#5: Kevin O’Leary

Known as: Co-founder of O’Leary Funds and SoftKey, Judge on Shark Tank

Net Worth: $400 million

Children: 2

While Shark Tank enthusiasts recognize Kevin O’Leary as the no-nonsense arbiter of innovative concepts, there’s a surprising twist to his financial philosophy when it comes to his children’s inheritance. Contrary to the expectation of securing their financial future, O’Leary is resolute in his belief that it’s his parental duty to compel his offspring to stand on their own two feet.

In an interview with Time Magazine, O’Leary articulated his unconventional perspective: “If you don’t commence your life with the fear of not being able to provide for yourself and your loved ones, what impels you to seek employment? Fear propelled me, and it will propel them.”