When his skateboard-deck business venture hits the wall, twentysomething graphic designer Ben agrees to fund a "sure thing" leather-jacket hustle proposed by good-times best friend Cam. The scheme morphs into downright desperation when Camʼs cousin Rene gets out of jail, looking for repayment of an old loan. Meanwhile, Ben is bummed to discover his ex-girlfriend Rachel is dating Darren, a hot hotelier, and finds little comfort in his horny pursuit of a sexy young thing during her late-night party. With Rene threatening bodily injury if Cam and Ben donʼt ...

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Using $3G they got via yet another high-interest loan from Rene, Ben and Cam buy up a roll of hot premium-denim material, then hit a series of dead ends in their search to find a manufacturer to make samples of their Crisp brand of retro-ʻ70s jeans. Along the way, they parlay a crashed late-night dinner with top fashion designer John Varvatos into a brainstorming meeting that may, or may not, hold the key to their entrepreneurial success. Meanwhile, both Ben and Rachel realize that they havenʼt totally moved on, and vow to try harder in the future.

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While Ben and Cam track down a tailor to re-imagine some ʻ70s-era jeans, Rachel, who works at an interior-design boutique for her eccentric boss Edie, rethinks her future after reconnecting with a friend in the Peace Corps. Eager to get a bigger marketing commitment for his fledgling Rasta Monsta drink, Rene makes a buyout offer his marketing partners better not refuse. After Cam peddles some of Benʼs skateboard decks to upper-crust Manhattan kids, they round up enough money to pay the tailor, deliver the denim and launch Crisp NYC.

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It's Rachel's birthday and both Darren and Ben are invited to the party.

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Ben finally receives the prototype of his jeans design, but feels a failure because it looks slightly sissy. Ben therefore shies away from asking help form design school buddy Pete Powell, but partner Cam still gets them presented to Japanese buyer Haraki, who orders t-shirts instead. Darren handles more souvenirs of Ben at Rachel's well, while her boss scolds her insensitivity. René hoped to recuperate the $100,000 he hid in a relative's home, but finds him expelled by is bitch-wife's restraining order, and the cash was 'found' by contractor Flaco while converting ...

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Ben and Cam have a hard time finding enough vintage 50% cotton t-shirts to print Crisp's Japanese order of 300 on. Ben is too often on the phone and takes time off without permission, so he ends up fired from his clothes sales job, but gets the t-shirts by inadvertently seducing salesgirl Julie. After a hot night he can't remember due to his hang-over, Darren sweetly insists on driving her to her next appointment. Warned by his confessor, René confronts Flaco, knocks him down like in their school days but end sup believing he didn't steal the cash.

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To investing partner Kappo's delight, working Crisp partners Ben and Cam finally have everything together for their first sale, albeit it 'just' t-shirts. That will cover their bet with René, but a day late, so he makes them 'work for it' as sample clerks for the Caribean energy drink he's marketing in New York for white Jamaican John Lardner, a fellow ex-con and hence a recipe for disaster according Rene's parole officer Larry. They play hookey to collect and deliver the t-shirts, but the truck ends up being stolen. Meanwhile Darren gets his board to engage lover ...

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Ben feels all is lost after the 200 t-shirts were stolen in the Jamaican power drinks van, resigning to odd jobs. Partner Cam however confronts uncle Rene Calderon, whom he suspects rightly of staging the theft. After secretly recovering their load while the van is burnt for insurance fraud, the boys deliver to Hiroshi's agent, who enthusiastically orders jeans too, but insists on 'customs evasion'. Lover Darren and boss Edie are startled when Rachel chooses to resign, dumping both of them and Ben to start over elsewhere.

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