#31: Mid-Day Squares - Creating fans and not customers, building a company as a family, and the power of social media

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grown Up. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome to this episode with the co founders of midday squares. 1. When I came across Nick, Leslie and Jake of Midday Squares, I was immediately drawn in. They have a massive ambition to disrupt chocolate and to build a hundred million dollar business. Then I saw all their videos on Instagram and LinkedIn and I saw they're both building a startup and also kind of creating like a reality TV show at the same time. They want to create fans, not customers. That's what they told me to make it even more interesting. They're not just co founders, they're family. Nick and Leslie are husband and wife and Jake is Leslie's brother. They see a therapist every week, Dr. Gavin, to make sure they stay on track with their personal and their co founder relationships. So I hope you could see why I jumped on a plane to Montreal to go see them in their podcast studio to record this episode. We cover a lot of ground here, including how they got the idea to build a functional chocolate company and why chocolate even needs disrupting. They talk about why they build in public and use social media so much and they also talk about how the business has impacted their personal relationships. Both Nick and Leslie's the husband and wife and Jake and his girlfriend Melissa. Melissa, by the way, actually joins us in the podcast studio. They talk about how much they get out of their therapy with Dr. Gavin and all of those insights are useful for all co founders, even if you're not husband and wife or brother and sister. Now, Leslie couldn't join us at the start, so she comes in in the middle. It's kind of a circus and super fun. Leslie, Jake and Nick are also just super honest about the struggle of entrepreneurship and how they cope with it. This is an incredibly fun and rich discussion. So please enjoy my conversation with with Leslie, Jake and Nick, the co founders of Midday Squares.

Hello everybody. Usually I say at this moment, welcome to the podcast. But actually I'm gonna say, first of all, welcome to MeToo Montreal. Why am I in Montreal? Because I'm here visiting this incredible company, Midday Squares, with these incredible entrepreneurs. And I'm so excited for you to get to know today. So welcome to the podcast, Jake, Carl's and welcome to the podcast, Nick Saltarelli. We're hoping that the third co founder Will also make an appearance. Leslie Carls. But in the meantime, welcome to the podcast. Thanks for joining me in your own podcast studio here in Montreal.

Are you having fun?

I'm having fun. So much. Can you tell?

It's exciting to see you. We've known each other for months and we got to hang once in New York. We had dinner together and that was so fun. Obviously Nick and Leslie didn't get to experience that, but when you told me you were coming here, I was like, this is going to be epic.

I had a great time last night. So I had the privilege of having dinner with you last night. I got intimacy. I didn't have Jake, I didn't have Les. It was just you and I.

So he lasted long. Hey, you stayed late, he stayed out late. We stayed out late because he doesn't do stay.

When I'm stimulated, I could be there forever.

That makes me so happy. And I feel the same way. And before we get too much further, I want to ask maybe both of you to answer. Take me back to the time maybe. Nick, I'll start with you. Take me back to the time when where you were starting the company and paint the picture of what was going on and how you decided to start this company. We wanted to hear about what the history of midday scores and what midday squares is.

Okay, so we gotta go back to 2017. You gotta go back to me being 29 at that point in time. Cause I'm 33 and I've been doing entrepreneurship like I started at like 16, wanting to play with it. 19, I got really serious about it and it's been a grind since then. And so just to set the stage, you gotta remember, I'm a human that's swung a lot of times, missed a lot of times, had a bit of success. And here we are, my wife and I, who's not even my wife at the time. Two people that had found each other, that were motivated by each other's entrepreneurial spirit, that wanted to do something together that was like the clearest piece. So when people always ask, how did Midday Squares start? It didn't start as midday Squares. It started with two people deciding that they wanted to continue working together. And I say continue because I had invested in a clothing company she was working in. I had sold out of a company that I was part of, had a two year non compete. And so I was in a discovery space. And basically when I had made the investment in her clothing company, we also decided that I was going to help her operationally. So we had A really good foundation of getting to work with each other. Fast forward when that business didn't work out. We then spent basically all of 2016 figuring out what we wanted to do. And then going into 2017, not only did we get married, but we decided that.

Big transition.

Yeah, huge transition. We decided that Midday Squares was this thing that we wanted to bring to fruition, and it had existed, but we knew we wanted to be in the food business. We felt like this was a real thing. And so we spent 2017. I like the word. Plotting. Plotting how we were going to make this happen.

And.

And that takes us to Jake, who ended up joining the company in early 2018. He was out there building a clothing company, and we had seen him do magic when it came to community building. And so that was really the catalyst for three people coming together and us decided that we wanted to take this on by charge. And I say this story in this way, why do I paint the picture is that it's important for the listener to understand that these were three people that have been trying entrepreneurship for a long time and that we didn't come together because we were. We were family members. We came together because we felt that three of us had the skill set to do everything required at that time to launch this business. We didn't need to rely on a single soul. And that. That was an important learning for me, at least in my past career.

Wait, so I want to double click on a lot of that. Well, Nick, so you married Leslie, and then you said, you know, you wanted to build. You knew you were going to build Midday Squares. What is Middle Day Squares? Because my understanding is that she was making chocolate in the kitchen and you were all like, eureka, we're going to make chocolate. This is not a normal thing. My friends don't make chocolate in the kitchen. Okay.

Yeah. I think if Les was here, she would tell you she has more certificates than any person on the planet. I mean, she had tried everything to the point where she wanted to be a chef. At one point in her life, she got very into the culinary scene in Montreal. She was going to go to Coram Bleu. And. And I think we called the period of when we were working together in a creative space our little renaissance. And during that period, she was in the kitchen losing it in plant based, like, I'm talking everything. Not just desserts, not just everything. She was getting really good at it. Data drove everything for us. And in early 2017, I got a report that really was like a punch in the face where it Was so obvious that there was this real chocolate movement that was growing. And I had not seen a growth curve like that in a long time. And plant based protein was still on a tear. You'd have to be living under a rock at that point to know that plant based protein wasn't on a tear.

Right.

