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SCHEDULE 13D/A 0000898860 XXXXXXXX LIVE 26 Common Stock, par value $0.0005 per share 08/19/2025 false 0001460329 34380C201 Fluent, Inc. 300 Vesey Street, 9th Floor New York NY 10282 Daniel Barsky, Esq. (646) 669-7272 300 Vesey Street, 9th Floor New York NY 10282 0000898860 N Phillip Frost, M.D. a OO N X1 8334.00 7294403.00 8334.00 7294403.00 7302737.00 N 28.3 IN (1) Frost Gamma Investments Trust ("Gamma Trust") beneficially owns 7,294,403 shares of common stock, which includes 66,667 shares of the Issuer's common stock underlying the convertible subordinated promissory note entered into pursuant to that certain securities purchase agreement, dated August 19, 2024 (the "Convertible Note"), 909,297 shares of common stock underlying warrants issued on May 19, 2025, and 571,429 shares of common stock underlying the Unregistered Pre-Funded Warrants (as defined below) on August 19, 2025. Dr. Phillip Frost is the trustee of Gamma Trust. Frost Gamma L.P. is the sole and exclusive beneficiary of Gamma Trust. Dr. Frost is one of two limited partners of Frost Gamma L.P. The general partner of Frost Gamma L.P. is Frost Gamma, Inc., and the sole shareholder of Frost Gamma, Inc. is Frost-Nevada Corporation. Dr. Frost is also the sole shareholder of Frost-Nevada Corporation. (2) Based on 24,268,299 shares of the Issuer's common stock outstanding as of August 18, 2025 (as reported in the Issuer's Form 10-Q filed with the Securities and Exchange Commission on August 19, 2025). Y Frost Gamma Investments Trust a OO N FL 0.00 7294403.00 0.00 7294403.00 7294403.00 N 28.3 OO (1) Gamma Trust beneficially owns 7,294,403 shares of common stock, which includes 66,667 shares of the Issuer's common stock underlying the Convertible Note and 909,297 shares of common stock underlying warrants issued on May 19, 2025, and 571,429 shares of common stock underlying the Unregistered Pre-Funded Warrants on August 19, 2025. Dr. Phillip Frost is the trustee of Gamma Trust. Frost Gamma L.P. is the sole and exclusive beneficiary of Gamma Trust. Dr. Frost is one of two limited partners of Frost Gamma L.P. The general partner of Frost Gamma L.P. is Frost Gamma, Inc., and the sole shareholder of Frost Gamma, Inc. is Frost-Nevada Corporation. Dr. Frost is also the sole shareholder of Frost-Nevada Corporation. (2) Based on 24,268,299 shares of the Company's common stock outstanding as of August 18, 2025 (as reported in the Company's Form 10-Q filed with the Securities and Exchange Commission on August 19, 2025). Common Stock, par value $0.0005 per share Fluent, Inc. 300 Vesey Street, 9th Floor New York NY 10282 This Schedule 13D is filed by the Reporting Person with respect to shares of common stock, par value $0.0005 per share, of Fluent, Inc., a Delaware corporation (the "Issuer" or the "Company"), formerly known as Cogint, Inc., formerly known as IDI, Inc., the successor to Tiger Media, Inc., SearchMedia Holdings Limited, Ideation Acquisition Corp. and ID Arizona Corp. The principal executive offices of the Issuer are located at 300 Vesey Street, 9th Floor, New York, New York 10282. EXPLANATORY NOTE This Amendment No. 26 (the "Amendment") amends and supplements the statement on Schedule 13D filed on December 6, 2007, as amended by Amendment No. 1 to the Schedule 13D filed on October 15, 2008, Amendment No. 2 to the Schedule 13D filed on April 13, 2009, Amendment No. 3 to the Schedule 13D filed on May 1, 2009, Amendment No. 4 to the Schedule 13D filed on July 14, 2009, Amendment No. 5 to the Schedule 13D filed on December 24, 2009, Amendment No. 6 to the Schedule 13D filed on November 22, 2011, Amendment No. 7 to the Schedule 13D filed on July 20, 2012, Amendment No. 8 to the Schedule 13D filed on August 23, 2012, Amendment No. 9 to the Schedule 13D filed on January 17, 2013, Amendment No. 10 to the Schedule 13D filed on July 12, 2013, Amendment No. 11 to the Schedule 13D filed on February 14, 2014, Amendment No. 12 to the Schedule 13D filed on April 6, 2015, Amendment No. 13 to the Schedule 13D filed on January 20, 2016, Amendment No. 14 to the Schedule 13D filed on March 29, 2016, Amendment No. 15 to the Schedule 13D filed on May 18, 2016, Amendment No. 16 to the Schedule 13D filed on July 21, 2016, Amendment No. 17 to the Schedule 13D filed on December 28, 2016, Amendment No. 18 to the Schedule 13D filed on December 22, 2017, Amendment No. 19 to the Schedule 13D filed on April 6, 2018, Amendment No. 20 to the Schedule 13D filed on February 14, 2019, Amendment No. 21 to the Schedule 13D filed on September 25, 2023, Amendment No. 22 filed on May 20, 2024, Amendment No. 23 filed on August 26, 2024, Amendment No. 24 filed on April 2, 2025 and Amendment No. 25 filed on May 23, 2025 (together the "Original Schedule 13D"), by Phillip Frost, M.D. ("Frost") and Frost Gamma Investments Trust ("Gamma Trust") (collectively, the "Reporting Person"). No material change. No material change. No material change. No material change. No material change. No material change. Item 3 is hereby amended and restated to read as follows. The information set forth or incorporated under the heading "Explanatory Note" and in Items 4 and 5 is incorporated by reference in its entirety into this Item 3. The source of funds used by the Reporting Person for the acquisition of securities of the Issuer reported herein is the working capital of Gamma Trust. Item 4 is hereby amended and restated to read as follows. On August 19, 2025, Gamma Trust entered into a securities