Online gambling is a global multibillion dollar business that dwarfs all other forms of entertainment, and yet business and marketing research about it is scarce (Mizerski, 2013). The focus of gambling research has been on problem gamblers who ultimately represent a rather small, albeit important percentage of the gambling population. However, in the current Age of Chance (Reith, 2002) gambling, whether as a game of chance or taking risky action in the hope of a desired result (Lexico.com, 2019), is said to be at the very heart of our society. Indeed, business often operates in an environment of uncertainty that is increasingly online. This thesis seeks to address the paucity of marketing and business research in online gambling to better understand aspects that customers consider when gambling online. In doing so, the thesis commences by investigating semantic differences in the text used to achieve market positioning on the websites of online gambling firms. It proposes a new methodology that employs a combination of lexical and statistical analyses to understand how customers view content and how this is related to market positioning. Results show that firms that emphasise low certainty (or risk) are better positioned in customers’ mind than those that put emphasis on action or certainty. The thesis proceeds to explore the literature for drivers of customers’ online gambling intention and identifies perceived fairness and enjoyment, particularly anticipated enjoyment, as overlooked concepts. Anticipated enjoyment is defined as the enjoyment felt prior to the actual experience while perceived fairness encompasses procedural, distributive and interactional fairness. The research employs the theoretical frameworks of  the Theory of Reasoned Action (Ajzen & Fishbein, 1980; Fishbein & Ajzen, 1975) and the Unified Theory of Acceptance and Use of Technology – UTAUT (Venkatesh et al., 2003; Venkatesh, Thong, & Xu, 2012). Anticipated enjoyment and perceived fairness are used as additional motivational drivers to enhance the models and better understand customers’ online gambling intention. Data are collected via surveys and analyses using mediated regression and PLS-SEM suggest that both anticipated enjoyment and perceived fairness strongly impact customers’ online gambling intention, whereas some of the UTAUT constructs fail to exhibit significance. Shorn of irrelevant relationships, a new Gambling Intention Model (GIM) is put forward. While the context of this study is online gambling, the resultant GIM may have broader application and can also potentially be applied to stock market traders and the insurance industry.