STOCKHOLDERS’ EQUITY | NOTE 8 – STOCKHOLDERS’ EQUITY The Company has authorized the issuance of up to 100,000,000 0.01 5,000,000 0.0001 5,000 1,610,000 3,385,000 On June 8, 2021, the Company filed the 2021 Shelf. Under the 2021 Shelf at the time of effectiveness, the Company had the ability to raise up to $ 150 60 58.5 59.5 32 Series A Preferred Stock As noted above, in September 2021, the Company entered into the Preferred Underwriting Agreement and the Common Underwriting Agreement with B.Riley. Pursuant to the Preferred Underwriting Agreement, the Company agreed to sell 1,400,000 3,833,334 55.3 The Series A Preferred Stock ranks senior to the Company’s common stock with respect to the payment of dividends and liquidation rights. The Company will pay cumulative distributions on the Series A Preferred Stock, from the date of original issuance, in the amount of $ 2.21875 8.875 25.00 Holders of the Series A Preferred Stock have no voting rights except in the case of certain dividend nonpayments. If dividends on the Series A Preferred Stock are in arrears, whether or not declared, for six or more quarterly periods, whether or not these quarterly periods are consecutive, holders of Series A Preferred Stock and holders of all other classes or series of parity preferred stock with which the holders of Series A Preferred Stock are entitled to vote together as a single class will be entitled to vote, at a special meeting called by the holders of record of at least 10 The Series A Preferred Stock is perpetual and has no maturity date. The Series A Preferred Stock will be redeemable at our option, in whole or in part, at the following redemption prices, plus any accrued and unpaid dividends up to, but not including, the date of redemption: 1) on and after October 15, 2022 and prior to October 15, 2023, at a redemption price equal to $ 25.75 25.50 25.25 25.00 25.00 Upon the occurrence of a delisting event or a change of control, each holder of Series A Preferred Stock will have the right unless we have provided or provide notice of our election to redeem the Series A Preferred Stock, to convert some or all of the shares of Series A Preferred Stock held by such holder into a number of shares of our common stock (or equivalent value of alternative consideration) per share of Series A Preferred Stock, or the “Common Stock Conversion Consideration”. In the case of a delisting event or change of control, pursuant to which shares of common stock shall be converted into cash, securities or other property or assets (the “Alternative Form Consideration”), a holder of shares of Series A Preferred Stock shall receive upon conversion of such shares of Series A Preferred Stock the kind and amount of Alternative Form Consideration which such holder would have owned or been entitled to receive upon the delisting event or change of control, had such holder held a number of shares of common stock equal to the Common Stock Conversion Consideration immediately prior to the effective time of the delisting event or change of control. Series B Convertible Preferred Stock On August 27, 2020, the Secretary of State of the State of Delaware delivered confirmation of the effective filing of the Company’s Certificate of Designations of the Series B Convertible Preferred Stock, which established 5,000 The shares of Series B Preferred Stock have a stated value of $ 1,000 3.25 13 The Preferred Dividends shall accrue and be cumulative from and after the date of issuance of any share of Series B Preferred Stock on a daily basis computed on the basis of a 365-day year and compounded quarterly. The Preferred Dividends are payable only when, as, and if declared by the Board of Directors of the Company (the “Board”) and the Company has no obligation to pay such Preferred Dividends; provided, however, if the Board determines to pay any Preferred Dividends, the Company shall pay such dividends in kind in a number of additional shares of Series B Preferred Stock (the “PIK Shares”) equal to the quotient of (i) the aggregate amount of the Preferred Dividends being paid by the Company in respect of the shares of Series B Preferred Stock held by such holder, divided by (ii) the Series B Issue Price (as defined in the Series B Designations); provided, further, that, at the election of the purchasers holding a majority of the shares of Series B Preferred Stock then outstanding, in their sole discretion, such Preferred Dividends shall be paid in cash or a combination of cash and PIK Shares. Notwithstanding the