tl;dr: start with whichever language your best friend is most comfortable with.

When a person sets out to learn programming, two outcomes are possible. Either they succeed, or they give up. If you don’t give up, you’ll eventually succeed.

People usually give up on learning to code either because they get bored, or because it takes too much effort (i.e. they keep getting stuck). The former problem is easy to avoid: pick a language (and/or project) that‘s really interesting to you. Most people get this part right. The latter one is where I think people mess up — people fail to learn programming because they get stuck and give up.

With this in mind, I now tell all my friends to learn Ruby. Why Ruby? It’s not really easier to learn than, say, Python. The difference is that I know Ruby really well. If a friend of mine has a question about Ruby at 3 A.M. on a Saturday night, they can call me and I’ll probably still be able to give a helpful answer. …


Last year I organized HackMIT, one of the biggest hackathons in the world and the first ever hackathon of its scale at MIT. HackMIT had 20 organizers, 1,050 attendees and a $250,000 budget raised from over 70 sponsors. This post is based on my experience organizing HackMIT and input from other hackathon organizers.

To first-time hackathon organizers: Hackathons cost a lot of money. It’s important to make a budget in order to know how much money you’ll need to raise and to prevent going into a deficit. …

Ishaan Gulrajani

Cofounder @Watchsend (YC S13), ex-@HackMIT.

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