Summary

Ouroboros Group is a private equity firm headquartered at 875 Washington Street, New York, NY 10014. It claims a $1 billion fund target, a proprietary AI investment platform called "Serpentel," and a thesis around "Community Wellness" measured in quality-adjusted life years. Its website features photos from cocktail events at Pebble Bar Townhouse at Rockefeller Center, the Harvard Club, the Metropolitan Club, and the Parrish Art Museum in Water Mill.

A primary-source investigation — court filings, SEC databases, property records, corporate registrations — reveals a different picture: a 2-3 person operation with zero SEC filings, 2-3 completed deals in eight years, a co-founder who allegedly forged a UBS proof-of-funds letter during an acquisition, a personal bankruptcy, and a $60M biotech investment announced in January 2026 that appears not to have closed.

Corporate Structure

Entities:

• Leigh Holdings, LLC d/b/a Ouroboros Group — Massachusetts LLC (operating entity, per court filings)
• OBG Management Company, LLC — management entity (per website)
• Ouroboros Group, LLC — Delaware LLC, general partner is Samantha Ory (per court filings)
• OBG OpCo, LLC — Delaware LLC formed specifically for the Honey Dew acquisition (per court filings)
• Ouroboros Family Founders Fund I, LP — named fund vehicle (per website and PR releases)

Address: 875 Washington Street, New York, NY 10014 (West Village). Earlier sources (Axial, Trivest interview) list Boston, MA. Phone: (813) 308-9273 — Tampa, FL area code.

Website: obgfund.com (built on Squarespace)

Size: 2-10 employees per LinkedIn. Axial profile shows 2 team members. The firm appears to consist of the two co-founders and one VP.

The People

Samantha Leigh Ory — Founder, General Partner, CIO

• Education: BBA Design & Management, Parsons (summa cum laude); MBA Finance & Economics + Social Policy, Brandeis International Business School (top 5%)
• Career: Morgan Stanley Capital Markets (consumer sector) → unnamed startup quant hedge fund (algo/back-testing) → Corporate Fuel Advisors (M&A advisory) → Generation Equity Capital (investment team) → Ouroboros (founded ≈2016-2017)
• Other: Licensed MA real estate salesperson since 2016. Developer of "Carmen" (original AI tool) and "Serpentel" (current branding). Treasurer at WorldBeing (youth wellness nonprofit). Committee roles at The Met, Frick, MoMA.
• WorldBeing bio lists hobbies: Golf, blackjack, skiing, electric guitar, competitive distance running, MMA
• Source: WorldBeing team page

Richard Seth Tannenbaum — Co-Founder, Managing Partner (JD)

• Education: BS Biological Science & Economics, Florida State; MS Microbiology & Molecular Biology, University of South Florida; JD Suffolk University School of Law; MBA Suffolk University
• Career: Foundation for Orthopaedic Research and Education (Tampa, research) → Moffitt Cancer Center (tech transfer) → defense contractor in Cambridge (≈$250M contract, role unclear) → Outcome Capital (mid-market life science investment bank, "$100M in transactions") → CEO of Medblob (patient health record system) → CEO of unnamed cannabis company (claims "22x multiple" exit) → Ouroboros
• Source: Trivest interview, Feb 2021

Vignesh Idya — Vice President

• Education: Master's in Finance, Brandeis International Business School (2018-2019)
• Prior: Deloitte India
• Note: Same school as Ory (Brandeis connection)

The Business Model

Ouroboros operates as an independent sponsor (also called "fundless sponsor"). This is confirmed by the Trivest "Independently Sponsored" interview series, which profiles firms that operate without committed capital.

What this means: Unlike traditional PE firms that raise a committed fund from LPs, then deploy that capital into deals, independent sponsors source deals first, then raise capital deal-by-deal from co-investors. The firm does not have a pool of committed capital.

This is important context for every claim Ouroboros makes about fund size, deal capacity, and investment range.

