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What Is It?

Legal Contract--a form of Buy-Sell Agreement

A trusteed cross purchase agreement is a form of buy-sell agreement, a legal contract between the owners of a closely held business. This type of agreement is basically a cross purchase buy-sell agreement with the addition of a third party (the trustee) to ensure that the agreement is carried out. The trusteed cross purchase agreement is also called a custodian agreement or an escrowed agreement.

Establishes Buyer for Your Business Interest

Under the trusteed cross purchase agreement you and your co-owners agree to buy each other's interests in the business under terms and conditions set forth in the agreement. This creates a market and guarantees a buyer for your business interest.

Defines Events Triggering Sale of Business Interest

The buyer named in the agreement (and there could be more than one buyer) is obligated to purchase your interest in the business at the occurrence of some specified triggering event and you or your estate are obligated to sell your interest. Likewise, you are obligated to buy all or part of a selling owner's business interest after a triggering event. You, your advisors, and the other parties to the agreement will determine the triggers appropriate for your business situation. Possible triggering events include those shown in the following table:

Typical Triggering Events

Other Possible Triggers

  • Death
  • Long-term disability
  • Retirement
  • Divorce
  • Personal insolvency or bankruptcy
  • Conviction of a crime
  • Loss of professional license
  • Withdrawal prior to retirement
  • Termination of employment

Utilizes Trustee to Ensure Terms of Agreement Carried Out

Under a trusteed cross purchase agreement, the sale of your business interest is overseen by a trustee, who is responsible for seeing that the obligations are carried out between you or your estate, and the buyer. The trustee is a neutral party and handles all the administrative paperwork that might arise from the transaction. The trustee monitors the funding of the agreement, making sure, for example, that the cash fund is established or the life insurance policies are bought and paid for.

The use of a trustee frees your family or estate from having to deal directly with the buyer of your business interest when you die. Although called a trustee, the role of the third party is generally more of an escrow agent, in that the trustee under this arrangement does not necessarily manage assets held under his or her custody.

Here's how it works: Say you are a business owner bound under a trusteed cross purchase buy-sell agreement. When the trusteed cross purchase agreement is established, you endorse the stock certificate representing your share of the business and deliver it to the appointed trustee. When you die, the trustee collects the money from the buyer for the sale of your business interest and pays your family or estate. The shares representing your interest in the business are transferred to the buyer named in the agreement.

When Can It Be Used?

You Own a Business

You are an owner of a closely held business. The business can be organized as a sole proprietorship, partnership, C corporation, S corporation, limited liability company (LLC), or professional corporation.

Tip: If you are a sole proprietor, your buy-sell agreement might be in the form of a one-way buy-sell, a variation of the cross purchase. A trustee can be used to oversee the obligations and transaction between you and your buyer.


Includes All the Strengths of a Buy-Sell Agreement

The trusteed cross purchase agreement, like other buy-sell agreements, can do the following things:

  • Can provide a guaranteed buyer for the business interest
  • Can provide liquidity for payment of estate taxes and settlement expenses (but only if agreement is funded)
  • Can avoid potential conflicts of interest
  • Can establish taxable value of the business, if structured properly
  • Can maintain stability of business operations
  • Can improve creditworthiness of the business
  • Can maintain tax status of your S corporation, partnership, or Professional Corporation (if relevant)

The Trustee Handles the Paperwork and Headaches, So You Don't Have to

The trustee holds the paperwork (such as the stock certificates) and is responsible for seeing that the obligations of the parties are carried out. When a triggering event occurs, the trustee collects payment from the buyer and delivers it to the seller. In addition, when you fund the buy-sell agreement with life insurance, not only is the trustee responsible for overseeing the policies, but fewer policies may be needed. The trustee might even be the actual owner of the policies.

Can Simplify Purchases under Buy-Sell Agreement When More Than Three or Four Owners

The trusteed cross purchase can eliminate some of the complexity of the cross purchase agreement, which generally works best for a business with only two or three owners. When there are more owners than that, the cross purchase agreement can become very complex. At the occurrence of the triggering event, there could be multiple buyers of your interest in the business.

