Mezzanine Equity and Stockholders' Deficit | 13. Mezzanine Equity and Stockholders’ Deficit Convertible Redeemable Preferred Stock The authorized, issued and outstanding shares of convertible redeemable preferred stock and liquidation preferences were as follows (in thousands, except share amounts): September 30, 2022 Series Authorized Shares Issued and Outstanding Liquidation Carrying Series A 14,497,716 10,678,459 $ 10,918 $ 16,953 Series B 11,980,730 5,216,044 8,407 9,578 Series C 18,526,490 10,836,279 23,844 22,761 Series D 45,812,043 44,439,418 294,940 191,841 Series D-2 2,712,109 — — — Series D-3 5,344,476 5,344,476 50,773 49,587 Series E 23,960,873 18,987,106 72,910 51,709 Series E-1 22,286,950 22,286,925 68,465 56,609 Series E-2 23,437,500 6,784,347 7 8,356 Series E-3 17,829,563 1,244,801 1 3,622 Total 186,388,450 125,817,855 $ 530,265 $ 411,016 December 31, 2021 Series Authorized Shares Issued and Liquidation Carrying Series A 14,497,716 10,678,459 $ 10,918 $ 16,953 Series B 11,980,730 5,119,213 8,251 9,338 Series C 18,526,490 10,836,279 23,844 22,761 Series D 45,812,043 44,439,418 294,940 191,841 Series D-2 2,712,109 — — — Series D-3 5,344,476 5,344,476 50,773 49,587 Series E 23,960,873 18,987,106 74,939 51,709 Series E-1 22,286,950 22,286,925 68,465 56,609 Series E-2 23,437,500 6,784,347 7 8,356 Series E-3 17,829,563 995,924 1 3,214 Total 186,388,450 125,472,147 $ 532,138 $ 410,368 During the nine months ended September 30, 2022, 248,877 Series E-3 1:1 basis for Series E-3 1.64 per share based on the fair value as of September 30, 2022 (See Note 15 - 300,000 Series B warrants to purchase were exercised into 96,831 Series B convertible redeemable preferred stock at $ 2.47 per share based on the fair value as of the exercise date (See Note 15 - Warrants). Common Stock The issued and outstanding shares of common stock were as follows: September 30, 2022 December 31, 2021 Class B Non-Voting 285,937 285,937 Common Stock 61,204,103 57,297,091 Non-Voting 22,155,719 22,155,719 Total 83,645,759 79,738,747 During the nine months ended September 30, 2022, 176,463 common stock options were exercised and 810,967 RSUs vested in exchange for 987,430 shares of common stock. Additionally, in June 2022, 2,919,582 shares of common stock were issued to settle the outstanding contingent compensation liability associated with the put and call options structure related to the acquisition of Drivy in April 2019 (See Note 4 - Contingent Compensation). Shares of common stock reserved for future issuance are as follows (in whole shares): September 30, 2022 December 31, 2021 Convertible redeemable preferred stock 125,817,855 125,472,147 Stock options and restricted stock units outstanding 19,432,132 18,702,704 Warrants for convertible redeemable preferred stock 28,259,306 28,808,183 Warrants for common stock 374,353 354,353 Shares reserved for future award issuance 8,000,613 3,390,543 Contingent compensation put and call options — 2,919,582 Total Reserved 181,884,259 179,647,512 | 14. Mezzanine Equity and Stockholders’ Deficit Convertible Redeemable Preferred Stock The authorized, issued and outstanding shares of convertible redeemable preferred stock and liquidation preferences were as follows (in thousands, except share amounts): December 31, 2021 Series Authorized Shares Shares Issued and Liquidation Carrying Value Series A 14,497,716 10,678,459 $ 10,918 $ 16,953 Series B 11,980,730 5,119,213 8,251 9,338 Series C 18,526,490 10,836,279 23,844 22,761 Series D 45,812,043 44,439,418 294,940 191,841 Series D-2 2,712,109 — — — Series D-3 5,344,476 5,344,476 50,773 49,587 Series E 23,960,873 18,987,106 74,939 51,709 Series E-1 22,286,950 22,286,925 68,465 56,609 Series E-2 23,437,500 6,784,347 7 8,356 Series E-3 17,829,563 995,924 1 3,214 Total 186,388,450 125,472,147 $ 532,138 $ 410,368 December 31, 2020 Series Authorized Shares Issued and Liquidation Carrying Series A 14,497,716 7,702,462 $ 7,875 $ 12,093 Series B 11,980,730 4,715,258 7,600 8,582 Series C 18,526,490 10,718,119 22,834 22,508 Series D 45,812,043 44,327,922 293,150 191,328 Series D-2 2,712,109 — — — Series D-3 5,344,476 5,344,476 50,773 49,587 Series E 23,960,873 18,582,697 71,358 51,093 Series E-1 22,286,950 22,286,925 68,465 56,609 Series E-2 23,437,500 6,706,750 7 8,055 Series E-3 17,829,563 — — — Total 186,388,450 120,384,609 $ 522,062 $ 399,855 In September and October 2020, the Company received $42,200,000 from the sale of 11,072,394 shares of Series E convertible redeemable preferred stock (Series E) at $3.84 per share, net of issuance costs of $319,000. For each purchase of Series E convertible redeemable preferred stock, each investor received preferred stock warrants exercisable into Series E-2 one-to-one E-2 E-1 E-3 convertible redeemable preferred stock valued at $1.20 per share based on the fair value and treated as a warrant liability on our Consolidated Balance Sheet as of December 31, 2020 (see Note 16 — Warrants). In September 2020, in contemplation of the Series E financing, all outstanding 98,573,564 shares of convertible redeemable preferred stock (Prior Preferred) were converted into non-voting one-to-one non-voting one-to-one non-voting non-voting additional-paid-in non-voting non-voting non-voting In September 2020, the three convertible notes outstanding from June 2020 (see Note 11 — Notes Payable for further discussions) were converted into 6,982,108 shares of Series E convertible