The American Dream of Business Ownership Is Alive and Well – But Evolving

As the United States turns 250 years old, Square data shows how entrepreneurs are adapting to each era of disruption, while holding onto the principles that have always defined small business success.

Katz’s Delicatessen has been slicing pastrami on Manhattan’s Lower East Side since 1888. Baker St Cafe turned Thai recipes and traditions passed down through generations into a digital-first, neighborhood favorite. Vines & Rushes transformed a four-generation dairy farm into a winery, into a wine club, into an event space, and beyond. These businesses’ founding dates span more than a century, across different states, selling different products – but they share something that no era of disruption has managed to erode: the conviction that building something of your own is worth it.

As America marks its 250th anniversary, the story of small business ownership is not one of decline. It is one of relentless adaptation. From big-box retail, to ecommerce, to a global pandemic and now the rise of AI enablement, entrepreneurs have faced down every disruption their era presented – and Square data shows the results.

What has changed is almost everything about how a business is built and operated. What has not changed is why.

Main Street Meets the Mainframe: How New Businesses Are Born

For most of American business history, starting a company meant finding a physical space – a storefront, a counter, a workshop. In 2016, that held true: 98% of new Square sellers launched as brick-and-mortar only businesses. By the first half of 2026, that figure dropped to 74%, and the share of businesses launching as ecommerce-first grew from just 1.3% to 22%, a nearly 17-fold increase in a single decade.

• 17x increase in ecommerce-first business launches among new Square sellers since 2016.

The pandemic marked the clearest inflection point – ecommerce-only new businesses spiked from 4% in 2019 to 14% in 2020 – and the trend continued to accelerate after reopening. The shift reflects more than a change in tactics. It represents a generational change in what it means to start a business in America. Today’s business owner is expected to manage digital storefronts, accept online payments, and maintain social media channels from the outset – capabilities that did not exist in the small business toolkit a generation ago.

Donnie McClanahan, a longtime restaurant operator and founder of Table & Ledger, where he helps independent restaurants put AI to work on the floor, sees this shift as a fundamental democratization of expertise. “Distance barely matters anymore. I can do business with someone almost anywhere, whereas my parents were limited to who walked through the door. And I can see my own business clearly: why it’s working or why it isn’t, instead of guessing the way they had to,” McClanahan says. “But the biggest change sits under all of it. Technology compressed knowledge. The expertise you used to have to afford – the consultant, the specialist, the back office – it’s open to anyone willing to sit down and understand it now. It used to take money to know what to do. Now it takes the will to learn it.”

Adapting Without Abandoning: The Rise of the Omnichannel Entrepreneur

Square seller data points to a defining characteristic of this era: businesses are not choosing between physical and digital – they are layering atop and operating both. In 2016, fewer than 2% of active Square sellers operated across both physical and digital channels. By 2025, that number had grown to nearly 14%, an 8x increase. The share of brick-and-mortar sellers who added ecommerce has grown steadily every year since 2016.

• 8x growth in omnichannel sellers operating both brick-and-mortar and ecommerce since 2016.

Physical retail remains a cornerstone of American small business. Digital channels have expanded the reach of those businesses, not replaced them. The same entrepreneurial instinct – being where customers are – is now playing out across more channels simultaneously than any previous generation of business owners has had to manage.

For Ryan Prellwitz of Vines & Rushes, a fourth-generation family farm in Wisconsin that he transformed into a winery, event space, and café, that layering is both a data challenge and a philosophy. “We have a weather station on site, an events calendar, a staffing calendar, social media advertising metrics – and we can cross-reference all of it,” he says. “But that doesn’t take into account what’s happening in town on a specific day, graduation parties, events in the region. No matter how far you take the data, there’s only so much you can build into a formula.” His solution mirrors the omnichannel instinct: blend both. “Knowing when to lean on the data and when to lean on the relational side – that’s one of the most critical things we can do.”