For example, say that your business is an S corporation, with a maximum allowable 100 shareholders. When you die, the cross purchase plan could require as many as 99 transactions between the surviving co-owners and your estate. It is the responsibility of the trustee to coordinate the transactions and cash flows.

The Transaction Probably Won't Be Considered a Dividend

When a corporation distributes money to a shareholder, it is generally considered a dividend to the shareholder. There are exceptions to dividend treatment when certain conditions are met, but with a trusteed cross purchase plan, dividend treatment is avoided if your closely held business is a corporation. Individuals are the parties to the sale, and no company money is used, so there is no risk of the transaction being considered a dividend payment.

Tip: In general, the American Taxpayer Relief Act of 2012 permanently extended the preferential income tax treatment of qualified dividends and capital gains. Capital gains and qualified dividends are generally taxed at 0% for taxpayers in the 10% and 15% tax brackets, and at 15% for taxpayers in the 25% to 35% tax brackets. However, capital gains are generally taxed at 20% for taxpayers in the 39.6% tax bracket. Also, as a result of the Affordable Care Act of 2010, an additional 3.8% Medicare tax applies to some or all of the net investment income for married filers whose modified adjusted gross income exceeds $250,000 and single filers whose modified adjusted gross income is above $200,000.

Tip: There remains a significant advantage in classifying a transaction as a sale or exchange rather than as a dividend distribution despite the fact that both types of transactions are subject to tax at long-term capital gains tax rates. That is, in the case of dividend treatment, part or all of the distribution is first treated as a dividend, any remaining distribution is then received tax-free to the extent of basis, and any distribution still remaining is taxed as capital gains. In the case of sale or exchange treatment, however, the shareholder pays tax only to the extent that the amount paid by the company exceeds his or her basis in the stock. If the sale or exchange of your shares occurs after your death, your shares will generally have a basis equal to the fair market value of the shares at the time of your death, and little or no tax may result. Thus, more may be subject to tax with dividend treatment than with sale or exchange treatment.

Transactions Not Subject to Attribution Rules, Which Can Complicate Family Corporation Transactions

There are additional tax rules that apply to company payments, called attribution rules. The attribution rules can eliminate possible favorable tax treatment of the sale of an interest in a business when owners are related. The trusteed cross purchase agreement avoids application of the attribution rules in the same way it avoids general dividend treatment--assuming that no company money is involved.


Restrictions Can Affect Personal Estate Planning (You May Not Be Allowed to Give Away Your Share of the Business)

Gifting strategies are important estate planning tools for owners of closely held businesses. Lifetime gifts of your interest in the business to your children may be part of your estate planning strategy to pass your business interest to your heirs and reduce the total value of the estate. Use of the trusteed cross purchase agreement could prevent you (and your co-owners) from passing all or part of your interest in the business as a gift. The parties to the agreement, therefore, must consider whether to restrict transfers by gift.

Tip: If your buy-sell agreement allows gift transfers, the group of permissible donees should generally be defined. The donee group should probably be subject to the terms of the buy-sell agreement.

Restrictions Could Limit Your Access to Outside Credit

Restrictions within the trusteed cross purchase agreement could prohibit you from pledging your own interest in the business as collateral for outside credit, or could require the consent of the other owners. Without the ability to pledge your business interest, a lender might turn you down for a loan.

Trustee Must Be Paid

The services of the trustee are not free, and you and the other parties to your buy-sell agreement must decide how the fee will be split.

Tip: Shop around for a trustee. Discuss the fee structure and the services provided by the trustee before you make any definite arrangements.

How to Do It

There are certain steps required in every buy-sell agreement. There are also some levels of detail that are not required but could save you trouble if they are included.

Things to Do Now

Decide What You Want to Happen to Your Share of the Business

You should consider all of your financial, tax, and estate planning goals. If you have co-owners who will be part of the agreement, you will need to talk with them about it.

Consider Terms of Agreement

You should consider possible components to the agreement, some of which are shown in the following table:

Components--Trusteed Cross Purchase Buy-Sell Agreement


The parties

Who is selling? Who is buying? Who is trustee?

