Entrepreneurs often choose limited liability companies to incubate their businesses. An LLC offers a simple entity structure, it lets the members claim start-up losses on their own tax returns, and it eliminates the double tax imposed on a corporate structure once the venture turns profitable.
But an LLC has a tax defect that its owners frequently don’t understand until it’s too late: because it is not a corporation an LLC cannot participate in a tax-free corporate reorganization. So when the owners sell their LLC interests to another company for stock, the transaction is a taxable event to them but they don’t get cash to pay the tax on any gain.
If the stock trades publicly the owners can sell some of it to raise cash for the taxes. But they may not want to do that, and there may be SEC- or deal-driven lockups that prohibit them from selling before the tax is due. If the stock doesn’t trade publicly, they may need to find cash somewhere else.
The buyer may have a number of reasons for wanting to acquire membership interests of an LLC using its stock as currency: it may not have the cash itself, or want to use it, or it may want the sellers to continue to have an equity interest in the company and be motivated to help it succeed. The buyer may propose a stock-for-stock exchange, a stock-for-assets exchange, or a merger. All of these transactions could be tax-free to the sellers who own the target – but only if the target is a corporation.
There are solutions to this problem, but each solution carries tax risks. The sellers can incorporate their LLC (or elect to have it treated as a corporation for tax purposes) before the acquisition and then exchange their stock in the new corporation for stock in the buyer. But this approach will usually generate a so-called “step-transaction” analysis: if the IRS decides that the conversion of the LLC into a “C” corporation and the subsequent stock exchange were all part of the same transaction, and that there was no non-tax reason for the conversion, it will disregard the first step – the conversion – and treat the transaction as a taxable sale of the LLC interests. The closer the conversion occurs to the acquisition, the more likely the step-transaction doctrine will be applied.
Another solution is to structure the exchange as a tax-free “Section 351 transfer”. Section 351 transfers can involve property (as opposed to just stock). In a section 351 transfer the seller contributes his LLC interests (or the LLC’s assets) to a new corporation, and the buyer contributes stock (or other property) to the new corporation, and if together the seller and the buyer control more than 80% of the new corporation, then the transfer is tax-free.
But this solution has its drawbacks, as well. For one thing the stock that the seller now owns is not stock in the buyer but in a corporation that is a subsidiary of the buyer. That stock probably won’t be sellable. After a decent interval (which could be as long as a year) the parties could liquidate the subsidiary into the buyer and distribute stock in the buyer, but if they do that too soon then — you guessed it — the step-transaction analysis is applied once again. And if the buyer uses treasury stock to capitalize the subsidiary, there is an unsettled legal question as to whether the transfer is still tax free to the seller. In any event, the section 351 transfer forces the buyer to hold the target’s business in a subsidiary company, something it may not wish to do.
There are also non-tax solutions: the deal might require the buyer to provide enough cash consideration for the seller to pay the tax, but then the amount of cash becomes a negotiating point and chances are the seller gives up something in return for it.
The best solution to the LLC problem is to plan ahead. Way ahead. Do you need an LLC in the first place – will the tax benefits of the losses justify the potential tax problem on a sale for stock? Would an S corporation serve as an alternative to an LLC? (It’s not an alternative if there are foreign, corporate or (in some cases) trust owners, more than 100 owners, or more than one class of equity.) If you plan to sell the business before it turns a profit (and then there would be no benefit to the tax flow-through) should you just start with a corporation in the first place? There are no boiler-plate answers to these questions; the alternatives need to be analyzed in the context of the business and the exit strategy.
If you already have an LLC and plan to sell, the best solution is still to plan ahead. If today you foresee a sale of your company in a year or so, now may be the time to convert it to a corporation. The further in advance of the sale that you do so, the more likely you are to avoid the step-transaction doctrine. (LLCs can usually be converted to corporations tax-free.) Again, there is no one-solution-fits-all, but you will have more options if you address the problem well in advance of the sale.
The corporate tax-free exchange rules of the tax laws are among the most complicated in the Internal Revenue Code, but people have been dealing with them for decades and a solution is often available, as long as you leave yourself enough time and flexibility to find it.
Written by Michael Savage, Esq.
The information in this article is for general, educational purposes only and should not be taken as specific legal advice.
