I now write on Medium here. You can find some of my old essays below.

How to Fail at Presenting to Hackers

I don't usually like pointing out others' failures (I prefer to focus on my own), but one particular demo by a startup at this past Tuesday's New York Tech Meetup is particularly instructive in How to Fail at Presenting to Hackers. A brief guide to failure, courtesy this demo:

Expect your connections to high profile individuals will build credibility: Exceptions include Richard Stallman, Cory Doctorow and probably Steve Jobs. Don't rattle off a list of Silicon Valley investors and expect us to be impressed. We'll just wonder why you're not showing us a product.

Put the conclusion before the story: It's fine to say that you're raking in cash or you have amazing clients, but do it after you show us the product you used to get there. Otherwise the story seems backwards and you seem full of yourself. Explain how something was built from the ground up, gained traction and eventually convinced people with money to buy your product and support you. That's a story that resonates with hackers.

Ignore the allegiances and perspectives of the audience: This is more of a general presentation rule, but this company couldn't have blown it worse with a hacker crowd. For instance: if your product has applicability to hiring for both Fortune 500 companies and early-stage startups, don't show examples of how Fortune 500 companies can use it to gain leverage over potential employees. You seem to be enabling a corporate culture that your audience is rebelling against.

Send someone who isn't a cultural fit with the audience: I'm sure your company has hackers. Even an executive CTO or VP of Engineering. Send them, not the business development executive you just recruited out of an investment bank.

Like any audience, presenting to hackers isn't hard. But just as it wouldn't be a good idea to wear jeans and Birkenstocks when making a presentation to the board of a Fortune 500 company, pitching a crowd of hackers requires a level of understanding and respect of the group's culture. Anything less is simply going to waste everyone's time.