It was in the media, it was everywhere. There was headlines, there was companies going public on nothing but an idea. Yeah, it felt like the Internet, but in like the food right space. Felt like 2000 in the food space. And so it was like that's where the eureka moment came. And it wasn't the typical eureka moment where it was like, oh, I have a eureka moment. Let's go make a product. It was a eureka moment that was, holy crap, there's a massive market here and there's a product that we have that fits right into this white space. Let's go make that a reality.

Let's go make that a reality. So the two of you are making it a reality. And then Jake, Leslie's brother. Right. How do you get involved with these two?

So I was throwing parties on college campuses. I love humans and I always wanted the freedom to do something different. And I wasn't an academic. I did study to be an actuary, actually. And what's funny is I just.

An actuarial.

An actuarial, yeah. So basically someone that does statistics and math. And I didn't do it for me, I was doing it for other people to show the world that I could do it. And I think that, again, that's not being authentic to myself. And I was struggling inside, internally. I was having tremendous difficulties at college. I was trying to, like, escape in different things.

And.

And I knew that I couldn't do the statistics. I just couldn't. It wasn't for me. When you don't love something, you're not willing to go that 150%, which to be an actuary, you need to know math and stats. And when I graduated, I decided to launch a business. That was the first thing. I couldn't get a job. So I decided to launch this business. And it was a clothing business. And what it turned out to be was, first it was clothing, then it was candles or, sorry, candles first, then clothing. And the kicker was, was I knew that storytelling was really important. I used Snapchat at the time. Huge. It was. It was on its fire trend right at that moment. And I basically took and I said, how do I share the stories of college kids? Because they want to share. They want us talk. You know, and they're A lot of the time they're quiet, actually, and they're scared of what people think of them. So I said, what if I did it as a platform? And then I threw parties that would bring the community together and then I would sell the clothing as a way to represent it. Cool thing was everyone was wearing the clothing. Everyone was like this. This person's like. They're like, this guy's the queen, you know, on campus, the king on campus. And I really wasn't, though, because from an operational standpoint, I was struggling tremendous. Again, playing not to my skill. My skill was more community building. But running a business, you have to do accounting, you have legal, you have all this stuff. And I was struggling. So I went to people around me and I went to Nick and I was like, can you help me with this? You know, and we would. We would, you know, play hockey, like ping pong, rally with each other about this. And. And they approached me in July 2018, and this is when I was kind of burnt. I was burning out. I was burning out from the college, partying, all that stuff and building the stuff. But they said, we have this great product, chocolate product. We have data that's driven, it's built, it's commercialized, it's ready to go. We need a third piece to this business where we've watched you over the last two and a half years enjoy building the community of your business, but you had trouble with the actual operations. We are now gonna be the operational engine. All you need to do is what you were great at in that business, but now apply it to this business. Very similar front facing. Do all that, the community, the loudness, that storytelling. And I looked at them at first for. For like two, three weeks at least, and kept rejecting because I was like, I'm not a foodie at heart. And again, doing something that's not authentic is dangerous. Just like I did with actuarial science. I didn't love it. I didn't want to be part of it. But then I started going to the grocery store and I started going through the aisle. There's 40,000 products on average in a major supermarket. 30 to 40,000. And I said to myself, not many connect with me. Nothing really, like, is touching my heart and saying, like, I'm obsessed with this product. I'm obsessed with this brand. And then I was thinking of the other industries like cosmetics, beauty, fashion. They had communities, they had people that were customer obsessed. So then I said to Nick and Leslie, I said, oh, my God, what if we built a community that's built in all those other industries that create this massive obsession of fandom in the food space. And that's when it all clicked in my head. It was full circle. It was like, okay, I'm good at that part. I now actually have a business running behind me, which I do like the product a lot. They're great entrepreneurs. And that's when we joined the company.

I love what you're saying and I actually want to talk about that, about the sort of the co founder relationship, because, you know, well, I just want to lay this out because I want to talk about each of these things. So Nick, you and Les are married and then Jake, you and Les are siblings. So that's a whole interesting dynamic. But just on the topic of co founders, because my listeners are always thinking about, should I co founder? How do I deal with my co founder? What do you think is the secret? I'm going to ask you first Nick, and then you, Jake, what are the secrets that you have of your strong co founder relationship?

So for sure, very defined understanding of your own strengths. Very defined is really, really important because the partnership is supposed to be that. A partnership of where you're trying to make a Lego part and you need the pieces to make the part that you do. And if you don't attract the right pieces, then you're just not going to make the part. So that's one. The number two is this incredible ability to get into a space to be able to have safe, hard conversations. Because what will happen during. I've been through three partnerships. This is the healthiest one I've ever been part of. You go through a pressure cooker and anxiety and fear manifest as anger and blame game and pointing fingers. And it creates a very ugly. It creates a very ugly person when they're in that experience. And what will happen is, is that if you are not in safe places, figuring out how to communicate that you're scared or anxious or any of these things, you end up imploding on each other. And that's really, really important for me. So there was a defined conversation that we had before the partnership. It was like, hey, this is how it's going to go. These are the expectations of each other. And we're gonna commit to seeing a coach and therapist every single week. Whether it's good, bad, ugly, doesn't matter, we show up. So even if like, hey, the partnership's hunky dory, everything's great, still show up. Everything's shit. Show up. Like, it's just It's a muscle that needs to be going there and then you gotta sprinkle out ego death in there. Like, you have to. I mean, you just have to. To the point where I always talk about this, I've been asked a question before, like, is it. Does it ever bother you that your co founder's out and about and building and doing his brand or stuff like that? And we've had this conversation before, too. It's like you have to be so dialed into what your internal goal is and then where ego would come into play. And this is what I speak to other founders, especially if you're in a situation where one founder is really on the road and getting everything. The attention of it is that if you trust that human. So it always stems back to trust is the most important. Then you know that the bigger celebrity they become, the bigger your product or brand will become. Regardless if it's Midday Squares or Jake Carl's, regardless if it's Nick Saltarelli or Midday Squares or Leslie Carl's Midday Squares. So if you take that approach of like, hey, we're going to have defined roles, we're going to see a therapist, and we're going to reduce the amount of ego that we have amongst each other, because ego is a real thing. I think you succeed.

I love that. Jake, what do you want to add? And also, Jake, you might want to speak to the. I just saw a LinkedIn post that you put about, like, some of the principles that you create in your partnership. Additional principles.

