brands. ⁓ Maybe. Monica Challingsworth (03:36) I think one of the first three brands to work with Uber Eats when Uber Eats was doing these deployments where they would pick up a hundred lunch boxes from us and they would put Uber drivers all over the city and then turn on the platform. And it was kind of like this free for all that whoever could get these lunch boxes, they sold out within like 10 minutes and come to the cars to pick them up from the drivers and be on their way. It was just one of the coolest things. So. Daniel Tsentsiper (03:56) Wow. Monica Challingsworth (04:02) So with Bottega, I really started getting into, you know, how do we create programs that generate a ton of money for brands, but also is operationally feasible. I mean, granted our team when they're making 800 lunch boxes in the morning, you know, didn't totally love me. So took a while for us to really understand that piece and all be able to come together. And I was recruited to Lemonade by my mentor that I talk a lot about, Helen Lau. and I was brought onto Lemonade to build our catering programs. So that was, we went from 800,000 to 5.6 million in just a year and a half and just drop off catering alone. Yeah, we had an amazing team and we were growing and it was just, it was incredible. So with that catering was... Daniel Tsentsiper (04:40) in catering alone. Wow. Monica Challingsworth (04:50) really knew kind of in our space. so I had a couple groups reach out to me on LinkedIn to be like, how did you do this? Will you help us? But I was employed by Lemonade at the time. So I could only really give some friendly advice. And we were acquired by Modern Market. And when that happened, the whole Lemonade leadership team was let go. And I found myself like, what do I do? And I figured I'd go back and get another real job. you know, the next like six months or something. And so I reached back out to those companies and said, you know, I have no idea what I'm doing. I'm not a consultant. I don't like that word, but I can help you in the meantime. I'm bored senseless. So let's do it. And honestly, that's how Eustris started. Daniel Tsentsiper (05:33) Amazing. ⁓ It's kind of walked me through when you are thinking of, let's imagine we're working with a brand that doesn't have a catering program, right? That wants to, like you said, expand, diversify its revenue stream, right. And earn some more money. What would be kind of like the first step in, figuring out if a catering program is feasible for that brand. Monica Challingsworth (05:40) Mm-hmm. You know, it's all about the people at end of the day. So how aligned is the leadership team? Do they have the capacity to do it? I mean, even simple things of do you have enough storage space for packaging? there's factors that go with it. Like we have a brand we're working with now, which is kind of cool. Their CFO is the CFO who brought me into kind of my first restaurant groups and was my CFO at Lemonade back in the day. And it's been fun to kind of Daniel Tsentsiper (06:05) Right. Monica Challingsworth (06:22) see him in different size restaurants. And now he has a little passion project of just two smaller stores. And it's interesting how different like the other programs work as they these massive operations. had ton of people, tons of capacity. mean, everything, the resources for the right technology tools, the everything. And now this one, you know, they're small and they're hungry and they're growing, but they only really have you know, a couple of team members who work in the restaurant every single day, they have their operator, but you know, he is already pulled really thin. now we're talking into like outside resources. So there's new catering connections that started, which are basically like an outside sales team. You know, they don't have their own delivery drivers. So we've worked with Deliver That for years. So love bringing on all these other partners. you know, I think Daniel Tsentsiper (06:57) Yeah, for sure. Monica Challingsworth (07:14) over building this for, I don't know, whatever 12-ish years that now we really know like who the best partners are to help connect them. So if they're a smaller brand but they have the eagerness to do this and the willingness to kind of put in the work, then we love working with them and helping, you know, just put the right people in front of them. whether it is a little mom and pop or, you know, a massive operation, it all starts with the people. Daniel Tsentsiper (07:40) I agree. And we talked about this before. It's for you. You mentioned that the types of clients that you want to take on with Eustris and Demeter are not the ones that bring you the most money. You're looking for, you guys have been in the game for a while now and you respect your sanity. So you want to work with up and coming brands that are led by good people, right? maybe if my audience here to get some help, what would be the type of Monica Challingsworth (07:46) Mm-hmm. Daniel Tsentsiper (08:05) customer, operator that you would want to work is your maybe you can tell us about one of your favorite clients that you've had in the past. Monica Challingsworth (08:13) Absolutely. I'm a big gut feeling kind