MEZZANINE EQUITY AND STOCKHOLDERS’ EQUITY | NOTE 10: MEZZANINE EQUITY AND STOCKHOLDERS’ EQUITY Preferred Stock The Company is authorized to issue 5,000,000 shares of preferred stock, no par value, of which 1,500,000 shares were designated as Series A-1 Preferred Stock, 2,000,000 are designated as Class C Preferred Stock, and 1,491,534 are undesignated Preferred Stock. The Series A-1 Preferred Stock is convertible at any time after issuance at the option of the holder into shares of common stock at the original issue price of the Series A-1 Preferred Stock. The Series A-1 Preferred Stock was also subject to mandatory conversion provisions upon an initial public offering raising $15,000,000 or more and is not redeemable. To prevent dilution, the conversion price of the Series A-1 Preferred Stock is to be adjusted for any issuance of securities, excluding exempt securities, which change the number of shares of common stock outstanding. The Series A-1 Preferred Stockholders are entitled to equal voting rights to common stockholders on an as-converted basis and receive preference to the common stockholders upon liquidation. Except as otherwise required by law or expressly provided in the Company’s Second Amended and Restated Articles of Incorporation, as amended, each share of Class C Preferred Stock has one vote for the election of directors and on all matters submitted to a vote of shareholders of the Company. The Company is not obligated to redeem or repurchase any shares of Class C Preferred Stock. Shares of Class C Preferred Stock are not otherwise entitled to any redemption rights, or mandatory sinking fund or analogous fund provisions. On August 14, 2023, the Company filed a Certificate of Designation of Preferences, Rights and Limitations (the “Certificate of Designation”) designating 8,466 shares out of the authorized but unissued shares of its preferred stock as Series D Convertible Preferred Stock with a stated value of $1,000 per share. The holders of Series D Preferred Stock will be entitled to cumulative dividends at the rate of 8% per annum, accrued daily and compounded monthly. Dividends are payable quarterly on January 1, April 1, July 1 and October 1, beginning on the first such date after the date of the first issuance of any shares of the Series D Preferred Stock and on each date in which a holder of Series D Preferred Stock delivers a notice of conversion in cash. The shares of Series D Preferred Stock have no voting rights. Upon any liquidation, dissolution or winding-up of the Company, whether voluntary or involuntary, the then holders of the Series D Preferred Stock are entitled to receive out of the assets available for distribution to shareholders of the Company an amount equal to 100% of the stated value, plus any accrued and unpaid dividends thereon and any other fees or liquidated damages then due and owing thereon, prior and in preference to the Common Stock or any other series of preferred stock. Each share of Series D Preferred Stock is convertible (1) at any time at the option of the holder, into that number of shares of Common Stock (subject to certain beneficial ownership limitations), determined by dividing 125% of the conversion amount by $1.20 or (2) upon the Company’s common share price exceeding 300% of the conversion price. During the three months ended September 30, 2023, 104 shares of Series D Preferred Stock were converted into 108,963 shares of common stock. As of September 30, 2023 and December 31, 2022, there were 5,542 and no 2023 Third Purchase Agreements On August 15, 2023, the Company entered into a securities purchase agreement (the “Third Purchase Agreement”) with certain investors (collectively, the “Third Purchasers”). The Third Purchase Agreement provides for the sale, in a private placement, by the Company of an aggregate of (i) up to 8,471 shares of the Company’s 8% Series D Convertible Preferred Stock, stated value $1,000 per share (the “Series D Preferred Stock”), initially convertible into an aggregate of 1,760,298 shares of the Company’s common stock, no par value (the “Common Stock”) at a conversion price of $1.20 (the shares of Common Stock issuable upon conversion of the Preferred Shares, collectively, the “Conversion Shares”), and (ii) warrants (the “Warrants”), to purchase up to an aggregate of 14,110,835 shares of Common Stock (the “Warrant Shares,” and together with the Series D Preferred Stock, and Warrants, the “Securities”). For purposes of conversion into Common Stock, the Series D Preferred Stock has a stated value of $8,471,000, which represents an original issue discount of 20%. The