Startup Weekend Strategies

UPDATE  while I have the unfair advantage of knowing the winners of Nov @nycSW:

  1. GRAND PRIZE –  Waag.it
  2. Design –  Postd.com
  3. Tech –  CK Tech
  4. Biz –  Reading Buddy
  5. Microsoft – (same as GrandPrize)
  6. My Turnstone – JDecker, JBerman
  7. Mashery –  MotiveList
  8. CloudMine –  TaxiNomi
  9. Twilio –  ClosedCapp

CONGRATS to you all, great work, great weekend.  VERY tight call in the judges room!

I thoroughly enjoy Start-up Weekends.

Having been to 4 now (mentoring & judging two), I’ve generalized some strategies / approaches that seem to derive the most value from the rapid-paced 2 day hack-a-thons.

Like any event, haters are gunna hate.  The only major problem I’ve seen is misaligned expectations about the event (usually from first-time participants).  Come to SW with the understanding that:

  1. Your idea will (probabilistically) not be picked.  This is NOT a problem.  I can’t tell you how many sore loosers with pipe dreams of building the next $xB business over the weekend stomp away after the initial pitch session muttering how much they’ll show everyone.  Don’t be a sore looser – that’s not the point NOR the main value of the event.
  2. Don’t pitch the wrong idea.  Certain ideas are better lent to making significant progress over a weekend.  Apps, eTailers are.  New cars, new drugs aren’t.
  3. Landing amazing tech talent is (still) hard.  Just cause you bought at ticket, then made it through/joined a team, you’ll still have to fill out the team.  Just because someone says they are technical, doesn’t mean you should automatically take them
  4. Weirdness around equity is foolish and counterproductive.  Join a team, chalk it up as a learning experience, and make new friends.  Obsession about who owns what is a waste of time and shows you aren’t there for the right reasons.  It’s a WEEKEND.  You aren’t going to build anything worth fighting over that couldn’t be replicated in ANOTHER WEEKEND.  Do your best to be an awesome teammate and people will want to work with you in the future (when it matters).


STRAT #1:  Working on progressing a (real, existing) start-up.  Some people come to get free help on their existing startup.  This tends not to work for several reasons:  a) Other participants realize they are unlikely to really be a part of the team, just a mercenary.  b) Even if they do join, the end discussion is now a bit harder as there is more at risk.  The way this CAN work: carve out a small project within your general business that can serve as validation to the bigger idea or a specific strategy.

STRAT #2:  Fun weekend idea.  IMHO – the best strategy is to come with a bordering on silly / fun / potentially viral idea that could be thrown together quickly.  Why?

  • You can actually get a MVP up by the end, and things that work tend to do much better in the final judging
  • Use it as a pseudo-audition.  You’ll work with these people in a situation that roughly replicated some of the stresses associated with building a business.  Check out how you work with your teammates – are they potential long term partners?  A missed opportunity is walking around and briefly checking what others are making and how they are working.  Are there people on other teams that are rockstars that you can keep in touch with?
  • You’ll enjoy your time if it is fun and something that the other participants will want to try.

STRAT #3:  From scratch -> big, complicated biz.  Given all the other comments, it should be obvious why I’m not such a fan.  Unclear if you can make meaningful progress or validation.


Misc. general advice:
  1. Be proactive and energetic.  In my first SW, I had one of the top ranked ideas in the initial pitch session.  I then sat back expecting it to rain programmers to help.  It didn’t.  The girl whose idea ranked near the bottom ran around the room telling programmers that they walked on water and she was moses…Guess what?…She had a the largest team of good tech talent that weekend.
  2. Use the service providers and mentors.  SW usually attracts some great mentors, judges, service providers ready to give you time and even help you build your product.  Please, it merits repeating: USE THEM.  This access can be invaluable.
  3. Be transparent about your expectations.  I’d start with something like: “that you for working on this idea with me for this weekend.  Let’s have some fun and focus on pushing it as far as we can.”
  4. Remain open to suggestions and critiques.  People just don’t want to work with you if you come across as a dominating figure, convinced you’re always right.


…and props to my friends at CloudMine for their newly announced Gold Sponsorship!  They help you with the backend to quickly build your mobile apps – use away!

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Posted on November 18, 2011, in Venture & Start-ups. Bookmark the permalink. Leave a comment.

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