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Jack, Bryn, Olivia, Derek and Aaron face uncertainty about their future as Gemini Corp CEO Andy Corvell calls an all-hands meeting. When friends and co-workers Aaron, Olivia, Jack, Derek, and Bryn are downsized by their eccentric CEO, Andy Corvell (Craig Bierko), they decide to make the 'leap' toward the unknown, rent an office, and start their own businesses. Things get complicated when each receives the same anonymous e-mail from a mystery investor promising half a million dollars to the start-up that impresses them the most four months from today.

Five friends. Five start-ups.