How Midday Squares Built a Brand Out of Unaverage Decisions

Hey everyone,

Welcome back for another bite to chew on.

Consumer brands are no longer competing on product alone. They are competing for attention, and attention now belongs to whoever makes people feel something. In a feed of billions of posts, the brand that gets scrolled past is the one that played it safe.

Jake Karls knows this better than most, because he failed his way into it. He started Midday Squares with his sister and brother-in-law, took the CMO title for the ego of it, and stepped down after eight months. "I just wasn't good at managing organization and execution," he said. His partners told him to figure out his strengths and go all in. What he found was that he was built for relationships, not operations. So he gave himself a new title: Rainmaker.

That decision helped turn a condo-kitchen chocolate bar into the first functional chocolate brand in 10,000+ stores, with more than 85 million squares sold. Along the way Midday Squares broke a Costco sales record, survived a revenue crater, and reinvented its entire product line through a cocoa crisis. None of it came from following the herd.

On the Menu:

(BTW, this is just a taste of our chat with Jake. Listen to the full recording here).

Jake's whole job is to make bets that do not pay back for years. His partners "just know when I swipe the credit card in different cities," chasing relationships where, in his words, the return "could be an ROI in six years."

That is the real cost of growth. The trip, the roadshow, the retail-media test, the two-year innovation runway: the card swipes today, but the payoff lands months or years out. The gap between the spend and the return is exactly where most growing brands run out of room. Flex was built to close it.

Flex gives high-growth brands a true Net-60 card, so the money you put down on a long-term bet does not come due before the bet has a chance to work. Pay a co-packer or fund a launch today, and settle up when the revenue actually shows. And for the partners who never take a card, Flex lets you pay them on credit anyway.

Click here to get net-60 credit built for growing brands.

Jake's first principle is internal. "The story that you're gonna tell yourself is the most important story you'll ever live by," he said. The founder who decides they cannot create content, do not have time, and will only hurt the business by trying has already lost. That story compounds into negative momentum until you conform to whatever everyone else is doing.

The fix is to write a different story and act on it. Jake's was simple: I have an interesting business, I have a real story, I am going to share one small thing a day. He was not good at it at first, and that was the point. Sharing is a muscle. The reps build the conviction, and the conviction sharpens the story.

The payoff was not subtle. His LinkedIn went from 10 views a post to 250,000. Those views turned into financing, retail partners, team members, and friends, all because he decided people should hear his story from his own mouth.

Midday Squares has documented the good, the bad, and the ugly since August 2018. The thesis Jake pitched his partners on day one: if we get people to care, they pay attention, and then we can sell to them. So they told a raw, emotional, unfiltered story across personal and brand accounts, the wins and the genuine hardships both.

The result was a roster of relationships that existed before any meeting. Investors watched the journey unfold on LinkedIn and Instagram without ever liking a post, then arrived already knowing the brand got into Target or launched a margin-crushing innovation. Retailers reached out to the brokers, or directly, asking Midday Squares to come sell. The storytelling put one foot in the door. Due diligence and the business model handled the rest.

Jake is careful about why it works. The content is not about the protein, the fiber, or the clean ingredients, even though he rates all three. "If I hounded that down to you every day, you'd eventually be like, this brand is so boring." Instead he shows the human moments, like his sister stepping down as CEO for an eight-month sabbatical after a health scare. That is what makes a stranger want to cheer the company on.

In a world of billions of posts, facts and figures get swiped past. Post the same thing as the brand next to you, Jake said, and "it's literally going to be swiped, scrolled by or fast forwarded." The job of content is to make people feel something, because relatability is what registers.

That reframes the metric, too. A post with 100 views is a failure or a win depending on who saw it. If 70 of those viewers are retail buyers at accounts you want to crack, you are crushing it. Jake's filter before posting is two questions: what emotion do you want to evoke, and do you even like your own content? If both check out, hit post and stop polishing for four hours.

He has lived through the doubt. Early on, industry experts and friends alike called the content gimmicky and a little cringe. Midday Squares blocked the noise and kept going. The same people later marveled that the brand landed Walmart Canada and Target. "The compounding effect is real," he said.

What you can do: Pick the one true, emotional thing about your business you have been too polished or too scared to post, and share it this week without editing it for four hours.

