Extant research has documented various sources of informational advantages enjoyed by company insiders including firm size, analyst following, dividend payout policy, book-to-market ratio, and the presence or absence of R&D investments. Surprisingly, despite this large body of work, virtually no research has investigated the contribution of advertising investments to information asymmetry. This omission is particularly glaring since: (a) advertising investments constitute a significant fraction of many firms' ongoing expenditures, and (b) the received literature provides strong theoretical arguments relating advertising investments and information asymmetry. Accordingly, the primary objective in this study is to empirically address this gap. Using advertising and insider transaction data at over 12,000 firms from 1986 to 2011, we find that insider gains are significantly greater at firms characterized by advertising investments. Specifically, a zero cost portfolio that is long on firms with net insider purchases and advertising investments, and short on firms with net insider purchases and devoid of advertising investments, garners annual abnormal returns of 5.5%. In addition, we find that investors' reaction to news of insider purchasing is significantly more pronounced at firms characterized by advertising investments - investors rationally recognize the greater information content associated with insider purchases at these firms. (c) 2013 Elsevier B.V. All rights reserved.