Yeah, I think I agree what he said. There's just trust is a really big one. Trust into doing what you got to do. I think you still need an ego. Any entrepreneur out there has to have an ego, because to have that type of ambition or the type of craziness that people find that you're doing something so different, it has to be in your head that it's okay. Right. I think what's interesting about what he said is we're in an era right now. It's different than ever before because we have platforms like crazy. We have people addicted to entertainment or education through police platforms is personal branding is the most important thing than it's ever been in the past. Used to just be for, you know, Hollywood politicians, people like that. Now personal branding is for every career, every person, everyone. And whether you're a banker, whether you're working at a cinema. But I think that it's not for everyone to go out there and be loud, crazy, wild, be the front attention. But in a partnership, it's necessary, I think now for everyone to try to figure out their own branding and have individuality as long as they have also have the brand. If you don't have that, it's gonna be very hard to grow in today's world. So when I'm out there loud and crazy and wild, yes, I'm getting a lot of it. I'm getting the radio, the tv, all that stuff while they're digging deep in the operations. But then I think about it, and people have asked me the same question that you did about, well, what do you. You're doing this, and you get to do the fun stuff, but your partners are grinding and doing the, you know, what I call the not fun stuff. That's my opinion. And I say to them, okay, let's take that as an example. But then let's go back and say, okay, I spoke to a group of 200 people yesterday. Two retailers came out of it. If we don't have those retailers, then that their operation can't get to work to keep the. Keep the factory going. So it's like you need both. The problem is, is if you have that ego that he was talking about earlier, it will get in the way because the spotlight shows fun, it shows energy, it shows the excitement when there's stress happening. And then it would create this animosity together, and it would actually defeat the partnership, because then this person would be like, well, why the hell are you getting mad? I'm trying to build out this whole thing. And then they're like, well, we're not getting that fun. So I think we've balanced it very well in our partnership. But that's through the therapy. That's through understanding who we are as individuals and not getting angry on certain things and not getting caught up in all this noise out there. You know, people try to hit you off your game, and we get it a lot because we're loud. And what happens is when I hear things like that, when someone asks you a question, I initially, right away, I'm on defense, which is not the right way. It's more like I want to inform, which is a better way. But when it comes back to everything, Trust, communication and the ability to have defined roles. Yeah, very defined.

Yeah, very defined. And actually, I do want to also set a little more context, because people are like, what do you mean by crazy? So I want to also talk about how you differentiate yourselves and how unusual it is that you're launching a product, really, but you're also launching the community. So just to clarify, Nick and les are co. CEOs, and you're focused on operations, and you have your own roles. Inside of that, you're the rainmaker. Right. If I'm not mistaken. And so you're the rainmaker. Jay, can you talk about.

Look who's coming in.

Oh, are we having a guest coming on?

Look who's coming in.

Oh, my gosh, is she coming?

Yay.

Les is here. We have our co CEO here. Hello, everyone.

Amazing. We got good news from Mike. He tried FaceTiming us.

What happened?

I don't know. I couldn't answer.

Well, that's a call. Right now.

Let's do a live.

Do it live. Yes, Mike Fatter. No, Mike Scavuzzo.

I know it is.

Well, how do you know?

I know. Let's take a bet before it happens.

Wait, are we Kroger back on? Okay, we have an inter. We have an interruption.

A legit breaking news alert.

Breaking news.

So we have a breaking news alert. Okay, we have no idea what it is.

Wait, wait, wait. Mike, we are literally in the middle of recording a podcast.

It better be.

This is a fire podcast. This is her podcast, not our.

This better be good.

And Les was like, Mike called us for something, so she's like, you know what? Let's get it on the show. Well, Mike said that, so I got you. Okay, Jason, I got you on the recorder.

This is the big reveal.

Tell us, Mike.

We're going national in Target.

Yeah. Ole, ole, ole, ole, ole, ole, ole, ole, ole, ole. All day.

All day. Okay, Mike, we love you. We love you after. We'll see you soon.

That's pretty wild. First of all, the reason why that's so wild is because Target does not usually take a new brand nationally, so they like to test it into stores.

Wow.

When you go national, it is extremely rare in food and beverage. Extremely rare.

National in Canada.

No.

U.S. target closed in Canada years ago.

You're in Midday Squares. Okay, we only fuck national.

I got.

I got that.

Yeah, we fuck national. Stop the party.

Oh, my gosh.

Party's just getting started.

I see that. Everyone, go look for Midday Squares in your Target. In your local Target. It's happening now in October, right?

October. October 2022.

It shows out in August.

Let's just say October.

Wow. Amazing. Okay, so back to what we were talking about. First of all, congratulations. That's amazing. And isn't that so true of the ups and downs of the journey? On the one hand, it's like, everything sucks because of these reasons, but I'm.

Like, oh, my God.

Exactly.

It's a paradox, Alyssa.

You know, it's crazy. I was reading something from this guy, Adam Merkel, I don't know the author, phenomenal writer. And he wrote in his book about. I think it was Adam Merkel, I can't remember, so don't quote me on that, actually. But he wrote, someone wrote in the book, and I was reading it, it said it was about burnout. And he said that the moment you stop enjoying certain milestones and you can't feel it inside is the moment you are burnt out. It means that your neurons can't register, you cannot accept, experience it. And I was going through that recently, where wins would happen. I think they called me one time for Costco. We went to Costco Canada in January and they FaceTimed me and I was away, and I actually didn't even feel the moment. And Costco is a dream. It's an absolute dream to be in. It's a phenomenal partner. Target is a phenomenal partner, and that's a dream come true, too. So I think it's important to take a second. For anyone listening that goes through that, just be aware when the second you stop and join those, those wins, how big or small they are, is a scary moment that you need to take back a step back and say, what's going on?

So important.

So I want to know, how did you guys truly feel in this moment? I want the truth, Les. We'll start with be honest. Be honest.

