This Isn't Really About Chocolate

What a Mid-Day Squares founder taught me about doing this for a long time

Ain't gonna lie. I eat Mid-Day Squares daily on my trips to Whole Foods. I go everyday and always come back with one. Like the sun coming up.

So when I got on the phone and actually had the chance to talk to Jake Karls I was ready to geek out on chocolate if there is such a thing.

Jake is the Chief Rainmaker of Mid-Day Squares, the Montreal-based chocolate company he built with his sister Lezlie and her husband Nick starting in 2018. I always knew their bars but then I was loosely introduced to Jake through a friend.

I spent my time watching Jake on TikTok for a while — he is high-energy, always on camera, always selling.

I did my research on Mid-Day Squares and got my seven questions ready.

Some of them were the questions he normally gets. Some of them were meant to get him off the rehearsed track. I wanted to know what he thought about the ten-year version of a brand built entirely on the visibility of three founders.

We got there. Which was cool. But then we went completely somewhere else which was better.

By the time we got off the call, I realized I hadn't been interviewing a 32-year-old wizard quasi Willy Wonka about chocolate. I was chatting with another founder about what happens when you do this for a long time. Two guys separated by twenty+ years of experience finding out we were actually working on the same problem in different phases of the same career.

Here's what I took from it.

We stopped talking about the business pretty quickly.

The first question I asked Jake — the one about the customer experience — I opened by telling the truth - I eat Mid-Day Squares almost daily because the bars are 150 calories, which meant I wouldn't overeat, and they taste like a treat. I told him that was the whole reason. Full stop. Not the story he tells on social. Not that founder narrative of his. Just: I like these because they're portion-controlled and they don't taste like health food.

He didn't push back - didn't seem flustered. He said it aligned with what he was seeing in customer trends — people looking for functional, portion-controlled indulgences that fit into an afternoon routine. That was the moment I realized we would have a real conversation, not a canned pitch. Most founders would have redirected to the mission. Jake just agreed.

He set the right tone.

The brand's future is about evolving, not disappearing.

Mid-Day Squares has spent seven years being three people on camera. Jake, Lezlie, Nick. Their faces, their voices, their family drama, the "good the bad the ugly" of building it. That has been the whole engine. It's what got them to Whole Foods and Target and 30 million dollars in annual revenue.

Jake was clear with me about something worth naming here, because I want to get this right. Storytelling isn't going anywhere. It's still one of the biggest pillars of Mid-Day Squares' strategy and of Jake's personal brand. They still believe in building out loud. The relationships with retailers, investors, and their community were built on that foundation, and they're not walking away from it.

What's changing is how they tell the story. In the early days it was much more of a 24/7 documentary — every disagreement, every legal battle, every therapy session was potential content. Today they're more intentional about what they share. Authenticity is still the center of everything. But the format is evolving. Jake told me they've got some campaigns coming that reflect that new approach, and separately, the brand itself has to be able to stand on its own without the three of them being the faces of every single story.

That's a subtle but important distinction, and I want to sit with it for a minute because I think it applies to more than chocolate.

Building a brand on personal visibility gives you tremendous early leverage — nobody else can replicate you being you. But the leverage compounds only if the brand can eventually operate without every story requiring the founders in the frame. The move Jake and his family are making isn't to abandon what got them here. It's to build the version of the brand that can carry the same storytelling philosophy into a scale where the three of them can't personally be in every piece of it. That's a much harder move than either "stay on camera forever" or "stop telling stories." It's the middle path, and almost nobody executes it well.

The 24/7 trade show is real.

I asked Jake a question I'd been thinking about for weeks. Not about content strategy. About the personal cost.

He called it a "24/7 trade show." That was his phrase. The way he described it, being on camera every day for seven years - talk about exhausting. There's no offstage. Every meal could be content. Every conversation could be content. Every disagreement, every legal battle, every moment of doubt is potentially something the audience wants.

He works with a coach. What I love is that like me, he guards his mornings hard. He said something that stuck with me: that rest isn't the opposite of performance, it's a component of it. Without rest, you can't sustain the performance long enough for the business to actually work.

This is the moment I recognized we were talking about the same thing from opposite ends. I've been running Rotary for nine years now. I've watched what it takes to be publicly present as a founder for a long stretch of time. I know what happens when you don't protect the first part of the day. Jake is 32 and figuring out at year seven what I'm still figuring out at year nine. The lesson is the same regardless of the age gap.

Protect your mornings. Rest is not weakness. This isn't a sprint and it isn't a marathon — it's just a damn long time. The people who last are the people who don't waste away before year 10.

Delusional self-belief.

The phrase Jake used, when I asked him what actually gets a founder through seven years of pressure, was "delusional self-belief."

He was making a specific point. He said that anyone who does the math on entrepreneurship the way a rational person would — expected value, risk-adjusted returns, probability of success would probably work in banking. The people who become founders are the ones who somehow realize that the math doesn't work. Rejection is a temporary condition. That the current pain is not the permanent state.

I laughed when he said this because it's obviously true and almost nobody says it out loud. Most founders talk about grit and resilience and vision, etc. Delusion is the right word. You have to believe something that the market has not yet given you any reason to believe. And you have to keep believing it after the many stumbles and failures that try to tell you are wrong.

The trick, Jake said, is that the delusion has to coexist with the actuals: shipping products, serving customers, building the business. Delusion without execution is just that - delusional. Delusion with execution is what carries you through year three when the numbers are rough and year five when the co-founder tension peaks and year seven when the strategy that got you here starts running out.

The years are slightly different for me at Rotary, but the pattern is the same.

Morning routines.

We ended up spending real time on this, and it was one of the more surprising parts of the call.

Jake protects his mornings for personal time. He said it builds momentum for the day and maintains the curiosity he needs to keep being interesting on camera and in meetings.

I told him about mine. Oil painting most mornings, sometimes padel at Ballers in Fishtown. I paint under the name Daub — a small daily practice I've kept up for a while now. Each painting gets paired with a song. It's not a business. It's the thing that sets the tone for every day.

We agreed, in a way that neither of us said out loud but both of us understood, that the morning practice is the thing that keeps the rest of the day functional. You can't be creatively empty in the afternoon if you started the day making something. You can't be reactive if you started the day being deliberate about your life.

Jake plays padel too, at a place called Kopa in Montreal. We're going to try to hit the courts together next time he's in New York. Should be epic.

What I took from all of it.

The piece I thought I was writing was about chocolate and how a small brand survives in a crowded category. That piece would have been fine I guess.

The piece I ended up wanting to write is about what happens when two founders in different phases of the same career recognize each other's actual problems. Jake is on the front end of figuring out how to sustain the personal cost of being a founder in public. I'm further into it. We ended up trading notes on things neither of us would have expected to talk about at the start of the call. Morning routines. The specific weight of being on camera for years. The delusion required to keep going. How to hit a better Bandeja. The eventual challenge of building something that doesn't need you.

Mid-Day Squares is still about chocolate. But Jake is really building a company that has to teach him how to run it for another twenty years without breaking him. That's the same company all of us are building, at whatever stage we're at.

If you're a founder who's been at it for a while, or just starting, take one thing from this. Protect your mornings. Believe delusionally in the version of your business that doesn't yet exist. Rest is a strategy, not a break from it. And find the version of your work that can scale beyond your daily visibility, because eventually you'll need it.

Also, the chocolate is really good. You should probably try one.

Take a look at what Jake and his family are building at middaysquares.com.

— Sean