Y2K. With no experience nor training, Simon Boisvert embarks on a journey of writing and producing self-financed micro-budget narrative films. Nine years later, he had produced and distributed six feature films. This documentary, interspersed with various excerpts from his films and personal archive footage, recounts his journey through thick and thin, and as a laughing stock.

When he learns that a co-worker is friends with his old high-school girlfriend, Jennifer, stockbroker Gary helps his former flame get a job at his company in order to pursue her affections all over again. But when Jennifer rejects his advances and dates other men, Gary becomes increasingly obsessed with winning her back.

A womanizer decides to start a dating service to make money and take advantage of vulnerable women.

Desperate for a fresh start at life after a tragedy on her watch, a suspended air traffic controller finds herself sucked into a world of financial fraud and manipulation when she throws in her lot with her secret lover.