The Great Retirement: How Searchers Are Fueling the Next Wave of Small Business Ownership

A quiet revolution is happening in the small business world.

Every single day, 10,000 baby boomers retire, a trend that will continue until 2030. And with that millions of small businesses such as plumbing companies, accounting firms, HVAC services, and more are about to go through one of the biggest transitions in ownership we’ve ever seen.

Roughly 8–10% of boomers own a small business. That’s millions of privately-held companies poised for sale, transfer, or, in some unfortunate cases, closure.

Here’s the thing: most of their kids don’t want to take them over. And the owners? Many don’t even realize they can sell or should be planning for succession.

That’s where the “searchers” come in.

Who Are the Searchers?

Searchers are ambitious entrepreneurs, often millennials or Gen Z who aren’t looking to start a business from scratch. Instead, they’re seeking to acquire an existing business and grow it.

It’s a smart move. Buying a business often means instant infrastructure, a customer base, cash flow, and established brand equity. With the right support, these new owners can bypass the most painful startup years and build something even stronger.

But here’s the truth: buying a business isn’t easy. Most of these companies are what online educator and influencer Codie Sanchez calls “SOWS”:

• Stale: Little innovation or growth in recent years
  
• Old: Long-standing, deeply entrenched operations
  
• Weak: Limited competition but not optimized for scale
  
• Simple: Straightforward business models that still work
  

That simplicity is exactly why they’re valuable. But it also means they come with serious financial and operational blind spots.

Why Financial Strategy Matters More Than Ever

This wave of transitions isn’t just an interesting economic trend, as recently discussed in Forbes. It’s a call to action for financial professionals, CFOs, and strategic advisors.

Here’s why:

1. Financial Due Diligence is Critical

Most small businesses weren’t built to sell. Their books might be messy. Revenue may be inflated. Profitability may rely too heavily on the owner. If you’re a searcher, you need to understand the real financial health before signing anything.

2. Old Systems = Missed Opportunity

Outdated tech, manual workflows, and a lack of digital infrastructure are common in boomer-run businesses. Financial advisors are important to identify where upgrades are needed, and what they’ll cost.

3. Owner Dependence is a Red Flag

If the current owner is the face of the company, the chief salesperson, and the one holding all the client relationships, you’re not buying a business—you’re renting one until they leave. Financial and operational strategy helps reduce risk and build a plan for independence.

4. Growth Requires Vision AND Numbers

Buying is just step one. The next challenge? Scaling. That means pricing strategy, hiring plans, financial forecasting, and systems built for growth. 

The Great Wealth Transfer Is Already Underway

By 2030, an estimated $68 trillion in assets will change hands as boomers retire. That includes roughly $5.1 trillion in small business value alone.

But here’s the harsh truth: not all of these businesses will find buyers. That’s a massive loss. Not just economically, but for the communities they serve and the teams they employ.

At KBS CFO, we believe there’s another path.

We partner with both searchers and business advisors to bring clarity and confidence to the business buying process. Whether you’re assessing an acquisition, building infrastructure post-sale, or planning a sustainable growth strategy, our team brings decades of experience to help you succeed.

If you’re a searcher looking to acquire your first business or an advisor supporting someone through the process, don’t do it alone. Let’s talk about how we can help. Visit us at KBSCFO.com to get started.