Jake Karls: Crafting Authenticity and Success from a Home Kitchen to a Global Brand

What if success in business isn’t just about strategy, but about authenticity and emotional intelligence? In this episode, Jake Karls, co-founder of Mid-Day Squares, shares his journey from making chocolate in his home kitchen to building a global brand. Jake emphasizes the power of transparency, personal support, and community in shaping his success. He opens up about how his marriage and family relationships serve as pillars through the challenges of entrepreneurship.

Jake also explores the transformative role therapy plays in business. Initially hesitant, he now sees it as an essential investment in both personal and professional growth. In a candid discussion, he highlights the importance of balancing ambition with mental well-being and how therapy has strengthened his leadership at Mid-Day Squares.

Tune in as Jake reflects on his Forbes 30 Under 30 recognition, navigating burnout, and staying true to his mission of connection and authenticity. Through stories of failure, resilience, and family dynamics, this episode offers invaluable insights for entrepreneurs looking to build not just successful companies, but meaningful, purpose-driven lives.

Presented by: Lerners LLP Hosted by: Mark McAuley Executive Production: Natalee Davis Project Management: Dylan Willems Audio Engineering: Aaron Murray – Charterhouse Studios (Season 1,3), Chandra Bulucon - Puppy Machine Recording Studio (Season 2) Graphic Design: The Branding Firm Inc. (Season 3), Jen Luchka and Dawn Yan Theme and Underlying Music: Mark McAuley and Randy McAuley

Chapters

• 0:19 Entrepreneurship and Marriage Balance
• 8:57 The Power of Therapy in Business
• 17:40 Finding Authenticity and Connection in Business
• 27:53 The Power of Authentic Storytelling
• 36:33 Lessons From a Favorite Failure
• 46:51 Building a Strong Business Partnership

Transcript

Mark: 2:06

Welcome to another season of Anything but Law, where we talk about anything but law. It's literally in the name. This season, we continue to dive into the minds of exceptional people, from entrepreneurs and business leaders to gold medal winning Olympians and thought leaders. We bring you inspiring stories and valuable insights from those who have truly made a mark in their fields. In each episode, we explore the success mindset, the art of overcoming adversity and the powerful lessons learned from failures that have launched extraordinary success. Our guests share their journeys, challenges and the pivotal moments that have defined their paths to greatness. So, whether you're looking for motivation, strategies for success or simply an inspiring story and great conversation, you've come to the right place. Let's get into it.

Jake: 2:06

I love it. I love the studio that we're in. I think it's epic, it's OG I do a lot of podcasts and I feel like there's just something to this vibe right now that I'm excited about, and that was a great intro as well, so I'm fired up to be here. Thanks for giving me a voice, man. That means a lot.

Mark: 2:22

Oh man, I'm actually thrilled to talk to you. I've been watching, uh, in preparation, I've been watching your talks and I've been reading, um uh interviews with you and, uh, I was uh actually thinking, you know, sometimes when we have these conversations and like, what are, how are we going to fill the time? And what I keep thinking is, like, do we have? Because I feel like we're going to run out. I know, I know you're full of energy, I know you got, you know, um, you like, uh, you're a self-professed hype man, so I'm uh, I'm going to, I'm going to meet your energy today, but, like, I'm so glad you're here today and I have to say two things.

Mark: 2:54

One, Western University represent. We are here today, um, and you were at Western earlier and, going back to Western, I'm going to shout out to our hometown university, University of Western Ontario. We're both alum. Thank you, Western. And we referenced the studio. The studio that we're sitting in is actually the studio that I first recorded in as a child, so it feels like being home again, nostalgic, yeah. Yeah, before we started, you were talking about the kind of things you got to get wrapped up before you're heading back home, and it's funny because that was like one of the last questions I wanted to ask you, which was? You just got married this year.

Jake: 3:31

Yes yes.

Jake: 3:33

I got my ring on my necklace actually, because I don't like wearing things on my fingers. So there you go. No, but I think marriage, especially during the entrepreneurship journey, is crucial. And I don't mean the idea of getting married, I mean the marriage of two individuals as a support system and love. I think you know something I've noticed in the last five years of Mid-Day Squares Squares before that I did two other businesses for five years before that.

Jake: 3:59

It's painful. There's a lot of adversity, there's a lot of hardship, depression, loneliness, being misunderstood, judged and you know, people always see the glamorous side and like the cover of Forbes Magazine, that shit's, that's cool and all. Don't get me wrong, but most of it's the other side and, um, I want to shout out my, my wife now she's now wife, but she, she was my girlfriend at the time throughout this journey is the support that she's given, because it's not easy for her either, for someone that travels every week, that's always out of town, that's exhausted when I get home. These are like real things that people don't talk about, and I think it's important that without that support system, I probably wouldn't be even sitting here with you today. I wouldn't be back in London, Ontario, where I'm a proud alumni of Western and love this city. But I'm here because I have a strong support system, from my wife to therapy, to my partners, to family friends. But, yeah, marriage of an individual with somebody that cares and loves is super critical to this journey.

Mark: 4:55

I couldn't agree more, and there's a lot of. Scott Galloway, one of my favorites, said the most important decision you make in life is the person who you spend your life with.

Jake: 5:08

That's like one of the biggest determinants of success, and so I want to also shout out to your wife to your lovely wife, melissa.

Mark: 5:11

Her name's Melissa. Hi, Melissa, and you know the reason. I wanted to circle back on that later but the reason why I was going to ask you know kind of how your approach to entrepreneurship is impacting your marriage is because your brand is kind of synonymous with openness and authenticity and having exposure to all the things that you do the ups and downs, as you've already alluded to and so how has being married now, how does that play into? Now there has to be some more barriers drawn around. You got to ring fence some things that are a little more sacred. So how has that impacted this kind of open and authenticity, openness and authenticity?

