The Talk Nobody Wants to Have

Authored by Eryk Johnson

Building a business is hard. Planning for what comes next is often overlooked entirely.

Nobody wakes up excited to plan for the day they can't run their business anymore, or the day they're not around. It's easier to put off. There's always something more pressing — a deadline, a deal, a Tuesday. But in working with business owners through major transactions, one pattern shows up again and again: it's shocking how many people just don't do this.

It's not a matter of priorities. It's because nobody wants to think about what it actually means: retiring from a business built over a lifetime, or planning for a day you won't be here to see. What follows is succession planning in plain language — what it really is, why even smart, successful people put it off, and what a small investment of time up front can protect down the road.

A Real Story

Consider a deal from a few years back. The business owner was in his 70s and had built a solid transportation and logistics company over decades. At the time, he had a basic will that hadn't been updated in years, no trust, and had already survived two heart attacks. The company eventually sold for roughly $65 million.

Here's the part that stops people cold: if he had passed away while he still owned the company, the estate tax bill alone could have run in the tens of millions — money his family might not have had sitting around in cash, because most of that value was tied up in the business itself. Sell first and then something happens? Still a rough outcome, once income tax and estate tax both take a bite.

Neither scenario is a good one. In this case, slowing the deal down to look at the full picture bought enough time to plan around it. Not everyone gets that lucky.

Most People Are Worth More Than They Think

One pattern comes up constantly: people genuinely don't know their own net worth. Not because they're careless, but because nobody ever sits down and adds it all up in one place.

Picture someone who owns a profitable business, a home, and a rental property. Ask them what they're worth and they might say "three or four million," thinking mostly about their bank accounts. Add up the real value of the business, the properties, the retirement accounts, and the life insurance, and the honest number might be closer to $19 million or $20 million.

It's easy to see how people miss that. It's not something most of us wake up and think about every day. Business owners in particular tend to think in terms of what the company earned last year, not what it's actually worth if they sold it, retired, or passed it down.

Why Your Advisors Might Not Catch It

Here's the uncomfortable truth: the professionals already in your corner may not have the full picture either. A CPA files your taxes, but might not know your savings habits or what your business would fetch on the open market. A wealth manager sees the account you invest with, but may have no idea the business behind it is worth $50 million. Everyone has a slice of the picture. Almost nobody has the whole thing.

That gap is exactly why business owners and high-net-worth families benefit from sitting down and mapping out the whole picture — not just this year's tax bill, but everything they own, what it's really worth, and what happens to it under different scenarios.

So... When Should You Actually Start?

There's no wrong time to start looking at this, with one honest exception. If the cost of a planning conversation would genuinely hurt your finances, this likely isn't needed yet. If it wouldn't, it's probably worth doing, because that means there's already something built worth protecting.

There is no wrong time to start, because nobody's promised tomorrow. That's true whether it's a 20-something entrepreneur just getting started, or a business owner in their 60s thinking about retirement. Life doesn't send a memo before something changes.

What Are the Options?

Once someone understands the full picture, the path forward tends to fall into a few buckets, and there's no single "right" answer. It depends on the goals and the family involved.

• Keep it in the family — put the business in a trust structure designed to let it grow for one, two, or even three generations without being eaten up by estate tax at each transfer.
• Plan, then sell — get the estate and tax structure in place first, so a future sale doesn't trigger a bigger tax bill than it should.
• Grow, then sell — build additional value into the business (or make it less dependent on the owner personally) before bringing in a buyer.
• Give strategically — charitable giving using appreciated stock, for example, can be far more tax-efficient than writing a check, while accomplishing the same generosity.

The common thread: define the goal first, then work backward to find the right tools. A cookie-cutter plan isn't really a plan.

How Nichols Cauley Can Help

This is where the Nichols Cauley approach stands apart. Most firms are strong in one lane — tax, or estate law, or wealth management. Nichols Cauley brings tax planning, estate strategy, business valuation, and M&A expertise together under one roof, plus insurance solutions to fill any gaps that turn up along the way.

It starts with a succession planning diagnostic — a guided conversation that lays out everything a client owns, what it's really worth, and where the biggest risks and opportunities sit. Most clients can get through it in about two to three hours of their own time, spread across a couple of meetings, with results back in one to two weeks.

From there, the plan can go as far as it needs to — from a simple will and a clear-headed view of one's finances, all the way to a full "master estate plan" built alongside estate attorneys, tailored to individual goals, family, and business.

And it's delivered in plain, practical language — not jargon that leaves clients more confused than when they walked in.

The Bottom Line

A little planning now can avoid a lot later.

There's no need to have all the answers before starting the conversation — just a willingness to have it. Whether the assets in question are a business, a portfolio of investments, or both, the Nichols Cauley team can help clients see the whole picture — clearly, honestly, and without the sales pitch — and build a plan that fits their goals and their family.

Ready to see where you stand? Reach out to your Nichols Cauley advisor to schedule a succession planning diagnostic.

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