A ROUNDPEG FOR A SQUARE PROBLEM

January 7, 2026 by Daniel Castaneda

BY: CATHLENA SPENCER

For many small business owners, the hardest part of the job isn’t serving customers- it’s the invisible battle with inventory. Knowing what to reorder, how much, and when can feel like a constant guessing game, even for well-run shops. Nathan Wakefield, a local entrepreneur and First Place Idea Stage winner of the 2025 Grow Ada Pitch Competition, knows this struggle intimately. His startup, RoundPeg, was born on the aisles of his own organic grocery store, QUNO, right here in Ada.

Nathan describes the “perfect” retail scenario as one where every product sells out just before the next shipment arrives- a completely efficient sales engine. While that may be unrealistic, every retailer understands the cost of falling short. “I’d place an order with a supplier, only to realize three days later that dark chocolate chips had run out and we’d have to wait a month to reorder them,” Nathan explains. “Other times, I’d order extra kettle chips because it seemed like they were selling faster, only to discount the extras months later when demand didn’t materialize.”

These painful gaps aren’t minor inconveniences. Every slow-moving product sitting on a shelf ties up cash, and every missing item risks lost sales and weakened customer trust. While large retailers like Walmart or Amazon have teams and advanced systems dedicated to optimizing inventory, small business owners are often left relying on instinct.

That gap is exactly where RoundPeg comes in.

Most local retailers use Square for payments and inventory tracking. However, Square shows what happened in the past- it doesn’t always help owners decide what to do next. As Nathan puts it, RoundPeg’s unofficial tagline captures the idea perfectly: “Sometimes you need a RoundPeg to fill a Square hole.”

By connecting directly to a business’s Square account, RoundPeg transforms raw sales data into an intelligent ordering engine. Instead of relying on habit or gut feeling, RoundPeg helps owners:

Determine exactly how much to reorder based on actual purchase patterns
Identify the optimal time to restock so shelves stay without overinvesting
Flag “shelf-wasters”-products that take up space but don’t move

Since the pitch contest, Nathan has been using an early version of RoundPeg at QUNO. In just a few weeks, it has already saved the store hundreds of dollars by preventing over-ordering on products that would have sat on the shelf for months.

While RoundPeg is launching with retail stores in mind, Nathan sees a much broader horizon. Coffee shops could use it to right-size orders for beans and milk, restaurants could identify rarely ordered menu items, and mechanics could ensure critical parts are always on hand. Beyond individual businesses, Nathan envisions RoundPeg will foster local collaboration- helping retailers discover complementary suppliers or even place centralized orders together to meet vendor minimums and secure better pricing usually reserved for big-box stores.

For Nathan, this work is about more than software- it’s about the health of Ada and Pontotoc County. “For large companies, addressing these inefficiencies might mean a few million or billion extra dollars for shareholders,” he notes. “For small businesses, ordering more efficiently can be the difference between surviving a slow season, hiring another local employee, or keeping prices competitive.”

If you’re a retailer using Square and want to be part of the beta testing group, you can sign up for the waitlist at roundpeg.store.