Cuesta Partners LLC v. Jamie Reingruber, et al.

District Court, S.D. New York·Decided July 8, 2026·No. 1:26-cv-03602·Unknown

Opinion

UNITED STATES DISTRICT COURT SOUTHERN DISTRICT OF NEW YORK --------------------------------------- X : CUESTA PARTNERS LLC, : : Plaintiff, : : 26cv3602 (DLC) -v- : : OPINION AND JAMIE REINGRUBER, et al., : ORDER : : Defendants. : : --------------------------------------- X APPEARANCES:

For Plaintiff Cuesta Partners LLC: Eric A. Savage Sara Elgndy Littler Mendelson, P.C. 900 Third Avenue New York, NY 10022

For Defendant Jamie Reingruber: Tina B. Solis Paul Fitzgerald Downs Nixon Peabody LLP 55 West 46th Street New York, NY 10036

For Defendants Leo Berwick LP and Leo Berwick AI, LP: Peter Andrew Stokes Anthony Lauriello Kelly Potter Norton Rose Fulbright US LLP 1301 Avenue of the Americas New York, NY 10019

DENISE COTE, District Judge: In March of 2026, Jamie Reingruber resigned from Cuesta Partners LLC (“Cuesta”) after downloading a massive amount of its files. He had accepted an employment offer from Leo Berwick AI, LP (“Berwick AI”), a Cuesta competitor. On May 1, 2026, a temporary restraining order was issued against Reingruber, Berwick AI, and its affiliate Leo Berwick LP (“Berwick”). This

Opinion contains the findings of fact and conclusions of law following a preliminary injunction hearing held on July 1. At that hearing, the defendants Reingruber, Berwick AI, and Berwick were enjoined from possessing and using confidential information regarding Cuesta and its clients, and from otherwise violating or inducing violations of Reingruber’s employment agreement with Cuesta.

Findings of Fact Cuesta was founded in 2019 as a data, AI, and IT diligence firm, working with private equity and corporate clients on technology, data, and AI strategy. Its principal place of business is in Chicago, Illinois. It currently has six partners, twelve individuals holding the title of principal, and over one hundred other employees. Reingruber was Cuesta’s first hire. He was hired in 2020 as a senior associate and by August of 2021 was promoted to manager. On or about the time of that promotion, Reingruber executed an Employee Confidentiality, Non-Compete and Non-

Solicitation Agreement with Cuesta Partners (the “Agreement”), which bears an effective date of August 6, 2021. Among other commitments, the Agreement bars Reingruber from “disclos[ing] . . . or remov[ing] from the premises of the Company . . . any Confidential Information,” “both during and

after the term of this Agreement” in a provision entitled “Non- Disclosure of Confidential Information.” It also requires Reingruber to “return” any confidential information in his possession upon Company request. In another provision entitled “Return of Company Property,” the Agreement requires Reingruber to “return to the Company all Company property including . . . computers [and] Confidential Information” upon termination of his employment. It also bars him from “procur[ing]” or “copy[ing]” any Company property, including its confidential information, “in anticipation of . . . termination of his employment.” The Agreement contains two restrictive covenants that

Cuesta seeks to enforce through this litigation. First, the Agreement bars Reingruber from, “for a period of six months . . . following termination of . . . employment,” “render[ing] to or for any Client any services of the type rendered by the Company.” It defines “Client” in three categories, as follows: • (i) any customer of the Company that had project work in process or pending with the Company on the date of Employee’s termination of employment or in the twelve (12) months prior to the Employee’s termination, • (ii) any prospective customer of the Company to which the Company had made a business presentation during the twelve (12) months immediately prior to the Employee’s date of termination, or • (iii) any prospective customer of the Company to which the Company makes a business presentation during the six (6) months after the Employee’s date of termination where Employee participated in such initial business discussions prior to the date of termination. The second restrictive covenant bars Reingruber from, “for a period of twelve (12) months after [termination],” “soliciting any employee, consultant, officer or director of the Company . . . for employment, consulting or other services,” “soliciting or interfering with any Client,” and soliciting “any Client using Confidential Information.” Reingruber was promoted to senior manager in January of 2023 and in May of 2023 received the Cuesta Employee Handbook, which includes additional confidentiality provisions. Reingruber was then promoted to principal in July 2024. At about that time he became a Co-Lead of the Technology Strategy Practice. As Co-Lead, Reingruber defined the practice’s strategy, go-to-market approach, delivery methodology, asset investment plans, and human capital needs, and had access to virtually all of Cuesta’s confidential information and trade

secrets. Reingruber’s total 2025 compensation consisted of a $225,000 salary and a $64,174 bonus. During 2025, Cuesta engaged in conversations with other entities about being acquired. In anticipation of its acquisition, Cuesta and Reingruber entered into a Transaction Bonus Agreement on January 30, 2025, which entitled him to a bonus in the event of “(i) a sale of all or substantially all the assets or ownership interests of the Company or (ii) a recapitalization of the Company” (i.e., a “Transaction”). The Transaction Bonus Agreement required Reingruber to be “employed in good standing” by Cuesta through the closing of the transaction in order for the bonus to be paid out. The

agreement also specified that 50% of any bonus would be paid to Reingruber at the time the transaction closed and the remaining 50% would be paid upon the one-year anniversary of the closing. Cuesta was ultimately acquired by Riveron in February 2026. Before that occurred, however, Nick Kato, Berwick’s Chief Operating Officer, approached Cuesta about a possible acquisition. Those discussions ended at some point in the Fall of 2025. In late 2025, the predecessor of Berwick AI was formed under the name Tenon Point, LP. It became Leo Berwick AI in early 2026. Omar Khalifa is the Chief Executive Officer of Berwick AI, and together with Kato, solicited Reingruber to join

Berwick AI. Berwick and Berwick AI began to recruit Reingruber in December of 2025. During telephone conversations in the following weeks,1 Khalifa and representatives from Berwick 0F explained their business plans for what became Berwick AI and informed Reingruber that they were well funded. They inquired in general terms about what Reingruber did for Cuesta and whether he was, in his view, adequately compensated for his work. They inquired about what kind of work he did for clients, how he would develop clients for their new business, how individual projects should be staffed, and how projects for clients should be priced. They also told Reingruber that it would be “critical” for him “to help [them] identify other members of [his] team that need to come along and be part of this,” ideally 5-10 individuals. They offered Reingruber a

1 Cuesta provided AI-generated transcripts of these conversations. These transcripts were produced by a company named Otter.AI after Reingruber personally purchased Otter.AI’s software to record the phone conversations and generate the transcripts. The defendants have objected that the transcripts are unauthenticated and may not be accurate, although Reingruber acknowledged that he still has access to recordings of these conversations and has not compared the transcripts to them. $500,000 signing bonus, which they noted would, in essence, be “commensurate” with the transaction bonus to which he would be entitled from Cuesta if he remained “employed in good standing.”

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Cuesta Partners LLC v. Jamie Reingruber, et al., (S.D.N.Y. 2026).

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