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From the outside looking in, startups can appear to be sexy and glamorous. When most of us encounter people working at a startup, they're usually basking in the media spotlight, speaking at a conference or appearing on stage during a demo day. It's all very heady stuff.

The reality, however, is that startup life involves a lot of work, hours and hours of toiling, plenty of frustration and never-ending challenges.

This behind-the-scenes world is what David Chan wants to show in a new documentary about startups called Day Job.

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The project involves five startups that were selected as part of the latest cohort at Extreme Startups, a Toronto-based accelerator. For five months, Mr. Chan and his team will follow each startup to provide insight into what happens during the daily grind of building a company.

Mr. Chan said the idea for the documentary popped up when he was doing videos earlier this year for some of the startups within Extreme Startups.

"The project resonated with me because we are technically a startup," he said of his company, Fidelity Format, which started a year ago. "The instant connection was I'd love to tell a story about all these companies and the day in, the day out struggles they go through."

Shooting began in late August, when the startups applied to the Extreme Startups program. Each startup received $50,000 when they were invited into the program, they get $30,000 in the middle of the program from SmartStart, and a $150,000 convertible note from the Business Development Bank of Canada when they graduate.

The filming will include Demo Day on Nov. 28 when the five startups make public presentations in front of investors. Mr. Chan hopes to follow up for another month to provide insight after the startups graduate from the accelerator program.

One of the big challenges Mr. Chan faces is getting authentic insight into what it's like to work for a startup without trying to manage or orchestrate the situation. At the same time, he needs to be careful about not being too intrusive because the entrepreneurs are busy.

"Think about it as herding cats because we need to stay on top of five companies," he said. "The difficulty is they are busy and we do not want to interfere with what they are doing but, at the same time, we need to know when it's happening."

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Another issue, Mr. Chan said, is he wants to show the personal side of working for a startup but be careful about making them uncomfortable or exposing too much information.

"The challenge is how we bring them out of their shells. Some of the stuff on the trailer takes the right interviewing skills," he said.

To date, the documentary has been self-financed but Mr. Chan said he hopes to raise $25,000 through a campaign on IndieGoGo, a popular online service that lets companies or individuals raise money from individuals.

Depending on the success of that campaign, Mr. Chan said he's hoping Day Job will be ready by December or early January.

Mark Evans is the principal with ME Consulting, a communications and marketing strategic consultancy that works with startups and fast-growing companies to create compelling and effective messaging to drive their sales and marketing activities. Mark has worked with four startups – Blanketware, b5Media, PlanetEye and Sysomos. He was a technology reporter for more than a decade with The Globe and Mail, Bloomberg News and the Financial Post. Mark is also one of the co-organizers of the mesh, meshmarketing and meshwest conferences.

Join The Globe's Small Business LinkedIn group to network with other entrepreneurs and to discuss topical issues: http://linkd.in/jWWdzT

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