How do you know when it's time to 'throw in the towel'? It's a question most of us face at some point in our lives, especially when it comes to relationships and jobs. And, it can be even more complicated when dealing with money, as "giving up" has huge implications for our financial stability and physical survival. But what if giving up isn't the only option? Or rather, what if it makes sense on paper—like it did for chef Reem Assil, who opened a restaurant during a pandemic—but it isn't something you're willing to do?

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?

Nancy Pfund is the mind behind the money of Tesla and Pandora. She’s a venture capitalist with a vision for change, just like Kim Colaprete and Chavi Hohm—the bombastic personalities behind Team Diva, one of Seattle’s most progressive real estate groups. Nancy and Team Diva have never met, but they’re both changing how we think about money and define profit. And they’re part of a movement that is ready for revolution.

Bradley Paul’s words are money. He's written for some of Hollywood’s best television studios, and his credits include AMC’s hit drama "Better Call Saul" and the upcoming "Lodge 49." But is he getting paid what he’s worth? This is the question we pose to a poet and writer who went from a cash-strapped childhood in Baltimore to a career in Hollywood, but almost gave up along the way.

Dr. Donna Beegle is the founder of a consulting firm that works to break the cycle of poverty in America. Here, Dr. Beegle talks about her uncommon life as migrant-worker, welfare-recipient and homeless mother. She discusses how our economic future may not rest in the hands of experts with money, but in the untapped genius of those without.