Advanced Markets

Your business is worth one number. Your family ends up with another.

Tax, risk, succession, and estate gaps sit between the two. We find them for owners of companies doing roughly $10M to $40M a year, and your CPA and attorney help decide what to do about them.

$16Mbuy-sell funding gap after an agreement went 11 years without review

40%+of revenue from just 3 customers, riding on one owner's relationships

90%of an owner's net worth locked inside the company he plans to sell

Illustrative figures from the case examples below.

Where value leaks on the way to your family

Flip the switches below. Each yes opens a leak at the checkpoint where it happens. Tap a picture to jump to its questions.

No leaks marked yet. Tap yes on each one that fits.

This shows where money can slip away. It doesn't estimate dollars. A review with your advisors does that.

Owner Wealth Review

Your opportunity map

0gaps marked

Your map fills in as you answer the questions above. Each gap comes with the question to bring to your CPA or attorney.

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Situations we see

Illustrative examples with hypothetical figures. Pick one.

The business that depends on one person

The facts

$30M revenue, $4M EBITDA
The owner holds the top customer and bank relationships
3 customers bring in 40%+ of revenue
Sale planned within 3 years

What's at risk

If the owner dies, is it still the same company?
Customers leave and lenders get nervous
The sale gets delayed and earnings slip
Value drops at the worst possible time

What we'd look at

Put a dollar figure on losing that person
Plan how the business keeps running, and how to keep key people
Check the insurance already in place and pay for the handoff
Decide whether to carry that risk or insure it

The question to askHow much would this business lose if one person disappeared tomorrow?

The buy-sell nobody has reviewed

Business value today

$22M

Buy-sell funding

$16M gap

$6M

The facts

Two owners
Valued at $6M when the agreement was written
Now worth $22M
Buy-sell written 11 years ago

What's at risk

The funding still reflects $6M
That leaves a $16M funding gap
The owners think they're covered
It's documented, but not funded

What we'd look at

Update the valuation method in the documents
Match the funding to what the business is worth today
Review how the company is owned and set up
Work it through with the attorney and CPA

The question to askIs the buy-sell funded, or only documented?

When insurance and valuation collide

The facts

Business worth $20M
Two 50/50 owners, $10M each
The company owns the life insurance
The policy is meant to buy back a deceased owner's shares

What's at risk

After Connelly v. United States (2024), the payout is added to company value
The buyback obligation does not offset it
That means a higher estate-tax value
The insurance meant to protect the business raises its taxable value

What we'd look at

Compare a company buyback with other ways to fund the buy-sell
Check who owns each policy and who the beneficiary is
Estimate the estate-tax hit and check cost basis
One common fix: a trust (called an ILIT) buys a new policy outside the company. A cross-purchase agreement or an insurance-holding LLC can also work. Moving an existing policy can set off tax problems, so the CPA and attorney decide.

The question to askWhen the company receives the insurance money, what happens to its value for estate tax?

Where will the estate find the cash?

The facts

The owner is worth about $25M
About $18M of that is the business
Little cash outside it

What's at risk

Estate taxes and expenses come due at death
Death becomes a sale with no planned buyer
The family may be forced to sell the business

What we'd look at

A trust-owned (ILIT) policy provides cash outside the estate
The estate borrows from, or sells assets to, the trust
The family avoids a forced sale
Planned around the current federal estate-tax exemption

The question to askIf most of the net worth is the business, where does the tax bill get paid?

Treating heirs fairly

Estate today

$24M

Business $18MReal estate $4MLiquid $2M

The facts

Founder owns an $18M business
$4M in investment real estate, $2M in liquid investments
Three children, only one works in the business

What's at risk

How are the other two treated fairly?
Pulling $12M of cash out of the company to even things up?
The family balance sheet is lopsided
Nobody has planned where the money comes from

What we'd look at

Plan how each child gets a fair share
Use trust-owned insurance to provide for the non-business heirs
Keep the business intact for the child running it
Coordinate the transfer with the family's attorney

The question to askDoes the child running the business inherit it, and how are the others treated fairly without draining the company?

The owner whose exit is the retirement plan

The facts

58-year-old founder
$35M revenue, $5M EBITDA
90% of net worth is inside the company
“My retirement plan is selling the business.”

What's at risk

Almost everything rides on one asset
A delayed exit derails retirement
A lower sale price hits right when the money is needed
No plan B for income

What we'd look at

Build retirement savings now, through a qualified plan
Build wealth outside the business
Plan cash flow and income after the sale
Pay for the handoff to the next owner, if there is one

The question to askWhat happens to retirement if the exit is delayed five years, or the price comes in lower?

A $30M business with a basic 401(k)

The facts

55-year-old owner
Established middle-market company
Strong, stable taxable income
An existing 401(k) with no advanced design

What's at risk

Deductions left unused
The company grew up. The plan didn't.
Nothing designed around age, employees, or pay
Nobody notices until closing

What we'd look at

Model a cash-balance or defined-benefit plan
Use the deductions before the sale
What we need: company type, ages, pay, employee list, and timeline

The question to askBefore the sale, has anyone checked whether the retirement plan itself is well designed?

How a review works

DiscoveryWe learn about the business and what's coming up.
ReviewWe check all five checkpoints.
Opportunity mapYou get every gap we find, in writing.
Your advisors weigh inCPA, attorney, TPA, valuation expert.
SetupWe put in place only what the review supports, and compare several A-rated insurance companies.

0 gaps markedSee my map

For M&A brokers, CPAs & advisors

You keep the relationship. We work behind you, never around you.

How many conversations are sitting in your book?

Enter your own numbers. Every lit square is an owner with at least one gap worth a second look.

Business owners you work with 60 Have two or more owners 12 Depend on one key person 15 Plan to sell within 5 years 10 Profitable, over 50, basic retirement plan 8

15 to 45 owners in your book likely have a gap worth a second look.

The low end assumes the groups overlap completely, the high end that they don't overlap at all.

What you see, and the planning problem behind it

We help solve each one without replacing the CPA, attorney, valuation professional, or your role. Tap a row.

You don't need to know the solution

Your job isn't to become a tax expert. It's to recognize when the conversation needs to go deeper, then bring us in.

What you notice

Owner is profitable

Owner has tax exposure

Owner has a partner

Owner wants to exit

Owner depends on a key executive

Wealth is concentrated in the business

What we diagnose

Retirement plan design

How cash moves

Insurance for key risks

Funding gaps

Ownership setup

Cash for estate taxes

Who validates

CPA

Attorney

TPA / actuary

Valuation professional

Insurance company specialists

Insurance underwriting

What we will not do

Name the concern, and we'll put the commitment in writing. Tap one.

Bring us one business.

One profitable owner you already trust. We run the Owner Wealth Review and send the opportunity map to you. It costs nothing, and your client hears about it from you.

Start a conversation

Introduce us as your advanced-markets team.
We run the Owner Wealth Review.
We write up the gaps we find.
Nothing gets built without the client's professionals.
We report back through you.

Important disclosures. This page is educational and is not tax or legal advice. Examples are hypothetical and shown to explain how strategies work; they are not quotes, projections, guarantees, or recommendations. We identify potential planning opportunities for evaluation with the client's CPA, TPA, ERISA counsel, and attorney, and we do not replace the client's professionals. Outcomes, including plan contributions, policy loans, company-owned and trust-owned insurance, and Connelly-related structures, depend on facts, design, performance, and current law. They are modeled, never promised. Connelly v. United States, 602 U.S. ___ (2024). Confirm current law before any client work.