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thecoolisnfinite · 9 years ago

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14 Tips on How to Crush a Hackathon. (Bonus: video of my pitches)

I’ve won 5 hackathons and wanted to share some tips for what I’ve learned. Here’s a guide to getting the most out of a hackathon along with embeds of most of the actual demos I gave. Enjoy!

14 Tips on how to crush a Hackathon:

(1) Start with the Pitch

Most hackers don’t realize it because they are so focused on coding but the pitch can easily be 95% of your grade. It is often an afterthought, something a team spends a few minutes considering well after 18 hours of programming. But the reality is you’re often pitching to VC types and “idea” people - not coders. And never underestimate the general audience (more on that later). So realize that no one gives a shit about the backend technologies. Like anything in life, you have a very limited time to impress the shit out of a group of adults with blackberries and short attention spans.

It’s always an emotional sell. A good pitch of a smart idea will almost always beat a meandering pitch explaining the best tech. I met someone at a recent hackathon who was perplexed: “Doesn’t the team with the best developers basically win?” No, not by a longshot.

Start the hackathon with the pitch. Nail it, test it on 10-20 people (by phone, skype, whatever) and learn what “works”, what sucks, where a joke works or doesn’t work, and crucially, what your idea actually is and if it’s captivating.

(2) Know your time limit

If it’s a decently run hackathon, the MC will strictly enforce a 60-second or 2-min time limit. I’ve been to other ones where they allowed people to go on for 10 minutes - those are generally run by first timers who are scared to pull hackers off stage. My favorite enforcement of this rule was at Music Hack Day (2 minutes) where the organizers assembled a handful of non-judges to sit in the front, and at 2 minutes, they’d all just start clapping - which triggered the room to applaud, and that gently cut the presenter off. It worked great.

60 seconds may not feel like much time, but hey, if it’s enough to boost a car, it’s enough to convince someone to tweet your URL or plant a seed in the judges’ heads that will last through the next few presenters. If you’re not prepared, 60 seconds, 2 minutes, 10 minutes - it all sucks.

At Music Hack Day, I watched the second team present. The guy spent nearly 60 seconds thanking everyone for the opportunity, he had a lot of fun, yadda yadda. He literally didn’t explain their (absolutely amazing and technically awe-inspiring) hack. Then time was up. They didn’t win. They did, however, have one of the best pieces of technology in the room and with the right pitch, they definitely would have placed or at least enjoyed a lot more attention.

Docracy (winner of TechCrunch Disrupt Hackathon 2011) is a great example of a flawless pitch. I remember watching them go on first or second last year. Their service was objectively pretty useful and neat, but there were lots of other cool ideas too. The difference was that they gave a perfect pitch. They had obviously practiced. It was clean and simple, crammed the whole idea into 60s and smoothly articulated the value and why they rocked. They won. Months later they raised $675k.

(3) What’s in a pitch

Hook . Tell an interesting story. Remember that your hack is 1 of 100. It’s boring as shit unless you tell a cool story and give a yawning, texting judge a reason to perk up and care.

Pain : Ok, great story, now weave it into the larger pain everyone has. Again, answer: Why do I give a shit?

Solution - ie, your hack. What did you build that makes that pain go away and is insanely entertaining at solving it. Just show the most compelling stuff.

Leave them wanting more : Finish this sentence: “This is the best fucking app you’ll see all day because…” Or “You will tweet this because…” If the rest of that sentence isn’t authentic, convincing and clear, then people are just waiting for you to get off stage and not in “I have to tell friends about this” mode.

(4) Branding > Technology

Might not seem too important, but come up with a catchy name. The easiest way is to be popular by association. Pick something already popular that is on people’s minds and tie your hack to that. That’s what we did with Poorsquare. It was originally going to be called “freebiecrawl.com”. But then, just as I was about to name our database, it smacked me: POOR SQUARE! Seconds later, knowing the Occupy Wall St demonstrations were going on, I came up with the slogan: “I am the 99%. Show me some free deals.” That hook to national news turned out to be incredibly helpful in being more “tweetable”. Just saying you’re showing deals because you’re cheap is pretty dull. But showing deals because you’re part of the 99%… that’s branding!

(5) Go live or go home

If you’re going for viral in addition to a win, I would opt for a web application that is live when you present. Building an iOS app may seem cool, but it’s not very “tweetable”. In other words, if no one can play with it immediately, there’s no way to capitalize on any immediate success or publicity. Chances are the audience and their followers aren’t going to share it and your product will be dead by the end of the day.

Poorsquare went viral (50+ tweets per hour, 19 major publications and blogs picked it up). It was only because the site was functional. Our first order of business for the hackathon was to buy the domain, get it set up and push our code immediately. I literally edited PHP files directly on the server - no git, no testing, just saving. Playing with fire? Yeah, but who cares, it works.

(6) Work backwards

This took me a while to learn and is an extension of (1). Work backwards. Just hardcode everything and run through the pitch early on. Most hackers spend way too many hours on bullshit stuff that doesn’t make its way into the pitch anyway and then forget about super important, highly visual stuff that the pitch will rely on. The earlier you practice your pitch with the site itself, the more efficient you’ll be at nailing down the parts that matter. “Make this button do this.” “Put in some fake data here so it works, then we’ll populate it with the foursquare API later.” Whatever. You’ll quickly find that your demo won’t even get into the 3 features you spent all night coding, so why the f did you waste your time on them? Ideally, you’ll be doing pitches every 1-2 hours - agile-like - and reassess what the priorities are.