Claimed strategy:

• Target fund size: $1 billion
• Investment range: $5-100 million
• Structure: "Dequity" — convertible notes, junior capital, growth equity
• Target companies: $5M+ EBITDA, $10-300M revenue, founder-led/family/employee-owned
• Sectors: Healthcare, consumer, manufacturing, distribution
• Claims 50+ operating partners on bench (per FINTRX)

"Past Deals" page: Password-protected (HTTP 401). Cannot verify track record.

Known Deal History (8 Years of Operation)

Deal 1: Honey Dew Donuts — FAILED ($25M attempted acquisition, 2019-2022)

Attempted acquisition of Honey Dew Donuts, a ≈120-location franchise chain founded in 1973 by Richard "Dick" Bowen. Negotiations ran from June 2019 through May 2022, when the deal collapsed. This deal is the subject of a major lawsuit (detailed below).

Deal 2: C&W Electric — COMPLETED (date/size unknown)

Regional union commercial electrical contractor in the Northeast. Listed on PitchBook as an Ouroboros portfolio company. No deal details (size, date, structure, outcome) publicly available.

Deal 3: Unnamed Veterinary CRM — COMPLETED (date/size unknown)

Growth capital investment described in the Trivest interview. The company built a pet product line to drive CRM adoption. No name disclosed, no details available.

Deal 4: Cytotheryx — ANNOUNCED, UNCONFIRMED ($60M Series A, January 2026)

Announced as a $60M Series A lead during JPM Biotech Showcase week. Language says "term sheet" and "will lead." No closing announced as of March 30, 2026. Detailed below.

That is the entire publicly identifiable deal history for a firm founded in 2017 claiming a $1 billion fund target.

The Honey Dew Donuts Lawsuit

Honey Dew Associates, Inc. v. Leigh Holdings, LLC d/b/a Ouroboros Group

Court: Suffolk Superior Court, Business Litigation Session (BLS1), Case No. 2284cv01901 Filed: August 19, 2022 Full complaint with exhibits: Universal Hub PDF (23 pages + exhibits, primary source) Federal docket: CourtListener 1:24-cv-11974 State docket: Trellis.law Press: Universal Hub

The Plaintiffs

Richard J. "Dick" Bowen — opened his first Honey Dew Donuts in Mansfield, MA in 1973 after Army service in Germany as a donut baker. Grew it to ≈120 franchise locations across Massachusetts, New Hampshire, and Rhode Island with ≈65 franchisee families. Established the Honey Dew Donuts Scholarship Fund (1999, 1,500+ scholarships awarded) and the Honey Dew Family Foundation (2008). He retained an investment banker to explore selling as he approached retirement.

His brother Robert P. Bowen co-owned a sub-franchisor entity. Together they represented the plaintiffs alongside their corporate entities (HDA, HDO, BRI, BII).

Timeline

June 11, 2019: Confidentiality Agreement signed between Sellers' Investment Banker and Ouroboros LLC (signed by Ory). Honey Dew opens its books — confidential financial data, franchise agreements, operations.

2019-2021: Two years of negotiations. A non-binding LOI was executed October 20, 2020. But no binding agreement materialized. Bowen expressed frustration at the cost and pace.

October 4, 2021: Tannenbaum creates a letter on UBS Financial Services Inc. letterhead (Tampa, FL office), stating:

"Ouroboros Group has been a valued client since February 12, 2018, and as of the close of business on September 28th, 2021, Ouroboros Group account value is at least $25,000,000."

The letter included a contact: "Wade Kornblith" at 813-775-4364 (Tampa area code). It carried UBS branding, a "Confirmation" badge, and SIPC membership language.

October 5, 2021: Tannenbaum emails the letter to Sellers' Investment Banker. Message: "Please see attached."

October 2021 - March 2022: Based in part on the UBS letter establishing financial capacity, negotiations intensify. 240+ pages of Purchase & Sale agreements are drafted covering ≈120 franchise locations, 12 real estate parcels across 3 states. Total price: approximately $25 million.

March 2022: Final P&S agreements signed. Tannenbaum signs on behalf of OBG OpCo. Terms include $150,000 real estate escrow deposit and a $50,000 termination fee (guaranteed by Leigh Holdings). Closing deadline: July 31, 2022.