foregoing, the Preferred Dividends may be paid in cash at the election of the Company if, and only if, (a) the purchasers holding a majority of the shares of Series B Preferred Stock then outstanding consent in writing to the payment of any specific dividend in cash, or (b) at any time following the twenty-four (24) month anniversary of the Closing, (i) the prevailing volume-weighted average price (“VWAP”) of the Common Stock over the trailing ninety (90)-day period is equal to or greater than $ 15.00 40,000 The holders of Series B Preferred Stock rank senior to the Common Stock with respect to payment of dividends and rights upon liquidation and will vote together with the holders of the Common Stock on an as-converted basis, subject to beneficial ownership limitations, on each matter submitted to a vote of holders of Common Stock (whether at a meeting of stockholders or by written consent). In addition, as further described in the Series B Designations, if at least 30 If at any time following the twelve (12)-month anniversary of the Closing (a) the prevailing VWAP (as defined in the Series B Designations) of the Common Stock over the trailing ninety (90)-day period is equal to or greater than $ 15.00 3.00 40,000 plus divided by th In the event of a Forced Conversion, a holder may elect, in its sole discretion and in lieu of the Forced Conversion, to have each then-outstanding share of Series B Preferred Stock held by such holder be redeemed by the Company (a “Forced Conversion Redemption”) by delivering written notice to the Company (a “Forced Conversion Redemption Notice” and the date such Holder delivers such notice to the Corporation, a “Forced Conversion Redemption Notice Date”) prior to the Forced Conversion Date, which notice shall state (a) the number of shares of Series B Preferred Stock that are to be redeemed, (b) the date on which such Forced Conversion Redemption shall occur, which date shall be the tenth (10th) Business Day following the applicable Forced Conversion Redemption Notice Date (the “Forced Conversion Redemption Date”) and (c) the wire instructions for the payment of the applicable amount owed to such holder. Each share of Series B Preferred Stock that is the subject of a Forced Conversion Redemption shall be redeemed by the Company in cash at a price per share equal to the sum of (1) the Series B Issue Price, plus (2) any accrued but unpaid dividends on such share of Series B Preferred Stock, including the Preferred Dividends (the “Per Share Forced Conversion Redemption Price”). If a sufficient number of shares of Common Stock are not available to effect the conversion of the Series B Preferred Stock outstanding into Common Stock and the exercise of the Warrants, each holder shall have the right, in its sole and absolute discretion (in addition to and not to the exclusion of any remedy such holder may have at law or in equity), to require that the Company redeem (an “Optional Redemption”), to the fullest extent permitted by law and out of funds lawfully available therefor, all or any portion of such holder’s Series B Preferred Stock then outstanding by delivering written notice thereof. The Series B Preferred Stock contains certain Change of Control provisions that preclude permanent equity classification. Securities Purchase Agreement On August 28, 2020, the Company entered into a securities purchase agreement (the “Purchase Agreement”) with an investor (the “Investor”), to purchase from the Company an aggregate of 3,500 1,000 400 5 4.60 3,500,000 2,892,500 607,500 As a result of the Purchase Agreement, the Company recorded a deemed dividend to the holders of the Series B Preferred Stock of $ 3,500,000 3,500,000 455,000 4,565,822 Options and Warrants During the year ended December 31, 2022, the Company issued an aggregate of 90,400 90,400 During the year ended December 31, 2022, the Company issued an aggregate of 29,691 During the year ended December 31, 2022, the Company issued an aggregate of 22,000 38,500 During the year ended December 31, 2021, the Company issued an aggregate of 375,000 670,750 During the year ended December 31, 2021, the Company issued an aggregate of 873,047 During the year ended December 31, 2021, the Company issued an aggregate of 162,033 480,609 Common Stock Common Stock Transactions During the Year Ended December 31, 2022 During the year ended December 31, 2022, the Company issued an aggregate of 306,250 During the year ended December 31, 2022, the Company issued 400,000 Common Stock Transactions During the