Business Owners: The Most Underserved Clients

You likely already know a handful of business owners. Clients, neighbors, people you see at church or run into at community events. They're driven, they've built something real, and by most measures, they look like they have it together.

But here's what's easy to miss: the majority of them are carrying serious planning gaps that no advisor has ever helped them identify. Not because they don't care, but because nobody has asked the right questions.

• Their attorney treats them like a transaction.

• Their CPA is focused on what already happened.

• Their insurance agent feels more like a salesperson than a strategic partner.

Nobody is looking at the whole picture.

That's the central argument Greg DuPont makes in the March to a Million podcast—WSN's ongoing miniseries for estate planning attorneys. The business owner segment, Greg argues, represents the single greatest opportunity in most practices. Not because they're wealthy, but because they're systematically underserved. And if you can position yourself as the one professional who actually sees their blind spots, you become irreplaceable.

This article breaks down the key insights, including the most common planning gaps, the right questions to ask, and how to start conversations that open doors no other advisor has walked through.

Why Business Owners Fall Through the Cracks

It's counterintuitive. Business owners often have more advisors than anyone else - a CPA, an attorney, a financial advisor, maybe an insurance agent.

So why are they still underserved?

The answer is coordination. Or, more precisely, the lack of it.

Each advisor operates in their own lane. The CPA handles taxes. The attorney handles entity formation or a will. The financial advisor manages investments. But nobody is synthesizing all of that into a coherent strategy. Nobody is asking, "Does all of this work together?"

Greg traces his commitment to this problem back to watching his own father, a small business owner who never received truly integrated guidance, navigate gaps that proper coordination could have closed. That experience became the foundation of WSN: the belief that a financially-minded estate planning attorney, one who understands the full landscape, can fundamentally change the trajectory of a business owner's life.

When you can articulate a client's blind spots, you stop being one of many advisors. You become the advisor.

The Planning Gaps You're Most Likely to Find with Business Owners

Several recurring vulnerabilities show up in business owner planning. Knowing these gaps before you sit down with a client gives you an immediate edge.

The Entity Structure Trap

The LLC, S-corp, or C-corp a business owner set up 10 or 20 years ago may no longer be the right structure for where they are today. For example, a client whose business has grown from a side hustle into a decades-old business with dozens of employees—still structured exactly the same way it was at the start. A restructuring conversation can save that client thousands of dollars in unnecessary taxes.

Business owners rarely revisit these decisions on their own. And many of the attorneys who set up those original entities never flagged the downstream tax implications of staying in the same structure as the business scaled.

The Exit Strategy Vacuum

Most business owners assume they'll eventually sell. The plan, to the extent there is one, is usually vague: work hard, grow the business, find a buyer when the time comes.

The painful reality is that very few of these businesses are actually sellable at the value the owner expects. The professional class is aging—and countless businesses will simply close their doors rather than transfer cleanly, because no one took the time to build a transferable operation.

The opportunity for estate planning attorneys is to start the exit planning conversation with clients early. Helping a business owner build a business that's both transferable and self-managing isn't just good exit planning—it makes the business easier to run today.

The Unfunded Buy-Sell Agreement

Many business owners have a buy-sell agreement. Far fewer have a funded one. Without a liquidity mechanism in place, the agreement is largely theoretical. When a triggering event occurs—a death, a disability, a partner dispute—there's no cash to execute on it. The business gets managed by an estate trying to recover value, with no clear plan and no means to act.

This gap is common. It's also entirely solvable. But only if someone raises it.

Paper Rich, Cash Poor: The Retirement Problem

A significant number of successful entrepreneurs hit a stage where their business generates strong, predictable cash flow—and yet they have almost nothing set aside for retirement.

The profits are real, but they're flowing into taxes rather than long-term wealth.

Greg describes working with clients who are generating well over six figures more than they need every year, with no strategy to capture that surplus. With the right tools—captive insurance, executive benefit plans, ESOPs, and others in the WSN toolkit—you can help those owners build protected, long-term wealth while significantly reducing their tax burden.

This is where the estate planning attorney with financial services knowledge become uniquely valuable. A traditional estate attorney can draft the documents. A WSN-trained attorney can show the client why those documents need to exist and what's at stake if they don't.

Attorneys: Ask Better Questions

WSN's diagnostic approach is built on a simple observation: most advisors stop one or two questions short of where the real planning conversation begins.

The right questions don't feel like a sales pitch. They signal genuine curiosity.

Here are three questions Greg recommends for your next business owner conversation:

• "How do you see the next five to ten years unfolding for your business and your family—and what has to have happened for you to feel like it went well?"

• "What's one thing about your business that only you truly understand?"

• "When was the last time your buy-sell agreement was reviewed?"

Each of these opens a door. The first gets at goals and gaps. The second surfaces the owner's own awareness of concentration risk. The third is a direct diagnostic—and the answer is almost always "not recently."

Lead With A Legacy Conversation

The most effective framing for a business owner conversation, Greg argues, isn't tax savings or exit strategy. It's legacy.

A business isn't just an asset. For most owners, it's an expression of who they are—what they've built, what they've sacrificed, what they want to leave behind. Starting a planning conversation with "What do you want your business to mean for your family?" naturally opens the door to everything else: succession, exit strategy, tax efficiency, key employee retention, and long-term wealth building.

Legacy is the universal language of business owners. It's also the entry point that no other advisor has found.

Your Next Five Conversations Start Today

Here's a direct call to action. Write down five names—business owner clients, peers, people from your community who have built something and probably haven't had a real conversation about what happens next.

Then pick up the phone.

Not to pitch. Not to sell. Just to connect.

Something like: "Hey, I really admire what you've built. I'm curious—have you given much thought to your legacy and what you want the next five years to look like? I might have a few things worth sharing if you're open to a quick coffee."

That's it. That's the first step.

The business owner opportunity is one of the most underutilized advantages available to estate planning attorneys today. The clients are already in your network. The gaps are real. What's missing, in most cases, is an intentional conversation—one that only you, with the right training and the right questions, are positioned to start.

Listen to the Full Episode

For a deeper dive into the business owner opportunity—including more on Greg's approach to legacy-first conversations—listen to Mini Series Episode 6 of the March to a Million podcast, available wherever you stream podcasts.