Bottom line: High risk — managing partner is the alleged author of a forged bank reference letter used to advance a $25 million acquisition; the fraud lawsuit is active with RICO claims and a pending court sanctions proceeding for fraud on the court and spoliation; and the entity has filed zero securities disclosures in a decade of claimed private equity operations, including for a $60 million Series A announced 73 days ago that has not closed.

What They Are

  • Legal structure: Leigh Holdings LLC (Delaware) d/b/a Ouroboros Group. Acquisition vehicle: OBG OpCo LLC (Delaware). Claimed fund: Ouroboros Family Founders Fund I, LP. Two employees per Axial platform data. All three entities filed Chapter 11 bankruptcy simultaneously on May 8, 2024.
  • Address: Claimed HQ is 875 Washington St, NYC 10014 — a Soho Works coworking space (desks from $400/month). Phone number (813) 308-9273 is Tampa FL area code. Actual operational address per OBG OpCo bankruptcy filing: 1402 W Swann Ave, Tampa, FL 33606. Prior listings showed Boston, MA.
  • History: Founded 2016–2017 as a self-described "fundless sponsor" in lower-middle-market manufacturing, healthcare, and consumer. Pivoted to claiming a $1 billion target fund and "community wellness" branding. No Form D for any fund has ever been filed with the SEC.
  • Claimed technology: A proprietary AI deal-sourcing tool — called "Carmen" in early materials, rebranded as "Serpentel®" on the current website. No patent filing, no technical documentation, no independent reference to either tool outside company-controlled materials. The "Dequity Funding Model" promoted on the website is not a recognized finance term.

Track Record

Honey Dew Donuts — $25M, failed, active fraud litigation. In 2019, Ouroboros approached Richard Bowen, founder of Honey Dew Donuts (Plainville, MA; 120 franchises across 3 states; founded 1973). Negotiations ran ≈2 years. In October 2021, Tannenbaum submitted a "UBS Letter of Reference" to Bowen's investment banker stating Ouroboros had been a UBS client since February 12, 2018, with at least $25 million in accounts. Based on that letter, Honey Dew compiled 240 pages of confidential franchise data. In March 2022 both sides signed a final purchase and sale agreement for $25M with a July 31 closing target; Ouroboros deposited $200,000 in escrow. In May 2022, Honey Dew conducted a forensic examination and contacted UBS directly. UBS confirmed no account, no client relationship, no affiliation of any kind. Tannenbaum had authored the letter himself — using a genuine UBS document as a template — the day before submitting it. Deal killed. Litigation active; see RED FLAGS.

C&W Electric — claimed acquisition, unverified. Listed on PitchBook as a portfolio company (union commercial electrical contractor, Northeast). No press release, no SEC filing, no independent confirmation of closing. PitchBook private company profiles can be self-reported.

Cytotheryx — $60M Series A, announced January 2026, not closed. On January 16, 2026, Ouroboros announced it would lead a $60M Series A in Cytotheryx Inc. (Mayo Clinic spinout, preclinical cell therapy for liver disease, Rochester MN). The press release explicitly states "subject to closing." No Form D on EDGAR as of March 30, 2026 — 73 days post-announcement, 58 days past the 15-day Reg D filing deadline. The deal has not closed. Cytotheryx is a real company: a separate $2.1M investment by Fernwood Investment Management (Quincy, MA) was properly documented with an SEC Form D filing in May 2024.

RED FLAGS

1. Forged bank reference letter — alleged, civil, litigation active. Tannenbaum is alleged to have fabricated a UBS Financial letterhead document claiming Ouroboros had $25M in accounts. He authored it using a genuine UBS template the day before submission. UBS confirmed zero affiliation. Forensic examination traced authorship to Tannenbaum. Source: complaint PDF, Suffolk Superior Court 2284CV01901-BLS1 (August 19, 2022). Allegation, not adjudicated. Case active.

2. Active RICO claims + pending state court sanctions for fraud on the court and spoliation. The complaint was amended to add RICO. Separately, the state court scheduled an evidentiary hearing for May 2, 2024 on sanctions against Tannenbaum and Leigh Holdings for fraud on the court, violation of court orders, and spoliation. That hearing was aborted — see #3. The case returned to Suffolk Superior Court October 4, 2024. Whether the sanctions hearing has since been rescheduled and ruled upon is unknown; MA trial court dockets are not publicly web-indexed. A judicial finding of fraud on the court is not an allegation — it is a ruling, with case-dispositive consequences. Source: D. Mass. 1:24-cv-11974 remand exhibits, PACER, August 2024.

3. Coordinated three-way bankruptcy to evade state court sanctions. On May 8, 2024 — the day the sanctions evidentiary hearing was due — Tannenbaum simultaneously filed Chapter 11 petitions for Leigh Holdings LLC (8:24-bk-02625: assets $0–$50K, liabilities $1–10M), OBG OpCo LLC (8:24-bk-02626: assets $1–10M, liabilities $100K–$500K), and himself personally (8:24-bk-02507). The filings triggered automatic stay and removed the Massachusetts case to Florida Bankruptcy Court — Tannenbaum's home jurisdiction. All three dismissed within 20 days for failure to file required paperwork or retain counsel. The Florida Bankruptcy Court abstained and remanded to Massachusetts on June 25, 2024. Source: FL Middle Bankruptcy Court records.

