For Business Owners

Most of your net worth is one asset
and you can’t sell it on a Tuesday

For most owners the business is not part of the portfolio. It is the portfolio. Four things worth working out well before that becomes a problem.

If a client came to us holding most of their wealth in a single stock, we would have a long conversation about concentration risk. Owners are holding the same position — except this one has no ticker, no daily price, no buyer standing by, and they also work there.

That is not an argument for selling. It is an argument for knowing what you are actually holding, and for building something outside it while you still have the earning power to do so.

Two numbers make the case better than any argument. Of the businesses that go to market, only around 20% to 30% actually sell. And roughly half the privately held businesses in the country are owned by baby boomers who intend to transition within the decade. Most of those owners will find out what their business is worth at the worst possible moment: when a buyer tells them.

The work that matters happens years before the transaction, or it does not count. A buyer pays for evidence, not intentions — and evidence takes reporting periods to accumulate. This is the rare planning problem where starting early is not merely tidier. It is worth money.

Four questions, in the order they matter

Each of these is a full guide. Start with whichever question you cannot currently answer.

One
What is my business worth?
Price is earnings times a multiple. Owners spend years on the earnings and never touch the multiple — which is where the larger number usually is. What buyers subtract for, and the gap between value today and value after cleanup.
Read the guide →
Two
What would I actually keep?
The headline price is not the number that reaches your account. Asset versus stock sale, the Illinois replacement tax, QSBS under the 2025 rules, and why the structure of a deal moves your proceeds more than the price does.
Read the guide →
Three
What am I building outside it?
A cash balance plan can shelter six figures a year for an owner in their fifties, on top of a 401(k). What it costs, what it obligates you to, and the deferred tax bill it creates — so the sale price matters slightly less.
Read the guide →
Four
Am I ready, and is it?
Exit planning around three questions: is the business ready for a sale, are the finances ready, and are you. Most owners who struggle afterwards were unprepared personally, not financially.
Read the guide →

Why that order

The sequence is not arbitrary, and getting it backwards is the most expensive mistake we see.

An owner who starts at question four — deciding to sell, then finding out what the business is worth — has already lost the ability to do anything about the answer. Every lever that lifts the multiple takes two or three years of history to be believed. By the time a broker is engaged, the price is largely already set.

An owner who starts at question one has time. If the honest number is lower than expected, there is room to fix the reasons. If it is higher, there is room to plan around it properly. Either way the answer is useful, which is exactly what makes it worth getting early.

Where we fit

We are not business brokers, and we do not appraise businesses for a fee. We sit on the owner’s side of a transaction most owners go through once: establishing an honest starting number, working out which gaps matter, sequencing the work so a buyer will credit it, coordinating the accountant and attorney and eventually the banker, and planning what the proceeds have to do afterwards.

That last part is the piece we are licensed for. The rest is the part that determines whether the number was ever going to be big enough — which is why we would rather talk about it first.

Related: the planning tools, including a twelve-question exit readiness assessment, and the Insights archive.

Where does yours stand?

Twelve questions across the three things that decide how a sale goes: whether the business is ready, whether the finances are ready, and whether you are. Scored separately, because an average hides the one that is about to break.

Take the Exit Readiness Assessment Schedule a Conversation

Three minutes, free, and your results are emailed to you.
Bayworth Capital serves clients across the North Shore and greater Chicago.