Jake: 5:47

piece. So you're right. And what my promise and my partner's promise was when we launched Mid-Day Squares Squares was to be radically transparent, show good bad ugly, meaning cameras would be following us in our homes when I travel, you know, in life, and we agreed to that because we really believe that that was a way to disrupt an industry that has not been disrupted. Right? So that was a commitment. That, again, when I was dating Melissa, that was an agreement that was made, but she didn't want to be really in the camera side and she's a private, she's very private, and she just doesn't need the spotlight. And I like spotlight. I'm a loud guy. You see me, I'm crazy, you know.

Jake: 6:23

So when we got married officially in June, there was a conversation that said how much longer are you going to be this character, which is authentically who I am? But it's a side that you know, you see, as the energizer, as the hype man, as the one that's traveling every day doing crazy stuff, and I burnt out twice on this journey, like major burnouts, and she asked me just seriously she's just like when does that stop or slow down? And she doesn't want me to stop it. She says when you want to stop it, you stop it. But I told her I have about three to five years of this energy in the tank and I said how long do you have? Oh, right, and she said you know, three to four years max. And I understand, because when I come home sometimes from west, I'll come home from London tonight, Montreal, and I'll get home and she'll ask me how my day was, and I won't even have the energy because I gave it to everybody else, right, and that's the difficult part that could erode a marriage, because what really does matter is Mid-Day Squares.

Jake: 7:19

Squares is very important, don't get me wrong. It's part of my life. It's not my identity, but but it's part of my life. But the people I surround myself every day with my family, my friends, her is actually what truly matters and sometimes I forget, and that forgetting is dangerous. So I've been working with my therapist to come up with strategies on how to prioritize that, because that is truly what I want to prioritize. But the addiction to it's going to sound crazy, but the addiction to wanting to win, disrupt, build is powerful. It's a powerful force that I get caught up into, right, yeah, so I need to learn the balance and we've had the discussion. So it's, it's, there's barriers. Now it's not just. You know, free for all, live your life and do you know, do everything without thinking of me. It's now, you know we're, we're a unit. Yeah.

Jake: 8:04

We always were a unit, but it's, we're a unit and that should be the number one focus first, rather than Jake and building his brand.

Mark: 8:11

Yeah, and then when the kids drop in it's kind of it's actually something entirely different altogether. Then there's like a fortress.

Jake: 8:17

Yeah. Then it's like okay, the you're right. Then there's a major fortress, there's a barrier.

Mark: 8:20

There's a moat.

Jake: 8:21

Changes the game a little bit.

Mark: 8:22

Oh yeah, it changes things up, but it's funny because one of the things you always talk about and I wanted to get to and I love how open you are with this is the idea that therapy not on occasion, but constantly is important to success, and one of the themes the through thread that's going to be running through everybody I speak to this season because it's important to me and it's become more important to me over the last few years as I navigate building a practice and being a dad and trying to be a good husband and trying to be present for my family is making sure I take care of that mental space.

Mark: 8:57

So I know it's important to you and I know that that's something that you have. You are probably the first entrepreneur I heard who said it's important for me to have that like business therapy sessions with my people, and I thought as soon as I read that I was like I read that again, and then I read it again, and then I read it again. I was like fascinating. So how crucial is that to maintaining the forward success of your business?

Jake: 9:21

It's everything. So I think that what I've noticed, um, when, when I was graduating Western actually I was on like a high horse of like, I was a good, I was a good athlete, good at hockey. I was in a fraternity. I was studying to be an actuary at the time, didn't do so well in that, but I did try, um, but I was very confident and I thought I was the happiest guy on the block and I thought that therapy meant at this time of my life, when I was 22, 23, 24, 25, I thought therapy meant weakness, meant that you're depressed. The word depressed scared me, right, it always is as if I'm embarrassed. It's embarrassing and I was so naive, I was so immature to even like, think like that, but that's what society kind of made me feel right.

Jake: 10:02

And when my partners said to me in day one I'll never forget, august 4th of 2018, they said if we're going to do this together as a partnership, you need to sign an agreement that says that you're committed to coming to therapy with the three of us together once a week, in good or bad times. And I looked at them. I said absolutely not. I said I'm happy. Look at me, I'm killing it. I was dating at the time I was, I was on fire in my I thought I was at least and they said, well then we can't do this. And I said you're going to throw all of this away, all of what we just worked on for a therapy session. And they're like, yeah, and the reason why they said that is they've had difficulties in the past. They've been going 10, 12 years now and they said the personal growth is inevitable. So I said I'll give you five chances, five opportunities of sessions together, and after that, if I don't like it, I'm done, I'm leaving the business. And I was mad, I was angry, I was fearful. This is what the emotions were going through. I didn't admit the fear.

Jake: 11:00

So I went to the first session. It was from a place of love, but it was criticism to build the business Right and it was a partnership. And I said I basically got out, you know, the first session. I waited till to the moment they stopped and my therapist said do you want to take a break? And I was actually like no, I was like just keep going. And they kept going and I felt this pain, really deep pain, and I thought that they were attacking me personally.

Jake: 11:21

Then I realized in that moment that it wasn't nothing to do with personal, and the fact that I didn't even know that it had nothing to do with personal attacks, that it was a way to constructively work together to build something, was the moment I realized that therapy is everything for me. It helped me see things differently, to put perspective, to understand, to be more empathetic because we're all empathetic most of us in the world, hopefully but it just has to come out right. It just has to come out a little more. So I did those five sessions and then I fell so in love with therapy that I realized that this is the best investment to build yourself, you as a human part of the one world that we live in. You can invest in that.