Triggering events

Could include death, disability, retirement, divorce, bankruptcy, or other events


Is purchase mandatory or optional?


Could include first-offer provisions or rights of refusal, ability (or lack of) to pledge shares for collateral, ability (or lack of) to use shares in gifting strategy, or other restrictions

Price (or method of determining)

Could be agreed upon dollar value or a valuation method based on formula, appraisal, adjustment, or percentage of book value

Sale terms

Lump-sum cash, installment payments, combination, or other

Trustee provision

Who is trustee? What are trustee's duties and obligations? How will trustee be compensated?

Time period for transaction

For example, how soon after triggering event should sale occur? Should there be a waiting period before sale for disability? How long should installment payments continue?

Funding method

Could be cash, borrowings, life insurance proceeds, or other method

Modification provisions

Could be used to provide for valuation update or changes to or termination of agreement

Factors such as the size, structure, and tax bracket of your business and the number of co-owners, if any, will influence your choices in setting up your trusteed cross purchase buy-sell agreement. This is where your tax advisor, financial planner, and/or attorney can be helpful.

Request Guide TRG

Pay Special Attention to These Agreement Clauses

You may want to pay special attention to the following parts of the agreement: Price: You don't necessarily have to name a dollar value. There are several ways to set the value of the business. For instance, there may be a valuation method commonly used in your industry that you could easily use in the agreement.

Caution: It is important that the valuation method used in the agreement represent the fair market value (FMV). The agreement is a legal contract, and the price (or method of determining price) specified will lock in the sale price. Unless the agreement is drafted carefully, the sale price could be different from the taxable value. The IRS is not obligated to accept the sale price as the FMV for taxation. If the IRS determines that the sale price is less than FMV, your estate will be taxed on the FMV. This means it is possible that the estate could be required to pay tax on value it did not (and never will) receive (assuming there is an estate tax).

Sale terms: The specific triggering events in your agreement may influence the terms of the sale. For instance, a lump-sum payment is appropriate in the event of a death, while an installment payment plan over some specified period of time may be suitable for retirement.

Trustee provision: The trustee provision can be part of the cross purchase buy-sell agreement itself or a separate agreement. This provision can be used to identify the trustee, its responsibilities, and fees. It might be a good idea to include a provision for the replacement of the trustee, in case circumstances change.

Tip: If a corporate trustee such as a bank or trust company is used instead of an individual trustee, the potential problems arising from the death of the individual trustee are eliminated. A corporate trustee can't die, which could be important, as the buy-sell agreement could be in place for many years.

Restrictions: State property laws favor the right of business owners to transfer an interest in a business to whomever he or she wants, whenever he or she wants, at whatever terms he or she wants. Restrictions in a buy-sell agreement that are extreme will generally be viewed as unreasonable and therefore unenforceable.

Meet With Your Attorney

Setting up a buy-sell agreement can be very complex because it involves legal and tax issues, so you should consult an attorney. Each party under the agreement should have his or her own attorney. Your attorney can help ensure that conditions in the agreement will be reasonable and enforceable under state law and can help set up your trustee arrangement.

Fund the Agreement

The parties to the agreement must set up the cash fund, buy the life insurance policies, and make arrangements for whatever method has been chosen to fund the buy-sell agreement. Without the funding to back it up, the agreement won't be effective.

Select a Trustee and Hand over Your Stock Certificates

Select your trustee. Generally, the stock certificates representing the shares subject to the buy-sell are endorsed and delivered to the trustee. When a triggering event occurs, the trustee will be responsible for collecting the money for the sale of your interest under the cross purchase transaction, paying you or your estate, and delivering the certificates to the buyer. Although the trustee would have physical custody of the stock certificates, you would retain normal ownership rights, such as the right to vote your shares of stock and receive dividends.

