13. Common shares, preferred shares and warrants

Common stock

As of December 31, 2017 and 2016, the number of issued shares of common stock was 61,631,573 and 53,717,996, respectively, which included shares of treasury stock of 352,523 and 160,235, respectively.

The change in the number of issued shares of common stock during the year ended December 31, 2017 was a result of the following issuances:

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An aggregate of 4,001,808 shares of common stock were issued as a result of the vesting of restricted stock units (“RSUs”) and the issuance of restricted stock, including 192,288 shares of common stock withheld to pay withholding taxes upon such vesting, which are reflected in treasury stock.

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On October 17, 2017, the Company entered into certain amendment agreements (the “Intracoastal and Anson Warrant Amendments”) with Intracoastal Capital, LLC (“Intracoastal”) and Anson Investments Master Fund LP (“Anson”), representing warrants to purchase a total of 861,769 shares of the Company’s common stock, previously granted to such warrant holders. The Company agreed to reduce the exercise price of all warrants described above to $3.00 per share. In October 2017, Intracoastal and Anson exercised such warrants and the Company issued an aggregate of 861,769 shares of common stock, and the proceeds from the exercise of $2,585 were received in October 2017.

The Intracoastal and Anson Warrant Amendments also provide that the Company deliver to Intracoastal and Anson an additional warrant for common stock equal to 25% of the number of shares exercised, that is, an aggregate of 215,443 additional warrants, at an exercise price of $5.35 per share (the “Additional Warrants”).

A loss of $1,005 was recognized into other expenses, net during the year ended December 31, 2017, as a result of the Intracoastal and Anson Warrant Amendments, using a Black-Scholes pricing model.

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On November 3, 2017, the Company issued an aggregate of 300,000 shares of common stock to Whitehorse resulting from the exercise of the Whitehorse Warrants, pursuant to the Whitehorse Warrant Amendments. Gross proceeds of $900 in total were received in November 2017. See Note 11, “Long-term debt, net,” for details. Together with the exercise of warrants by Intracoastal and Anson, as discussed above, during the year ended December 31, 2017, an aggregate of $3,485 were received as a result of the exercise of warrants to purchase 1,161,769 shares of common stock.

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On November 3, 2017, the Company issued a total of 2,750,000 shares of common stock to settle the acquisition consideration payable in stock in relation to the Q Interactive Acquisition. See Note 4, “Acquisitions,” for details.

The change in the number of issued shares of common stock during the year ended December 31, 2016 was a result of the following issuances:

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On February 22, 2016, the Company’s Series B Preferred, 450,962 shares in total, automatically converted into 22,548,100 shares of the Company’s common stock, by multiplying each such share of Series B Preferred by 50, pursuant to the Company’s Series B Preferred certificate of designation.

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On March 11, 2016, the Company issued 1,800,220 shares (the “Series A Earn-out Shares”) of the Company’s Series A Non-Voting Convertible Preferred Stock, par value $0.0001 per share (the “Series A Preferred”) and 900,108 shares (the “Common Earn-out Shares”, and together with Series A Earn-out Shares, the “TBO Merger Earn-out Shares”) of the Company’s common stock, which shares represent “earn-out” consideration paid in connection with the TBO Merger between Tiger Media and TBO consummated on March 21, 2015, upon a determination by the Board of Directors that certain financial targets had been achieved as set forth in the TBO Merger. In 2016, all such earn-out liabilities under the TBO Merger Agreement have been settled.

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On March 11, 2016, the Company amended the certificate of designations of the Series A Preferred to provide for the conversion of the Series A Preferred into common stock on a one-for-one basis. Previously, the Series A Preferred were convertible in connection with a sale of any such shares to a non-affiliate of the Company. As a result, all the outstanding shares of Series A Preferred converted into 6,672,022 shares of common stock.

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During the year ended December 31, 2016, the Company issued an aggregate of 1,069,728 shares (“Exchange Shares”) of common stock in exchange for warrants previously issued to four stockholders of the Company, including Frost Gamma, resulting in a loss on the exchange of warrants of $1,273 recognized in other expenses, net. No additional consideration was paid by the warrant holders and the old warrants were cancelled. In addition, new warrants to purchase 320,102 shares of common stock (the “New Exchange Warrants”), at an exercise price of $10.00 per share, were issued to one of the warrant holders as part of the exchange of warrants.

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During the year ended December 31, 2016, 14,500 restricted shares of common stock were issued to two vendors of the Company as additional consideration for services rendered.

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An aggregate of 1,434,562 shares of common stock were issued as a result of the vesting of RSUs, of which, 360,235 shares of common stock were withheld to pay withholding taxes upon such vesting, which are reflected in treasury stock.

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In December 2016, an aggregate of 200,000 shares of common stock were sold to an investor. These shares were issued out of treasury stock.

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An aggregate of 3,000,000 shares of common stock were issued in registered direct offerings (“Registered Direct Offerings”) to certain investors, pursuant to the securities purchase agreements entered into on May 17, 2016 and November 28, 2016.

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On June 8, 2016, an aggregate of 2,369,190 shares of common stock were issued to Selling Source in connection with the Q Interactive Acquisition.