redeemable preferred stock based on a fair value of $2.96 per share, along with the issuance of 6,982,108 preferred stock warrants exercisable into series E-2 During September and October 2020, 6,706,750 Series E-2 E-2 In January, February, May, and April 2021, the Company received $1,528,000 from the sale of 404,409 shares of Series E convertible redeemable preferred stock (Series E) at $1.52 per share, net of issuance costs of $26,000. For each purchase of Series E convertible redeemable preferred stock, each investor received preferred stock warrants exercisable into Series E-2 one-to-one E-2 E-2 E-2 E-3 E-3 In January, February, and May 2021, 3,609,608 shares of non-voting one-to-one Common Stock The issued and outstanding shares of common stock were as follows: Year ended December 31, 2021 2020 Class B Non-Voting 285,937 285,937 Common Stock 57,297,091 43,294,342 Non-Voting 22,155,719 25,765,327 Total 79,738,747 69,345,606 In September 2020, the Company amended its Certificate of Incorporation. The Company is authorized to issue 572,688,450 shares, each with a par value of $0.00001 per share, of which 287,000,000 shares shall be common stock, 99,000,000 shall be Non-Voting non-voting The September 2020 amendment authorized the creation of 23,960,873 of Series E convertible redeemable preferred stock, 22,286,950 of Series E-1 E-2 E-3 In September of 2020, 3,207,974 common stock warrants were exercised for the same number of shares. During the year ended December 31, 2021, the Company settled a portion of the liability related to terminated vehicle leases with the issuance of 327,991 shares of common stock. Shares of common stock reserved for future issuance under the Amended and Restated 2010 Stock Plan (Stock Plan) are as follows (in whole shares): Year ended December 31, 2021 2020 Convertible redeemable preferred stock 125,472,147 120,384,609 Stock options and restricted stock units outstanding 18,702,704 26,876,324 Warrants for convertible redeemable preferred stock 28,808,183 29,477,295 Warrants for common stock 354,353 354,353 Shares reserved for future award issuance 3,390,543 8,891,681 Total Reserved 176,727,930 185,984,262 The rights, preferences and privileges of the holders of the common stock, non-voting non-voting C-1 C-1), C-2 C-2), D-2 D-2), D-3 D-3), E-1 E-1), E-2 E-2) E-3 E-3) Dividend Rights The holders of shares of convertible redeemable preferred stock shall be entitled to receive dividends, on a pari passu basis, out of any assets legally available therefor, prior and in preference to any declaration or payment of any dividend (payable other than in common stock, non-voting non-voting non-voting non-voting D-2, D-3, E-1, E-2 E-3,respectively, non-voting non-voting Liquidation Preference In the event of any liquidation, dissolution or winding up of the Company, either voluntary or involuntary, the holders of convertible redeemable preferred stock, on an as adjusted basis, shall be entitled to receive, on a pari passu basis, prior and in preference to any distribution of any of the assets of the Company to the holders of common stock, non-voting non-voting D-2, D-3, E-1, E-2 Series E-3,respectively, Conversion Rights Each share of voting preferred stock, on an as adjusted basis, shall be convertible, at the option of the holder thereof, at any time after the date of issuance of such share, into such number of fully paid and non-assessable D-2, D-3, E-1, E-2, E-3 Redemption The convertible redeemable preferred stock is redeemable at the option of the holder in certain situations if the Company sells, conveys or otherwise disposes of all or substantially all of its property or business, or if the Company sells, leases or enters into any agreement involving the exclusive, irrevocable license of all or substantially all of the Company’s intellectual property. Voting Rights Series A, Series B, Series C, Series D, Series D-2, D-3, D-4, E-1, Series E-2, E-3 E-2 D-2 D-2 E-2 as-converted one-half As long as 2,445,000 shares of Series D are outstanding, the holders of such shares of Series E shall be entitled to elect two directors of the Company at any election of directors. As long as 2,445,000 shares of Series D are outstanding, the holders of such shares of Series D shall be entitled to elect two directors of the Company at any election of directors. As long as 2,445,000 shares of Series A, Series B and Series C are outstanding, the holders of such shares of Series C shall be entitled to elect one director of the Company at any election of directors. As long as 2,445,000 shares of Series A are outstanding, the holders of such shares of Series A, Series B and Series C shall be entitled to elect one director of the Company at any election of directors. The holders of outstanding common stock shall be entitled to elect three directors of the Company at any election of directors. The holders of at least 55% of the voting convertible redeemable preferred stock and the holders of a majority of the common stock, voting independently as separate classes, shall be entitled to elect one director of the Company. The holders of voting convertible redeemable preferred stock and common stock, voting together as a single class on an as-converted In addition, the Company cannot take certain actions without first obtaining the approval of a majority of the then-outstanding convertible preferred shares voting separately as a class on an as-converted Non-voting |