Jake: 11:57

And education we invest for education, to learn to be a lawyer, to be an accountant, to potentially be an entrepreneur, but why not learn how to be a better human to the world? And that was when I realized now, today I go sometimes twice a week, I'm a huge advocate for therapy and I try to break the taboo feeling that I felt when I was 21 to 25, that has nothing to do with weakness, it's actually to do with strength and now I've become a lot more emotionally intelligent. I would say simply, just because I've decided to take that leap, to invest constantly, not once, not five times, but weekly and it's an investment. It's expensive, but what else are you investing in to make yourself better? So look at it like that.

Mark: 12:37

It's the thing that I always say to people. It's like, oh, therapy sounds expensive and I'm like, yeah, and I admit that having access to it should be less expensive and easier for everybody to get their hands on. But at the same time I'm like listen, if we went out to a couple of fancy dinners, like we would cover off the cost of two or three of these sessions, anyways, we would spend.

Jake: 12:55

I would eat this in sushi or steak or whatever it is, or going out, if you go out, yeah, if I go out for a night with a bunch of friends.

Mark: 13:02

I could pay for X amount of therapy sessions, which will build me up as a person.

Jake: 13:07

And then make you stronger. And then, if you believe in you know your goal is to make financial success, being a better person, better leader, will allow your vision to come true faster or in a more, you know, impactful way. And I think that that's where people don't understand. And I hear the expensive one is the number one excuse. It's expensive having found the right person, find the right person. There's many great people out there you could test and learn but expensive.

Jake: 13:32

I see these same people that say expensive as going out, like you said, every night, three times a week. They go on vacations lavish and I'm all for that, by the way, do you and do whatever you got to do. But but then when you feel that, that that weird feeling inside of you, you just know that there's a way to fix that over a time period. There's a way to invest in, you know, building and getting better at whatever you're going through, simply by going to therapy. And therapy doesn't just mean they talk about depressing things. You talk, you work through major, hard conversations that you may not have.

Mark: 13:59

I, uh, I swear by my sessions. I think they're the best way for me too. The way I think about it is you zoom in and out of what you're doing. This is me in the riding around in this little as one of my friends like to call it in a meat suit, like doing the things that I think I'm supposed to do. And then when I sit down with somebody to talk about it, I get to zoom out and see like, is that getting me to where I wanted to go? Is that working for my wife? Is that working for my daughter? Is that working for my coworkers?

Mark: 14:24

And then being able to kind of zoom in and out of your life, kind of in real time, as you were saying before feeling attacked, it's like no, it's not actually about being attacked. There's nothing better than knowing in real time when you're making a mistake and being able to. Actually you can correct faster if you're able to identify those things within yourself. So I do think as soon as I heard that I was, you know, when I was listening to your interviews I was like oh yeah, actually that doesn't make a lot of sense to not have ego hijack something, to not have my perception of self hijack, this business proposal. I'm not going to make a decision based on ego. I'm going to make a decision based on the things that are best for us, based on the things that we want to do, and then being able to have those conversations with people in real time, I think is very smart. So I found that very fascinating.

Jake: 15:11

Just two days ago, like two days ago, me and my sister got into an argument and a disagreement about some sort of touchy, sensitive subject and we were going at each other for like 20 minutes, not like calling each other names, there's no name calling it was just about the facts of what was happening and how we felt. And then we came to a solution of and it was led with love and empathy and after we left that I walked away and she walked away and we messaged each other saying, wow, I'm proud of our communication. We disagreed and we were emotional at one point and within 20 minutes we were able to get somewhere. Because we both are invested into understanding, communication, understanding, empathy, understanding love for each other, vision, alignment and usually, if that happened three years ago at the beginning, or four or five years ago, we're going to slam the door and left and it would have been a day's worth of energy gone. Think about that day's worth is now saved just because we know how to communicate a lot better now.

Mark: 16:09

Yeah, and in our industry, you know we have hourly rates, so you know how much time is wasted, how much, how many workable units am I wasting on energy that really doesn't need to be expanded, how we can get past that. So, anyways, I found that fascinating and so, um, I'm, I'm a, I'm going to start saying, saying to people over and over again, as we, as I sit down with new business owners and they're talking to me what they want to do. I will add that to the toolkit of things that you might want to consider. Oh, you guys are partnering up Cheryl's agreement. Great idea.

Mark: 16:38

Have you considered doing therapy together? I'm just going to say, not a bad idea. You know I'm going to start throwing that in. And so I want to ask something you, you, you glossed over something that I actually meant to mention at the top, but, like Forbes, 30 under 30, you know you're talking about this period of time in your life of successes and failures, the resistance to the therapy piece, and how you, what you, what your inner process was. Then how do you feel getting through all of this and then being named 30 under 30, like dropping into that category? It must feel surreal.

Jake: 17:17

Yeah, so that was a dream of mine since I was 19 years old, and the reason why it was a dream was because I liked a lot of the people that were on that were part of the Forbes 30. So at the time there was a lot of the tech booms, there was a lot of creatives that I really respected, there was a lot of people doing really cool stuff. So I said to myself, how could I be like that? And like then, 10 years later, I was on it and I wasn't just on it, you know, as a, as an honoree or something like that. I was gone. The magazine, like, actually, which was a crazy cool, you know something that you know.

Jake: 17:44

At first I thought it was all about here and I went through a burnout because during that time I got engaged, I got. I had so much going for me. I got the Forbes 30 cover. Mid-Day Squares Squares business was on fire. I was on TV every week, radio, anything you name it.