I felt good. I definitely felt fired up, but I think I'm very tired. Like, I'm in a point in my life right now. I guess the last couple of days, I'm feeling very exhausted just from the long hours. So I'm really fired up about it. But I think for me, on my journey of entrepreneurship, what I've really been focusing on is not getting caught in the hype, because the hype makes the lows. Like, shooting myself really high makes the lows really low for me. So for me, I like to live in the middle. Like, that's something I've learned over the last four years. Is as for myself, what works for me is not to live in the highs and the lows of the business, but to live in the middle, because the middle allows me to stay the most level headed and it allows the hard moments to not be as hard. So I'm really fired up about it, but I'm not. Like, adrenaline is just spiked. Like, I feel like I did some sort of drugs. You know what I mean? I'm fired up and I'm good, but I'm ready to continue tackling the everyday. Yeah, that's how I feel about it.

I felt one, I was worried about not getting the national just because, you know, I want that volume really, really bad coming through the door. And. And then two was when we went and rocked Target recently in la. It's really the set that they've built for where we're going into is shocking that like Midday Square started in 2018, the fact that it's going to be national and Target is a really big deal. Third biggest retailer. Yeah.

Well, that's why I was saying the same thing about watching Walmart leave yesterday. Even Walmart 9, Walmart Canada, nine pallets leaving. I mean, it's incredible, right?

Just to be clear, for those of you on my podcast, we're filming this whole thing and we're. We just announced this news live on this podcast. This is all real. And Les really was, I think lying down and now she just came in. This is all happening now. Jake, tell us about the strategy of building in public.

Oh, I love building in public. You know, there's a lot of great leaders out there that do it more and more recently. But in 2018, August, before coming on to Midday Squares, I showed a slide to Nick and Leslie that had the ratings from Keeping up with the Kardashians. Great, great drama in there. Great show that people had a community around. Actually Shark Tank, where I found that the celebritization of entrepreneurship was happening live. Like chefs were getting celebritized in like 2005, but entrepreneurs with Shark Tank, which are great shows to inspire more entrepreneurs, they're dragons. Then there's ones in the UK all over were inspiring that. And then you had Elon Musk as a founder who was really loud and bold in who he believed, what he was expressing it all the time, whether people liked it or not, it was still building the Tesla brand and SpaceX and et cetera.

So in public, I would say, I would argue Tesla and SpaceX have been built in public.

Public and being true to who he is. And we have a live call that is really bad. So I think that I showed that slide. I said, if you combine these three things, you really set yourself apart by basically creating something that we like to call fandom, not just customers. And I said to you earlier today, and what it meant was we were going to create a reality show on entrepreneurship show, the Good, the Bad, the Ugly, but really take the raw format of it and actually give people a view on what it is. To build a business, whether it goes from zero to 100 million to a billion to failure, wherever that is, but actually showing the good, the bad, the ugly. And what that did was it separated us from completely all the food companies and beverage companies in that grocery store. That was the first thing it did. So naturally, when you sell a product, you don't see just the chocolate bar, which is a phenomenal product, but you now see the humans. You see the story, you see the emotions, the journey, and you actually could partake in it and be on that roller coaster up and down when you want to. So you strap in and you strap out. And I think that what's exciting about it is when we did that in 2018, there wasn't a lot of brands doing it. Now, if you just go on LinkedIn, I could promise you go on it right now, you will see brands sharing that journey more than ever before and going really behind that curtain. And it's exciting because now I know a lot more about, instead of being 10 products out of that 40,000, now I maybe know 500. Big difference. So that was really what building allowed has done for us. It's allowed us to get out there and people to get to know who we are as individuals and our team characters.

Yep. And you expose so much. And actually, I'm going to play now a clip from one of your podcasts. And Les, I'm going to ask you to respond to this. And then Jake probably you. So here is the clip.

Just 20 minutes ago, we weren't gonna make this podcast.

What happened? Take the audience through what happened.

So this morning we show up 8am to record the show. Jake's here. I roll in, you know, Jake, and I start chit chatting, you know, and he tells me that last night he had a good cry. I asked him what's going on. He just said, you know, the transition's really hard for me, you know, from the two square to the one square, where we're getting hit from from all angles. And last night I was in the Facebook DMs, and there's a lot of negativity. And then that triggered me, because what's the negativity? Well, we're gonna get into that, but I think what's really important to know is, like, we're all going through really hard times right now. You know, we're all feeling beat to the ground, demoralized and depressed.

Slightly depressed, yeah. That's the downside. I mean, one thing about entrepreneurship is, like, you get the great news, but on the other Side, as you just said, you're feeling exhaust. So what's that? What was going on with you when you were sort of sharing that? Can you remember? And how is that connected today?

Yeah, I think, you know, it's, it's generally, I think the, the, the business has so many different stages and moments, and you're just showing up and giving it, putting your best foot forward every single day. Right. The idea is, how can we continue to build this, this company, make it viable, sell really good product and build a community around it. And so when you get backlash, you put yourself out there, you do open yourself up for opinions and people's feedback, which is part of it. But it's still never easy to hear things that are not true. And the reality is, and I think Elon Musk actually said, this is be who you want to be, because people are going to make the judgments anyway.

Right.

Or so for us, it's like people are never going to see us the way we want them to see us. People are never going to interpret things the way we want them to. People will make their own ideas and stories of why we did things or what we're saying. And even when talk about the storytelling, I mean, a lot of times people think that it's staged. You know, we'll hear that a lot. It's like, did you guys stage that? It's like, no, that was a real therapy session, like you said. Yeah, 10 minutes ago, we had a live call and I was staged. That's it. Nothing was staged. Right. You see it, you're here, you're seeing everything is filmed. So people are always going to interpret things the way they want. That doesn't mean that it's not going to hurt us. We're human, we have feelings. But I think when it goes to, you know, building in public and why we really took that path, I mean, Tad, onto what Jake said is, historically, stories have been the most powerful thing to exist. I mean, so many things are based off of stories. Right. And I don't need to get into those things today. But storytelling is powerful and it creates a connection. And I think that's what we've done with Midday Square is we've really created a connection with our customers. And Jake likes to call it that fan base, because they are invested more than just the product. They get to see what the journey actually is. And I think you and I touched on this briefly last night, which is a lot of people, when they see entrepreneurship, it's romanticized. Oh, I'm a founder. I'm an entrepreneur. It's not glamorous, you know, and most of the time it doesn't work out. Right. A 1% or less works out. So I think the beauty of what we can offer the people is showing them that we went for this not knowing what was going to happen. And we are showing you as we build it, you know, what is happening in real time. And I think it gives a better idea of what entrepreneurship is instead of what's actually out there. You know, I listen to a lot of podcasts or I read a lot of stories and it's like, oh, I mortgaged my house and I'm worth $100 million. That's not the reality. Right. There's so much uncertainty in the journey. So I think it's really powerful showing the story. That being said, it makes it complicated. Right. Sometimes we get messages from our investors being like, is everything okay? Like, you put that story out, I don't know about that story, you know, and we get pushback, but again, it's true to who we are. We just really are showing the good, the bad and ugly of this journey. The complexities of being in a family business, brother and sister, husband and wife, brother in law, brother in law. Like, it's complex.