Warrants

During the year ended December 31, 2017, as a result of certain amendments of warrants, as discussed above under common stock, the exercise price of warrants to purchase an aggregate of 1,161,769 of common stock were lowered to $3.00 per share, and such warrants to purchase an aggregate of 1,161,769 of common stock were subsequently exercised.

As of December 31, 2017, warrants to purchase an aggregate of 1,273,776 shares of common stock were outstanding, which includes:

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Concurrent with the Registered Direct Offering in May 2016, as discussed above, warrants to purchase an aggregate of 500,000 shares of common stock were issued to five investors, including 375,000 shares to Intracoastal and Anson, with an exercise price of $8.00 per shares, which are exercisable beginning November 21, 2016, six months and one day from the date of issuance, and expire 24 months from the date they became exercisable. As a result of the Intracoastal and Anson Warrant Amendments entered into on October 17, 2017, warrants previously issued to Intracoastal and Anson were amended and exercised, with an exercise price of $3.00 per share, which resulted in remaining warrants to purchase 125,000 shares of common stock as of December 31, 2017.

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The Intracoastal and Anson Warrant Amendments also provide that the Company deliver an aggregate of 215,443 Additional Warrants to these two investors, at an exercise price of $5.35 per share. The Additional Warrants are exercisable from the date of issuance and expire on the earlier of the close of business on the two-year anniversary of (i) the date the registration statement registering the resale of the underlying shares is declared effective by the SEC, or (ii) the commencement date that such Additional Warrant may be exercised by means of a “cashless exercise.” These Additional Warrants do not participate in the Cash Dividend or Spin-off of the Business Combination Transaction.

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Concurrent with the Registered Direct Offering in November 2016, warrants to purchase an aggregate of 1,000,000 and 100,000 shares of common stock, with an exercise price of $3.75 and $5.00 per share, respectively, were issued to four investors, including Intracoastal, and related agents, respectively. These warrants issued to the four investors are exercisable beginning six months and one day from the date of issuance and expire 5 years from the date they became exercisable, while the warrants issued to related agents are exercisable beginning 6 months and one day from the date of issuance and expire 24 months from the date they became exercisable. As a result of the Intracoastal and Anson Warrant Amendments, warrants to purchase 166,667 shares of common stock, previously issued to Intracoastal, were amended and exercised, with an exercise price of $3.00 per share, which resulted in remaining warrants in aggregate to purchase 833,333 and 100,000 shares of common stock, with an exercise price of $3.75 and $5.00 per share, respectively, were issued to the remaining three investors and related agents, respectively.

As of December 31, 2016, warrants to purchase an aggregate of 2,220,102 shares of common stock were outstanding, which includes:

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New Exchange Warrants to purchase 320,102 shares of common stock were issued to an institutional investor as part of the exchange of warrants, as discussed above. The New Exchange Warrants will expire twenty-four months from the date of issuance, which were subsequently amended and exercised during the year ended December 31, 2017.

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Warrants to purchase 200,000 shares of the Company’s common stock were issued as part of our Term Loan of $45 million, with the exercise price being amended to $5.08 as a result of the Amendment No. 2 to Credit Agreement entered into on September 30, 2016. As part of the Amendment No. 2, we issued additional New Whitehorse Warrants to purchase 100,000 shares of common stock, with an exercise price of $5.08 per share and an expiration date of September 30, 2026. As a result of the amended and newly issued warrants, an aggregate of $492 was recognized in additional paid-in capital. Such warrants to purchase an aggregate of 300,000 shares of common stock were subsequently amended and exercised during the year ended December 31, 2017.

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Concurrent with the Registered Direct Offering in May 2016, as discussed above, warrants to purchase an aggregate of 500,000 shares of common stock were issued to five investors, with an exercise price of $8.00 per share, which are exercisable beginning six months and one day from the date of issuance and expire 24 months from the date they became exercisable.

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Concurrent with the Registered Direct Offering in November 2016, warrants to purchase an aggregate of 1,000,000 shares and 100,000 shares of common stock were issued to four investors and related agents, with an exercise price of $3.75 and $5.00 per share, respectively. These warrants issued to the four investors are exercisable beginning 6 months and one day from the date of issuance and expire 5 years from the date they became exercisable, while the warrants issued to related agents are exercisable beginning 6 months and 1 day from the date of issuance and expire 24 months from the date they became exercisable.

Preferred stock

As of December 31, 2017 and 2016, we had 10.0 million shares of preferred stock with par value of $0.0001 per share authorized, and there were no shares of preferred stock issued or outstanding. Of the authorized preferred stock, 6.8 million shares and 1.0 million shares are designated Series A Preferred and Series B Preferred, respectively.

Treasury stock

As of December 31, 2017 and 2016, the Company held 352,523 and 160,235 shares in treasury, with a cost of $1,274 and $531, respectively.

During the year ended December 31, 2017, the increase in treasury stock was due to 192,288 shares that were withheld to pay withholding taxes upon the vesting of RSUs and restricted stock.

During the year ended December 31, 2016, the increase in treasury stock was due to 360,235 shares that were withheld to pay withholding taxes upon the vesting of RSUs and restricted stock, which was decreased by the sale of 200,000 shares of treasury stock.