Jake: 18:04

I was getting so much spotlight and then it all collapsed, fell off a cliff, and that cliff was so deep that I felt rock bottom. I felt depressed. I felt rock bottom, I felt depressed. I felt I was so hurt, I didn't. I couldn't talk to anybody. I was like almost two months zero communication with anyone, no working, had to see therapy every day, because I started to feel like I lost my identity, my purpose and everything.

Jake: 18:30

I got caught up into this game of hype and um and just wanting to be doing everything for everyone else. But what does Jake actually want, right? And I had to do that deep soul searching then, and I did, and this was like only months ago. This was like six, seven months ago, it wasn't even that long ago, but it was a crazy moment, like I felt like I was on top of the world and this was all happening and I got to experience and meet really, really cool things. I was on billboards in Times Square. I was on all this crazy stuff that like I dreamt of as a kid, and then it actually happened. But then it's like how do you keep that up? So you start playing weird games.

Jake: 18:59

Oh yeah, and that games took me to the cliff where I jumped. Well, I fell off and I hit rock bottom and I was physically injured. I was mentally injured and I was unable to be a person to anyone that mattered to me. So it ended up being going from top to bottom real fast and now I'm climbing back, but I'm a lot more careful and I'm a lot more purposeful and intentional on what I want.

Jake: 19:23

And Forbes is amazing. I was just in Cleveland for the Forbes 30 conference and you know I did an interview with them and it was a blast and their team is phenomenal and they help Mid-Day Squares Squares, they give us a voice all the time and the network they've introduced me to. But there's more than just press and awards and all that stuff. You know AM building a business, which is the main focus, but also not losing sight of what who really matters and, as we talked about at the beginning, is that's the focus that I need to stay focused on, because if I just jump into the game of that hype and all that stuff, you start to do things that aren't necessarily authentic to you and that's when you lose yourself and you lose your game.

Mark: 19:59

So here's I guess here's my question. I was going to ask you how you rally back, as you say it's a process, but because I do find this, with entrepreneurs, business leaders that we work with that are clients of mine, people in my profession, lawyers, who wrap their identity around the thing that they do all day, every day, how did you find, like, where did you find the resolve to kind of separate out Jake, the identity, from, like, the authentic Jake, like that journey inwards? You know, you, you journey inwards to find your authenticity, which is, by the way, is a lifelong journey, and then you have the, the mask that you wear.

Mark: 20:40

I'm not saying it's not authentic, but you know what I mean. We all do the exact same thing. I'm a different person outside of my house than I am at home. Um, how did you rally back to to find that kind of core identity?

Jake: 20:51

Yeah, so you're right, it's a lifelong journey. I've definitely not figured it out, but what I have noticed is I started to notice what truly matters to me outside of just business, because I really tied myself originally to Mid-Day Squares Squares. That was Jake Jake the chocolate guy, Jake the Mid-Day Squares Squares guy, Jake the guy that's on Forbes. I started tagging my identities to all these things, but then I started to realize that that's not who I actually am. I'm so much more than that and those things are great, every single one of them. I love my business, I love Forbes. I love, I love the things I get to do every day. But there's, there's something outside of that, and identifying that and working towards that is, like you said, a lifelong journey. That will still take time. But I start to notice what I'm really there meant to be and what I learned is my purpose more is not to make chocolate bars. I'm allergic to my product, which is even funnier. Yeah, I heard that story yeah, so it's real, that's real.

Jake: 21:47

So that goes to show you that my purpose is way more than that.

Mark: 21:55

I actually think in watching you and I don't want to cut you off I think in watching you and you, the way you talked about your previous businesses in your other interviews and other um uh materials, is that I actually think that your, your, um, your purpose is connection. That I, when I see you in talking in front of people or in the interviews, I'm like no, no, no, Jake loves connecting with people, that's his thing. His thing is connecting with people. The product is connection, or the road is connection and the product rides on that road, and so I kind of see that as your. I don't know it's not an addiction you were saying before, but this feeling is like that's the thing that kind of fuels you, it's the connection and the connection is the thing that keeps you going. Can you speak to that? Am I accurate? Did I miss?

Jake: 22:36

it, you literally hit it. So it's to go out there and literally spread energy, show people that they could win by being themselves, and to just inspire. And I think that how I and I struggled with this early on because I was like, how does it even relate to anything to do? And it relates to everything because, at the end of the day, why I'm even in London right now is to connect and inspire. It's literally to show people I'm authentic, I'm not some fraud, I'm not bullshit, and I'm here to give an individual an opportunity to be like hey, I should be me a little bit more, I should take more risks. And by me talking about the good, the bad, the ugly, I'm literally giving you my life. I'm putting everything out there that I can hopefully help you. I mean you as in the people that I'm meeting today and that is my purpose. I'm not trying to sell you a chocolate bar right now. I'm not even talking about the chocolate bar, but we're talking about life. We're talking about real things that can actually help people that are listening to this to be like yeah, I don't need to be in a square box, I don't need to be tied to one thing. What's more important is to just be yourself. Because when you're yourself, you know and I know this you start winning. You start winning and I don't just mean financially, I mean like in life, like the game of life, friendships, family experiences, moments, capitalism, if you're a capitalist, and that's when you really start to win big.

Jake: 24:04

And I always respected Jeff Bezos when he said early on, when Walmart I think it was Walmart was the big player and still is a big player. But people would say to him aren't you worried about your competition? And I think he responded something like I acknowledge it, but I don't worry about them, because I'm only focused on making the best experience for my customer. And I obsessed with that. And when I heard that it all made sense, why compare yourself people? Why not play your game? Because when you're on your game, you're at your best, yes, and when you're at your best, people feel it yeah. So that's my mission is, if I'm not at my, when I'm not at my best, I'm being somebody else. Right, I'm doing yard sticking, I'm doing all that jazz, but when I'm unapologetically myself, you feel that. You will feel it. You will feel that energy and the genuineness. You will see it and be like, even if I don't agree with what he's saying.