But also, why did we connect last night? Because you were here on the late shift, right? So also, it's just a lot of work.

It is, right?

Like, why were you even here on the late shift? Can you talk us about what's going on in the business that makes you have to work so hard?

So right now, I mean, I'm stuck in like 16, 17 hour days. You know, it's not going to be forever. It's for, you know, an X amount of time. We had to let go of our plant supervisor on Monday, and we made that decision for various reasons. It was the right decision. That being said, someone needs to step in. And the reality is I don't want to burn my AM team out. And so we decided to take that on, you know, so we need to make sure that business goes on as usual. It's our responsibility at the end of the day.

And.

And so right now I'm filling in for that shift to make sure the team feels supportive, that they feel motivated to come to work every day. When your leader gets let go, it's very discouraging. So seeing the owner, one of the owners, and Jake and Nick are also there to support in other ways. Seeing us step in motivates them and gets them to be fired up and want to put their Best foot forward every day. I mean, since I stepped in on Tuesday, we've only seen success. We've only seen more positive attitude, completing our tasks and our goals and really creating a strong transfer shift from the PM to the am so the ecosystem right now is turning better than ever. I'm exhausted, I'm tired. But at the end of the day, what makes, you know, what actually fires me up? We just talked a little bit. What's firing me up? What fires me up is that like, that gets me fired up. The fact that we are seeing things happen and we are getting out of this kind of downtime and the turnaround has begun. That being said, it's fucking hard and no one's going to do it but the founders. And the reality is when the founders are putting in that kind of work, it just creates a different energy on the entirety of the team. Like you could see right now, the whole team is working harder than ever. And so it does create a really powerful energy. That being said, it can't go on for that long because burnout is real. And.

And it takes a cost.

It takes a cost.

It takes a serious cost.

Yeah, absolutely. You know, I want to come back to also what you talked about in terms of the complexity. So we already talked about what makes a great co founder relationship, which actually everybody can relate to. And so important to all my listeners who are, you know, dealing with either deciding to do co founders or to build their co founder relationship. I have the co founder prenup in my book From Startup to Grownup. But you guys are also in a family dynamic. So I'm curious. Nick, I'm going to start with you. How has this changed or maybe tested your marriage?

Yeah, I mean, there's been two components. I think Les and I came into this environment with the idea of where we want to protect the relationship over the business at all cost. Because if you're going to get into a relationship with your spouse, there's really nothing uglier than succeeding at the task and failing at the relationship. Right. Because then you're just like, what was the point of this whole thing to begin with? So that was priority number one. And not just between, between Les and I, between this entire relationship of the tripod was just like, if we get through this with everybody hating each other a la Metallica, the goal will just have been failed. And so that was a huge priority. I think what Les and I had realized is we designed our life in a really peaceful manner of where we had learned to deal with each other under Arrested circumstances, under non pressured circumstances. We had a really rough period for the first 24 months. Adjusting to our relationship under exhaustion and high pressure and needing different things to re. Energize. That was a new dynamic. That was like a. Whoa. Where did it just. This just come out?

What's an example, when you say rough period? Like, what's an example of that rough period?

Oh, just one point where I like, I felt that she just hated me, you know, like, like literally just that. And I felt like, okay, there's, there's. My communication sucks right now. I'm not doing a good job at that aspect. Everything that we do is rough. When we were speaking, it was just always ending in a really shitty energy. And you would go to sleep demoralized. You'd be like, this is a pretty toxic experience. Right. Where the safe place is no longer safe.

Yeah.

Home is no longer a haven.

No. And that, that needed.

You're agreeing like this happened.

Yes, we, it was a rough period for us. And I mean, we invest in therapy, the three of us, from the day we started, it's been four years and the results are. I mean, I always think, like people talk about therapy, the ROI is huge. I mean the, the way how far the three of us has come as a unit, as individuals is massive. And we each do therapy individually sometimes. Nick and Jake. Nick and I. Jake and I. And Nick and I. When we were in turbulent times, we did therapy every single week with the same.

Your same physical therapist.

Exactly.

He sees you all individually and as a group and as two dyads.

Exactly.

Wow. Yeah.

Yeah.

And he's there.

Great perspective.

Just two weeks ago, we were doing therapy almost every day, so sometimes twice a day because it was so rough around here. And so Nick and I were in turbulent times and we committed to therapy once a week and we got through and we had to learn how to communicate. And some of the examples were like, Nick and I met at 14 years old. Okay. We've been best friends forever. I'm 32. And he was the person I confided in, I looked up to, I talked to, I asked advice from. And when Midday Square started happening, he was no longer that person that was able to be there for me in that way because he was exhausted, he didn't have capacity. You know, I like to come home and talk everything through and you know, and talk about the day. And it's like we couldn't do that anymore. Right. Because number one, he was, he was no longer just talking to somebody that wasn't involved he was directly involved in the things that I was saying.

Implicated.

Implicated. And so he couldn't just listen because he would want to react or help, and I just needed a support system, and he couldn't be there for me. And that was really hurtful. And the same. I couldn't be there for him. And even times, I mean, Jake's even been in the conversation where I'll say, or Nick will say, I can't be there for you right now. I can't support the needs that you need. And that's painful to hear from your lover, your best friend, your partner. But we've worked our ways around it and we've. We've done a lot of work. We have symbols now and we have.

What do you mean, symbols?

Like the sign. Like this means, like waving the white flag.

