DOT - The FilmI recently viewed a profoundly funny and very real motion picture about a Chicago startup company that soars then goes bust—a must-see for anybody in the entrepreneurial community and a great way to teach what not to do. I’m providing a link to the streaming version. It’s also available on DVD (see below).

Filmed in a heady era a the dot-com era, DOT is as fresh as if made yesterday. It’s Hollywood quality work in the style of the subsequent Christopher Guest/Eugene Levy movie series and the TV show “The Office.” The humor is outrageous and priceless, and could only come from creative yet lucid minds with a deep understanding of what makes business work and not work.  I love the opening line of dialogue, spoken softly, in all sincerity:  “We wanna make the most amount of money in the least amount of time with the least amount of effort.  Basically, that’s about it.”

DOT - The Film

The Makers

I met the makers of the film, Brett Singer and Simeon Schnapper, at the Chicago Loop offices of Youtopia—a real startup that offers a promising solution to community service requirements in public schools. I caught their company presentation at the 2012 Funding Feeding Frenzy—it was one of the top three contestants—and again at the July meeting of BNC Venture Capital. As you’ll find abundantly clear in the movie DOT, these guys know the odds of success for a startup. That means they possess a good dose of panache.

The Making

Singer tells me they created a detailed story and outline of 120 typical scenes any startup might go through, but the dialogue process was DOT - The Filmstrictly improv. They shot the film in 12 days over 6 consecutive weekends, generating more than 40 hours of content. They edited that down to 83 minutes, and I might add, with a great deal of expertise and talent. If these guys want to go into the filmmaking business, they’ve got the tools.

“Most of the actors had very little experience working at a startup,” said Singer. “Before we shot each scene Simeon and I would have a few minutes with the actors to relate to them how a ‘real world’ staff meeting or equity discussion, might be. We were lucky to have such a wildly talented group of improvisers.”

I was surprised to learn that the candidate interview scene was footage of real interviews. Another quirk—the actor who plays the CTO/techDOT - The Film guru had no technical experience at all. “He expressed concerns on in his ability to play the role of a coder/CTO convincingly,” said Singer. “We gave him one note – He’s by far the most intelligent of the bunch. He won’t waste his breath trying to explain or even speak technically around this group. Basically we told him, don’t say anything. Just be annoyed with everyone and occasionally we’ll feed you some lines. We are always told that the most spot-on characterization is the CTO”


The film had a great festival run, winning a number of awards. It won BEST FEATURE at The Dances with Films Festival in Santa Monica, CA. Said Singer, “After the awards ceremony the judges came up to congratulate us. When we asked, ‘Why did we win?’ they answered, ‘We watched your film first and it set the bar for the whole festival. No other film was better.’” DOT subsequently aired on the Showtime Networks for years.

“Years later we still get emails or Facebook notes on the film,” said Singer. “It’s very quotable and has a small, rabid following. I think it’s ripe for another generation to appreciate it.”

I enthusiastically agree with that. See the entire movie free on streaming media below:


Dot from Brett Singer on Vimeo.

DOT the feature film streaming

Get your copy of DOT on Amazon

For more information, contact Brett Singer at

Their real company – YouTopia –

Funding Feeding Frenzy

BNC Venture Capital

Comment on this article — Name and email optional

Find Chicago Venture Magazine at Comments and re-posts are welcomed and encouraged. This is not investment advice – do your own due diligence. I cannot guarantee accuracy but I give you my best.

Copyright © 2012 John Jonelis – All Rights Reserved


Filed under BNC Venture Capital, Chicago Venture Magazine, Chicago Ventures, Entrepreneurship, FFF, Innovation, Innovation and Culture, Invention

4 responses to “DOT – A FILM

  1. Ann Brice

    That’s a stich! Ha, ha! So many companies are just like that!

  2. Jim Kren

    That movie chronicles a fictitious company that has everything but an idea. It’s the same now but we see ideas with no company.

  3. Janet Case

    I say if they have the smarts to dramatize what’s wrong, they have a good handle on what’s right.

  4. Pingback: FUNDED TONIGHT! | Chicago Venture Magazine

Leave a Reply to Jim Kren Cancel reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s