Things to Do Later

Periodically Review the Agreement

You and your buy-sell participants should review the agreement on a regular basis, perhaps yearly. You want to be sure that the agreement still meets your objectives. The valuation provisions may specify an annual valuation of the business, which should be conducted. You should review the pricing method if there is a significant change in the business. It is hard to say exactly what type of change is considered significant and will require a price change, especially when the courts use language like "unusual intervening events or circumstances," but there is a chance your price might not set FMV after the change.

Caution: Failure to update an agreement when called for within the agreement could lead to problems.

Tip: You might be able to avoid the problems that could result from a failure to update your agreement by assigning the trustee the responsibility for either making sure the updates happen or actually doing the updates. If the trustee is responsible for the updates, and they are not done, you could take legal action against the trustee.

Change Percentages of Ownership When Making Purchases Under The Trusteed Cross Purchase Agreement, If Desired (And Agreed Upon)

With a trusteed cross purchase agreement, the buyers can purchase the business interest in any agreed-upon proportions. The percentages of ownership can be adjusted to whatever ratio the owners agree upon.

Example(s): Say you own a business with two co-owners, Bert (your son) and Ben (no relation). You own 40 percent, Bert owns 40 percent, and Ben owns 20 percent. All of you are bound under a trusteed cross purchase agreement. You die. The fair market value (FMV) of the business when you die is $100,000. The FMV of your 40 percent interest equals $40,000. Bert buys one-fourth of your interest at the FMV price of $10,000 by delivering the payment to the trustee. The trustee issues a certificate to Bert reflecting the purchase. Bert's interest in the business is now valued at $50,000 and has increased from 40 percent to 50 percent. Ben buys the remaining three-fourths of your interest at the FMV price of $30,000 by delivering payment to the trustee and receives a certificate reflecting the purchase. Ben's interest is now valued at $50,000 and has increased from 20 percent to 50 percent. The trustee delivers the proceeds from the sale to your estate.

Tax Considerations

Income Tax

Normally No Capital Gain to Seller's Estate

When you die, your stock receives a new basis equal to the fair market value (FMV) typically determined at the date of death (called a step-up in basis). When the sale price under the trusteed cross purchase plan is accepted as the FMV, there shouldn't be any capital gain or loss realized by your estate.

Example(s): Assume you paid $50,000 for your share of the business (your basis). You die. Your estate sells your business interest to your co-owners through the trustee and receives $150,000, representing the sale price for your interest under the agreement. This value is accepted as the fair market value for taxation. The basis of your interest is stepped-up from your original $50,000 to the new value of $150,000, and your estate does not need to recognize any capital gain.

Capital Gain with and without Step-Up


No Step-Up

Estate Receives Step-Up

FMV/Sale Price Basis Capital Gain







Even though this seems clear-cut, it still would be wise to consult a tax advisor.

Caution: If an estate of a person who died in 2010 elected out of the federal estate tax, estate property may have received a carryover or modified carryover basis and not a step-up in basis.

Buyers Receive Increase in Basis

When surviving co-owners buy a business interest under the trusteed cross purchase agreement, their basis (investment) in the stock is increased (stepped up) by the amount of the purchase price. This leads to a reduced capital gain if the stock is later sold.

Example(s): You and Noah originally invested $100,000 each in your boat-building business (original value $200,000, basis is $100,000 each). The fair market value (FMV) of the business is now $1.5 million. Noah dies. You buy Noah's interest in the business from his estate for $750,000, representing the FMV of his half. Your basis is $850,000 as shown in the following table:

Your Original Basis




Stepped-up Basis


Example(s): You are now the sole owner of the business valued at $1.5 million. If you sell your interest during your lifetime, you will recognize a capital gain of $650,000.


Basis Step-Up

No Step-Up

Current FMV


Capital Gain







As you can see, without the step-up in basis, your taxable gain on the sale during your lifetime would be $1.4 million.

Gift and Estate Tax

Your Stock Is Included In Your Gross Taxable Estate

When you die, the value of your stock is included in your gross taxable estate. The value of your stock for estate tax purposes generally should be equal to the sale proceeds of the stock.