Like putting your hands over each other. Yeah.

Like we're suffering.

Yeah.

This is not the right time.

I don't want to kick the dog.

I don't want to kick the dog. I love you. I know you're suffering. I'm suffering, too. Like, let's just either reset the room or park it and come back to it, you know? And Jake, I know himself has had the same challenges in his relationship.

Yeah. I think that's a whole other topic. Is entrepreneurship is destructive. No.

For any relationship.

No. You understand.

I've met so many founders. I think I've met like over, like 200 in the last four years. Like, 200 founders from different industries. This past week alone, four different individuals have had destruction in their relationships. And my girlfriend's in the room right now, so, like, it's kind of awkward.

But her and I listen to this.

Anyways, but her and I are having. Her and I are having trouble. And the reason being is I'm not present. I'm. I don't know how to be present. And it's. It's due to exhaustion. It's due to stress and anxiety. And the baby that I currently want so bad is this to work because it's truthly purposeful. But then if you look back, what's important, it's not just that that's important. Right. And when I talked to someone that's one of our investors and advisors and a friend, Mike Fatah, he told me that he. He had a bad situation, his relationship, during his journey. He's doing another one now, and he's changing certain things. And I was listening to it, and he's like, it was the Mike Fatah show when he was in his first relationship. And what that Meant was it was all about him, even though he didn't want it to be about him. But that's what it turned into and that's what's happening. I'm realizing that's happening to me. And if you just go and ask and you're honest about it and you truly are aware, you can start fixing it. And I see her crying right now. She's crying because it's true and this is true. It's destructive and it's hard. It's fucking hard. I see them with their struggle and they're working together, but when someone's not involved in the business, it's almost as hard because they're not there in the moment.

It's harder in some ways.

Yeah. And when I go home, I don't want to talk. I don't want to talk. And if I do, it's 10 minutes and I'm very closed off and then all my mind is doing is, okay, we have customers that are really unhappy. I'm going to spend four hours doing that right now because that's going to give me that re energy, that's going to give me the adrenaline I need to even function.

Yeah.

You know, and, and, and again, the four founders I met with this week, unfortunately the odds were stacked against them and they all failed and they succeeded in terms of their businesses. Each one of them had great exits, that's what they wanted. But they've lost their, their, they lost the person that was with them on that journey and they, some of them have regret.

Yeah. It's something that we just don't talk about. Right. That sort of, that part of the journey and that sort of difficulty and I would just say the consumingness of the relationship or. Sorry, the consumingness of the business and wanting it to succeed. You know. Scott Belsky who wrote the Messy Middle, is a very well known entrepreneur and sold Behance to Adobe. He talks about not being present even on his honeymoon.

Right.

Like there was part of his mind that was still with the business. Right. Also he talks about pulling over to the side of the road because he was so nauseous with anxiety.

Right.

And that's kind of what it's really like. So I guess I would love to ask you more actually Jake, let me ask you also, how about you in this dynamic, in the co founder dynamic, do you ever feel left out because like they're married or how does it, how has it affected your relationship with your brother in law, with your sister?

At the beginning I was probably more, felt more left out I just want. I wanted to know what was going on and. And they were doing their own stuff, which is not purposeful or anything like that. But now I'm so, like I said, I'm so separated from what they do that I just trust whatever's happening is happening. Obviously, I'm cheering them on to make sure that their relationship works out in the end. But all I can do is either suggest, use the tools you have, be there if they're in hurting, if I. If I know that they're hurting, so ask questions, or just watch and make sure that things don't just go too chaotic because at the end they're going to work what they're going to have work to work out. They know what they have to do. They know the big vision they're committed to. A vision that we all agree on. So if you trust your partners to do that, they will figure it out. Obviously, when they're down on the ground, it's important to lift them up. But sometimes we're all down.

Yeah.

And when you're all down, you can't even figure it out.

Yeah.

And Jim, Jim comes in.

Jim's a legend. Dr. Gavin.

Talk more about Dr. Gavin. So I'd be curious how you guys met Dr. Gavin. And then could you talk about the specific tools like you just mentioned? One tool where you put your hands together to kind of indicate like, hey, white flag.

Hey, don't.

Right.

What other specific tools? Nick, I'll start with you. What specific tools have you learned from him that you can now use to continue to build your own relationship skills?

Monitor my exhaustion level throughout the day because that really defines my mood and my ability to. I actually become as. So if the morning I start, I'm the most resilient to being able to deal with human conversation because you're. When you're in deep conversation and understanding, there's a lot that's going on. As the day progresses, I become less and less capable of doing that. And so I would set myself up for failure a lot. And I think one of the big things that we're doing right now that I'm doing right now is monitoring that I'm trying to wave the white flag when I'm like, hey, it's 4 o'. Clock. I know everything seems like a big deal to me right now. I know it's not a big deal. It just feels like a big deal. It feels like I have no capacity to deal with it and trying to avoid getting caught in conversations when it happens. So you're being A lot more preventative and proactive in that essence. Another big thing is really letting people know your primary feeling rather than anger. So I'm feeling anxious right now. I'm feeling scared right now. These are very.

So it's like you think you're angry but you tap into what's really going on is anxious or fear or something that's so important.

We have enough understanding now. And you know, this has been studied by psychologists for a long time. That anger is not a primary feeling.

Yeah.

So it is not the. No matter what, if you feel angry, you have to tap. There's something leading to anger.

Yeah. Yeah.

And that's, that's the piece now. Are we perfect at it? No, but wow. Those tools have helped me avoid a lot of blowouts with both of them.

That's amazing. Jake, how about you? What specific tools have you learned from.

Your experience with Dr. Gavin to be more empathetic? The big one. That's the one thing is I didn't believe in therapy actually, to be honest, you. When we started, when they, when these two told me that that was part of the gig that we had to do. Otherwise this can't, this can't start this like I can't be part of it. I thought they were out of their mind because I come from the schooling of. I don't mean school school, I mean the schooling of. I thought I was perfect. I swear. It's a weird. It's very ego driven this.

But why you don't think, you don't think you're perfect.

