Social media and their accompanying smartphone apps have opened brands to consumers in unprecedented ways. Of these sites, none, with the exception of Facebook, are more popular than Instagram, a social networking app that is image-centric and image-driven. As a free platform for potentially reaching, attracting, and engaging with millions of consumers, Instagram offers brands an unprecedented avenue for free advertising—all on a relatively level playing field. This means that brands, even startups, have the same access to potential followers as larger, more established brands. This advertising is more fluid, more frequent, and more inconspicuous than traditional advertisements; e.g., magazine spreads, billboards, or commercials. To better understand what elements are commonly found in startups image posts on Instagram, as well as to learn if or how those elements translated to engagement, this study employed a content analysis to deconstruct 438 image posts aggregated from the Instagram accounts of ten U.S. startups. Images were coded for salient image features, viral advertising appeals, fundamental image functions, and creative message segments as outlined by Taylor's seminal advertising model, the six-segment message strategy wheel (1999). Likes and comments were recorded during coding in order to measure engagement. Two approaches to analyzing the data were then taken. First, descriptive statistical analyses were applied to the data to determine how frequently elements appeared among startups' image posts. The second approach involved two phases. In Phase 1, crosstabs were conducted to discover what interrelationships exist among these elements. In Phase 2, a qualitative content analysis of the data compiled from the initial content analysis was conducted to determine if certain schema were commonly manifest among posts with high and low engagement in respects to likes and comments. The subsequent findings indicated that object(s) were the most common image feature, informing was the most common function, ration was the most common image function, and humor was the most popular viral advertising appeal, although as a whole, viral advertising appeals were rarely manifest. The qualitative content analyses suggested that more schema negatively affected engagement than schema that positively affected it, though several important themes and base combinations were perceptible among the top 10 percent of posts in relation to engagement.