The research is conducted for LearnVest. The research discusses the website elements employed by LearnVest. In doing so the research has analyzed the type of brand personality that LearnVest exhibits to its customers. LeranVest is a financial services planning tool. It is a convenient and a comprehensive tool. The dissertation compares LearnVest by means of a Case Study with another financial services planning tool. Secondary research data is used collected from observational study. Primary research data is collected about the usability of the two sites and these data are discussed under Key Advertising Elements of Endorser, User Imagery and the Big Five attributes of Sincerity, Excitability, Ruggedness, Sophistication and Competence. The analysis also includes the hypothesis testing for whether LearnVest’s CEO style of brand advocacy was helpful. The data collected shows that LearnVest is indeed stronger in terms of its use of advertising elements and big five attributes for reinforcing brand personality.