Mark: 24:59

I respect him because he's being myself Cause he's being real right now.

Mark: 25:03

It's. It's when you talk about winning. It's funny because I think you know If I can be so bold as to assume that when you're talking about winning, what you mean is winning at life, in the sense that you're no longer swimming upstream Like why are you always fighting against it? Why are you fighting against your nature? Why are you avoiding the things that make you who you are? Why not be who you are instead of spending all of your life until you qualify for a pension being something that you're not? It seems tiring. It seems like a lot more work. It's our system.

Jake: 25:33

Unfortunately, the system we live in and it's great for a lot of things and I'm grateful that I got to experience some of the great things from the system but a lot of it pushes us into a herd way of like being a certain way, and that's dangerous, because I know a lot of even my friends, my best friends, who are great. They have great careers, great careers. A lot of them aren't doing what they actually want to do and the way I know it is is I feel their sadness, I feel it and some of the stuff that they say. It's like well, I see them, Well, why don't you just do that? And they're like I can't, I can't and a lot of it's fear. Because, at the end of you, everyone has bills to pay. Let's remember this right Humans all over the world have bills to pay. Some are grateful, Some are in zones of they're very wealthy and that's fine and all that jazz, but everyone has to pay a bill. So you as a human will figure it out.

Mark: 26:22

Yeah.

Jake: 26:22

But would you rather have your bills paid and then live in a mental prison your whole life, yeah, or would you want to try to figure out, explore, try, experience, meet? These are things that we're scared of doing. So my goal is can I show that by building a very impactful business? Can I show it by being me in that if I could do it, anyone could do it? I didn't do well in school. I tried. I love Western University dearly, but my grades they could show it to you, they weren't great and I struggled. I couldn't get an investment banking job. I tried. I love Western University dearly, but my grades they could show it to you, they weren't great and I struggled. I couldn't get an investment banking job. I tried. I really wanted to fit in into the stuff that I was doing. I couldn't, and I still figured it out. Daddy, it's time to take a break.

Mark: 27:03

Are you a new business owner, starting out on a new venture, or perhaps you're at the other end of your entrepreneurial journey, eyeing a smooth transition to retirement? Maybe you're planning to expand and take on the next chapter of your business. Whatever your need, Lerners Business Law Group is here to help. Our team has the expertise and dedication to help you achieve success. With decades of experience in business law, we provide personalized solutions tailored to your unique situation. Whether it's navigating complex regulations, securing contracts or planning for the future, we've got you covered At Lerners Business Law Group. Your success is our mission. Let us guide you through every step of your business journey, ensuring peace of mind and a solid foundation for growth. Ready to take your business to the next level, contact Lerners Business Law Group today and let us help you achieve your goals.

Jake: 27:51

And now back to the show.

Mark: 27:53

You have described yourself as weird, which I think is awesome, by the way. I think we're all strange. And how much do you think that neurodivergence has played into your ability to kind of? I mean, it must be a success. It's got to be one of those things where it's like, yeah, it is like a superpower, and then sometimes it's like, yeah, it is like a superpower, and then sometimes it's like kryptonite. You know how much do you think that would play into it?

Jake: 28:17

yeah, I think being weird is definitely a superpower, but I think that what it can do is it could be your kryptonite in terms of some people aren't gonna like it and you have to be able to take that. So, being out there and being weird and being myself you know, I can't please 100% of the people and there's a lot of people on the internet that are just mean no offense, and you know, at the beginning, yeah, but at the beginning the trolling was terrible and for me, being weird, I was getting made fun of like you're ugly your teeth are this, you're that die in hell. And ugly your teeth are this you're the die in hell. And I yeah, raw hell, mean people. How am I? They call my sister fat, like it was just horrible stuff and we were all just being truly ourselves and trying to put our front foot forward in a way that we're trying to build a business and in a fun and real way, and we were getting shit on for it and at first I would cry and I'd actually take it personally and get mad and it would ruin my day for like seven hours and then I would have to see therapy and do that stuff.

Jake: 29:16

Then I started to realize that this isn't a me problem, this is a them problem, the people that are doing this. They're suffering. So how can I help those people? How can I actually be there for them? So my weirdness would then take over and be like the person would call me ugly and I'd be like yo all good, like is everything okay? Like, can I get on a call with you, can you want to come for dinner? And I was actually genuine about it.

Jake: 29:35

And guess what? Six out of seven out of 10 times these people would just say I'm so sorry, I had a bad day, let's jam. And I actually have some of these people who are my friends now, who said such mean things, and I don't even blame them. It's just that they were going through a moment in their where their insecurities came out and they took it out on me. So that's the kryptonite. There is not. If you're not able to deal with that, your weirdness will then change back to the herd, because you will slowly start to change yourself to fit in, yeah, and you'll try to slide yourself back into that.

Mark: 30:05

In other words, there's a line from a little known song I don't even bother quoting, but I love it all the time, I think about it all the time is that this way of life is so designed to snuff out the mind that moves. So we take ourselves, you know, we, we, we mute and numb ourselves so that we can just kind of fit in and try not to stick out, which I think is super boring. Um, but also there's no um, there's no reward without risk, and and the risk isn't just financial the risk has to be putting yourself out there. I think, looking at the model that you have built, I think it's kind of proof, positive, the fact that in the modern age and in the future, kind of showing people what goes into the sauce is important. People want to know.