offering is to occur in two tranches. The first closing of the transaction with gross proceeds of $4,300,002, and net proceeds of $4,225,002, after cash placement agent fees, occurred on August 15, 2023 (the “First Closing”). In addition to the cash placement agent fees, the Company issued 269 share of Series D Preferred Stock and 448,334 warrants as placement agent compensation for the August 15, 2023 offering. A total of 5,646 shares of Series D Preferred Stock were issued in the First Closing. The second closing of the transaction can only occur after the date that the Company has received shareholder approval of the transaction and the Common Stock underlying the Securities has been registered with the SEC, subject to the satisfaction of customary closing conditions (the “Second Closing”). As of September 30, 2023, the Second Closing has not yet occurred due to the low trading volume of the Company’s Common Stock. The Series D Preferred Stock is classified as a mezzanine equity and is recorded at fair value at the time of issuance. The fair value of the Series D Preferred Stock was determined to be $4,418,015 utilizing a binomial lattice model at the date of issuance. The assumptions used in the lattice model were a 1.90-year term, risk free interest rate of 4.97%, risk adjusted rate of 30.00%, and an annualized standard deviation of stock price volatility of 117.25%. Share issuance costs of $158,787 were accounted for as a reduction in the Series D Preferred Stock totaling a carrying value of $4,259,228 on the date of issuance. The value of the Series D Preferred Stock is accreted to redemption value of $4,377,422 at September 30, 2023. The Company recorded a reduction to additional paid in capital of $118,194 related to the redemption value accretion for the three and nine months ended September 30, 2023. Each Warrant has an exercise price of $1.50 per share and is exercisable upon the earlier of (i) six months from the First Closing date or (ii) the date that the Company has received shareholder approval of the transaction and the common stock underlying such Warrants has been registered with the SEC for resale (the “Initial Exercise Date”), subject to certain ownership limitations and will expire on the fifth anniversary of the Initial Exercise Date. The Company has determined that the Warrants are liability classified. The fair value of the Warrants was determined utilizing a Black-Scholes model at the dates of issuance. The assumptions used in the Black-Scholes model were a 5.00 year expected term, risk free interest rate of 4.30%, and an annualized standard deviation of stock price volatility of 111.09%. The grant date fair value of the Warrants was $9,618,708. The Warrants were remeasured at fair value using a Black-Sholes model using a 4.88 year expected term, risk free interest rate of 4.6%, and an annualized standard deviation of stock price volatility of 113.57% resulting in a fair value of $5,930,349 at September 30, 2023. The Warrants are classified as a current liability on the Condensed Consolidated Balance Sheets. As a result, the Company recorded an unrealized gain of $3,688,359 for the three and nine months ended September 30, 2023 in the Condensed Consolidated Statements of Operations. The second tranche right associated with the Second Closing was determined to be a liability classified freestanding financial instrument that requires bifurcation from the initial Series D Preferred Stock issued. The fair value of the bifurcated derivative at issuance was $2,264,629 and is remeasured at a fair value of $1,195,018 at September 30, 2023 as is recorded as a current liability on the Condensed Consolidated Balance Sheets. The fair value was measured as the difference between the forward value of the second tranche less the expected proceeds to be received. The conversion options on the Series D Preferred Stock from the First Closing were also determined to be liability classified freestanding financial instruments that require bifurcation. The fair value of the bifurcated derivative at issuance was $4,365,786 and are remeasured at a fair value of $2,239,309 at September 30, 2023 as is recorded as a long-term liability on the Condensed Consolidated Balance Sheets. The fair value was measured as the difference between the Series D Preferred Stock with and without the conversion options. Both of the derivatives are measured at fair value each reporting period with the change in fair value recorded in the Condensed Consolidated Statements of Operations. The Company recorded an unrealized gain of $3,196,088 for the three and nine months ended