May 6, 2022: Sellers issue Notice of Default — OBG OpCo failed to provide required real estate subordination documents. 5-day cure period.

May 13, 2022: Buyers fail to cure. Sellers issue Notice of Termination. Sellers demand $150,000 escrow release and $50,000 termination fee.

May - August 2022: Ory and Tannenbaum attempt to resurrect the deal. During this period, sellers discover the UBS letter is forged. Per the complaint (paragraph 37): "Sellers were shocked to discover that the UBS Letter of Reference dated 'September 29th, 2021' was not issued by UBS Financial Services, Inc., but was actually authored by Tannenbaum himself on October 4, 2021."

UBS denied any account or relationship with Ouroboros when contacted directly.

Per the complaint (paragraph 42): Tannenbaum and Ory "maintain that the UBS Letter of Reference was not fabricated" but "have failed, despite Plaintiffs' requests, to provide proof from UBS that it is a genuine UBS document."

Dick Bowen "wanted nothing further to do with Ouroboros Group, Tannenbaum, Ory or the Other buyers for whom they were acting as agent."

August 19, 2022: Lawsuit filed. Four counts:

1. Ch. 93A Sections 2, 11 — Unfair and deceptive trade practices (all defendants)
2. Fraud, Misrepresentation (all defendants)
3. Breach of Contract — $150,000 escrow (OBG OpCo)
4. Breach of Contract — $50,000 termination fee (OBG OpCo, Ouroboros Group, guaranteed by Leigh Holdings)

Prayer: damages, multiple damages for knowing/willful 93A violations, $150K escrow, $50K termination fee, attorneys' fees.

The Second Alleged Forgery

Per Mass Lawyers Weekly and Law360 (paywalled, extracted via Grok):

April 29, 2023: A fake letter was sent to Judge Peter B. Krupp, forged to appear as if from Joanne D'Alcomo — Honey Dew's Of Counsel attorney. The letter:

• Purported to "confess" to misrepresentation in the case
• Accused Jack Mikels (Honey Dew's lead attorney) of actually creating the UBS forgery
• Enclosed a fabricated letter from Mikels to Citizens Bank

May 8, 2023: D'Alcomo discovered the forged letter.

June 12, 2023: Hearing before Judge Krupp. He referred the matter to the Massachusetts Attorney General for investigation.

July 13, 2023: Judge Krupp denied a motion to impound the documents, stating, quoting Justice Brandeis: "Sunlight is the best disinfectant." He said: "The existence... of these forgeries cannot be undone."

Tannenbaum's Response

November/December 2023: Some claims against Ory personally were dismissed — LLC member status shielded her from personal liability on certain counts under G.L. c. 156C Section 22. Fraud and breach claims regarding the UBS letter dismissed as to Ory; 93A and breach regarding Confidentiality Agreement retained.

May 14, 2024: Tannenbaum files personal Chapter 11 bankruptcy in the Middle District of Florida (Case 8:24-bk-02507).

July 30, 2024: Tannenbaum removes the case to federal court (D. Mass. 1:24-cv-11974). Assigned to Judge Indira Talwani.

August 1, 2024: Tannenbaum files a 50-page Amended Counterclaim with ≈295 pages of exhibits, alleging Honey Dew:

• Falsified financial documents through related-party structures
• Misrepresented income
• Violated federal franchise regulations (16 CFR 436.6(a) and 436.5(u)(1))
• Committed wire fraud (18 U.S.C. Section 1343)
• Fabricated evidence and submitted perjured affidavits

The wire fraud allegation is how the case received RICO classification (Nature of Suit 470) in federal court.

August 5, 2024: Tannenbaum files motion to transfer venue to Middle District of Florida — where his personal bankruptcy was filed.

September 25, 2024: Case remanded back to state court. The federal claims did not sustain jurisdiction.

Late 2024/2025: Case reportedly settled. Terms undisclosed.