Mark: 30:49

It's a hyper-connected age. People want to be involved. They kind of want to know you and they want to be able to. They will. They will buy what you're selling. I think you had noted in one of your things in one of your interviews I was like the Kardashians they will buy what they're selling if they can if the story speaks to them, and so I guess, if you had advice for entrepreneurs who are coming up now about how to uh storytell, how to build a story in a way that's authentic. I know you've already said be yourself, but like what would be your, your top piece of advice for, for branding in this, like in this hyper-connected age?

Jake: 31:26

So I like that we keep saying hyper-connected, because the purpose, my mission, like you said, connection right. So this is part of that, right, being out. There is definitely a way. So first step to any entrepreneur out there that's going to tell their story is get out of your way, like you are the only one in your way. And what I mean by that is a lot of my friends, fellow entrepreneurs. They're scared. They're scared to tell the story. They're like no one's going to listen, no one cares, it's boring, it's dumb, it's not fun. And I look at them and I say why do you say that? And they'll say to me well, I don't find it that interesting. And I look at them again and I say you find it not fun or boring because you live it 24-7, every minute, every second of the day. It's you, but not everyone lives your story. So what do you have to lose to get it out there? What someone's not going to like you? Because you said you like the Toronto Blue Jays or you're going to a Maple Leafs game or a Habs game. This is my thing. It's like I'm always interested to know about humans. I'm interested to know about you and that's why this company Humans in New York, or whatever that thing is, does really well, because it's the stories of humans, and we, as humans, crave a type of authenticity and storytelling, and it's not a new thing.

Jake: 32:39

We've craved it for as long as we've been human. So today, as a business, you have a great opportunity that you didn't have necessarily 15 years ago. Social media has given you vehicles that have access to almost anyone, whether it's Kim Kardashian, the government, whoever you want to meet you could potentially get in touch with by sharing your story. All it has to do is resonate, so you might as well put it out there. As long as you're a kind soul and you're not a mean person, you don't have hate in you, then share your story every day and proudly share it, and you won't please everybody, but who cares? Those people don't even deserve to be on your journey if they don't care for it.

Mark: 33:16

Yeah, it's funny, I remember there was. I've probably said this before, even on the podcast. But you say one true thing, right, like, say something that's true and authentic to you. Trying to create something that is inauthentic will be ferreted out and it's not going to last long. But you had said in one of your interviews, like, they can't duplicate you. But the other thing that you realize is that your perspective, as unique as it might be from your social location, I'm not the only person who feels this way. I'm not the only person who thinks this way.

Mark: 33:43

Say something true about you and you will find people who will rally around. And especially in this day and age where we can actually just create a community, essentially by having, uh, like, uh, a profile on a social media platform, and I just say, hey, you know not feeling great today. Uh, this is what I'm kind of dealing with, but you know we're working through it. By the way, you know this is kind of what we're doing and you just kind of you know, press stop. Somebody out there is going to be like I'm also not having a great day, or somebody's going to say, hey, man, hope you feel, hope you're feeling all right, like I think there's this counterintuitive thought, I'm sure with people where it's like no, I get the business, I know what the actual thing on the balance sheet is, but the part that drives people back to this is the fact that we're authentically connecting with them.

Jake: 34:33

Done and I think that you said it right. There's no two feelings that are the same in this world ever, but they can be relatable and the way that you make people feel somebody else can't necessarily do that. We each make people feel something deeply that's different than anybody else, and I always say they can copy your product and copy you know the branding but they can't copy you and how you make them feel, and that's something that we can do by sharing your story, being yourself every day and and and showing up. That's all it is, and if you hide behind all that, then how would someone feel anything from what you're doing?

Mark: 35:10

Yeah, and it's, you know, it's, it's remarkable, it's such a counterintuitive way to look at business and that's why I was, you know, kind of tripping over this all the time.

Mark: 35:17

I'm like there's gotta be something here that's a little more kind of stock off the shelf where you can talk about when it comes to business. I'm like no, it's actually the passion here is connection, and it's an odd thing to think okay, because that's not going to show up on the balance sheet, it's not going to be in the assets or liabilities, it's not going to be how many people we made smile or feel a certain way today, but it is kind of the part of the fuel that drives all this. So I want to take another step back, because you often talk about documenting the good, the bad, the ugly, the ups and downs of business and something I've been asking people, because I think we learn the most from failure it's hard to learn a lesson when things are going well, because everything's shiny and bright and all the cracks are obscured, but you always take time to reexamine when things go kind of wrong.

Jake: 36:13

So what is your favorite failure? I think that my favorite failure that we've gone through is most definitely well, we made a huge mistake and I said it in this event in Toronto, we changed our product from two squares to one square and that was a big change because you've changed a UPC code change and in my gut it was telling me to do it. Like all three of us were like, do it. But we knew that the whole business can be on the line and we didn't really realize how long it would take. And when we did the change, we raised prices 27% of the time. We changed some ingredients. We did, and we told our customers everything. We were open about it. And when we did it, we thought give it a two-month break. And then next thing, you know things weren't going so well, you know we were losing. You know went from a million five a month or something to $500,000 a month, and that's scary for a small business, right? And we realized that. Did we just throw the whole business away? And the reason why it was a failure was not because of the decision. The decision ended up being the correct decision. The reason why it was a failure was not because of the decision. The decision ended up being the correct decision. Eight months later, it's now working. It was working phenomenal. It made a lot of sense. Today it makes sense.

