How to hack a pitch competition

BlueChilli > Blog > Blog > How to hack a pitch competition

This week a wide range of Sydney’s early-stage startups were on stage at ATP Innovations for the finals of the Sydney Challenge Cup, part of Washington DC incubator 1776‘s global search for the most interesting startups in Education, Energy, Health and Cities.

It would be un-Australian if BlueChilli wasn’t there 😉 Linda Glassop, founder of one of our most promising startups, Comwriter made it through to the finals and landed the Runner-Up position in the Education category against an exceedingly strong field of competitors at all stages of the startup journey.

Linda Glassop


I was one of the judges in the Sydney Challenge Cup and had to declare my conflict of interest in being asked to judge a startup in which I had an indirect financial interest (via BlueChilli) but it wasn’t my only conflict of interest (via Startmate I’m also about to become a very minor shareholder in drone data startup Propellor Aerobotics).

Indeed, the 1776 folks remarked upon how unusual it was for their Challenge Cup judges to have so many conflicts of interest but Sydney and the Australian startup scene in general is still so relatively small, even compared to the startup scene in Washington DC. After all, what Australian startup accelerator would have the money and resources to mount something like the global Challenge Cup, visiting 16 cities around the world and bringing back 40 startups all expenses paid, to compete in for USD650,000 in prizes? We’ll get there, but we’re not in that league yet.

Challenge Cup judges deliberate



Pitch competitions have their shortcomings — to some extent even the best-organised events are entertainment for the audience, publicity for the organiser, grist for the media mill, and easy diligence for investors. The needs of the startups involved are important, but sometimes aren’t the highest priority.

But even in Australia pitch competitions seem to get bigger and richer every year, and like them or lump them, it seems they’re here to stay. How do you optimise your chances of succeeding?


You’re all individuals, except you’re the best

Organisers usually  keep the criteria for choosing the pitching startups from the online applicants close to their chest; for good reason — organisers know a good pitch competition is to some extent entertainment, and good entertainment requires variety. Every organiser wants to make sure they have a couple of way-out-there moonshot ideas, a couple of likely-to-blow-it-in-a-funny-way pitches, a couple of earnest-hard-workers-with-real-metrics, some revenue-unlikely-but-social-benefit-huge feel-good stories, and one or two ‘pitch stars’ — startups and founders already in the limelight, already known for doing a killer pitch.

Recognise at the outset what category you and your startup are in, and then make sure you’re the best you can be in your category. There’s nothing more likely to fail than trying to be the pitch star when in reality you’re likely to blow it in a funny way. Don’t try to be the founder with the early traction metrics if you’re a social enterprise and are unlikely to ever be a $1B business. Celebrate what makes you unique, but make sure you know which group of unique people you belong to 😉


The pitch competition begins long before you’re accepted

When considering applicants, evidence of a broad social footprint tells the organisers they may sell more tickets or get more free attendees if they include you in the roster. If there’s a best time to invest in building your presence on social media, it’s a few weeks before entering the big pitch competition of the year. If you’re accepted, use your social media connections to promote the heck out of the pitch competition. Does everybody know yet? Are you encouraging them to get a ticket? Are you giving them reasons to share it with their friends and colleagues? Because if your audience isn’t full of your diehard fans, which startups will they be tweeting about during the competition? How are you going to get the biggest roar of applause at the end of your pitch? No, applause doesn’t determine the winner of a pitch competition, but the startup with the quietest audience reaction definitely doesn’t win.


Be prepared, and not with your investor deck

Pitch competitions are a kind of theatre, and they are a very different kind of theatre to an investor pitch — as different as rom-com is from police procedural. Investors ask you to work off a standard problem/customer/solution/market potential/team/ask template because they try to keep emotions out of their investment decisions. Pitch competitions are all about eliciting emotions, and the best way to do that is to bring your investor pitch to a pitch competition.

Pitch competitions almost always run to a very strict schedule, and you’ll get dragged off stage if you run over time, so in-between trying to elicit emotions and win over an audience, you need to be incredibly disciplined and rehearsed to pull it off successfully. Be brutal about what stays in and what goes from your pitch competition pitch, right down to leaving out information that would ordinarily be considered essential in other forms of pitch.

Can’t explain your market opportunity without a very detailed diagram? Detail kills emotion dead as the rational mind swings in to decode the meaning and pushes the emotional mind out of the way. Can’t explain your product without a detailed description of the features and technologies you’ve employed? Leave all that out and concentrate instead on the benefits of the technology. Describe the better world that is coming for customers of your product. Use “imagine if” not “In respect of”.

Allow 15-20% more time to pitch on stage than it takes you to deliver the pitch in front of the bathroom mirror. Walking across stage, correcting a laptop or Powerpoint problem, momentary spotlight blindness or waiting for the audience to finish laughing at your killer lines — all this takes time you don’t need in front of the mirror. Better to finish 30 seconds before the timekeeper’s bell than risk not being able to deliver your killer finish.

And have a killer finish. Not “So we’re Startup X and if you’re interested, come talk to us at the break”.


Dos and don’ts

  • Don’t walk into the beam of the data projector. Don’t walk anywhere except onto the stage, and then off the stage at the end.
  • Don’t turn to look at the screen. Don’t ever break eye contact with your audience. If necessary use a laptop on a lectern.
  • Don’t use a smartphone as a memory aid or slide controller — you break eye contact and they are too unreliable when you’re under stress.
  • Don’t ever express a negative opinion of any kind about any other team or founder. Nobody votes for anyone who might be a sore loser.
  • Do vary the pitch, pace and projection of your voice to increase the drama of your narrative
  • Do use relevant physical props — nothing breaks the tedium of endless Powerpoint slides better than a relevant physical prop (unless you’re pitching in an IoT event!)
  • Do network extensively with the judges, winners and influential audience members afterwards. That photographer is taking photos — are you in the shot? Will you be in the social media after the event? Will the journalist interview you even though you didn’t win because you were so interesting to talk to during drinks? Be the last to leave, and help the organisers tidy up before you go. Everybody likes a helper, and there will always be another pitch competition!

Thanks to the 1776 crew for having me as a judge for your Sydney Challenge Cup and I hope to find a way to join you in Washington DC for the global final!