September 30, 2023 related to the derivatives in the Condensed Consolidated Statements of Operations. As the fair value of the Series D Preferred Stock, Warrants and derivative liabilities was greater than the cash proceeds received from the offering, the Company recorded the excess of fair value over proceeds received of $16,283,349 as financing costs for the three and nine months ended September 30, 2023 in the Condensed Consolidated Statements of Operations. Common Stock The Company has reserved a total of 1,848,241 and 378,296 shares of its common stock pursuant to the equity incentive plans (see Note 11 – Stock-Based Payments) as of September 30, 2023 and December 31, 2022, respectively. The Company has 348,241 and 278,296 stock units, options and warrants outstanding under these plans as of September 30, 2023 and December 31, 2022, respectively. The Company has no Exercise of Stock Options and Warrants A total of 223 employee options, with an exercise price of $34.24 per share, were exercised for total proceeds to the Company of $7,636 during the three months ended September 30, 2022. A total of 2,202 employee options, with exercise prices ranging from $34.20 to $50.00 per share were exercised for total proceeds to the Company of $91,095 during the nine months ended September 30, 2022. No employee options were exercised during the three and nine months ended September 30, 2023. No warrants were exercised during the nine months ended September 30, 2023. A total of 400 employee warrants, with an exercise price of $50.00 per share, were exercised for total proceeds to the Company of $20,000 during the nine months ended September 30, 2022. A total of 15,336 and 20,136 employee restricted stock units vested and were converted into common shares during the three and nine months ended September 30, 2023, respectively. A total of 460 employee restricted stock units vested and were converted into common shares during the nine months ended September 30, 2022. Offerings of Common Stock and Warrants 2023 Purchase Agreements On January 18, 2023, the Company entered into securities purchase agreements (the “Purchase Agreements”) with certain investors (collectively, the “First Purchasers”). The Purchase Agreements provide for the sale and issuance by the Company of an aggregate of (i) 3,300,000 shares (the “Shares”) of the Company’s common stock, no par value per Share (the “Common Stock”), (ii) pre-funded warrants (the “Pre-Funded Warrants”) to purchase up to 700,000 shares of common stock and (iii) warrants (the “Common Warrants” and, together with the Shares and the Pre-Funded Warrants, the “Securities”) to purchase up to 4,000,000 shares of common stock. The offering price per Share and associated Common Warrants is $3.00. The offering price per Pre-Funded Warrant and associated Common Warrant is $2.9999. The Pre-Funded Warrants are immediately exercisable subject to certain ownership limitations, have an exercise price of $0.0001 per share, and may be exercised at any time until all of the Pre-Funded Warrants are exercised in full. The Pre-Funded Warrants were exercised immediately upon issuance. Each Common Warrant has an exercise price of $3.00 per share, will be exercisable immediately upon issuance subject to certain ownership limitations and will expire on the fifth anniversary of the date on which the Common Warrants become exercisable. Both the Pre-Funded and Common Warrants contain provisions regarding settlement in the event of a fundamental transaction that calculate the fair value of the warrants using a prespecified volatility assumption that was not consistent with the input used to value the warrants at issuance which causes the warrants to be classified as liabilities. The Pre-Funded Warrants are recorded at fair value on January 18, 2023 at $1,735,941. As the Pre-Funded Warrants were immediately exercised, the fair value is recorded in equity. The Common Warrants are recorded at fair value on January 18, 2023 at $7,951,393 and are remeasured at a fair value of $2,055,008 at September 30, 2023 and are classified as a current liability on the Condensed Consolidated Balance Sheets. As a result, the Company recorded an unrealized gain of $2,194,743 and $5,896,385 for the three and nine months ended September 30, 2023, respectively, in the Condensed Consolidated Statements of Operations. The offering resulted in gross proceeds to the Company of approximately $12 million. The net proceeds to the Company from the offering were approximately $11 million, after deducting placement agent fees and other expenses. The Company used $7,500,000 of the net proceeds from the offering to repay the September 2022 Note as disclosed in Note 9 - Convertible Notes, and the remainder of the proceeds for working capital and general corporate purposes. 