Jake: 37:22

The failure was is we took a lot for granted during that time when we did the change. There's a code thing that's called the UPC code and it's a barcode that's on each package and it basically retails. You scan it and basically retailers scan it right, but it keeps the stock, the inventory, it makes sure that so they can get their auto orders and all that stuff. And when we did the barcode, we didn't think twice about it. We were just like, okay, let's change it. We were negligible on little things, very little things. The big thing was, okay, prepping our retailers that were doing a change, the distributors getting ready, you know, getting the ingredients. The small little thing that costed $20 to check on a website, we didn't check, we just took it for granted. And when we shipped it I think it was a million something, bars or whatever it was it couldn't scan in stores. So when we shipped it, not only did we make consumers upset with the change, they were unable to buy the product Wow, unless you typed in the 10 numbers in small on the back. But imagine you bought 12 bars. You typed in 12 different times. The cashiers were livid, the retailers were mad, so they just started scanning it as a grocery item and guess what that does? It doesn't register as a Mid-Day Squares square, so no one was reordering.

Jake: 38:23

So we're like holy shit, we just bankrupt the company on this decision. But all it was was a $20 check and we didn't listen to people around us. People told us GS1, do all these checks, blah, blah, blah. All this process, this basic process stuff. And Today we learned that any type of change has to go through a process, a structure and a bit of bureaucracy, because without that you have these issues which you almost bankrupt a company on the smallest little thing. It wasn't that the change was made, it was that a barcode didn't scan. And it's my favourite failure because you will never see us do a mistake on things without checking and process before we do changes in our company. So we've already implemented all the changes process, safety, quality, everything from that moment. So I'm grateful that we went through it at the stage we went through it, rather than going through it when you're doing $100 million or $200 million and the opportunity cost could be $50, $60 million, right. So that was crazy. Like I was depressed during that time.

Mark: 39:25

I was like yeah, I could imagine.

Jake: 39:27

I felt like it was all out of control. I felt the whole company was done, the dream was over, the party was over and we lost it on a dumb mistake. How many yeah?

Mark: 39:37

yeah, I mean, I suppose that's the whole. When I say, when I'm talking about you know your favorite failure, what I'm talking about is how you pivot and learn from failures. That's you know. And then, in the like you might still like at this point it's still kind of near, kind of like near history. So it still feels like it stings a little bit. But some of mine I'm like I look back and I kind of laugh and I'm like I can't believe that I did that, like I can't believe I did this and expected a different outcome, if you know what I mean.

Mark: 40:05

So how many? How many employees do you guys have now? I think it's 60. 60? Fully automated factory.

Jake: 40:10

Yeah, 97% automated. We're almost fully automated. It's a custom factory, which is kind of cool. So we went to 26 co-manufacturers at the beginning. Not one of them was able to. We want to. So my sister went out and figured a way to make a manufacturing plant in Montreal which can support up to 70 million output a year. So we have to go build a second line within the current facility in the next 24 months likely.

Jake: 40:31

So how many bars do you move every year? We're we sold 20,. To date we sold 27 or 28 million chocolate bars. We're moving about this year we're looking to do about 24, $25 million of revenue and then next year maybe $60. So next fiscal year, as we do by fiscal. So our fiscal is May 1st, Nice, but that's all. Again, that's projections.

Jake: 40:53

But that being said, there's so much that could go wrong, right, and that's why I say, with a grain of salt, but that's what we're gunning for in our momentum and our strategy. But look, the world goes through all kinds of things and next thing, you know, like you know, your revenue could fall off a cliff 60%, you know. So I always, I'm always nervous, you know, I'm always like my stomach's always turning, you know, especially with food safety. You know people are consuming your product. It's not putting on a t-shirt or clothes where you know it's just an item. You're actually putting it in people's bodies. So having the perfect process and I mean perfect, trying to get as much perfection as you can in terms of safety and quality is our priority. So operations is the focus this year to continuously become, you know, hopefully world-class in that, and I could say that that would be a massive accomplishment for our business.

Mark: 41:44

So when you get those butterflies and that churning, other than going to therapy, what do you do? How do you study that? Or are you just one of those guys who chugs Pepto-Bismol and says like let's go?

Jake: 41:55

Yeah, no, I go to the washer. I definitely diarrhea a lot, but what I can tell you that happens is I talk to my partner, like my wife, about it in deep, deep, deep, deep detail, from a perspective of what's your opinion, and I trust her to give me honest, hopefully non-biased advice, which she has given over the last five years. But the second thing is you got to be peaceful, and this is the hardest thing about the whole journey. You need to be peaceful with it all falling apart and be okay with that, because it doesn't define you. Mid-Day Squares Squares doesn't define Jake arls, doesn't define my partners either, or the team members we have. So as long as we're giving it 150% every day and excited about that, then we're doing everything we got to do and the world will tell us what happens to the business.

Mark: 42:46

Do you think that comfort with having it potentially fall apart comes from the fact that you've had businesses work and fail before? And so you're like well it comes and it goes, and I'm still here, essentially.

Jake: 42:57

And yeah, so still here and all that. It's like also, just like you figure it out. And you know, my partner texted me yesterday, Nick, he was on his way to New York to meet an advisor and we basically had some sort of meeting happen. Before that there was something that didn't happen that was good for the business. It was just basically a, a, an opportunity that didn't work out.

Jake: 43:53

And he's like I'm deeply depressed, like I'm giving my all, and deeply depressed. And I looked at him. I said, dude, we know, like if it doesn't work, it doesn't work, man, like it is what it is. And then he's like I need like an hour and he took an hour. And then he texts me. He's like I feel good. He's like I feel good that you, me, leslie and the team are giving everything we've got to build this vision and that there's nothing really more we can do.

Jake: 44:12

And he's like, yeah, like I'm exhausted too, but like we're going to go down swinging. If we go down, otherwise we're building a unicorn business. So you know, I always say we're either going to crash, we're going to burn, sorry, we're either sorry. We're either sorry. No, no, we're not going to crash or burn. That's only that's two negatives. We're either going to build a unicorn billion dollar business or we're going to crash while doing it. And I'm okay with both, and trust me, we have shareholders, we have amazing community. We are gunning for the top, we are giving it all to the top, but there is a chance that it won't work.