of person. So when I meet, it's usually the CFO, CEO who hire us. And when we sit down, it's kind of a couple of things I look for. Let's just say we go out to lunch and they are rude to our server, cut them off, or that tip. Or anything even remotely in that category, we won't take on the project. I'll respectfully finish the meeting, but there's no world that Daniel Tsentsiper (08:29) Yes. That's a flag. Monica Challingsworth (08:40) that we would want to work with them. Or even if they just have a really poor reputation when it comes to how they treat their teams. So if we go in and we meet their teams and everybody's just, Yeah, yeah, yeah. Or they're like, yeah, that's such a great way to put it. Like if they're terrified of a consultant coming in because they think they're gonna get in trouble or whatever, somebody's gonna find something or they're really defensive. Daniel Tsentsiper (08:50) on guard, you know, like scared. Monica Challingsworth (09:03) Like that just tells me that they're not ready for that. And I don't want to be the person who's making them uncomfortable. I'm not going to put my team in that. And it also tells me a lot about the leadership side. And if I know right out of the gate that we're never going to make this company happy, we could generate $5 million and they'll still find a way to, you know, whatever, be unhappy in some form or another. then I don't want to do that. just, feel like, we work really hard and our team are extremely hands-on. So we're like on the line with them. We're packing these boxes with them. We're going through that entire process. So if they're miserable, I mean, we left working under somebody for a reason and didn't want to go back to that because now we do have the freedom to kind of choose who those, who the people are that we want to work next to. And so. I think that it really is like, how do you feel when you're around them? Do you want to be in the trenches with them? And do you want to spend all of this time? there's definitely been very large companies with a lot of money that we've turned down and we've collectively agreed as a group, we have our kickoffs and we sit back and say, how do we feel about this? Like, do we feel good? Is this going to be something that we're all really excited to work on? Or do we feel like... you know, we're going to leave at the end of the day and be exhausted and nobody's happy. And, and we've definitely, on our side fired several brands because they're just not the right fit. but we've ended it really respectfully and we've still gone out and like had drinks and stuff with them as people, but from a business standpoint, we are just not a good fit. And that is totally okay. Daniel Tsentsiper (10:27) I loved it. I love that firing your customers, Like you, ⁓ as for us, a small company, at the beginning, you're trying to take on any opportunity that comes your way. But as you start to scale, you have more leverage and you start to notice that certain customers that you started working with at the beginning might not be taking you down the best path, right? And they're not fun to work with. I would much rather work with someone that I like and someone Monica Challingsworth (10:43) Yeah. Daniel Tsentsiper (11:08) treats me with respect and sees me as a partner rather than just, a tool to, to accomplish, X, Y, and Z. So I love your philosophy. I absolutely love your philosophy. And has there been, without going into some of the bad ones, what has been some of your favorite projects that you've taken on? And I'm also curious, like what types of initiatives do you, do you help businesses with? Is it catering? Is it marketing? what are some of your projects that you've done with clients in the past? Monica Challingsworth (11:30) Yeah, originally when we first started, it was all catering. So we built the catering program for Takaya for Tartine, which we spoke about. then, know, true food kitchen, they were all kind of in right before COVID. And as soon as COVID hit, then, you know, I mean, I remember like, you know, as a small business owner, totally panicking and being like, my gosh, what is going to happen? Like we have all these invoices open. Daniel Tsentsiper (11:40) Yeah, big fan. Monica Challingsworth (11:58) They can't pay them. They don't know what's going to happen. I got to pay my team, but I don't know what's going to happen. And I emailed all of them and I said, do not pay our invoice. Just hold. I have no idea what's going on. You have no idea what's going on. You need to pay your team members first. I'm going to talk to my team. I will figure it out. We are not going anywhere. So let's just like figure this out. And with all of them, we worked through like, okay, let's just let's slowly see where we need to shift. Obviously people aren't getting together in groups. So let's about third party. you know, True Food and Tartine and all these brands are not really doing like DoorDash and Uber Eats at the time, but we need to pivot and we need to meet people where they are. And so we looked at, do we do like the grocery kits? Do we do meal kits? How are we gonna continue to keep our teams, but still be able to make money? And so we just shifted