Year Ended December 31, 2021 On February 11, 2021, the Company consummated the closing of the February 2021 Offering, whereby pursuant to the February 2021 Purchase Agreement entered into by the Company and certain accredited investors on February 11, 2021 the investors purchased 608,696 0.01 23.00 14.0 13.5 As noted above, in September 2021, the Company entered into the Common Underwriting Agreement with B.Riley. Pursuant to the Common Underwriting Agreement, the Company agreed to sell to B. Riley 3,833,334 21.8 During the year ended December 31, 2021, the Company issued an aggregate of 1,347,875 During the year ended December 31, 2021, the Company sold 70,786 493,481 WorkSimpli Software Restructuring Transaction (“WSS Restructuring”) Effective January 22, 2021 (the “WSS Effective Date”), the Company consummated the WSS Restructuring. To effect the WSS Restructuring the Company’s wholly-owned subsidiary Conversion Labs PR (now “LifeMD PR”), entered into a series of membership interest exchange agreements, pursuant to which, Conversion Labs PR exchanged that certain promissory note, dated May 8, 2019 with an outstanding balance of $ 375,823 37,531 Concurrently, in furtherance of the WSS Restructuring, Conversion Labs PR entered into two Membership Interest Purchase Agreements (the “Founding Members MIPAs”) with two founding members of WSS (the “Founding Members”) whereby Conversion Labs PR purchased from the Founding Members an aggregate of 2,183 225,000 In furtherance of the WSS Restructuring, Conversion Labs PR entered into a Membership Interest Purchase Agreement with WSS, (the “CVLB PR MIPA”), pursuant to which Conversion Labs PR purchased 12,000 300,000 The CVLB PR MIPA provided that the transaction may be completed in three (3) tranches with a purchase price of $ 100,000 100,000 Following the consummation of the WSS Restructuring, Conversion Labs PR increased its ownership of WSS from 51 85.58 Concurrently with the WSS Restructuring, Conversion Labs PR entered into option agreements with Sean Fitzpatrick (the “Fitzpatrick Option Agreement”) and Varun Pathak (the “Pathak Option Agreement” together with Fitzpatrick Option Agreement the “Option Agreements”), pursuant to which Conversion Labs PR granted options to purchase membership interest units of WSS. Upon vesting, the Fitzpatrick Options and the Pathak Options provide for the potential re-purchase of up to an additional 13.25 72.98 The Fitzpatrick Option Agreement grants Sean Fitzpatrick the option to purchase 10,300 1.00 2,500,000 4,000,000 8,000,000 The Pathak Option Agreement grants Varun Pathak the option to purchase 2,100 1.00 2,500,000 4,000,000 8,000,000 WorkSimpli Software Capitalization Update On September 30, 2022, Sean Fitzpatrick and Varun Pathak exercised their options to purchase 10,300 2,100 1.00 85.58 73.64 Stock Options 2020 Equity Incentive Plan (the “2020 Plan”) On January 8, 2021, the Company approved the 2020 Plan. Approval of the 2020 Plan was included as Proposal 1 in the Company’s definitive proxy statement for its Special Meeting of Stockholders filed with the Securities and Exchange Commission on December 7, 2020. The 2020 Plan is administered by the Compensation Committee of the Board and initially provided for the issuance of up to 1,500,000 150,000 On June 24, 2021, at the Annual Meeting of Stockholders, the stockholders of the Company approved an amendment to the 2020 Plan to increase the maximum number of shares of the Company’s common stock available for issuance under the 2020 Plan by 1,500,000 3,300,000 On June 16, 2022, at the Annual Meeting of Stockholders, the stockholders of the Company approved an amendment to the 2020 Plan to increase the maximum number of shares of the Company’s common stock available for issuance under the 2020 Plan by 1,500,000 4,800,000 1,732,163 The forms of award agreements to be used in connection with awards made under the 2020 Plan to the Company’s executive officers and non-employee directors are: ● Form of Non-Qualified Option Agreement (Non-Employee Director Awards) ● Form of Non-Qualified Option Agreement (Employee Awards); and ● Form of Restricted Stock Award Agreement. Previously, the Company had granted service-based stock options and performance-based stock options separate from this plan. During the year ended December 31, 2022, the Company issued an aggregate of 369,500 3.5 4 A summary of outstanding options activity under our 2020 Plan is as follows: SCHEDULE OF OPTION ACTIVITY Options Outstanding Exercise Price per Share Weighted