Basic premise is these two best friends (poker stars Phil "The Unabomber" Laak and Antonio "The Magician" Esfandiari) wandering around various places making random bets on shit: can you get someone to drive you somewhere, can you buy that guy's necklace, has that cop ever shot his gun etc. Standard bet is $500 but it can vary.
Framing the half hour is a larger bet like who can win a surfing contest, or who can get the most tips bartending, for higher stakes of around two to three grand.
On top of that there's a poker bet somewhere, such as Episode 2 where they coach two strippers on the game and have them play strip poker.
There's a certain stagedness around how the bets are dreamed up, but who wins is certainly not.
On at different times - check the listings. Certainly most recommended for poker fans, but I think it would appeal to people outside that range too. It's just a lot of fun to watch!