2026 Best Business Debt Settlement Lawyers in Boston

Best Business Debt Settlement Lawyers in Boston for 2026

The debt settlement companies can sound great on the phone. They go on and on about how they can save you money, cut your payments in half, get you on the road to financial freedom in no time. But they aren’t always up front about the hefty fees they collect, or that their savings estimates are about as real as a three dollar bill. On top of that, most funders will add fees and charges for ordinary problems: bad checks, stop payments, changing bank or merchant accounts. They also try to enforce these charges if your settlement deal fails, even though you may have already paid fees to the settlement company.

The UCC Lien

Judgments are a danger. But the UCC lien is far worse. A UCC lien doesn’t freeze money in your bank account. It freezes money that’s owed to you and has you as the payee. When you took the advance you agreed that they could take the money before it was even paid. When the funder has your bank statements or your customer list, it doesn’t have to prove anything to anybody. It just sends a letter to Paypal, Square, Stripe and the rest of the processors demanding your money. The kicker is that the funder is likely to send letters to your customers about the debt. Suddenly your customers know that you’re in trouble, which makes them uneasy. There’s no telling how many will say “I don’t want to work with a business that’s going under” and take their money elsewhere.

Back in the day, confession of judgments clauses were a huge threat. You give up your right to argue the facts in a trial. New York banned the confessions against out-of-state owners in 2019, so funders filed them in Texas, Illinois and Utah. But often funders just sue. Most of them do. In Massachusetts, most claims arising out of a contract must be brought within six years after the cause of action accrues. Funders are loading up on judgments in courts in other states, and “domesticating” them to reach assets in Massachusetts. It’s happening more often as the MCA industry grows and more borrowers default on their obligations to repay the advances. Chalk it up to tougher collections tactics among funders.

Really a Loan Disguised as Something Else

One of the biggest reasons to see a lawyer is to find out whether your MCA is really a loan disguised as something else. MCAs look just like business loans, but that isn’t what their funders say they are. Most MCA funders say that they’re “purchasing” your future receivables. In a real MCA deal, the funder is buying pieces of your future income. If you don’t make money, there’s nothing to buy. One difference between a merchant cash advance and a loan is that the funder in a merchant cash advance takes the risk. Some merchant cash advance funders make 100%, 200% or more in profit, and if the MCA is deemed a loan under the law, these rates are considered usurious in most states. But most contracts between funders and businesses like yours are not properly drafted to withstand a legal challenge. If it’s a loan, a judge might void it altogether.

A lot of the deception happens on the front end with brokers, because brokers get paid only if there’s a deal, so they want to make a deal at any cost. They don’t care if you repay. They often pack a series of advances from multiple funders to load you up with debt. One dirty trick is to say that if you pay on time for a month, they’ll be able to move you to a traditional loan. Keep in mind that a good business lawyer can bring a third-party claim against a broker.

Personally Guaranteed the Merchant Cash Advance

If you’re the owner of an LLC, you might think that if the LLC can’t repay the merchant cash advance, you’ve got nothing to worry about. But there’s a little problem with that. While your LLC can be on hook for the balance, you are likely to have personally guaranteed the merchant cash advance. Discharging your personal liability in a personal bankruptcy doesn’t end the company’s liability. Your business bankruptcy won’t touch your personal liability. A good lawyer should resolve both. Bankruptcy often comes as a last resort. You should ask whether your lawyer files personal Chapter 7 and Chapter 13, business Chapter 7, Chapter 11 bankruptcy, including Subchapter V for small businesses.

If you go with a debt settlement company instead, a legitimate outfit can’t charge fees until it settles your first debt and you make a payment under the agreement. The Federal Trade Commission Telemarketing Sales Rule is the basis for this rule. The ban on upfront fees applies to businesses and individuals.

If a debt is settled for less, the Internal Revenue Service usually treats debt that’s forgiven as taxable income in the year that the lender cancels it. But this is not always the case. Lenders send a Form 1099-C to the IRS if the forgiven debt was at least $600. If the borrower was insolvent before the lender canceled the debt, the borrower can exclude up to the insolvency amount on Form 982. Debt discharged in bankruptcy is excluded from income, as well.

When choosing a lawyer, ask who handles collections and litigation. You also want someone who understands contract law and bankruptcy, and has a track record. Interview several lawyers to make sure you hire the right one for your legal needs. The best debt lawyer isn’t the person on the TV, radio, or at the top of Google’s search results. The best lawyer is one with the qualifications, experience, and standing to advise you on your options and guide you out of debt.