Average Weighted Average Balance, December 31, 2020 720,000 $ 7.21 8.81 9.76 $ 7.73 Granted 1,354,500 4.57 21.02 8.99 10.34 Exercised - Cancelled/Forfeited/Expired (11,000 ) 13.74 9.48 13.74 Balance at December 31, 2021 2,063,500 $ 4.57 21.02 8.04 $ 9.41 Granted 169,500 2.30 13.74 3.78 6.12 Exercised - Cancelled/Forfeited/Expired (448,413 ) 3.68 13.74 7.99 7.66 Balance at December 31, 2021 1,784,587 $ 2.30 21.02 6.95 $ 9.54 Exercisable at December 31, 2021 636,229 $ 4.57 21.02 8.95 $ 9.18 Exercisable at December 31, 2022 1,185,153 $ 2.30 21.02 7.64 $ 9.62 The total fair value of the options granted during the year ended December 31, 2022 was $ 919,280 0 4 135.65 741.77 0.90 3.62 5,319,512 5,566,981 5,635,180 A summary of outstanding service-based options activity (prior to the establishment of our 2020 Plan above) is as follows: SCHEDULE OF OPTION ACTIVITY Options Outstanding Exercise Price per Share Weighted Average Weighted Average Balance, December 31, 2020 2,457,400 $ 0.80 7.95 5.25 $ 2.30 Granted 490,000 3.78 19.61 6.53 11.64 Exercised (1,122,000 ) 0.80 2.00 2.22 1.38 Cancelled/Forfeited/Expired (166,667 ) 1.50 7.50 8.74 4.51 Balance at December 31, 2021 1,658,733 $ 1.00 19.61 5.85 $ 5.45 Granted 50,000 4.12 4.01 4.12 Exercised (149,400 ) 1.00 2.00 1.23 Cancelled/Forfeited/Expired (120,000 ) 1.00 4.12 3.21 3.33 Balance at December 31, 2022 1,439,333 $ 1.00 19.61 5.63 $ 6.11 Exercisable December 31, 2021 1,019,164 $ 1.00 19.61 5.21 $ 3.60 Exercisable at December 31, 2022 1,158,764 $ 1.00 19.61 5.63 $ 5.25 The total fair value of the options granted during the year ended December 31, 2022 was $ 205,995 0 4 420.16 1.37 2,126,756 2,013,749 2,566,728 59,000 29,691 90,400 A summary of outstanding performance-based options activity is as follows: SCHEDULE OF OPTION ACTIVITY Options Outstanding Exercise Price per Share Weighted Average Weighted Average Balance at December 31, 2020 1,155,000 $ 1.25 2.50 4.94 $ 1.71 Granted - Exercised (235,000 ) 2.00 0.03 2.00 Cancelled/Forfeited/Expired (385,000 ) 1.25 2.00 3.94 1.67 Balance at December 31, 2021 535,000 $ 1.25 2.50 5.59 $ 1.60 Granted 150,000 4.12 3.01 4.12 Exercised - Cancelled/Forfeited/Expired (150,000 ) 4.12 3.01 4.12 Balance at December 31, 2022 535,000 $ 1.25 2.50 4.59 $ 1.60 Exercisable December 31, 2021 100,000 $ 1.75 2.50 1.96 $ 2.01 Exercisable at December 31, 2022 470,000 $ 1.50 2.50 4.58 $ 1.61 The total fair value of the options granted during the year ended December 31, 2022 was $ 617,980 0 3.5 444.0 1.37 423,188 222,897 215,877 Restricted Stock Units (RSUs) (under 2020 Plan) A summary of outstanding RSU activity under our 2020 Plan is as follows: SCHEDULE OF WARRANT AND RESTRICTED STOCK OUTSTANDING AND EXERCISABLE RSU Outstanding Balance at December 31, 2020 - Granted 459,250 Vested (77,875 ) Forfeited (6,000 ) Balance at December 31, 2021 375,375 Granted 922,500 Vested (177,125 ) Forfeited (92,500 ) Balance at December 31, 2022 1,028,250 The total fair value of the 922,500 2,716,440 2,626,654 1,001,536 3,955,850 177,125 111,250 RSUs (outside of 2020 Plan) A summary of outstanding RSU activity (outside of our 2020 Plan) is as follows: SCHEDULE OF WARRANT AND RESTRICTED STOCK OUTSTANDING AND EXERCISABLE RSU Outstanding Balance at December 31, 2020 - Granted 620,000 Vested (20,000 ) Balance at December 31, 2021 600,000 Granted 260,000 Vested (145,000 ) Balance at December 31, 2022 715,000 The total fair value of the 260,000 743,400 1,609,257 846,600 5,155,143 145,000 Warrants A summary of outstanding and exercisable warrant activity is as follows: SCHEDULE OF WARRANT AND RESTRICTED STOCK OUTSTANDING AND EXERCISABLE Warrants Outstanding Exercise Price per Share Weighted Average Weighted Average Balance at December 31, 2020 3,550,471 $ 1.40 5.75 6.85 $ 4.56 Granted 500,000 12.00 4.67 12.00 Exercised (162,033 ) 1.75 4.75 1.83 2.97 Balance at December 31, 2021 3,888,438 $ 1.40 12.00 5.85 $ 5.59 Granted - Exercised (22,000 ) 1.75 1.75 Cancelled/Forfeited/Expired (6,800 ) 2.00 2.00 Balance at December 31, 2022 3,859,638 $ 1.40 12.00 4.89 $ 5.60 Exercisable December 31, 2021 2,621,307 $ 1.40 12.00 6.36 $ 5.98 Exercisable December 31, 2022 3,836,993 $ 1.40 12.00 4.88 $ 5.63 Total compensation expense on the above warrants for services was $ 1,629,247 2,419,896 17,981 Stock-based Compensation The total stock-based compensation expense related to common stock issued for services, service-based stock options, performance-based stock options, warrants and RSUs amounted to $ 13,734,614 12,071,659 17,330,882 |