The book is structured around a story of three people in their late 20s visiting Roy, the title character, for lessons in financial planning. Each chapter of the book describes a different visit and a different element of financial planning. Each month along with their lessons the three students are required to start carrying out the actions prescribed by Roy. In addition to these individuals, Roy also shares his financial knowledge with the customers of his barber shop. The story (in Canadian editions) is set primarily in
Sarnia, Ontario, where Roy has been operating a barber shop for several decades. As a young man, Roy had planned to become a lawyer, but those plans were derailed. He ended up taking over his father's barber shop. Worried about money, Roy visited Mr. White, one of the town's wealthiest men, and asked for advice on financial planning. This advice paved the way for Roy's accumulating wealth. The basis of the book is Roy's advice to "save 10 per cent of all that you earn and invest it for long-term growth." In that, it draws from the advice first set forth in
The Richest Man in Babylon. Subsequent chapters discuss wills and life insurance,
RRSPs, buying a home, income tax and saving and spending. Roy (and thus Chilton) is not as harshly anti-debt as some other authors, like
Dave Ramsey. However Roy does advise that extra money should go to pay off debt, and that credit cards are "
anathema" to well-run personal finances. Roy does believe that if you are investing 10% and maxing out your RRSP, day-to-day spending doesn't matter too much to your overall financial picture. A U.S. version with discussion of topics such as
IRAs was also released; the third edition was published in 1997. The updated 2025 edition of the Canadian version adds discussion of additional account types and products introduced in Canada since 1989, including
TFSAs,
FHSAs, and
ETFs, as well as the impacts of
social media influencers on financial behaviour. ==Main characters==