Sec Form 4 Filing - Kennedy Michael W @ RumbleOn, Inc. - 2023-12-13

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Kennedy Michael W 2. Issuer Name and Ticker or Trading Symbol RumbleOn, Inc. [ RMBL] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Executive Officer (Last) (First) (Middle) C/O RUMBLEON, INC., 901 W. WALNUT HILL LANE, SUITE 110A 3. Date of Earliest Transaction (MM/DD/YY) 12/13/2023 (Street) IRVING, TX75038 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Stock options (Right to purchase) $ 5.85 12/13/2023 A 825,000 ( 1 ) 11/01/2033 Class B Common Stock 825,000 $ 0 825,000 ( 1 ) D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Kennedy Michael W C/O RUMBLEON, INC. 901 W. WALNUT HILL LANE, SUITE 110A IRVING, TX75038 X Chief Executive Officer Signatures /s/Mathew W. Grynwald, Attorney-in-fact for Michael W. Kennedy 12/15/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )These options vest when the minimum closing price of RMBL common stock remains at or above the minimum closing price for at least 30 consecutive trading days ("Target"), subject to his continuous employment and the other terms of the grant. Vesting at each applicable Target is as follows: 125,000 at $12; 175,000 at $17; 200,000 at $22; 225,000 at $35; and 100,000 at $40. The award was granted outside of the Company's shareholder-approved stock incentive plan as an inducement to Mr. Kennedy's entry into employment and approved by the Compensation Committee of the Board of Directors, in accordance with Nasdaq Listing Rule 5635(c)(4). Pursuant to Mr. Kennedy's employment agreement, the award was granted after the conclusion of two trading days following the completion of the Company's Rights Offering, which closed on December 8, 2023, and the exercise price per share was determined as the price of RMBL at the conclusion of trading on the day before the grant.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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