all of the clients that we were with and in about probably two months then, You know, we all felt better. Everybody paid their bills and they said to you there like you were the only vendor that we had that didn't like grab on to us and be like, you need to pay me right now and all that stuff. so I, you know, I think that that ended up building a much stronger partnership. So then we did new projects with True later on. And then that team went to Wetzel's Pretzels. We got to work with Wetzel's Pretzels to build out their food truck program. So now we've done a lot in the food truck space or Lowry's, we built Lowry's at home, which are all of the prime rib meals shipped nationally. And that was a COVID project because they didn't want to let go of anybody in their teams and they didn't have to because we were generating more revenue that way. So, a lot of it's been how do we pivot, again, how do we work with the teams, the people? figure it out together, get in the trenches with them and make sure that whatever we're creating, wanna say is successful, but we had another really great barbecue brand out here with just the best leadership team. They were so fun, they were amazing. We got to the very end of the project and we're getting ready to launch this barbecue national shipping. And we looked at the numbers and I called the CEO and I'm like, guys, I... I actually don't think this is a good idea. know, after we get like co-packing and packaging and the price point we want to stay in and who our guest is, I'm like, and I was like losing so much sleep over it because we're like, how do we tell them that all this money they spent all this time, all this everything, that it just isn't a good business decision? And it was really because they were so happy, so happy. I couldn't believe it. were like, you know, Daniel Tsentsiper (14:27) Yeah, that's tough. Yeah, of course. Monica Challingsworth (14:35) This has just always been something we wanted to try and we did it. We accomplished it. We figured out, we answered every question we had. And now we know that it just isn't a good part of our business model. And this is great. Like we are not upset at all. This has been, this has been such a fun project. The money was not wasted because we didn't have time to do it. You guys did it and then figured out that at the end of the day, the numbers just don't make sense. And then we ended up doing like four more projects with them on different things. So. Daniel Tsentsiper (15:03) That's right. Monica Challingsworth (15:03) Yeah, so Daniel Tsentsiper (15:04) Yeah. Monica Challingsworth (15:04) I was of like, you know, like, oh my gosh, you're gonna kill us. We failed. So like, didn't fail. you know, that was our number. Daniel Tsentsiper (15:10) No. And, and I love that. I love that. That kind of reminds me, I took a class back in college. was like one of these entrepreneurship accelerator classes where you get together with other students that are working on ideas. And the professor said there's three outcomes of this class, right? The first is, is you decide I'm going to keep, keep working on my idea. I'm going to keep going. I got the, the steam to, to keep pushing forward. The second was to, to pivot. Monica Challingsworth (15:24) Mm-hmm. Daniel Tsentsiper (15:39) Right. If you learned something along the way and you realize that, your business model is not viable or there's, there isn't the pain right in the market, then you should probably pivot. And the third one that always caught me by surprise is he said, you can also decide to quit and you can decide to stop, me, didn't really make sense. I'm the type of person that you going at all costs, but stepping back from something and realizing that, Hey, you know, maybe this isn't the right, have for me. I think it's also a very there's the I don't see it as quitting, I see it as learning. So you learn along the way. And I'm sure that with the experience that you got with that one customer, you now understand like all the intricacies of co packing how difficult it is. And, you know, you can and you can you can go to another customer and actually kind of show them the numbers and be like, hey, in order for this to make sense, all of these things need to be true. So I love that. Monica Challingsworth (16:07) Yeah. Yeah. Absolutely. You know, and I love the concept of like failing fast. I believe, I really believe in that this ⁓ is, guess, Dink and Dine is probably my fourth business now. I've learned on early ones too. And I have, I'm a very non-ego driven person. like failure, I don't look at it as failure. So I am like, okay, if we're going to fail, fail fast. Daniel Tsentsiper (16:33) Absolutely. Monica Challingsworth (16:52) know exactly how much money you can put into something before it's like, it's not going to get over the, it's not going get over the finish line. Or if, you truly can't be, you know, the best in the industry and you don't have billions of dollars to, you know, somehow get there, you just, you fail fast and it is a great thing. It's a very powerful thing. Daniel Tsentsiper (17:07) You should keep going, yeah. It is. And I think that's a, that's a good transition for us to talk about