Shareholders' Equity and Share-based Payments | STOCKHOLDERS’ EQUITY Authorized Shares The Company has 200,000,000 authorized shares of common stock and 10,000,000 authorized shares of preferred stock, each with a par value of $0.0001 per share. Sale of Securities On June 4, 2020, the Company entered into an ATM Sales Agreement (the “2020 Sales Agreement”) with National Securities Corporation, as sales agent (“National Securities”), pursuant to which the Company could offer and sell, from time to time, through National Securities, shares of the Company's common stock, by any method deemed to be an “at the market offering” (“ATM Offering”). On June 12, 2020, the Company entered into an amendment to the 2020 Sales Agreement to increase the amount of common stock that could be offered and sold in the ATM Offering to $40 million in the aggregate. On January 25, 2021, the Company entered into a new ATM Sales Agreement (the “January 2021 Sales Agreement”) with National Securities, pursuant to which the Company may offer and sell, from time to time, through National Securities, up to $35 million shares of its common stock, by any method deemed to be an ATM Offering. During the nine months ended September 30, 2021, the Company sold 11,186,084 shares at an average price of $4.16 per share for total gross proceeds of $46,544,688 pursuant to the 2020 Sales Agreement and January 2021 Sales Agreement with National Securities. As of September 30, 2021, the Company had sold a total of 26,005,824 shares at an average price of $2.88 per share for total gross proceeds of $74,999,784 pursuant to the 2020 Sales Agreement and January 2021 Sales Agreement with National Securities. The 2020 Sales Agreement and January 2021 Sales Agreement were terminated following the sale of all shares of common stock available to be sold thereunder. On June 21, 2021, the Company entered into a third ATM Sales Agreement (the “June 2021 Sales Agreement”) with National Securities Corporation, as sales agent, pursuant to which the Company could offer and sell, from time to time, through National Securities, up to $100 million of shares of the Company’s common stock by any method deemed to be an ATM Offering. No sales have been made under this agreement as of September 30, 2021. Equity Incentive Plans In May 2011, the Company’s Board of Directors (the “Board”) adopted the 2011 Equity Incentive Plan of IZEA Worldwide, Inc. (as amended, the “May 2011 Plan”). The stockholders approved an amendment and restatement of the Company’s May 2011 Plan at its 2020 Annual Meeting of Stockholders held on December 18, 2020, to allow the Company to award restricted stock, restricted stock units and stock options covering up to 7,500,000 shares of common stock as incentive compensation for its officers, employees, consultants, and advisors, including its non-employee directors. Shares of the Company’s common stock that are withheld (or not issued) to cover the purchase price of an option or any required tax withholding obligation will again be available for issuance under the May 2011 Plan. As of September 30, 2021, the Company had 3,602,509 remaining shares of common stock available for issuance pursuant to future grants under the May 2011 Plan. In August 2011, the Company adopted the 2011 B Equity Incentive Plan (the “August 2011 Plan”) reserving 4,375 shares of common stock for issuance under the August 2011 Plan. No additional awards may be granted under the August 2011 Plan following the tenth anniversary of its effective date, but awards theretofore granted may extend beyond that date. Restricted Stock Under both the May 2011 Plan and the August 2011 Plan (together, the “2011 Equity Incentive Plans”), the Board determines the terms and conditions of each restricted stock issuance, including any future vesting restrictions. On January 31, 2020, the Company issued its five independent directors a total of 390,625 shares of restricted common stock initially valued at $125,000 for their annual service as directors of the Company. The stock vested in equal monthly installments from January through December 2020. During the nine months ended September 30, 2021, the Company issued its six independent directors a total of 30,324 shares of restricted common stock initially valued at $147,329 for their annual service as directors of the Company. The stock vests in equal monthly installments from January through December 2021. The following table contains summarized information about restricted stock issued during the year ended December 31, 2020 and the nine months ended September 30, 2021: Restricted Stock Activity Common Shares Weighted Average Weighted Average Nonvested at December 31, 2019 31,282 $ 2.15 1.9 Granted 390,625 0.32 Vested (408,241) 0.39 Forfeited — Nonvested at December 31, 2020 13,666 $ 2.28 1.4 Granted 30,324 4.86 Vested (30,475) 4.24 Forfeited — 0 Nonvested at September 30, 2021 13,515 $ 3.65 0.5 Although restricted stock is issued upon the grant of an award, the Company excludes restricted stock from the computations within the financial statements of total shares outstanding and basic earnings per share until the restricted stock vests. Expense recognized on restricted stock issued to non-employees for services