Mark: 44:54

What do they call that? Beautiful risk. There's a book that I read a long time ago called Beautiful Risk, I highly recommend. I can't remember the name of the author, but I can see it in my mind right now.

Jake: 45:03

Daddy, it's time to take a break.

Mark: 45:05

Are you a new business owner, starting out on a new venture, or perhaps you're at the other end of your entrepreneurial journey, eyeing a smooth transition to retirement? Maybe you're planning to expand and take on the next chapter of your business. Whatever your need, Lerners Business Law Group is here to help. Our team has the expertise and dedication to help you achieve success. With decades of experience in business law, we provide personalized solutions tailored to your unique situation. Whether it's navigating complex regulations, securing contracts or planning for the future, we've got you covered At Lerners Business Law Group. Your success is our mission. Let us guide you through every step of your business journey, ensuring peace of mind and a solid foundation for growth. Ready to take your business to the next level, contact Lerners Business Law Group today and let us help you achieve your goals.

Jake: 45:54

And now back to the show.

Mark: 45:56

You were talking about Nick and I know you've described so. You're the chief rainmaker. You're also a hype man. You've described your sister as a rock star and like is Nick the strong, silent type, like he's the original taste tester.

Jake: 46:09

Yeah, he's the original taste tester.

Mark: 46:10

He's the original taste tester, but like. But you know that team that core that tripod. You know, what do you think is the strength that each of the three of you brings to this?

Jake: 46:23

The strength is that we're all out of our fucking minds excuse my language, I'm okay, we're whacked out and putting that together is great and that we all have three different skill sets. So my brother-in-law, Nick he's an operation genius and what I mean by that is he's a data guy. He's a software engineer by trade. He loves numbers and he's so brilliant when it comes to analyzing data. So when we make our decisions in the company, it's based on his findings and he loves that. Like that's what he genuinely has so much fun with. He feels at home, he's weird with it and that's who he is.

Jake: 46:51

My sister is a creator and a builder, so she is the one that built the factory, she created the product and now she's moving into the creative side of the business. But she's very bold in that sense and she's the most and I say this she's the most empathetic out of the three of us. So she holds us accountable to a lot of things that Nick and I would bulldoze through and she doesn't let. And then my job is simply to connect. Like you said, is to rain, make is to build, the friends of Mid-Day Squares Squares, the community, the brand, and when you put these three things together these three individuals that believe in the same vision and bring their skills, you have a very foundationally strong tripod where you have people only playing their strengths, not their weaknesses.

Jake: 47:33

I would never do any operational stuff. I'm horrible at that. My sister doesn't want to do necessarily the things that I do and my brother-in-law doesn't want to be, you know, doing what I'm doing, but he loves what he does. And then you know, we never cross each other, and that's the beauty of this business. And if we do cross each other, we have very strategic conversations about it.

Mark: 47:52

It's funny, I used to ask people this question. It's like if you could restart your business, you know, knowing, you know now who are the your, your first three people that you would enlist, and why. And I want to ask you that question because you have a tripod where you say, like you know, these people are complimentary, like this is how this works, and we all bring something different and that allows us to kind of spin forward.

Jake: 48:16

And, trust me, we're far from perfect, like we each have major downfalls and they come out. But the truth is one thing that we like to say is we're right more than we are wrong. And if we could keep being right more than we are wrong and staying in the pocket I say staying in the pocket meaning just withstanding the amount of pressure that is to build a business then if we step another day forward, then we win, and the longer we could do it, the more we win. And one of our mentors he's actually, I think, is alumni of Western as well, but he's also on our board Brilliant entrepreneur, older guy, 50 years old. He's jacked, good, looking, kills it. He's a philanthropist. It's a philanthropist Like. He's a like a rockstar entrepreneur. He always told me shut him out. He's such an amazing human. David Cinnamon His kids also went to Western. That's how I knew him actually was through his kids. But he's the nicest guy in the world. He has no ego. He's just somebody that elevates you when you're with him.

Jake: 49:12

He's simply elevating the world One day at a time, one person at a time, and he doesn't ask for anything in return. And he once told me and my partners we were feeling down and he just said he's like whoever withstands the most amount of pressure the longest wins, and whatever that means winning to you. And the more I go through this journey, the more I see how much pressure it is. It's a pressure cooker and the more I step forward and keep waking up the next day and going, the more we win as a business. So I stay true to that and I believe it tremendously.

Jake: 49:44

And the moment you you know most businesses fail. They don't fail because their products are bad or they're they're, they're they want out of capital. They actually fail because they can't withstand the pressure or they can't withstand the pressure of their partnership. They hate their founders, they fight, they get animosity. They can't deal with that pressure. I think that one thing that you can guarantee with Mid-Day Squares Squares is that we can withstand pressure and we will not misalign, because we invest resource, time, energy and love into our partnership.

Mark: 50:11

I think that's beautiful, and I don't think there's much more I can add, to be honest, and so I'm simply going to say thank you for being here, thank you for taking the time to connect with us today, and let me know when the fifth flavor comes out. It's coming. It's coming, all right, all right, all right. You heard it here first, folks there's going to be a fifth Mid-Day Squares Square flavor.

Jake: 50:31

Let's go.

Mark: 50:31

Jake, thank you so much for being here today. I appreciate you and I appreciate your time, appreciate you. Thank you. If you have any questions, feedback or would like to be a guest on the show, reach out to us marketing@ learners. ca. Anything But Law is a Lerners Business Law Group production. Thanks for joining us, cheers.