Jaak Roosaare is from Saku, Estonia. He is married to a Southwestern Advantage bookgirl, Maria, and they have two boys, Jako and Hugo, and a baby girl, Marie. Jaak was the number-one rookie in the Southwestern Baltics division and sold books for seven summers. He won Sizzler every single summer and was DSL of the year three times. He helped to start the Lithuanian division and also recruited in Poland.

In 2018, Jaak started the new Southwestern company called E1 Ventures. It did almost half a million dollars in sales and made a profit in its first year.

Jaak is also an active investor, founder of the 50% Club and a contributor to business newspapers in Estonia. He promotes financial literacy and investing in high schools and in society as a whole. He is the author of four best-selling books about personal finance and has coached hundreds of people on how to start investing. His book, Rikkaks Saamise Õpik ("Textbook for becoming wealthy") is the all-time number-one bestseller in the personal finance field in Estonia.

In his free time, he enjoys cycling and reading investing books and annual reports of Berkshire Hathaway.

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