YARMOUTH — Levee Breaks Investment Group LLC, a Yarmouth-based investment firm that said bankruptcy On October 21, 2021, let 55 investors hold the bag. The initial claims totaled approximately $4.5 million according to the trustee assigned to the case. The Times followed the bankruptcy case as it progressed through the court. Here’s what we know so far:

After:Yarmouth investment firm files for bankruptcy, investors risk losing money

Company history

Levee Breaks Investment Group LLC: Formed in 2015 by Brian Serpone to carry out activities for members, including residential and commercial construction, development, rehabilitation, management and sale of property, according to the Commonwealth Secretary’s website .

Brian Serpone: Principal Owner of The music room, a Yarmouth venue offering studio recordings, food, drink, an art gallery and live music featuring local and national musicians. It opened in the spring of 2021.

Dennis Serpone, Brian’s uncle, who sold unregistered securities or promissory notes for Levee Breaks but was not registered with the Commonwealth Secretary’s office, according to a Securities Division administrative complaint . Its registration was terminated by the SEC in 1998.

Headley Grange Investments LLC, was established in 2017 by Brian Serpone, to carry out the development, acquisition, renovation and sale of commercial and residential real estate, according to state records.


2015 : Levee Breaks is formed and begins selling promissory notes of $10,000 each. The tickets promised to yield 10%, paid in monthly installments, with a term of one year.

2017: Creation of Headley Grange Investments LLC.

2018: Levee Breaks is launching a profit-sharing program with a few tickets, which were sold in increments of $20,000. Investors could share the profits from the sale of a property or share the annual rental income from a property.

2019: Levee Breaks’ activities come to the attention of the state’s securities division when an investor files a complaint, according to Deb O’Malley, a spokeswoman for the office of Commonwealth Secretary William Galvin. The investigation revealed that Dennis Serpone and the Levee Breaks Investment Group LLC allegedly violated several general Massachusetts laws.

Brian Serpone in June 2021

May. 2020: Dennis and Brian Serpone accept a consent order from the Securities Division of the Commonwealth Secretary’s Office. A settlement offer is made, but never honored, according to state documents.

Week of October 11 to 15, 2021: The Securities Division filed an administrative complaint against Dennis Serpone and Levee Breaks for alleged continuing violations of general Massachusetts law. These alleged violations included offering to sell unregistered securities when doing business in the state was prohibited, employing an unregistered agent, and making false and misleading statements to the Section of l law enforcement during its investigation.

October 22, 2021: Levee Breaks Files for Chapter 7 Bankruptcy

October 22, 2021:Headley Grange Investments files for bankruptcy.

About $4.5 million in claims are filed in the bankruptcy case, according to trustee David Madoff. Fifty-five investors are concerned.

July 2022: Trustee David Madoff files petition to hire a forensic accountant to examine Levee Breaks’ bank accounts to see if any funds had been misappropriated.

September 21, 2022. Madoff is asking the court for permission to review four Citizens Bank accounts that received $4,454,000 in transfers before the bankruptcy filing. Information is sought on the identity of each owner, holder, beneficiary and signatory associated with the accounts according to court documents.

Bank statements and information regarding such transfers made by Levee Breaks Investment Group could potentially constitute preferential and fraudulent transfers. If this is the case, the estate could try to recover these transfers.

Contact Denise Coffey at [email protected]