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We just had our largest Startup Weekend in Singapore. Over the weekend of 20–22 January 2017, 150 passionate startup enthusiasts, including participants, mentors, and judges, gathered at Google’s stunning APAC HQ to hack out their next company. The event was full of networking, the most genuine entrepreneurial trials and community gathering at large.

Pitching is one of the most important skill-sets you will need in order to succeed as an entrepreneur.

“Everything from creating the right environment to vocabulary to when to push hard, when to yell, when to be gentle, when to be motivational, when to challenge. If you’re an entrepreneur and you want to reach your maximum potential, or you’re an investor or someone who works closely with them, this talk is for you.”

– Nicole Glaros, Partner with Techstars Ventures & Chief Product Officer of Techstars

The winners of 2017 Startup Weekend Singapore, Team GitHip

The winners of 2017 Startup Weekend Singapore, Team GitHip

There isn’t a single winning structure to pitch your startup ideas, and that is why it is often seen as an art form. There are however, some tricks and ways of presenting that seem to create better impressions (people always remember how you made them feel!) for your audiences and communicate your ideas better.

Also Read: How to really make your pitch stick and story resonate

Here are some of my observations that differentiated the wining teams at Startup Weekend:

1. Ask the right questions

Asking questions to engage the audience in your pitch is one of the most widely used tricks yet it is seldom done effectively. Almost 50 per cent of the teams asked questions to kickstart their pitch hoping to hook audiences’ attention but only one or two teams used this technique effectively. Teams should use this only if they have novel facts, unexpected insights or strong emotional triggers.

Example: Did you know that pork bacon can be healthier than turkey bacon?

2. Humour and honesty

Both are mutually exclusive. Humour can be the hardest but done right, it can be one of the most powerful tools one can use to create emotions.

Whether your pitch is funny or sad, one must always be honest with everything you do! People (judges) will see right through any shortcuts, laziness and lies. Entrepreneurs are truth seekers (customer validation, the problem, features, economics)!

So be honest with yourselves. If you don’t have the answer, don’t lie or try to pivot the solution.

3. Prepare for the Q&A Sessions

You get as much time for answering questions as you have for the pitch, so us the Q&A time more intentionally. This can be strategically utilised to cover the extra stuff. Spend some time and try to come up with as many questions as possible from the judges’ perspectives. Be your own devil’s advocate.

4. Know where you stand

Positioning matrix always seems to aid, especially if judges don’t have direct experience with the industry you are exploring.

5. Demo prevails over everything

Show, don’t tell. If there is only one thing you can do, it’s DEMO (given that you have some sort of MVP).

Also Read: Bootstrapping your MVP: 5 contrarian tips for doing your side hustle

6. TAM, SAM and how you will get your share!

Most people do a great job of demonstrating the size of their markets and customer segments. However, only few put enough energy into explaining how they will get their share of the market.

The most creative team, The Woodland Whisky

The most creative team, The Woodland Whisky

Additional tips:

  1. The team member (who is also the user) who understands the pain should have the opportunity to share the problem slide!
  2. Nobody is CEO: Please don’t use CEO, CFO, CIO in your team slide! It is not the best sign at this stage of your startup. It doesn’t paint the right image of you at this stage since people invest in people.
  3. When tech stops working remember your time! Be ready to continue even when the slides stop working.

Congratulations to the organising team and the Singapore Startup community!


Oko is the Techstars Regional Director of Startup Programs, Co-Founder of Startup Mongolia, and a Design Thinking Practitioner.

The views expressed here are of the author’s, and e27 may not necessarily subscribe to them. e27 invites members from Asia’s tech industry and startup community to share their honest opinions and expert knowledge with our readers. If you are interested in sharing your point of view, submit your post here.

This article was originally published on Medium.