I think I'm very imperfect and. But. But I become way more calm. It was very different. So what I thought before this journey was I'm happy, I'm in a fraternity, I played sports, I was popular. No. But I didn't believe in it. And I was shocked that that's what I was. That was part of the gig like that. I thought it nothing to do with my performance at the time because I was like, how could this even be related to that? You know? And I really was actually contemplating not joining because of that. I was like, I don't need it. And a lot of people come from that schooling. Unfortunately, it's dinosaur mentality in my opinion. And it's a way to like, you know. And I joined and I said, I'll give it a shot, I'll try just for the sake of trying. And I was not fully open minded, but I showed up because again, you trust a partnership, you give it a chance, you hear it out. It was the worst thing I ever went to in the first set, the first three sessions, I would say, I just thinking about that. No, it's horrible. It's horrible.

Jake would be silent.

It's horrible.

And there were shots, like, sulky. Yeah. No, no, no, no. He was taking shots from Nick and I of bullets. And at one point, Jim had to stop and say, jake, would you like to leave or take a moment? And Jake's like, no. And then I would say, for the first three months, you barely spoke in their.

I didn't want to. I didn't want to do this. And then there was a flicker in my mind where it's like, holy shit. This is a learning experience, because I'm starting to understand who they are, actually, who these people are, how I could work with them, where we can optimize with each other. And actually, this investment is making me a better human. So then I became a huge advocate for it, because the people I hang out with, they don't believe in it for some reason. So I started telling them again, I'm not giving people to do things. I'm just saying, here's what I learned. Here's how much benefit I got from it. And then people are like, oh, really? Next thing you know, you start talking about more consistently, and then those people are trying it. So therapy was that tool for me to become a. I think I've become more obsessed with learning from it, and I become more empathic, empathetic, which has made me a better human in both my professional life and my personal life.

Yep, I love that. Les, what's a typical session that with Dr. Gavin? I have to hear, like, what does it look like?

I mean, usually it's. It's either. Like I said, it's either a duo or the tripod. We get in and we really get right into it. So it starts with generally, like, how's everyone feeling? So we do a check in. Sometimes there's an agenda, so there's, you know, pent up something or there's a situation.

What's an example? A situation.

A situation. A perfect one was the video you showed. Right. So we came into work, we ready to film a podcast. Jake and I had a situation. Nick walked into it.

What do you mean by situation, though?

We were talking about the negativity, the haters, the comments, the negativity. And Jake and I were having a bit of a heightened conversation as well. We were finding our flow to then come down and get ready for the show. Jake and I are brother and sister. We talk very differently to Each other. Nick walked into the environment and got heavily affected by it. And he, at this moment, was like, I can't do the show anymore, and left. And Jake and I were just coming back to peacefulness and ready to do the show. Re energized. And so Nick had, you know, message Dr. Yavin, and he's like, we need a therapy session. So that was what. In that moment, Nick was heavily affected by the talk prior to the show, by the energy.

What were you affected by?

My biggest thing is I'm always. I don't want us to kick each other. The journey's too hard. That when we start turning on each other, which we do sometimes, and it's. We call it the kick the dog moment. It's because you want to punch a punching bag. There's nobody you can punch.

Yeah.

You're like, oh, you're a good target today. I'm gonna punch you.

So you felt they were punching each other? I felt that way.

Just an energy that I didn't want to be part of. I felt that they were punching each other even though they may not have been punching each other. And I remember them saying, hey, we don't need to do the therapy session.

We're good.

I said, no, you don't understand. It's not for you. It's for me.

Yeah.

I'm calling because I needed to get back on track with the whole thing. Yeah. So, like, that's it. That's an example. Sometimes the agenda will just be as simple as I. I get. I've been very insecure in moments on this journey to the point. Like I said, at one point, I thought Les hated me. At one place, I thought Jake just really couldn't stand me. I get in my head about it, and then I'm like, do they not actually like me? And I really am affected by that. And so a session will just be like, hey, I feel like you hate me.

Wow. Can we talk it through?

So that's safe space to be able to actually give voice to that.

Yes.

We talk about violent communication. We talk about how strategies on our teammates. Like, if we have an internal issue, how do we go about it, how do we handle it? So I think, you know, there's. There's many different things that we speak about, but it's really about, you know, the day to day, how we're feeling in the relationship or how we're feeling about the business and. And the roller coaster of emotions that we're going through, you know? Exactly. Nick. That sometimes I'm doing a Solo session. And I'm feeling, you know, insecure about, you know, me being me as a leader. Right. First time in my life, I'm a co CEO and taking on a lot of different divisions in the business. And so, you know, how am I showing up? And so there's just a lot of things that we work through.

I also think it's focus. So it's important. Like, it allows you to have a conversation with focus. Right. So it takes you out of the moments of everything else. So if bombs are exploding across the whole business and you're in that moment, the conversation has nothing to do with necessarily the bombs. It has to do with what's the current situation in this room. And it gives us the full attention to each other. The respect that we give to that session is so high that you are not on your phone, you are not looking at things, you are not thinking about things. This is a dedicated moment to a long vision, and this is what allowed us to survive till today. Otherwise, this would have been relationship. Relationships would have been done.

I do want to say, though, just to, like, wrap up that on therapy. And what we do is for anybody who's listening, who is thinking about getting them themselves, either a therapist or a business coach or whatever it is, you have to be ready to be committed. This is not something that happens overnight. It could take years. And it takes a lot of commitment. And a lot of people reach out to Dr. Gavin to see if he could take them on in his practice. And they say that they want to do. They want to have what Jake, Nick and I have. And he says, are you ready to put in the work? Because they are some of the most committed people I've ever worked with. And that's the reality is, like, we show up, we put in the work, we have very open, hard, honest conversations, and we've been doing it for four years.

And we know when to use the tool. That's a skill. He knew to use it. In that moment of the podcast, he couldn't function. He was frat. He was one of the most fragile states. And he broke it. Broke. And then he had to get back up in order for it to get back. We were able to do the show. What's even crazier?

Yeah. Just to say, I love what you just said, and I just want to say he could function because people can function, but it wouldn't have been his whole self.

You're right.

They would have functioned, like, irritable or insecure or less than in my head. Yeah.

Yeah.

And so that would have affected your performance. And I think that is the lack of self awareness. Like, I'm fine. And then you show up, not really fine. And bad things happen.

