{"schema_version":"secwatch.filing_event.v1","accession":"0001104659-25-075879","form_type":"8-K","ticker":"DRCT","cik":"0001880613","company_name":"Direct Digital Holdings, Inc.","filed_at":"2025-08-11T23:59:59+00:00","discovered_at":"2026-05-14T18:02:45.501820+00:00","generated_at":"2026-05-17T15:45:57.613298+00:00","sec_items":["1.01","3.02","3.03","5.03","9.01"],"event_type":"other_material","sentiment":"neutral","materiality_score":0.8,"calibrated_materiality_score":0.8,"confidence":"high","headline":"Direct Digital converts $25M term loans to Series A Preferred; debt reduced to $9.4M","bullets":["$25M of term loans exchanged for Series A Preferred stock issued to Lafayette Square; remaining term loan debt $9.36M.","Series A Preferred carries 10% cumulative dividend, convertible at $2.50/share, and liquidation preference up to 3x after Oct 15, 2025.","Credit parties must maintain minimum EBITDA of $1M for Q3/Q4 2025 and $500M thereafter; cash covenant set at $1.5M.","A $25M exit fee on preferred redemption is waived if fully redeemed by Dec 31, 2026; $1M closing fee due by Sept 30, 2025.","Preferred stock is senior to common, voting on as-converted basis, with protective provisions requiring majority holder consent for key actions."],"urls":{"canonical":"https://secwatch.observer/filing/0001104659-25-075879","json":"https://secwatch.observer/filing/0001104659-25-075879.json","markdown":"https://secwatch.observer/filing/0001104659-25-075879.md","text":"https://secwatch.observer/filing/0001104659-25-075879.txt","edgar_index":"https://www.sec.gov/Archives/edgar/data/1880613/000110465925075879/0001104659-25-075879-index.htm","edgar_primary_document":"https://www.sec.gov/Archives/edgar/data/1880613/000110465925075879/tm2523062d1_8k.htm"},"model":{"generated_by":"deepseek-v4-flash:cloud@v2","generated_at":"2026-05-17T15:45:57.613298+00:00"},"review":{"review_status":"machine_generated","human_reviewed":false,"corrected":false,"correction_note":null,"correction_timestamp":null,"superseded_by":null,"related_filings":[]},"source_grounded_claims":[{"claim_id":"6a8182a12afd6efa07aa8cc963303572aaf9c0d3","claim":"Direct Digital Holdings, Inc.: Direct Digital Holdings, Inc. filed a Certificate of Designation of Series A Convertible Preferred Stock with the Delaware Secretary of State on August 8, 2025, establishing the rights, preferences, and limitations of the Series A Preferred Stock (effective 2025-08-08).","evidence_excerpt":"on August 8, 2025, the Board authorized and the Company filed the Certificate of Designation of Series A Convertible Preferred Stock (the “ Certificate of Designation ’) with the Secretary of State of the State of Delaware, which established the Series A Preferred Stock.","evidence_source":"SEC 8-K Item 5.03/5.05/5.06","evidence_url":"https://www.sec.gov/Archives/edgar/data/1880613/000110465925075879/0001104659-25-075879-index.htm","confidence":0.95,"family_label":"Governance Changes","details":[{"label":"Change","value":"charter amendment"},{"label":"Effective","value":"2025-08-08"}],"fact_type":"governance_change"}],"license":"Source filings: public domain (SEC EDGAR). Summaries (headline + bullets): CC-BY-4.0; attribute https://secwatch.observer"}