Millions of Small Businesses Will Soon Be for Sale. Here's How Smart Entrepreneurs Are Cashing In

If you're serious about building real wealth and autonomy in 2025, your fastest path might be the family business down the street.

Over the next decade, millions of small businesses — an engine of America's real economy — will transition to new ownership. But this shift won't play out on public markets or through high-profile dealmaking. It will happen in quiet, negotiated transactions between retiring owners and the next generation of hard-working entrepreneurs.

The numbers prove just how large an opportunity this is:

• 70% of small business owners have no formal succession plans, despite nearly a third planning to exit within five years.
• 26% have accelerated their transition plans, signaling a growing urgency to find the right buyers before retirement forces their hand.
• 43% of owners prioritize legacy and continuity over sale price — meaning that they'll seek buyers who will protect employees, preserve community relationships, and carry forward the businesses they spent decades building.

In short, stewardship now matters as much as capital.

That data was collected in my company's 2025 State of Main Street report, which details how smart entrepreneurs are leveraging this market to their advantage.

By purchasing established operations with existing revenue, customer loyalty, and community goodwill, many buyers are skipping the rocky startup phase and stepping into profitable positions in America's most trusted sector.

The Rise of the Acquisition Entrepreneur

For years, entrepreneurship was synonymous with invention, raising venture capital, chasing scale, and aiming for billion-dollar outcomes. That model will persist, but another paradigm is gaining momentum: Main Street acquisition entrepreneurship.

Image Credit: Courtesy of Contrarian Thinking

Buying an existing business enables entrepreneurs to move beyond the unpredictable incubation of 0-to-1, early-stage startups and toward the more stable but still difficult work involved in 1-to-10 scaling.

What's cool is that Main Street interest is accelerating across sectors.

• Highly skilled technology developers are increasingly moving into Main Street, applying modern tools like AI to legacy industries.
• Deal-making knowledge, once the domain of private equity and family offices, is now being democratized through online communities, educational platforms, and public discourse, including our own.
• Media narratives are shifting from glorifying unprofitable hypergrowth to celebrating sustainable, profitable ownership.

We are entering an era where words like "cash flow," "acquisition," and "profitability" are once again markers of ambition and pride, not small thinking.

The New Playbook for Entrepreneurs

The next generation of entrepreneurs will not be defined solely by their ability to invent but by their ability to own wisely, operate skillfully, and steward responsibly.

For those willing to move beyond conventional startup mythology, ownership is not merely an aspiration. It is a discipline. So, what's happening on Main Street, and more importantly, what exactly are people doing about it?

Image Credit: Courtesy of Contrarian Thinking

These are the questions our 2025 State of Main Street report set out to answer. It's a look at the state of Main Street entrepreneurship from our unique perspective, shaped by a diverse mix of voices: business owners, bankers, policymakers, educators, startup founders, painters, window cleaners, and more. It's both macro and micro. Data and narrative. Strategy and sweat. Inside, you'll find:

• Small Business Acquisition Survey Data: Key trends, financial insights, and real-world data from our business-buying community.
• Business Owner Spotlights: Stories from members of our community who are actively buying, building, and scaling small businesses.
• Blue-Collar Boom: Insights from operators and founders in the trades, exploring what's working, where opportunities are emerging, and how industries are evolving.
• Main Street Technology: A look at some of the startups in our venture portfolio that are modernizing how small businesses operate.

Our goal is simple — that somewhere in the pages of this report, you find something that moves you. A story that resonates. A path you hadn't seen before. A tool you can use. We can't wait for you to read it.