4. Leigh Holdings disclosed $0–$50K in assets at bankruptcy — 20 months before announcing a $60M investment. The entity whose website claims a $1 billion fund target had essentially no assets when it filed Chapter 11 in May 2024. Source: bankruptcy petition 8:24-bk-02625.

5. Two federal court removals, both remanded as bad-faith. After the bankruptcies failed, Tannenbaum removed the case to D. Mass. in July 2024, pro se, asserting RICO jurisdiction via counterclaims he had never filed in state court. He simultaneously moved to transfer venue to Middle District of Florida — his third attempt to move the case out of Massachusetts. Judge Talwani issued an Order to Show Cause and remanded in 57 days. Both federal courts characterized the removals as abusive jurisdictional maneuvers to block the state sanctions proceeding. Source: D. Mass. 1:24-cv-11974, PACER.

6. "Emergency Motion to Impound Forged Letters" — plural. Plaintiffs filed an emergency motion (docket #78, May 19, 2023) to impound forged letters — not "a forged letter." The plural suggests additional fabricated documents beyond the UBS proof-of-funds. Their full scope is not publicly documented. Source: Suffolk Superior state court docket.

7. Defendants' counsel withdrew mid-litigation, 13 months in. The full defense law team (Brooks, Gens, Milkovich, Mullane) withdrew from representing Leigh Holdings and OBG OpCo in September 2023, requiring substitute counsel before the October 5, 2023 status conference. Tannenbaum subsequently appeared pro se in federal proceedings. Source: state court docket entries.

8. Contempt proceeding against OBG OpCo. Plaintiffs filed a Verified Complaint for Contempt against OBG OpCo on August 18, 2023, alleging violation of a court order — almost certainly a discovery order given the later spoliation allegation. Source: Suffolk Superior docket.

9. Zero securities disclosures, ever. No Form D for Ouroboros Family Founders Fund I, LP. No Form D for any prior offering. No RIA registration. No FINRA registration. EDGAR API queries on March 30, 2026: "ouroboros" + Form D (2016–2026) = 0 results. "leigh holdings" + Form D (2016–2026) = 0 results. "cytotheryx" + Form D (2026) = 0 results. Source: EDGAR full-text search API, direct queries.

10. Ory faces surviving c.93A claim for confidentiality breach. Separately from the forgery, Ory is alleged to have shared Honey Dew's confidential evaluation materials — 240 pages of franchise data — with third parties who then solicited Honey Dew for finder's fees on the same transaction. The c.93A (unfair business practices) claim against her survived the November 2023 partial dismissal. Under Massachusetts law, c.93A carries double or triple damages. Source: state court ruling, November 3, 2023.

11. Additional creditor in Tannenbaum's personal bankruptcy. Sheehan, Phinney — a real New Hampshire/Massachusetts law firm — appeared as a creditor in Tannenbaum's personal Chapter 11 (8:24-bk-02507). This implies at least one additional legal dispute not publicly surfaced. Source: bankruptcy petition.

GREEN FLAGS

1. Cytotheryx is a real company with legitimate prior investment. Mayo Clinic spinout, credible hepatocyte platform technology, real CEO (Dr. John Swart, prev. Exemplar Genetics). Fernwood Investment Management properly documented a $2.1M investment in April 2024 with a timely SEC Form D filing (CIK 0002021923). A serious biotech agreed to accept Ouroboros as a committed lead investor on a term sheet.

2. Conference presence in legitimate venues. Tannenbaum spoke at LSX World Congress USA (life sciences). Ory spoke at ACG Boston and Opus Connect Consumer Goods Summit. Not pay-for-play circuits.

3. Ory's prior employer traces. Generation Equity Capital is a real PE firm (Boston, founded 2006; family/small business focus). Her WorldBeing board membership confirmed at worldbeing.org. These are verifiable.

4. No criminal charges, no SEC enforcement. All allegations are civil. No DOJ indictment, no SEC enforcement action as of March 30, 2026.

Key People

Richard Seth Tannenbaum — Managing Partner, Co-founder. BS Biology/Economics FSU, MS Biology USF, JD/MBA Suffolk University (claimed). Career: research at FORE (Tampa), tech transfer at Moffitt Cancer Center (Tampa), legal/licensing at unnamed defense contractor (Cambridge MA), founder/CEO of MedBlob health records startup (Tampa FL, entity L15000173395, confirmed). No institutional PE or finance background. Alleged author of the forged UBS letter. Filed three simultaneous personal and entity Chapter 11s in Tampa to abort state court proceedings. Appeared pro se in federal RICO litigation. Moved to transfer venue to his home district (Middle District of Florida) three separate times across two removal attempts.

Samantha Leigh Ory — CIO, General Partner, Co-founder. BBA Design/Management Parsons, MBA Brandeis top 5% Finance/Economics (claimed). Career: unspecified role at Prada (claimed), M&A advisory at Corporate Fuel Advisors (claimed), Associate at Generation Equity Capital January 2014–January 2016 (employer verified, role claimed). Board member WorldBeing (confirmed). AngelList syndicate (confirmed). No senior PE operating history; two years as a junior associate is the full institutional experience. Partially dismissed from forgery count (did not personally forge the letter). Faces surviving c.93A claim for sharing confidential deal materials with third parties.

What's the nature of your exposure — are you a potential LP, a deal target being approached, a co-investor in the Cytotheryx round, or something else?