was $37,544 and $31,250 for the three months ended September 30, 2021 and 2020, respectively, and $109,784 and $93,749 during the nine months ended September 30, 2021 and 2020, respectively. Expense recognized on restricted stock issued to employees was $6,364 and $6,507 for the three months ended September 30, 2021 and 2020, respectively, and $19,371 and $27,175 during the nine months ended September 30, 2021 and 2020, respectively. On September 30, 2021, the fair value of the Company’s common stock was approximately $1.92 per share and the intrinsic value on the non-vested restricted stock was $25,949. Future compensation expense related to issued, but non-vested, restricted stock awards as of September 30, 2021 is $49,376. This value is estimated to be recognized over the weighted-average vesting period of approximately six months. Restricted Stock Units The Board determines the terms and conditions of each restricted stock unit award issued under the May 2011 Plan. The Company issued 84,994 restricted stock units on January 3, 2020 to Mr. Ryan Schram, its Chief Operating Officer, under the terms of his employment agreement. The restricted stock units were initially valued at $23,739 and vest in equal monthly installments over 48 months from issuance. The Company also issued 100,000 restricted stock units on January 3, 2020 to Mr. Schram as additional incentive compensation. The restricted stock units were initially valued at $27,930 and vest 12 months from issuance. During the twelve months ended December 31, 2020, the Company issued a total of 580,099 restricted stock units initially valued at $215,936 to non-executive employees as additional incentive compensation. The restricted stock units vest 12 months from issuance. During the twelve months ended December 31, 2020, the Company issued Mr. Edward Murphy, its Chief Executive Officer, 123,228 restricted stock units valued at $61,790 for bonuses owed under the terms of his amended employment agreement. The restricted stock units vest in equal monthly installments over 36 months from issuance. During the twelve months ended December 31, 2020, the Company issued Mr. Schram 41,824 restricted stock units initially valued at $14,052 for bonuses owed under the terms of his employment agreement. The restricted stock units vest in equal monthly installments over 48 months from issuance. During the nine months ended September 30, 2021 the Company issued Mr. Murphy 100,000 restricted stock units valued at $394,000 as a one-time bonus. The restricted stock units vest in equal monthly installments over 10 months from issuance. During the nine months ended September 30, 2021 the Company issued Mr. Peter Biere, its Chief Financial Officer, 4,286 restricted stock units valued at $8,101 for bonuses owed under the terms of his employment agreement. The restricted stock units vest in equal monthly installments over 36 months from issuance. During the nine months ended September 30, 2021 the Company issued an aggregate of 30,514 restricted stock units valued at $73,715 to 37 non-executive employees related to performance bonuses. The restricted stock units vest 12 months from issuance. The following table contains summarized information about restricted stock units during the year ended December 31, 2020 and the nine months ended September 30, 2021: Restricted Stock Units Activity Common Shares Weighted Average Weighted Average Nonvested at December 31, 2019 366,812 $ 0.42 3.2 Granted 930,145 0.37 Vested (172,441) 0.41 Forfeited (154,167) 0.30 Nonvested at December 31, 2020 970,349 $ 0.39 1.2 Granted 134,800 3.53 Vested (673,201) 0.73 Forfeited (3,336) 1.46 Nonvested at September 30, 2021 428,612 $ 0.84 1.4 During the three and nine months ended September 30, 2021, the Company withheld 18,398 and 200,942 shares of common stock valued at $40,682 and $437,644, respectively, to cover statutory employee withholding taxes due upon the delivery of common stock for the vested restricted stock units. Expense recognized on restricted stock units issued to employees was $147,044 and $44,636 for the three months ended September 30, 2021 and 2020, respectively, and $427,287 and $159,720 during the nine months ended September 30, 2021 and 2020, respectively. On September 30, 2021, the fair value of the Company’s common stock was approximately $1.92 per share and the intrinsic value on the non-vested restricted units was $822,935. Future compensation related to the non-vested restricted stock units as of September 30, 2021 is $278,669 and it is estimated to be recognized over the weighted-average vesting period of approximately 1.4 years. Stock Options Under the 2011 Equity Incentive Plans, the Board determines the exercise price to be paid for the stock option shares, the period within which each stock option may be exercised, and the terms and conditions of each stock option. The exercise price of incentive and non-qualified stock options may not be less than 100% of the fair market value per share of the Company’s common stock on the grant date. If an individual owns stock representing more than 10% of the outstanding shares, the exercise price of each share of an incentive stock option must be equal to or exceed 110% of fair market value. Unless