“Heads I Win, Tails You Lose” is a book advocating an alternative wealth-building strategy that centers around utilizing life insurance policies differently than the conventional approach. The author, drawing from personal experiences and anecdotes, critiques traditional financial planning methods involving Wall Street and 401(k)s, highlighting their inherent risks and advocating for increased financial literacy and self-reliance. The book details a multi-tiered wealth-building system, emphasizing the importance of establishing a strong financial foundation through insurance before pursuing higher-risk investments. It also stresses the significance of personal development and human capital in achieving long-term financial success and freedom. A companion study guide is offered to supplement the book’s content.