purchase agreement (the "Purchase Agreement") with the Company, pursuant to which Gamma Trust subscribed for $1,000,000 aggregate amount of (i) pre-funded warrants (the "Unregistered Pre-Funded Warrants") to purchase shares of common stock of the Company at a purchase price of $1.75 per Unregistered Pre-Funded Warrant and (ii) warrants (the "Warrants") to purchase shares of common stock of the Company with an exercise price of $2.21 per share of common stock. The aggregate exercise price of the Unregistered Pre-Funded Warrants (other than the nominal exercise price of $0.0005 per Unregistered Pre-Funded Warrant) was pre-funded. The Warrants are exercisable at any time on or after the date that is six months and one day following the date of issuance for a period of five years from the date of initial exercisability. In connection with the Purchase Agreement, the Reporting Person and the Company entered into a Support Agreement with the Issuer pursuant to which the Reporting Person agreed to vote shares of the Issuer's common stock beneficially owned by him in favor of certain actions subject to Stockholder Approval (as defined in the Support Agreement) at any meeting of stockholders of the Issuer and to vote against or decline to consent to any proposal or any other corporate action or agreement that would result in a breach by the Issuer of the Purchase Agreement or impede, delay or otherwise adversely affect the consummation of the transactions contemplated by the Purchase Agreement or any similar agreements entered into by the Issuer and the stockholders a party thereto in connection with the consummation of the transactions contemplated by the Purchase Agreement. Furthermore, in connection with the transactions described above, on August 19, 2025, Gamma Trust entered into a registration rights agreement (the "Registration Rights Agreement") with the Company, which provides that the Company is required to file a registration statement covering the resale of certain Registrable Securities (as defined in the Registration Rights Agreement). The closing of the sales of the Unregistered Pre-funded Warrants and Warrants under the Purchase Agreement occurred on August 19, 2025. The foregoing descriptions of the Unregistered Pre-Funded Warrant, Warrant, Purchase Agreement, Support Agreement and Registration Rights Agreement are not complete but are qualified in their entirety by reference to the full text of the form of the Unregistered Pre-Funded Warrant, Warrant, Purchase Agreement, Support Agreement and Registration Rights Agreement, copies of which are attached hereto as Exhibits 99.1, 99.2, 99.3, 99.4 and 99.5, respectively, and are incorporated by reference herein. The Reporting Person is the beneficial owner of 7,302,737 shares of common stock of the Issuer, which includes 66,667 shares of the Issuer's common stock underlying the Convertible Note and 909,297 shares of common stock underlying warrants issued on May 19, 2025, and 571,429 shares of common stock underlying of the Unregistered Pre-Funded Warrants on August 19, 2025, representing 28.3% of the Issuer's common stock. The percentage of beneficial ownership is based upon 24,268,299 shares of the Company's common stock outstanding as of August 18, 2025 (as reported in the Company's Form 10-Q filed with the Securities and Exchange Commission on August 19, 2025). The information contained on the cover page to this Amendment is incorporated herein by reference. Transactions in the Issuer's securities effected by the Reporting Person during the past sixty days: The information set forth or incorporated under Item 4 is incorporated by reference in its entirety into this Item 5. Not applicable. Not applicable. Item 6 of the Schedule 13D is amended by adding the following paragraph: The description in Item 4 and the agreements incorporated therein by reference and set forth as an exhibit hereto is incorporated herein by reference in answer to this Item 6. Exhibit 99.1 Form of Pre-Funded Warrant dated August 19, 2025 (incorporated by reference to Exhibit 4.3 on the Issuer's Form 10-Q filed on August 19, 2025). https://www.sec.gov/Archives/edgar/data/1460329/000143774925027383/ex_854690.htm Exhibit 99.2 Form of Common Stock Warrant dated August 19, 2025 (incorporated by reference to Exhibit 4.4 on the Issuer's Form 10-Q filed on August 19, 2025). https://www.sec.gov/Archives/edgar/data/1460329/000143774925027383/ex_854691.htm Exhibit 99.3 Form of Securities Purchase Agreement by and between Fluent Inc. and the purchaser parties thereto (incorporated by reference to Exhibit 10.7 on the Issuer's Form 10-Q filed on August 19, 2025). https://www.sec.gov/Archives/edgar/data/1460329/000143774925027383/ex_854692.htm Exhibit 99.4 Form of Support Agreement by and among Fluent, Inc. and the parties thereto (incorporated by reference to Exhibit 10.8 on the Issuer's Form 10-Q filed on August 19, 2025). https://www.sec.gov/Archives/edgar/data/1460329/000143774925027383/ex_854693.htm Exhibit 99.5 Form of Registration Rights Agreement, dated as of August 19, 2025 by and among Fluent, Inc. and the purchasers parties thereto (incorporated by reference to Exhibit 10.9 on the Issuer's Form 10-Q filed on August 19, 2025). https://www.sec.gov/Archives/edgar/data/1460329/000143774925027383/ex_854694.htm Exhibit 99.6 Joint Filing Agreement. Phillip Frost, M.D. /s/ Phillip Frost, M.D. Phillip Frost, M.D., individually 08/26/2025 Frost Gamma Investments Trust /s/ Phillip Frost, M.D. Phillip Frost, M.D., Trustee 08/26/2025