Credibility Assessment

The UBS forgery allegation comes from a sworn complaint filed under penalty of perjury by a 78-year-old franchise founder who spent decades building 120 locations and a scholarship fund. The actual forged letter is attached as Exhibit A and can be read in full.

Tannenbaum's counterclaim comes from the same person accused of two separate forgeries (the UBS letter and the letter to the judge), who filed personal bankruptcy, attempted to move the case to his preferred jurisdiction, and was acting pro se with paralegal assistance — possibly suggesting limited legal resources.

The case settled — meaning no court finding of fraud. But the settlement also means no exoneration. The allegations stand as allegations.

The SEC EDGAR findings are not allegations. They are database queries with binary answers.

The Cytotheryx Deal ($60M Series A, January 2026)

What Was Announced

Two PR Newswire releases during JPM Biotech Showcase week:

• January 12, 2026 (Cytotheryx): "a lead term sheet from Ouroboros Family Founders Fund I, LP for its $60 million Series A financing"
• January 16, 2026 (Ouroboros): "it will lead a $60 million Series A financing in Cytotheryx"

Board observer seat: "subject to closing."

What's Actually Confirmed

Total confirmed funding: ≈$10M. Total claimed: $60M.

The Company

Cytotheryx is a legitimate Mayo Clinic spinout (2019). It uses genetically engineered pigs as bioreactors to propagate human hepatocytes — real science with published validation. The Scientific Advisory Board is genuinely world-class (Grompe at OHSU, Nyberg at Mayo, Strom at Karolinska, Forbes at Edinburgh).

But it is a 12-person preclinical company with no IND filed, no clinical trials, and no disclosed regulatory timeline. The prior best-funded company in this space — Ambys Medicines, backed by Third Rock Ventures and Takeda with $107M+ — shut down in early 2023 without reaching the clinic. Cytotheryx acquired their IP at what was likely a distressed price.

The nearest competitor, LyGenesis, already has Phase 2a patients dosed (April 2024).

Media Coverage

A real $60M Series A in cell therapy would be covered by at least one major biotech trade outlet. None wrote original reporting.

Zero SEC Filings — The Complete Search

EDGAR full-text search (efts.sec.gov/LATEST/search-index) across all filing types:

EDGAR company search for "ouroboros" filtered to Form D: one result — Ouroboros Medical Inc (CIK 0001394735), San Diego, CA, medical device company, single Form D from 2009. Completely different entity.

SEC IAPD (Investment Adviser Public Disclosure): no results for Ouroboros Group, OBG Management, Samantha Ory, or Richard Tannenbaum.

FINRA BrokerCheck: no results.

Under Regulation D, Rule 506, an issuer must file Form D with the SEC within 15 days after the first sale of securities. "Ouroboros Family Founders Fund I, LP" — the entity named on the Cytotheryx press release and the firm's own website — has never filed a Form D. If the fund has accepted a single dollar from an investor, it is either in violation of securities law or does not exist as described.

The Presentation vs. Reality Gap

What the Website Shows

• $1 billion target fund size
• $5-100 million investment range
• Proprietary "Serpentel" AI investment platform with "Opportunity Detection," "Risk Assessment," "Lifecycle Insights," and "Trend Analysis"
• Photos from events at Pebble Bar Townhouse (Rockefeller Center), Harvard Club, Metropolitan Club, Parrish Art Museum (Water Mill)
• "Community Wellness" thesis measured in quality-adjusted life years
• "Member Login" portal
• Professional branding

What Primary Sources Show

• 2-3 person team (two founders + one VP)
• Zero SEC filings for the fund entity
• 2-3 completed deals in 8 years (one electrical contractor, one unnamed veterinary CRM, one possibly-pending biotech)
• One failed $25M acquisition with forgery allegations in court
• Co-founder personal Chapter 11 bankruptcy
• All press coverage is paid/branded content (NY Weekly: "This article features branded content from a third party." Disrupt Magazine: "All written content is for informational purposes only.")
• Password-protected "Past Deals" page
• Geographic inconsistency: NYC website address, Boston on Axial profile, Tampa phone number, Florida bankruptcy filing

