Chris Castig Co-founder of Adjunct Prof at Columbia University Business School.

How Not To Make It In New York

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We created How Not To Make it In New York because we wanted to tell the not-so glamorous side of New York City startup story: the hustle, the disappointment, and the comedy.

Whereas most depictions of the startup life seem outrageous and opulent (think: HBO’s Silicon Valley,  The Social Network, The Circle) we wanted to show the scrappy dreamers who may or may not ever get their big break.

I started writing How Not To Make It in New York with Sydney Flint back in October 2015.  At the time we had a simple longline: A risk-averse creative woman, and her overconfident male friend attempt to fake their way into the NYC startup scene with their idea for a meditation app.

Which later resulted in the series’s opening narration:

This is the story of two friends, who leave their corporate jobs to startup a startup.

These first few episodes show the two main characters Kate and Jackson gearing up to quit their corporate jobs (at the yoga mat company NamaStacy) in order to follow their passion of starting a startup.  What is to come in later episodes is their journey sneaking into a local co-working space called The Garage where they attempt to take over the world with their gamified meditation app.




Kate – Kate Dearing
Jackson – Kenny Kline
Paul – Mic Daily
Narrator, Director and Editor – Chris Castig
Producer – Sydney Flint
Written by – Chris Castig & Sydney flint
Director of Photography – Annakeara Stinson
Sound – Hannah Rimm

Pros: Things that worked

  • The people! Everyone we worked with was so awesome and supportive. Thanks everyone.
  • Friends that let us use their living rooms and offices!
  • Planning: We did lots of planning (maybe too much?). We used Google Spreadsheet to draft our initial call sheet and script outline. Here’s our Call Sheet Template [Word] [Pages] in case you’d like to use it on your project.

Cons: Things that didn’t work

  • We didn’t use a tripod on some shots. We experiment with handheld cameras which resulted in some shaky shots.
  • I think it took us some time to find our stride. That’s just a natural part of the creative process I suppose.
  • If I shot this again, I’d shoot it more lo-fi and use the extra time to on character development.
  • Improvising scenes. For us, this resulted in lots of extra takes, lots of film being shot, and therefore we had an exorbitant amount of footage to go through in editing.

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Chris Castig Co-founder of Adjunct Prof at Columbia University Business School.

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