So many people do that.

Yeah.

And I see it everywhere. And it. It. As you start working on yourself.

Yeah.

You have less patience for that type of.

Exactly.

Like it's a bad lie.

Yeah, it's a bad lie. Yeah.

Straight up a lie.

Yeah, totally. So. Oh, my God. We could talk all day. I just have three final questions that I want you all to respond to and they're about personal growth in particular. And Les, I'm going to start with you. What are some ways, one or two specific ways you've personally grown as you've built Midday Squares?

I would say so many ways. Every single day I'm growing and learning. I would say communication has been one of the biggest things for me on this journey is really learning how to listen, really learning how to respond, really learning how to have hard conversations. Hard conversations for me are the foundation of any relationship and any successful relationship. And like empathy and vulnerability, leading a team is extremely hard. And if you are a leader, you need to be an excellent communicator. And so I think that's been one of my biggest learnings. Aside from the. That's the personal growth in it all is. Is really becoming an expert communicator.

Beautiful.

Amazing.

Jake, how about you? Some ways you've. One specific way you've personally grown.

Blocking out noise, not getting caught up with everything around me and being so affected by it. I used to be as of eight months ago. So I think I've come a long way. I've worked with therapy on that. And a troll is a great example. So an Internet troll used to hit me at the heart and I used to get smoked for like four or five hours, six, seven, eight hours even, potentially even two days, three days. And I was so hurt. I didn't even know what to tell people because I felt like I felt alone from that. Right. And then now I've learned from those moments to actually have fun and be in spirits. And I'm not even pretending from. I'm actually having a good time with it. So, you know, we're doing a video right now on scammers. I thought it was gonna be about trolls, to be honest, but it was about scammers. It's not the same fun. But I actually asked our custom send me all the trolls so I could actually engage, because I'm not engaging from a negative standpoint. I'm actually trying to find out, like, a lot more, because I learned a lesson from this guy, Mike, from Nosh. He said, trolls want to love you. They just don't know how. So try to show them how. So I make it a mission every time. And if you do that with good spirits, it feels really good.

Nick, how about you?

One way you've personally grown having extreme empathy, and I'm, like, not even there yet, but I have a very low tolerance for what I deem a stupidity, and that's unfair. And what. Yeah, it's been a really, really challenging journey for me. That piece still remains the biggest, but it's the piece I feel like I've made the most progress on since starting, which is just having empathy for the people that are around me. Because at the end of the day, you can't just go through it being affected by things, because ultimately you yourself are probably the problem at some point, by not having communicated or coached a person through it properly, giving them enough attention, energy, you've made assumptions. You've failed yourself and them in that part. So that, for me, has been the biggest piece.

Great.

Thanks, Nick. Okay, Jake, what do you wish you had known earlier on your journey?

To play to my strength, not my weaknesses.

Beautiful.

Excellent.

I love it. I love it. Les, how about you? What do you wish you had known earlier on your journey?

I would say how hard it is to really build a team. Like, I. I didn't realize how hard it is to find and bring people together and have them rally behind an idea and a concept and how to navigate. I mean, Midday Squares is a true diverse company, and it has people from all over the world. And the biggest learning for me has been, how do you manage that? How do you unite people? How do you bring people together? How do you have them rally behind what you're doing? You know, because what you're doing, when you're taking nothing and building it into something, it is so hard. You cannot do it alone. And building a team is, for me, a good team. Near impossible. And now I understand why people purchase teams.

Yes.

And not ideas, you know, so don't.

You think that would be nice in the world if a leader did that to unite the countries? Maybe Leslie should run for politics. Maybe.

Maybe after this journey, I think I'm gonna resort to the mountains.

Exactly.

You won't be able to call me. There's no, you know, be off the grid. Off the grid.

Off the grid, baby.

Nick, what do you wish you had known earlier in your journey?

Journey still. Again, still struggling with it. But Getting there. Suffering and misery is a choice. It is a pure self inflicted choice. Yep.

Yep. So well said.

No matter what the circumstances are.

So well said. Okay, my last question I ask everybody, and I'm going to ask anyone can jump in when they want to. What advice do you have for founders as they embark on their journey to grow into leaders?

Mine. Simple.

Yeah.

Learn to be yourself and figure it out, because that is going to be your biggest superpower forever. Not just on your business journey, but in your life.

Beautiful.

Nick.

I'm going to stick with remove the fear of failure. And I think how you do that is by detaching your being to the outcome of a thing, meaning a business. Working or not working is actually not reflective of anything as to who you are. It was just a piece of the journey. And ultimately, when you're dead, it means nothing. So you have to really de emphasize what it means to fail. And then the closer you are to that peace with failure, I think the more unstoppable you become. I think the relationship is inverse and it's correlated.

Oh, my gosh. I love it. Thank you, Les. Bring us home.

Focus on five minute periods, though. It's overwhelming. That's, you know. So focus on the five minute periods and don't think past that. I mean, obviously in the spectrum of running a business, you need to look at the macro views sometimes, but focus on those five minute periods and just start. I think that's the most important thing. People are always trying to chase perfection or huge ideas, like, you gotta start somewhere. And that's the most important thing for me for entrepreneurship.

Amazing. I wanted to say thank you to the three of you for being on my podcast and we're spending this beautiful, precious time together and also for welcoming me into your community. I just appreciate it so much, spending the time and I love what you're doing. So keep going.

I appreciate it so much. I really enjoyed this and I can't tell you how much I enjoyed our time together.

I would agree with Nick. Your energy, your vibe. We were talking about it last night. It's just incredible. And I look forward to hanging more. Thanks for having us on your podcast. This was amazing. I know I wasn't here the whole time, but I really enjoyed it.

Thank you.

Thank you.

Thank you, everybody.

I'm thrilled that you're here. I just am. It's full circle. This is a full circle moment. People don't understand. This comes from a simple text from a person that we have mutual friends with, wanting to make magic with the two of us months ago. Connected, talked. Finally you made your trip to Montreal and I knew you would love everybody and it was a bet I made and it worked. So this is magical moment and it's got such a future ahead.

Beautiful.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple Podcast so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website alyssacon.com.