Oscar, a 34 year-old from East Jersey, has been a low-stakes grinder since he was 18. Like a lot of players his age, Oscar found early success in a soft game, but has failed to adjust to an increasingly sophisticated landscape. This documentary examines the benefits and detriments baked into the pursuit of a nontraditional career, and why it can be difficult to abandon something that has defined you for so long - especially in an industry where security is elusive, but extreme wealth is possible. Far from the glamour often associated with playing a game for a living, Oscar spends his days driving back and forth from the casino or playing online, hoping he can make $200 a day. Though he's aware his career has stagnated, Oscar's belief in his natural skill set keeps him from working at his game; his aversion to risk paradoxically blocks him from achieving financial stability. Unlike most grinders, Oscar has direct access to advice and coaching by elite poker players. His close friend and high school classmate, Christian, has overcome many of the socio-economic obstacles and industry changes that have hindered Oscar. Through Christian, Oscar is introduced to Berkey, a high-stakes pro and coach, who agrees to mentor Oscar - both on and off the felt. Leaving New Jersey for the first time in years, Oscar heads to Vegas to attend an advanced poker training academy run by Berkey's company, Solve For Why. In Vegas, Oscar is shown just how far he's fallen behind. He continues to resist change, even though he knows it's necessary, and begins to question whether he should abandon the only career he's ever known. Upon his return to Jersey, he loses the remainder of his poker bankroll and is forced to get a job for the first time since high school. Forced into a more-traditional lifestyle, Oscar struggles to find meaning outside of the game. After swearing off underground games years earlier when he was robbed at gunpoint, Oscar re-enters the underground poker scene and immediately starts winning again. He quits his job, believes he can continue winning without working on his game, and seems doomed to repeat his mistakes. Parallel to Oscar's experience, in an effort to fully explore the tenuous line between success and failure, intermittent interview segments featuring some of poker's biggest names describe how skill, opportunity, and endurance all factor into the creation of a sustainable poker career. These interviews give context as to how the game has changed, what "success" means in a lifestyle that's inherently unstable, and why Oscar's story is one small piece of a much larger one.