What Independent Sources Confirm

• FINTRX case study (they use legitimate LP-sourcing tools)
• Samantha Ory has verifiable Morgan Stanley background
• Ory's WorldBeing nonprofit board role (in good standing)
• Cytotheryx is a real company (Mayo Clinic spinout, real facilities, real SAB)
• C&W Electric appears on PitchBook as a real portfolio company
• Cytotheryx $7.6M real estate purchases confirmed via county records

The Pattern

A firm with no committed fund signs non-binding term sheets, issues PR Newswire releases timed to major industry events (JPM Biotech Showcase), and uses the announcements to signal legitimacy to prospective LPs, co-investors, and deal targets. The website creates an institutional veneer (Harvard Club photos, AI platform branding, $1B target) around what is functionally a two-person deal-sourcing operation.

The Honey Dew lawsuit — regardless of how one weighs the competing allegations — establishes that Ouroboros has previously been involved in a multi-year acquisition process that collapsed, with the sellers alleging fabricated proof of financial capacity.

Wikipedia Manipulation

The Honey Dew Donuts Wikipedia article contains a "Legal issues" section (last edited January 31, 2026) that reads like a defense briefing document rather than neutral encyclopedia content.

The section:

• Cites specific federal regulation sections (16 CFR 436.6(a), 16 CFR 436.5(u)(1)) — language that maps directly to Tannenbaum's counterclaim
• Names Honey Dew's CPA (Marc Cohen) and accuses him of simultaneously serving as auditor and CFO
• Alleges "wire fraud" (18 U.S.C. Section 1343) — the exact statute from the counterclaim
• Describes Honey Dew's corporate structure (Bowen Investments, BRI, HDO) as vehicles for "shifting income and expenses away from HDA"
• References a separate franchisee lawsuit (Goldman et al., Norfolk Superior Court) to create the impression of a pattern of behavior by Honey Dew
• Frames the UBS letter allegations in the most favorable light to the defense

The section does NOT mention:

• The second alleged forgery (fake letter to Judge Krupp impersonating opposing counsel)
• The MA Attorney General referral
• Judge Krupp's "sunlight is the best disinfectant" ruling
• Tannenbaum's personal Chapter 11 bankruptcy
• The attempted venue transfer to Florida
• That the federal removal was rejected and case remanded within two months

The edit pattern — highly specific legal language matching the counterclaim, asymmetric inclusion/exclusion of facts, defense-favorable framing — is consistent with reputation management via Wikipedia editing, either by defendants or their representatives. This is a common tactic documented by researchers (see: Wikipedia:Conflict of interest editing).

Sources

Court filings (primary):

• Full complaint + Exhibit A (forged UBS letter)
• CourtListener federal docket 1:24-cv-11974
• Trellis.law state docket 2284cv01901
• PacerMonitor — Tannenbaum bankruptcy

SEC (primary):

• EDGAR full-text search: efts.sec.gov/LATEST/search-index (7 queries documented above)
• EDGAR company search: "ouroboros" + Form D
• Fernwood Cytotheryx LP Form D (CIK 0002021923)

Press:

• Universal Hub — Honey Dew lawsuit coverage (Aug 2022)
• Law360 — "Honey Dew Says M&A Adviser Missed Fake $25M Letter"
• Post Bulletin — Cytotheryx $60M raise (Jan 2026)
• Post Bulletin — Cytotheryx $7.6M facilities (Mar 2026)
• PR Newswire — Ouroboros Cytotheryx announcement (Jan 16, 2026)
• LucidQuest diligence brief

Company profiles:

• Trivest — "Independently Sponsored: Ouroboros Group" (Feb 2021)
• WorldBeing — Samantha Ory bio
• Ouroboros website
• Axial profile
• FINTRX case study

Other:

• NY Weekly (branded content disclaimer)
• Disrupt Magazine (branded content disclaimer)
• Wikipedia — Honey Dew Donuts "Legal issues" (last edited Jan 31, 2026; section appears to reflect defendant narrative)