“Technology Helps Tremendously, But It Can’t Replace Perseverance”

Fon Khunsamart, owner of Baker St Cafe, a Thai kitchen and bubble tea shop, built her business on the foundation laid by parents who immigrated from Thailand, and operates it today with tools unavailable to prior generations.

“What has become easier today is access to information and technology. My parents built their lives through hard work, word of mouth, and determination,” she said. “Today, small business owners have tools that help them reach customers, understand their business, and compete in ways that weren’t possible before.”

The competitive landscape has shifted accordingly. A neighborhood restaurant today competes not only with businesses on the same street, but with every option visible on a customer’s phone. Consumer expectations have risen alongside that choice.

“Most customers discover us online before they ever walk through our doors. They read reviews, browse photos, visit our website, and learn about our story. Technology helps us share who we are before we ever meet them,” added Khunsamart.

Square data reflects this dynamic. Social commerce adoption – connecting a business’s Square presence to Instagram, Facebook, and other platforms – grew from essentially zero in 2018 to meaningful adoption rates by 2025. Health & Beauty has seen the sharpest growth, rising from 0.41% adoption in 2018 to 11.79% year-to-date in 2026.

The Timeless Principle: Regulars Are Everything

Across every generation of American business, one principle has held constant: the returning customer is more valuable than the first-time visitor.

Square data quantifies that dynamic. Regular customers – defined as those who visit at least four times per year – generate six times the annual revenue of one-time visitors nationally. In Atlanta, that multiplier rises to seven. Regulars tip 11% more on average, and regular customer revenue grew 7.67% in 2025, outpacing overall revenue growth of 6.97%, even as transient customer spending declined.

• 6x more annual revenue generated by regular customers versus one-time visitors.

Baker St Cafe illustrates what that loyalty compounds into at the local level. Loyal customers at the café spend nearly double what non-loyalty customers spend on subsequent visits – $104 versus $52 on average. Loyalty revenue accounted for 22% of the café’s total revenue in 2025, and the business has now served more than 5,300 unique customers in McMinnville, Oregon – roughly one in seven residents of the town.

Usage of Square Loyalty has nearly tripled since 2021. Long-tenured sellers – those active with Square for 10 or more years – use loyalty tools at roughly double the rate of newer sellers, suggesting that retention becomes an increasing priority as businesses mature.

Product consistency is a key driver of that loyalty. Among beauty businesses, 78% of regulars purchase the same products each visit. At food and beverage businesses, 59% of regulars place the same order. Businesses that identify and reliably deliver on those preferences are best positioned to build the repeat customer base that sustains long-term growth.

What the Data Says About the Dream

Business ownership in America has never come with guarantees. Each generation of entrepreneurs has faced its own version of disruption, and each has had to develop new capabilities in response. What the data shows is that they consistently do.

Businesses that launched in 1970 navigated the rise of suburban retail. Those that opened in 2000 had to establish a presence alongside the early internet. Today’s entrepreneurs are expected to operate across physical, digital, and social channels simultaneously – while continuing to deliver the customer experience that drives return visits.

Square’s data captures American entrepreneurship at this inflection point, and reflects that ongoing adaptation. The ecommerce share of new businesses has climbed steadily. The omnichannel base has grown every year. Loyalty tool adoption continues to rise. And in a small town in Oregon, a Thai immigrant family has built a customer base by bringing authentic family recipes to the platforms where the next generation of consumers spends its time.

Prellwitz, who took the same land his grandfather farmed and evolved it into a multi-concept business none of his ancestors could have pictured, sees that continuity clearly. “It’s not as simple as saying technology is moving faster than it used to,” he says. “In reality, it’s all relative to where you are in history. The opportunity was always there – we’re just on the cutting edge of doing cool stuff with our version of it.”

McClanahan puts it this way: “I believe in the American Dream more than ever, but it has changed at the root. People still want to build and own something, that part is alive. What’s different is what they’re really trying to own. It isn’t just the store anymore, it’s the freedom. People want to run their business their way, on their own time, because time is the one thing none of us can make more of.”