otherwise determined by the Board at the time of grant, the exercise price is set at the fair market value of the Company’s common stock on the grant date (or the last trading day prior to the grant date, if it is awarded on a non-trading day). Additionally, the term is set at ten one three A summary of option activity under the 2011 Equity Incentive Plans during the year ended December 31, 2020 and the nine months ended September 30, 2021, is presented below: Options Outstanding Common Shares Weighted Average Weighted Average Outstanding at December 31, 2019 1,357,837 $ 3.24 7.2 Granted 411,350 0.69 Exercised (369) 1.00 Expired — — Forfeited (56,012) 5.08 Outstanding at December 31, 2020 1,712,806 $ 2.56 6.9 Granted 266,594 2.64 Exercised (161,270) 0.34 Expired — — Forfeited (17,021) 3.50 Outstanding at September 30, 2021 1,801,109 $ 2.77 6.2 Exercisable at September 30, 2021 1,079,065 $ 3.68 5.2 During the nine months ended September 30, 2021, 161,270 options were exercised for gross proceeds of $54,105. The intrinsic value on exercised options was $454,123. There were 369 options exercised during the nine months ended September 30, 2020. The fair value of the Company's common stock on September 30, 2021 was approximately $1.92 per share and the intrinsic value on outstanding options as of September 30, 2021 was $971,773. The intrinsic value on exercisable options as of September 30, 2021 was $412,605. A summary of the nonvested stock option activity under the 2011 Equity Incentive Plans during the year ended December 31, 2020 and the nine months ended September 30, 2021, is presented below: Nonvested Options Common Shares Weighted Average Weighted Average Nonvested at December 31, 2019 600,779 $ 0.64 3.0 Granted 411,350 0.56 Vested (283,766) 0.72 Forfeited (12,877) 0.88 Nonvested at December 31, 2020 715,486 $ 0.56 2.5 Granted 266,594 2.81 Vested (251,647) 0.65 Forfeited (8,389) 0.92 Nonvested at September 30, 2021 722,044 $ 0.93 2.4 There were outstanding options to purchase 1,801,109 shares with a weighted average exercise price of $2.77 per share, of which options to purchase 1,079,065 shares were exercisable with a weighted average exercise price of $3.68 per share as of September 30, 2021. Expense recognized on stock options issued to employees during the three months ended September 30, 2021 and 2020 was $73,739 and $55,202, respectively. Expense recognized on stock options issued to employees during the nine months ended September 30, 2021 and 2020 was $182,137 and $166,955, respectively. Future compensation related to non-vested awards as of September 30, 2021 is $710,661, and it is estimated to be recognized over the weighted-average vesting period of approximately 2.4 years. The following table shows the number of stock options granted under the Company’s 2011 Equity Incentive Plans and the assumptions used to determine the fair value of those options using a Black-Scholes option-pricing model during the nine months ended September 30, 2021 and 2020: Period Ended Total Stock Weighted-Average Exercise Price Weighted-Average Expected Term Weighted-Average Volatility Weighted-Average Risk-Free Interest Rate Expected Dividends Weighted-Average September 30, 2020 410,215 $0.69 6 years 108.56% 0.46% — $0.56 September 30, 2021 266,594 $2.64 6 years 120.14% 0.94% — $2.81 Employee Stock Purchase Plan The amended and restated IZEA Worldwide, Inc. 2014 Employee Stock Purchase Plan (the “ESPP”), provides for the issuance of up to 500,000 shares of the Company’s common stock to employees regularly employed by the Company for 90 days or more on a full-time or part-time basis (20 hours or more per week on a regular schedule). The ESPP operates in successive six During the nine months ended September 30, 2021 and 2020, employees paid $5,222 to purchase 3,376 shares of common stock and $1,944 to purchase 9,665 shares of common stock, respectively. Expense recognized on the options to purchase shares under the ESPP was $1,892 and $2,223 during the three months ended September 30, 2021 and 2020, respectively, and $4,424 and $2,996 during the nine months ended September 30, 2021 and 2020, respectively. As of September 30, 2021, the Company had 392,237 remaining shares of common stock available for future issuances under the ESPP. Summary Stock-Based Compensation Stock-based compensation cost related to all awards granted to employees is measured at the grant date based on the fair value of the award and is recognized as an expense over the employee’s requisite service period utilizing the weighted-average forfeiture rates disclosed in Note 1. Total stock-based compensation expense recognized on restricted stock, restricted stock units, stock options, and employee stock purchase plan issuances during the three and nine months ended September 30, 2021 and 2020 was recorded in the Company’s consolidated statements of operations and comprehensive loss as follows: Three Months Ended Nine Months Ended September 30, September 30, September 30, September 30, Cost of revenue $ 1,898 $ 9,709 $ 5,315 $ 24,278 Sales and marketing 5,342 3,324 16,090 42,967 General and administrative 221,799 95,535 611,814 289,601 Total stock-based compensation $ 229,039 $ 108,568 $ 633,219 $ 356,846 |