---
schema_version: "secwatch.filing_event.v1"
accession: "0001880613-25-000110"
form_type: "8-K"
ticker: "DRCT"
cik: "0001880613"
company_name: "Direct Digital Holdings, Inc."
filed_at: "2025-09-22T23:59:59+00:00"
generated_at: "2026-05-17T06:00:37.071426+00:00"
event_type: "other_material"
sentiment: "negative"
materiality_score: 0.65
calibrated_materiality_score: 0.65
confidence: "high"
source: SEC EDGAR
---

# Direct Digital sells 700k shares at ~$0.39 each to New Circle for $276k under facility

## Summary
- Sold 700,000 Class A common shares for $275,993 cash with $8,997 discount since Aug 6, 2025.
- Sales made to New Circle Principal Investments LLC under previously disclosed Equity Reserve Facility.
- Filing triggered because aggregate shares sold exceeded 5% of outstanding shares as of Aug 6, 2025.
- Shares issued in reliance on Section 4(a)(2) accredited investor exemption.
- Implies significant dilution at approximately $0.394 per share, indicating need for capital.

## SEC filing metadata
- accession: 0001880613-25-000110
- form_type: 8-K
- ticker: DRCT
- cik: 0001880613
- company_name: Direct Digital Holdings, Inc.
- filed_at: 2025-09-22T23:59:59+00:00
- event_type: other_material
- sentiment: negative
- materiality_score: 0.65
- calibrated_materiality_score: 0.65
- confidence: high
- sec_items: 3.02
- EDGAR index: https://www.sec.gov/Archives/edgar/data/1880613/000188061325000110/0001880613-25-000110-index.htm
- EDGAR primary document: https://www.sec.gov/Archives/edgar/data/1880613/000188061325000110/drct-20250916.htm

## Machine-readable alternates
- HTML: https://secwatch.observer/filing/0001880613-25-000110
- JSON: https://secwatch.observer/filing/0001880613-25-000110.json
- Plain text: https://secwatch.observer/filing/0001880613-25-000110.txt

## Key facts
- Equity Issuances
  Direct Digital Holdings, Inc. issued 700,000 shares of common stock to New Circle Principal Investments LLC for an aggregate of $275,993 in cash consideration after a total discount of $8,997.
  - Security: common stock
  - Shares: 700,000 shares
  - Purchaser: New Circle Principal Investments LLC
  - Consideration: an aggregate of $275,993 in cash consideration after a total discount of $8,997
  source text: Since August 6, 2025, the end of the period covered by the most recent Report filed on any of Forms 8-K, 10-K or 10-Q under this Item 3.02 by Direct Digital Holdings, Inc. (“ Company ”), through September 16, 2025 , the Company sold 700,000 shares of its Class A Common Stock, par value $0.001 per share (the “ Class A Common Stock ”) for an aggregate of $275,993 in cash consideration after a total discount of $8,997. This Current Report on Form 8-K is being filed because the aggregate number of shares of Class A Common Stock sold in unregistered transactions during the foregoing period exceeded five percent (5%) of the total number of such shares issued and outstanding as of August 6, 2025. The sales of Class A Common Stock referred to herein were made to New Circle Principal Investments LLC (“ New Circle ”) pursuant to the previously disclosed Equity Reserve Facility under the Share Purchase Agreement (the “ Purchase Agreement ”) with New Circle.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1880613/000188061325000110/0001880613-25-000110-index.htm

This AI-assisted summary is a reading aid. Review the linked SEC EDGAR filing before relying on any specific claim.