2023 Second Purchase Agreements On June 12, 2023, the Company entered into securities purchase agreements (the “Second Purchase Agreements”) with certain investors (collectively, the “Second Purchasers”). The Second Purchase Agreements provide for the sale and issuance by the Company of an aggregate of 1,467,648 shares (the “Shares”) of the Company’s common stock, no par value per share (the “Common Stock”), in a registered direct offering and warrants (the “Warrants” and, together with the Shares, the “Securities”) to purchase up to 2,935,296 shares of Common Stock in a concurrent private placement (the transactions contemplated by the Second Purchase Agreements are referred to herein as the “Second Offering”). The offering price per Share and associated Warrant is $1.70. Each Warrant has an exercise price of $1.75 per share, will be exercisable six months after issuance subject to certain ownership limitations and will expire on the fifth anniversary of the date on which the Warrants become exercisable. The Second Offering resulted in gross proceeds to the Company of approximately $2.5 million. The net proceeds to the Company from the Second Offering were approximately $2.3 million, after deducting placement agent fees and expenses and offering expenses payable by the Company. The Company used $250,000 of the net proceeds from the offering to partially repay the Note payable - related party, and the remainder of the proceeds for working capital and general corporate purposes. The Company paid the Placement Agent a cash fee equal to $275,000 which was 5.0% of the aggregate purchase price paid by all Second Purchasers in connection with the sale of the Securities, and warrants to purchase a number of shares of Common Stock equal to 5% of the Shares (the “Placement Agent Warrants”). The Company issued 73,529 Placement Agent Warrants. The Placement Agent Warrants have a five-year term, and are exercisable beginning six months after the closing of the Second Offering at a price of $1.87 per share. The Company recorded the aggregate placement agent fees as financing costs in the Condensed Consolidated Statements of Operations. The Warrants issued to the Second Purchasers are recorded at fair value on June 12, 2023 at $3,906,366 and are remeasured at a fair value of $1,842,282 at September 30, 2023 and are classified as a current liability on the Condensed Consolidated Balance Sheets. As the fair value of the Warrants was greater than the cash proceeds received from the offering, the Company recorded the excess of warrant fair value over proceeds received of $1,404,374 as financing costs. The 1,467,648 common shares issued in the offering had a fair value of $2,362,914. The fair value of the common shares issued were recorded as additional financing costs in the transaction because the aggregate fair value of the liability classified warrants and the common shares issued exceeded the offering proceeds. The Placement Agent Warrants are recorded at fair value on June 12, 2023 at $95,740 and are remeasured at a fair value of $44,410 at September 30, 2023 and are also classified as a current liability on the Condensed Consolidated Balance Sheets. As a result, the Company recorded an unrealized gain of $1,686,806 and $2,108,424 for the three and nine months ended September 30, 2023 for the Warrants and Placement Agent Warrants in the Condensed Consolidated Statements of Operations. 2022 Offerings On January 14, 2022, the Company entered into an Equity Distribution Agreement (the “Sales Agreement”) with Canaccord, under which the Company may offer and sell, from time to time, through or to Canaccord, as sales agent up to $100,000,000 of its common stock. The Company intends to use the net proceeds of the sales pursuant to the Sales Agreement primarily for working capital and general corporate purposes. The Company issued and sold 188,664 shares of common stock during the three months ended September 30, 2022, in connection with the Sales Agreement at per share prices between $28.80 and $67.00, resulting in net proceeds to the Company of $10,177,356 after subtracting offering expenses. The Company issued and sold 391,985 shares of common stock during the nine months ended September 30, 2022, in connection with the Sales Agreement at per share prices between $28.80 and $143.60, resulting in net proceeds to the Company of $26,493,094 after subtracting offering expenses. There were no |