Dink and Dine. So three years, right? What, what was that journey like? You know, what was, tell me about the inception of the idea and what you and your team have been working on these last couple of years. Monica Challingsworth (17:26) Yes, so another COVID baby. So my business partner, Dave and I were speaking. I had COVID at the time and I was all cranky and sassy and I couldn't leave my house. And we were talking about the projects we were working on and how challenging it was to sometimes fix the problems as opposed to creating something right the first time. we were you know, part of it was like, gosh, wouldn't it be nice to like just do it the first time? And then, you know, we're thinking of, and then we're also talking about all the things that we miss and, being able to just be out and active. And Dave is a big pickleball tennis guy. And I had actually never played at the time. I do more now, but I was like, pickleball. Yeah, I've heard of it. That sounds fun. And I'm like, gosh, and even my, like my brother and his kids, like, I'm like, we're always looking for something fun to do, but you we want to have some drinks and have some food and hang out and run around and not just like sit at a bar, sit at a restaurant. And so we started really thinking through what it is that we personally were looking for and the people around us that we knew would be looking for. And we just kind of started talking about this idea of pickleball mixed in with food and beverage. and, know, Dink and Dine was really born from that. team, call ourselves the entertainment dream team because everybody are actual operators and we've all worked together on different projects in the past. So our CFO is one of the largest CFOs for big, big restaurant brands. He brought me my first, I would say probably five or six clients on the Eustris side. So him and I, again, been in the trenches together. Kelly, our chef owner. He owns Bruxy or did own, sold at Bruxy's Chicken and Waffles and him and I worked on projects and my Eustris team came over to help build everything from the operation side, marketing side. And so as we went on this journey, we were like, you know what, we are actually operators. We know how to do this. We know how to do this the right way, which is why it's taken so long because we wanted to have a very strong foundation. Daniel Tsentsiper (19:13) Big fan. Monica Challingsworth (19:34) in place for us to continue to grow and scale from there. And there's been competitors of ours who are, you real estate people who don't know anything about food and beverage. And that's their business model. And we've had others who were, kind of neck and neck with us in growth. And they've since disappeared because they raised too much money too quickly, got over their stuff too quickly and think about kind of all of the, realizations that need to happen in order to, do this slow and steady and not have a shaky foundation. So you have something very strong to grow from. Daniel Tsentsiper (20:08) Yeah, I think that's it. I like what you just said there, right? You got to have a strong foundation because if you're taking a, you know, what every single time I go to like one of these massive like pickleball arenas, I see it as like a real estate play, right? You're, you're buying out a massive factory or you're buying out a used to be like a Sears or a Bloomingdale's and you're converting it into a pickleball arena. But then if you're just adding food on top of it, have some drinks and food and you're not actually putting in like thought into the menu, into the experience, it feels very artificial, right? So are you thinking about in terms of the experience? do you envision if I was to walk into a dink and dine, what would I be looking at, right? Would I be coming in and would I be able to go and just only get food and drinks or do I have to, Monica Challingsworth (20:44) Yeah. ⁓ Daniel Tsentsiper (20:58) play some games in order to the lounge and all that good stuff. Like what is the, I'm trying to imagine what the experience would be like. Monica Challingsworth (21:02) No way. So we are all about community, people having fun. So no, I mean, if you just want to come in and listen to live music, we're dog friendly, which is my favorite part. So if you want to bring your dog, come and sit in the park, listen to music and not spend any money, you are just as welcome as the person who is there show up in the morning and play a game of pickleball, have lunch, play some games in the park, go to happy hour, play another game of pickleball and then. Daniel Tsentsiper (21:14) Nice. Monica Challingsworth (21:30) a private event with us. So we want everybody to feel welcome. So we're not doing memberships. we do have a pretty amazing loyalty platform and program that we've built because we want to encourage frequency. But, I don't want it to feel like it's a country club where, you know, Sue is paying $200 a month and, you know, Mark isn't paying anything and then he can't get on the courts and Daniel Tsentsiper (21:46) Right. Interesting. Monica Challingsworth (21:54) So we don't want that. We want everybody to feel welcome and just have a blast. So whether you're, you you've