TV series
Get rich or lie trying.
Explore the extraordinary measures taken by ten savvy individuals to pull off mind-boggling, high-stakes gambles. Each episode charts the exploits of an overzealous entrepreneur who may have gone too far in their pursuit of riches and recognition.
Availability
Generation Hustle premiered April 22, 2021. We don't have a confirmed streaming, rental or purchase option yet.
Explore the extraordinary measures taken by ten savvy individuals to pull off mind-boggling, high-stakes gambles. Each episode charts the exploits of an overzealous entrepreneur who may have gone too far in their pursuit of riches and recognition.
Choose an episode, then use the watch options above for the show.
Episode 1
Dreams and deception collide when a brilliant con artist impersonates high-profile Hollywood producers to scam aspiring young artists. After the FBI teams with a dogged investigator to hunt this fraudster across
Directed by Yon Motskin
Episode 2
Is Adam Neumann a brilliant salesman or a greedy false prophet so charismatic that he convinced an entire generation to follow him to the promised land? The last of Silicon Valley’s so-called "unicorns," WeWork;s extraordinary rise and fall is told through the eyes of some of the multi-billion-dollar company’s earliest disciples.
Directed by Yon Motskin
Episode 3
A teenager reinvents himself as scam rapper Teejayx6, using his songs to teach others how to con. When his music takes off, the master of deception manages to scam his way into a record deal with one of America's biggest labels before the age of 20. But as Teejay ascends, the real-life stakes increase.
Directed by Yemisi BrookesGuest stars Teejayx6, Kasher Quon, Chrys, Success, Poody, Propane
Episode 4
Aided by a masterful social media presence, the young, awkward Anna Sorokin transforms herself into glamorous German heiress Anna Delvey. But after she sticks her friend Rachel with the bill for their lavish vacation, Anna's world begins to unravel and she goes on the lam. Convinced her friend is a con artist, Rachel works with the NYPD to piece together clues to track Anna down.
Directed by Martha ShaneGuest stars Rachel Deloache Williams, Richie Notar, Marc Kremers, Sergio Corvacho, Elle Dee
Episode 5
Jeremy Wilson channels his good looks and effortless charisma to assume many identities: a decorated Special Forces Captain, a swanky Scottish music journalist, the love child of an infamous IRA bomber, and more. While this master of deception travels the country seducing, manipulating, and cheating friends and family, he manages to evade law enforcement for decades – until he's finally outsmarted by a New York City cop.
Directed by Jeremiah Crowell
Episode 6
When self-proclaimed Google alum Kyle Sandler bursts into the tiny town of Opelika, Alabama to launch the Round House business incubator, he promises to turn the town into the "Silicon Valley of the East." The enchanted residents throw themselves into the project, until a local 14-year-old inventor gains nationwide press for reportedly rejecting a $30 million outside buyout offer. Spooked Round House investors are left wondering: is Kyle who he says he is or were his promises built on lies?
Directed by Martha Shane
Episode 7
An orphan born in Colombia and raised by his adoptive parents in Michigan, Anthony Gignac developed a taste for the finer things – and to get them he assumes the persona of a Saudi Royal prince. Whether flying high with real-estate moguls or convincing banks to extend him lines of credit, Gignac earns his reputation through a combination of wit and bravado… but how long can he sustain the delusion before the authorities catch on?
Directed by Jeremiah CrowellGuest stars Perla Lichi
Episode 8
Young, aristocratic billionaire William Baekeland charms his way into an exclusive group of wealthy world travelers – only to disappear with their money. Is he a brilliant imposter who spins fabulous lies and invents fictional personas to con the rich or just a kid who went too far trying to escape his past?
Directed by Yon MotskinGuest stars Harry Mitsidis, Dominique Laurent, William Simon Beakeland., Kolja Spori
Episode 9
Shortly after pledging his college fraternity, Midwest math whiz Syed Arbab uses funds raised from fellow students, alumni, and high school friends to start a hedge fund. Flush with cash, Syed becomes a campus legend, until a market crash causes his hedge fund (and life) to implode. As this stereotypical "good kid" breaks bad – trafficking cocaine, packing heat, and defrauding investors – the feds close in.
Directed by George PlamondonGuest stars Syed Arbab, Will S., Will G., Anthony Moore
Episode 10
Building a business with nothing but blind ambition, Ian Bick transforms himself from a nerdy teen into a concert promoter almost as legendary as the bands he books. As the teenager's EDM raves pack houses and feed his emerging VIP lifestyle with first-class trips, high-end shopping, and brand-new jet skis, his fall is as dramatic as his rise – culminating in an FBI raid that shocks his family, friends, and hometown.
Directed by George Plamondon
Episode information updated Sep 19, 2026
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HBO Max
Jigsaw ProductionsUnited States