(7) Code only what people see

No one is looking at your code. No one even asks if the hack was actually done during the hackathon! No one gives a shit. Scaling doesn’t matter. Clean commented code doesn’t mean shit. (Amazingly, no one will even test you to see if your app works or, incredibly, if you just outsourced it to a dev team the month before. It is an unspoken rule that you did the work there, and honestly, it defeats the purpose if you roll in with something you’ve been building for 6 months. Not to mention it would be pretty obvious.) But the point here is that you shouldn’t waste time on superfluous shit that won’t make it in your (reasonably paced) pitch.

(8) Iterate your idea beforehand

Hash out your idea in advance. I recommend pitching your hack idea to a few dozen friends and see what their responses are. What do they find most compelling, if anything. What’s lame. Practice the general parts of the pitch long before the hackathon.

(9) Know the judges

If you have the time, it pays to understand who you’re pitching to. What are the judges interested in, what’s their focus, what are they tweeting about this week. All of that can be incorporated into your pitch and demo - use their names in the test data. Tell the demo story through their eyes. This is a classic case of “you have 10 seconds to grab my attention before I look back at my Blackberry.” If you call a judge out by name or mention their company or something they’re already interested in, you have that much of a better chance that they’ll remain interested.

(10) Be memorable / “why should I care”

You are one of many demos. Why is your shit better than the next person’s shit? Seriously. It may be cool but so is everyone’s hack. The burden is on you to be memorable. What are you going to say that stands out. Put another way, what are you going to say that’ll have the judges and audience continue to think about you even after the next several demos go on stage?

(11) Exposure often > winning

Winning isn’t everything! Poorsquare went viral and it had nothing to do with winning. (We were watching tweets start to blow up immediately. In fact, most press never mentioned that we won.) Recall that “group.lyl” didn’t win TCD, but did go on to become GroupMe. If your hack resonates with a few influential people in the room, it can spread with or without the judges’ blessing.

It’s a way to get 2 minutes on stage and be the center of attention. You get to talk directly to influential tech folks. Not a ton of people get this opportunity.

It’s a great way to hone your pitching skills and get comfortable with public speaking. Can you wow the audience? Most of the wow will come from your words, not your hack.

Try some jokes. Be different. Misha Ponizil gives the best pitches. Not a lot of people can pull that off, but you might as well try.

(12) Keep a hack journal

I think of hack ideas all the time, so I keep a hack journal. I jot down a 3-4 sentence pitch about what the hack would do and then if I’m feeling inclined I’ll describe it in more detail. That’s the list I draw from when I come to hack. I have my next 5 hacks already sketched and I’m always looking to see if anything like these ideas are already on the market. After all, they solve a problem I have, so if I can find a ready-made solution, hell yeah.

The trick here is to throw 5 or 10 of these random ideas at a bunch of friends and see what they want built immediately. That’s usually a good indicator of a good idea. Not great or revolutionary, but good enough to maybe get a few people to use it at first.

(13) Track your press

If you find you or your hack written in a blog or in some press, stay organized! After poorsquare I tracked down every blogger/journalist who wrote anything about us and said “hey, I’m the guy who did poorsquare, let’s stay in touch” and they all wrote back. Tech reporters are crazy busy so you want to use this as an opportunity (while you’re hot and somewhat recognizable) to connect. Then when you have an update, a new project or launch a startup, you can reach out easily. (I added them all to Google contacts and tagged them ‘poorsquare journalists’ so on a future release I could send a mass email in one step. Staying in touch with the press is something most techies don’t really think about. Right after your pitch is when you should think about it the most and ride that wave!

(14) Enjoy

I love to dream of products and build them. A hackathon for me is a way to unwind and relax the way you might with a book or on a vacation. It doesn’t have to be stressful - it’s free food, hanging out with cool, super smart people who all love to think of ideas. There is nothing I enjoy more than brainstorming ideas with creative people who know how to build the shit they’re talking about. I will take that over football or a trip to the Hamptons any day. Although now that I think about it… a hackathon at the beach?

You made it this far. Want to see some of my pitches?

* = win

Valentun.es @ Music hack day (Feb 2011) This was not my idea, nor my pitch, but it was my first hackathon and taught me a lot. We won the prize for best use of the Musixmatch API.

Cnvrge.com @ TechCrunch Disrupt (May 2011) I coded this myself through the night and presented an unprepared pitch. It was a blast and I continued work on Cnvrge, running a few events with it. Twilio even wrote a blog post about it. Here’s my (not so great) TC pitch.

* Poorsquare.us @ American Express “Reinvent Local” (Oct 2011) I coded the backend, Pinzler did front. We were selected by a group of small business owners and won $2,000. The hack went viral almost immediately and was featured in a ton of press.

* BandsNearby @ Music App Hack Day (Feb 2012) Demo. We won two prizes: from McDonald’s and State Farm Insurance.

* GCal integration into FareShare @ Google Apps Hackathon (Dec 2011) Won a RC helicopter.

* Spotify/Coke invite-only hackathon, codenamed “Placelists” - Six teams. We won. Here’s a video. And blog post.

* PoachBase.com @ Techcrunch Disrupt NYC 2012. Second place. Here’s the pitch filmed from the crowd, and from TCTV.

Kennedy on the left (part of Team Poachbase) and Jon on the right (part of Team Thingscription):

Who Do We Eat Next? @ Comedy Hackathon. An ok pitch/idea in a sea of amazing pitches by hilarious comedians.

Other pitches:

1. 2x presenter @ NY Tech Meetup for VocabSushi

FareShare (which was also at TechCrunch Disrupt 2010 Startup Alley)

2. Demo day at Blueprint Health for Patient Communicator (now dead)

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