Costco took three years. The sticking point was getting the product on shelf at all, and the opening they earned was a Costco Canada roadshow. So Jake set the bar at breaking the chain's roadshow record, and the team did everything in their power to hit it: rallying fans on social in real time, getting the press involved, bringing family and friends in to work the booth, making it an experience.

"Energy is a currency," Jake said. "No matter where you are, people want to feel something." The community wanted Midday Squares at Costco because the win felt like theirs too. Midday Squares blew past the number across four roadshows and started selling in Costco in January 2025.

The deeper lesson is about hearing no. A no can be a not-yet. A category a retailer passes on today might be hot in two years, and the brand that stayed respectful and in communication is the one that gets the call. Jake's posture is long-term: keep the energy up, keep building the relationship, and treat the retailer as a partner, not a shelf to rent.

There is no one-size-fits-all retail strategy. Jake is blunt about it: understand what each retailer wants and needs, then build a strategy specific to them. An FDM account might move product on its own with light marketing, while a grocery channel demands far more effort for the same brand. The format dictates the play.

This is especially true for a refrigerated product. Midday Squares does not get consistent placement, sometimes landing in dairy, sometimes produce, sometimes the HMR set. That inconsistency is a velocity problem, and velocity is survival. "Getting into store means nothing if you can't move the product," Jake said. Weak velocities get you kicked out of valuable real estate.

Jake names four levers for selling through. First, traditional retail marketing: price and promo strategy, packaging visibility, and placement in the store. Second, a retail-specific influencer strategy, with creators who do hauls at the exact grocery stores where the product lives, pointing shoppers to the merchandised spot. Third, content and paid media that tells the story of how the brand got into a retailer, so the sell feels like support, not a pitch.

Fourth, and the one most brands resist, is retail media. Jake got "so much bad advice" from operators who built their brands decades ago and called retail media a scam. Midday Squares ran the incrementality test on Walmart Connect, comparing months with spend to months without. The difference was night and day. For a refrigerated brand, retail media buys the front-row placement that the dairy case never will. Instacart, meanwhile, drives the trial that turns into repurchase. Jake calls the whole aim "bars to belly."

What you can do: Run a clean incrementality test on your largest retailer's media platform before you trust anyone's opinion about whether it works, including your own.

Around three and a half years ago, Midday Squares went from two bars per pack to one square and raised prices 30% to survive a supply-chain squeeze. The change came with a hidden landmine: the new UPC code was too small to scan reliably at retail. Stores rang the product up as a generic grocery item, so out-of-stocks went untracked and reorders stalled. Revenue cratered from roughly $1M a month toward $400K.

Jake's framing of the moment is the whole lesson. You have two options: sit still in inaction, or act. "Panic doesn't work," he said. The team felt the grief for a day, then chose movement, solved the problem, and brought revenue back over the following months. The same pattern repeated when COVID wiped out retail sales.

The strategy underneath was not clever. It was momentum. "Create action and let that compound," Jake said. You might be wrong, but you take the bet. Midday Squares took it, and the team got fired up watching the recovery happen.

Then came the cocoa crisis. Midday Squares was a chocolate company, and its largest input "went to 100 year high. It quadrupled." Raising prices was off the table for an already-premium product. That left one real option: innovate out of chocolate entirely.

They chose innovation, and it took two years. After more than five years as a functional chocolate company, Midday Squares launched its No Bread PBJ line, a brand-new product with no cocoa. It is now the company's number-one seller. The constraint did not just produce a workaround. It produced a better product and a repeatable innovation process, with a new flavor now possible every five to six months.

The kicker is timing. Because they refused to lean on price and built the new line instead, cocoa prices have since come back down, and Midday Squares gets the tailwind on its original products too. "If we raise prices, we'd probably be in a very different situation right now," Jake said.

Jake is direct that none of this scales on the founders alone. Midday Squares started as three people and is now around 55, and Jake says the team is smarter than the founders. The job became building an environment where their greatness and the founders' greatness combine.

He puts it in plain math. The cliché says one plus one plus one equals three. The real goal is to make it greater than three. Surrounding yourself with the right people creates a compound effect, the same force Jake credits for everything from content to retail wins. The founder's job is to assemble that force and then get out of its way.

What you can do: The next time an input cost or a channel collapses, give yourself one day to grieve it, then ask what you can build with the constraints you actually have.