never played or you are a seasoned pickleball player, our courts, which are really amazing. mean, it's cost us a lot of money to build them. They actually like state of the art courts. And then we have like drone cameras to for playbacks. have computers signing in. It's like, it's all really, really cool. And our, we have two indoor buildings. So our Daniel Tsentsiper (22:15) Wow. Monica Challingsworth (22:22) main pickleball building has eight indoor courts and a bar restaurant in the middle of it. And then it's roll up doors onto our park. And then we have another building, which is called the clubhouse that has two indoor courts, three private dining rooms, a lounge, and that opens up on the other side, like kind of behind the stage into the park. So everything is integrated and fun. And we have different price points, different menu options, different. food concepts kind of throughout the park, lots of bars. It's just a fun, safe place to be. Daniel Tsentsiper (22:57) was with a guest a couple of days ago talking about, she doesn't like the concept of third spaces, but she calls it an everyday affair, right? ⁓ I feel like we, we don't have a lot of places these days other than, maybe the gym or church. If you go to church where you can just come together and it's, you you bring the community, as you said, right. And you can just hang out you know, have a good time. Monica Challingsworth (23:05) That's fun. Daniel Tsentsiper (23:21) Where is your first location is in Arizona, right? Monica Challingsworth (23:25) Yes, Mesa, Arizona. Yeah, will probably do several in Arizona. ⁓ been in talks with several California locations, but California's very hard. mean, ⁓ yeah. Yeah, and we're large. We're looking for like three acres. So it's a lot of land ⁓ and what we had assumed and what our competitors who ⁓ Daniel Tsentsiper (23:27) You say Arizona. really stuff. We both from California, we know. Yeah. Wow. Monica Challingsworth (23:53) competing, found is the ground up builds are just astronomical. The time that it takes. So we are looking for a retrofit, but like you said, ⁓ about these like big box stores, we won't go into those because there's no park space. And then it's just, it's loud pickleball gymnasium and that's not us. So we are selective and where we're going. and, and staying true to our brand and our concept is. Daniel Tsentsiper (24:08) Right. I see. Monica Challingsworth (24:20) very important and so it might take us a little bit longer to get to 10 units, but we're gonna do it right and we're gonna be thoughtful as we do. But Mesa will be the first one, so we'll find out in a couple months. Daniel Tsentsiper (24:34) Amazing, going live, the grand opening is in 75 days. What are you doing to prepare for that? And am I invited? That's the question. Monica Challingsworth (24:42) Well, I'll be out there next week. Yeah, of course, everybody is. Yeah. So, well, you know, and it's a, it's going to be summertime in Arizona. So we kind of have like a phased opening. our two indoor buildings, like I mentioned, will be opening and then the park, like if somebody still wanted to play on our outdoor courts, they can. We have three outdoor courts, but it's going to be, you know, 115 degrees in Arizona. So then October 11th is the date right now. I hope it doesn't change, but that's kind of what we're planning is now the full, like the park is open and we have, it's called the Dink Dive, which is like a outdoor smoker barbecue concept that will be going. mean, everything will be engaged throughout the park. So that's the date I'm most looking forward to. Like my family is coming out and my dad's coming out from Pennsylvania, everybody from California, we're gonna get a big house and. And I want to be there to actually enjoy that day and not be working it. I'm going to be a guest and having fun and bringing our new home. Absolutely. Yes. Yeah. My family worked very hard to support me over the last three and a half years emotionally and mentally with all this. So I want to enjoy it with them and just have fun. Daniel Tsentsiper (25:41) All the fruits of your labor, just enjoy it. Amazing. Amazing. Amazing. Well, Monica, you've had an amazing career in hospitality. I'm sure you've helped hundreds and hundreds of operators and staff members and work that you've done on the consulting side and now with your own concept is fantastic. And I just want to say thank you for all the hard work you've done a difference in this industry. And I think now that you're entering this new chapter, your fourth business, what I think is a very difficult concept to execute well. I wish you the best of luck and where can our audience find you? Where can we find you how can we this movement that you're starting? Monica Challingsworth (26:25) Thank you. Absolutely. So I am still doing Eustress Indimeter. I don't think I will ever give that up. It is my baby. I love it. So EustressIndimeter.com. I'm also on LinkedIn and anybody can find me there or Dink and Dine Pickle Park. And again, we're opening in Mesa, Arizona this coming summer. Daniel Tsentsiper (26:47) Thank you so much Monica. Have a good rest of your day. Bye bye. Monica Challingsworth (26:49) Thank you. You too.