Caution: If the price received is determined to be less than the fair market value (FMV), the estate will also be taxed on the FMV determined by the IRS. This means it is possible that the estate could be required to pay tax on value it did not (and never will) receive.

Questions & Answers

Who or What Is The Trustee?

The trustee can be an individual, such as a lawyer or a CPA, or a corporate trustee, such as a bank or a trust company. The main difference between an individual and a corporate trustee is that the individual could die, and that could complicate your arrangements. Although there is a chance that a corporate trustee could go out of business, it can't die, providing added stability to your trusteed cross purchase agreement. The important thing for your trusteed cross purchase agreement is that the trustee be a disinterested and impartial third party and not the company's CPA or legal representative.

Is A Trustee Under the Trusteed Cross Purchase Agreement Different From Other Trustees?

A trustee under a normal trust would hold the legal title to property held in trust. The normal trustee has an active role with the responsibility of protecting and conserving the assets held by the trust for the benefit of the beneficiaries. The normal trustee is held to high standards of fiduciary duties and must pay taxes on behalf of the trust entity. The particular form of trust dictates whether the trust is taxed as an individual or a business.

The so-called trustee under the trusteed cross purchase agreement may or may not take legal title to the stock it holds for the benefit of the parties to the agreement, depending upon how the arrangement is established. If the trustee is assigned legal title to the stock certificates, the agreement should provide that the individuals would keep their rights to vote the stock and receive dividends. The primary purpose of the trustee in the buy-sell scenario is to hold documents in safekeeping and to see that necessary activities are carried out. The trustee may or may not be the party responsible for the action, just the motivation to get something done.

For example, the trustee may be responsible for seeing that the yearly valuation of the business is conducted as may be required under the cross purchase buy-sell agreement, but may not be the party to actually set the valuation. How much and what specific duties the trustee under the cross purchase is responsible for are a matter of choice and could be different in every trusteed cross purchase agreement.

What Would Be Considered an Unreasonable (And Therefore Unenforceable) Restriction?

A restriction that may be viewed as extremely prohibitive (thus unreasonable) is one that permanently and absolutely bans lifetime transfers of shares of a business's stock, along with a mandatory resale of the shares to the corporation at death for the original purchase price. A restriction like this could be viewed as a forfeiture; unreasonable, and therefore unenforceable. If the only condition for a profitable transfer of stock is a pure right of first refusal that requires the offer of the stock at the same price to the other parties, it does not restrict the transfer of stock, only the persons who may buy the stock. In this case, the restriction is not extremely prohibitive and would almost always be enforceable.

In general, if the terms of the restrictions were reasonable when the agreement was executed, such as rights of first refusal and rights to buy interests in the business based on a formula set price, then the restrictions would be enforceable. Whenever a buy-sell agreement is ambiguous, the courts will not uphold the enforceability of the restrictions. However, a carefully drafted, clearly outlined buy-sell agreement containing reasonable terms of restriction should be able to avoid any issues with state law.

What Happens If the Existing Agreement Calls for Periodic Updating, and It Isn't Done?

If the agreement requires an update, the failure to do the updating could have serious consequences. For example, if the agreement calls for a revaluation of the business at specified intervals, and the revaluation is not calculated, the value set under the agreement may be lower than the taxable value set by the IRS. If you die, your estate would be bound under the agreement to sell your shares at the agreement price. The taxable value assigned by the IRS could be higher, subjecting your estate to taxation on value it didn't receive (assuming there is an estate tax). In addition to the potential tax consequence, the failure to update the agreement when called for in the terms could affect the ability of the agreement to stand up in a court case.



This material was prepared by Broadridge Investor Communication Solutions, Inc., and does not necessarily represent the views of  The Retirement Group or FSC Financial Corp. This information should not be construed as investment advice. Neither the named Representatives nor Broker/Dealer gives tax or legal advice. All information is believed to be from reliable sources; however, we make no representation as to its completeness or accuracy. The publisher is not engaged in rendering legal, accounting or other professional services. If other expert assistance is needed, the reader is advised to engage the services of a competent professional. Please consult your Financial Advisor for further information or call 800-900-5867.


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