Jay Sunde on Why Buying the Business Is the Easy Part

by Natasha Wolff | January 15, 2026 9:12 pm

Entrepreneurship Through Acquisition is often sold as a rational alternative to starting a company from scratch. Buy an existing business, inherit customers and cash flow, avoid the chaos of zero-to-one. For many professionals, it feels like a cleaner, more controlled way into ownership.

Jay Sunde[1] doesn’t disagree. He just thinks most buyers misunderstand where the real risk lives.

“The deal is rarely what breaks people,” Sunde says. “It’s the year after the deal.”

Sunde has spent more than two decades acquiring and operating small and lower-middle-market businesses across industries that don’t lend themselves to abstraction—home services, construction, early childhood education, real estate. In his experience, the first twelve months after closing determine almost everything that follows.

What the Numbers Don’t Tell You
Acquisitions are built on diligence. Financial statements are reviewed, add-backs debated, cash flow modeled. That work is necessary, but it has limits.

Financials explain outcomes. They rarely explain dependence.

A business can look stable on paper while relying heavily on one person’s memory, relationships, or constant intervention. Those realities don’t surface cleanly in a data room. They surface when the owner stops answering the phone.

“People assume the systems are stronger than they are,” Sunde says. “A lot of small businesses run on judgment, not process.”

That distinction matters. Judgment doesn’t transfer automatically.

The Quiet Risk of Cultural Shock
Most buyers expect operational problems. Fewer expect cultural ones.

In closely held businesses, culture isn’t documented. It’s enforced. Expectations live in habits, not handbooks. Employees learn how to operate by watching the owner—not by reading policies.

When a new owner arrives, even sensible changes can feel destabilizing. Reporting structures shift. Decisions slow down. Long-standing shortcuts are questioned.

“Change always sends a message,” Sunde says. “If you haven’t earned credibility yet, that message isn’t always the one you intend.”

The mistake, he says, is treating improvement as neutral. It isn’t. Timing matters more than intent.

Where Most Acquisitions Strain First
Certain pressure points show up repeatedly.

Labor is one. Many businesses rely on a handful of employees who carry far more responsibility than their titles suggest. Their knowledge is informal, undocumented, and difficult to replace.

Legacy systems are another. Software, scheduling, accounting—often inefficient, often outdated, but deeply embedded. Replacing them is rarely a clean upgrade. It’s a period of disruption.

Then there’s owner dependence. In many deals, the seller functioned as the final decision-maker, the relationship manager, the problem solver. Once that person exits, authority doesn’t redistribute on its own.

“You don’t always see owner dependence until decisions stop moving,” Sunde says. “That’s when it becomes expensive.”

When Cash Flow Stops Being Academic
There’s also a shift that’s harder to model.

Before closing, decisions are hypothetical. After closing, payroll clears—or it doesn’t. Debt service isn’t a scenario. It’s a date on the calendar.

That reality changes behavior. Buyers become more conservative, sometimes abruptly. Growth plans slow. Liquidity starts to matter more than upside.

“The first year isn’t about optimization,” Sunde says. “It’s about survival without panic.”

Owners who recognize that early tend to stabilize faster. Those who don’t often find themselves reacting instead of leading.

The Questions Buyers Rarely Ask Early Enough
Looking back, Sunde believes many post-close problems could be anticipated—not eliminated, but anticipated—with different pre-close questions.

Who actually makes decisions day to day?
Which employees keep things from breaking?
What happens when the owner is unavailable for a week?
Where does knowledge live when something goes wrong?

“These aren’t comfortable questions,” he says. “But they tell you what kind of business you’re really buying.”

Ownership Starts After the Transaction
Buying a business is often framed as an endpoint. In reality, it’s an entry point.

The first year exposes whether the buyer understands the role they’ve stepped into. Ownership isn’t proven by closing a deal. It’s proven by navigating what follows—quietly, consistently, and without shortcuts.

“Acquisition creates the opportunity,” Sunde says. “The work afterward determines whether it was worth it.”

Source URL: https://dujour.com/uncategorized/jay-sunde-on-why-buying-the-business-is-the-easy-part/