Free trials! Free apps! Free samples! If so much is free, why are we so broke? Jeff Kreisler, an award-winning comedian and author of "Get Rich Cheating" talks me through all the ways that free can cost you big.

Did you come out of college knowing how to negotiate your salary? What about knowing your worth in a competitive market or how to ask stranger to give you money for an idea? Yeah, me either. Sara Benincasa, comedian and the author of "Real Artists Have Day Jobs" offers tips for the professionally challenged on how to make sure you're getting paid for your work and to ask for what you deserve. 

It's the World Series of Poker. You're sitting in Las Vegas with the best players in the world. The goal? Don't lose the $10G you came with and come away with a big score. Clayton Fletcher is a comedian and a career gambler. He talks about how he makes a living playing cards and how poker knowledge can be used to determine how to invest, whether or not to buy car insurance and of course, dating beautiful women. Clayton talks about the World Series of Poker and what it means to have the "the nuts." 

How much is too much Versace? Is there such a thing? When NYC stand-up comic Petey DeAbreu was 21 and making thousands of dollars a week hustling stolen goods in Miami, there was no such thing as too much. The money was flowing and everything was amazing -- until he got arrested. This week, he tells me everything he bought (and everything he lost) and how he makes a living as a comedian now.