under the CRW SPA. Effective February 4, 2022, the Company registered the resale of the shares of common stock issuable upon conversion of the Series A Preferred Stock on a Form S-3. Also on February 26, 2021, the Company entered into a letter agreement with CRW, granting CRW the right to designate one individual for election or appointment to the Board and Board observer rights. Under the letter agreement, for as long as CRW has the right to designate a Board member, if the Company, directly or indirectly, plans to issue, sell or grant any securities or options to purchase any of its securities, CRW has a right to purchase its pro rata portion of such securities, based on the number of shares of Series A Preferred Stock beneficially held by CRW on the applicable date on an as-converted-to-common-stock basis divided by the total number of shares of common stock outstanding on such date on an as-converted, fully-diluted basis (taking into account all outstanding securities of the Company regardless of whether the holders of such securities have the right to convert or exercise such securities for common stock at the time of determination). Further, under the letter agreement, the Company paid CRW Capital, the sole manager of CRW and a holder of a carried interest in CRW, a monitoring fee equal to $125,000 in 2021 and total monitoring fees of $25,000 as of September 30, 2022. Mr. Rubin is a manager and 50% owner of CRW Capital, and he shares voting and disposition power over the shares of Series A Preferred Stock held by CRW.
On December 7, 2021, the Company entered into a Securities Purchase Agreement with the Rubin Trust pursuant to which the Company issued a Convertible Note in the aggregate principal amount of $100,000 to the Rubin Trust for $98,000 in cash. The Convertible Note bears interest at 13% per year payable quarterly commencing March 31, 2022 in cash for the amount equal to the amount payable on such date as if the Convertible Note was subject to an annual interest rate of 9% with the remainder of the accrued interest payable as an increase to the principal amount of the Note. As of September 30, 2022, the Company has paid $7,430 of cash interest and no principal to the Rubin Trust under this Convertible Note. In addition, as of September 30, 2022, the principal amount outstanding under this Convertible Note is $103,302 as a result of accrued interest added to the principal amount. Mr. Rubin is the majority owner of the Rubin Trust and a beneficial owner of CRW. In October 2022, the Board appointed Mr. Rubin as a director to fill a vacancy on the Board.
Transactions with Entities Affiliated with Brian Ruden
The Company has participated in several transactions involving entities owned or affiliated with Brian Ruden, one of its former directors as of October 2022, a beneficial owner of more than 5% of the Company’s common stock, and a beneficial owner of more than 5% of the Series A Preferred Stock.
Between December 17, 2020 and March 2, 2021, the Company’s wholly-owned subsidiary SBUD LLC acquired the assets of a number of Star Buds retail dispensaries (collectively, “the Star Buds assets”). The Company previously reported the terms of the applicable purchase agreements and related amendments in the Company’s Current Reports on Form 8-K filed June 8, 2020, September 21, 2020, December 22, 2020, and March 8, 2021.
The aggregate purchase price for the Star Buds assets was $118,000,000, paid as follows: (i) $44,250,000 in cash at the applicable closings, (ii) $44,250,000 in deferred cash, earning simple interest at a rate of 12% per year, also referred to in this proxy statement as “seller note(s),” (iii) 29,506 shares of Series A Preferred Stock, of which 25,078 shares were issued at the applicable closings and 4,428 shares were held in escrow. Of the 4,428 shares held in escrow, 3,484 shares were released post-closing to the applicable sellers and 944 shares remain in escrow as of the Record Date. In addition, the Company issued warrants to purchase an aggregate of 5,531,250 shares of common stock to the sellers at an exercise price of $1.20 per share. The Company has not paid any principal and has paid an aggregate of $8,320,887 of interest on the seller notes as of September 30, 2022.
Mr. Ruden’s interest in the aggregate purchase price for the Star Buds assets is as follows: (i) $13,727,490 in cash at the applicable closings, (ii) $13,727,490 in seller notes, and (iii) 9,151 shares of Series A Preferred Stock, of which 7,778 shares were issued at the applicable closings and 1,373 shares were held in escrow for release post-closing to either Mr. Ruden or the Company depending on post-closing adjustments to the purchase price. In addition, the Company issued warrants to purchase an aggregate of 1,715,936 shares of common stock to Mr. Ruden. The Company has paid Mr. Ruden an aggregate of $2,577,212 in interest on his seller notes as of September 30, 2022.
Mr. Ruden was a partial owner of a majority of the Star Buds companies that sold assets to SBUD, LLC. Mr. Ruden owned 50% of Colorado Health Consultants LLC, 50% of Starbuds Pueblo LLC, 50% of Starbuds Alameda LLC, 47.5% of Starbuds Aurora LLC, 46% of SB Arapahoe LLC, 36% of Starbuds Commerce City LLC, 30% of Starbuds Louisville