Open Account with SuChin Pak Slate Group Studios/Umpqua Bank

If you could either retire at 35 or 65, which would you choose? What if retiring at 35 meant working long hours at a burger joint for two decades, and retiring at 65 meant working twice as a long, at a job you love, as an attorney? Suddenly the decision isn’t so easy. However, for Matt Bath and Sue Ra, this isn’t a hypothetical situation – and they wouldn’t trade their choices for anything.

If there’s one thing Jagpaul Badhesha learned as a farmer, it’s that you don't take money for granted. While Jag wouldn’t trade his family's 1,000-acre operation – or the personal satisfaction of a hard day’s work – for the world, it comes with incredible amount of responsibility and massive financial pressure.

Velma Davis bought her first house when she was 26 years-old. Although it would’ve been hard to know it then, Davis – a first-generation college graduate in the throes of the Civil Rights Movement – was on her way to amassing life-changing wealth. Now she has a new challenge: helping her daughter Kenya figure out how to steward her financial legacy. 

Bryan Clay trains hard, and works hard. It's what earned him a gold medal at the Olympics, and the title of "Greatest Athlete in the World." But his training only prepared him to win – it didn't teach him to deal with failure. That’s something he had to learn on his own. With no coach. No spotlight. And no money. 

For most people, money is impossible to escape. But Megan Jasper is not ‘most people.’ She’s the CEO of SubPop Records - the iconic music label behind Nirvana and The Shins - and one of those rare people who put her dreams before dollars. And in the process, saved one of music’s most iconic record labels.    

Three siblings discuss why people sometimes hide money troubles from loved ones. The story revolves around their family business and mother—who hid their father’s gambling addiction from them for 30+ years, only to “confess” when the family was on the verge of bankruptcy. Their tale begs the question: Can you ever go too far to protect the ones you care about?