That’s the daily reality of retail operations for small businesses, where every decision behind the counter affects margins, loyalty, and long-term survival.

In this interview, I sat down with Ebun Onagoruwa from Square to unpack what real support looks like for retailers in 2026. We talked about how data can help you make faster decisions, where most operators waste time and money without realizing it, and the practical moves that keep customers coming back even when costs keep rising.

Key points from the discussion:

• Square started with the little white reader, but it’s grown into a full business platform
• Block is the broader ecosystem, and Square is focused on sellers and local businesses
• What customers don’t see is what matters most: planning, inventory, margins, loyalty, and operations
• Small businesses juggle multiple roles, so tools must be simple and valuable
• Patterns of successful businesses: clarity of brand, obsession with customer experience, and practical tech adoption
• Square AI is built around practical scenarios inside the dashboard
• Cash still matters, and coin changes could impact daily operations
• Square’s message to entrepreneurs: plan, choose the right partner, and become a neighborhood favorite

The Conversation That Started It All: A Real-World Square Moment

I opened the interview with a simple story. I had my carpets cleaned, and when it was time to pay, the technician pulled out the small Square reader. Tap, paid, handshake, done.

That moment matters because it represents something bigger than a transaction. It’s speed. Trust. Ease. And for the business owner, it’s getting paid without friction.

Ebun told me Square is proud of those roots, but also proud of how far the platform has come. The goal is still the same: help businesses accept payments and run more smoothly. The scope is what’s expanded.

Block vs. Square: The Ecosystem Explained in Plain English

I asked Ebun to break it down clearly, because people hear “Block” and “Square” and don’t always know how it fits.

Here’s the simplest way she framed it:

• Block is the umbrella, the larger ecosystem focused on economic empowerment.
• Square is where she works, focused on helping sellers and businesses run, sell, and grow.
• Other brands in the ecosystem serve other audiences and use cases, like consumer financial tools and broader commerce options.

For the business owner listening, the practical takeaway is this: Square is built for the seller who wants to run better, serve better, and grow without adding chaos to their day.

What Customers Don’t See: The Real Work Behind the Counter

One of my favorite parts of the interview was when we used my Jamaican patty shop example from Brooklyn. I wanted to know what’s happening behind the scenes that customers don’t see.

Ebun walked through it like this:

Before a customer even walks in, the owner has decisions to make:

• What does the brand stand for?
• Who is it for, and who is it not for?
• What are the revenue targets and customer goals?
• How do we differentiate from other places nearby?
  

Then there’s the operational reality:

• Inventory planning.
• Supply cost pressure.
• Menu decisions tied to margin and demand.
• Staffing flow, from front counter to back of house.
• Loyalty and follow-up so customers come back.
  

This is especially true for retail operations for small businesses, where inventory, staffing, pricing, and customer experience all intersect in real time.

Why “Simple” Is Not a Nice-to-Have for Small Businesses

We also talked about something every entrepreneur feels: most small business owners don’t have five departments. They have one person wearing five hats.

Ebun described different “personas” that might use Square in a larger business:

• Frontline staff
• Back-of-house team
• Back office and management
• Owners tracking performance across locations

But then she made the point that matters most: for many businesses, all of that is one person. Which means the tech cannot be complicated.

I shared my own “standard”: if I need a manual for basic use, it’s already too much friction for most people. Tools should feel intuitive, especially at the point of sale.

What the Best Performing Businesses Do Differently

When I asked Ebun what patterns she sees among the most successful businesses, she gave three clear ones. These are worth repeating because they apply to almost every industry:

1) They know their brand

Not in a fluffy way. In a practical way.

Who are we serving? What do we stand for? What is our value proposition? What are our targets and revenue goals?

2) They invest in customer experience

Even when costs rise and pressure hits, the best businesses keep the experience strong. Customers remember how you make them feel. They come back for consistency.

3) They embrace technology with curiosity, but only when it creates value

This is where her line landed hard: “AI for ROI.”

The message wasn’t “use AI because it’s trendy.” The message was: use tech when it saves time, creates insight, improves decisions, or helps you serve customers better.

Square AI: What It’s Designed to Do in Real Life

We spent time on what “AI” means when you’re not living inside a tech bubble.

Ebun explained Square’s approach in a way I respect: build it with sellers, test it with sellers, and focus on real scenarios.

She gave examples of how it can help:

• Ask questions about what’s selling fastest, who your best customers are, and what trends are showing up.
• Reduce manual work by helping set up menus and catalogs.
• Support smarter purchasing decisions by comparing vendor costs and guiding order decisions.

That approach matters most in retail operations for small businesses, where tools need to save time and improve decisions without adding complexity.

The Penny Conversation: Small Detail, Big Operational Impact

I asked about physical coins and how changes around pennies could affect small businesses.

Ebun’s point was practical: cash transactions still matter, and coins still move through local businesses at high volume. If coin availability changes, it creates friction at the counter and slows down staff.

She shared that Square is piloting a penny rounding feature designed to:

1. Round cash transactions to the nearest five cents
2. Show the rounding clearly on receipts
3. Track it properly in reporting, so taxes and records stay clean

Even if this sounds like a small detail, anyone who’s ever stood at a busy counter knows how tiny disruptions stack up fast.

Ebun’s Message to Entrepreneurs: Become the Neighborhood Favorite

Near the end, I asked for her message to small business owners.

Her themes were clear:

• Entrepreneurs are the lifeblood of the economy.
• Plan, even while managing day-to-day realities.
• Choose the right technology partner, one that grows with you and listens to feedback.
• Keep the customer and community at the center, because that’s the real differentiator.

I loved the way she framed it. The tech helps in the background. The business wins by delivering value through craft, consistency, and experience.