What happened when Investors had to Pitch to Startups

This past week I attended a large gathering of entrepreneurs from around the world here in Taipei, Taiwan, where the hosts did something rather unusual: They made the 30+ angel investors and venture capitalists pitch to the startups. 

In this total role-reversal, the investors - extremely smart people who evaluate up to hundreds of pitches a year - now had to get onstage and be evaluated.

Their task was simple: to pique the interest of the startups in attendance, so they'll come and meet with the investor to talk potential partnerships.

The tough part? Each investor had only four minutes.

So how did they do?

Now, I know you may be thinking: "It doesn't even matter how they did, they've got the money! Startups would still flock to them!" 

Yep, you might be right. But most of us don't have $ millions lying around, do we? So let's evaluate their performance as if they really had to compete for the audience's attention and time. Because that's the reality for... well, everyone.

So in light of this, how did they do?

Um... let's just say the investors experienced first-hand how difficult it is to speak clearly and engagingly in fewer than five minutes.

Below I recap their struggles (and also successes), and then offer three practical tips on how to pitch more effectively.


Where they struggled

1. They fire-hosed the audience with facts

A majority of the speakers apparently thought they had 30 minutes and not four, because their slide count often ran into the 20s.

As a result, many were midway through their materials when the MC yelled "10 seconds!" And in their stunned state they had to skip to the last slide while muttering "ok I don't have time for this, or this, or this... so anyway, in summary...", before quietly shuffling off-stage.

Now, the investors are obviously highly intelligent and knowledgeable, but it's precisely the intelligent and knowledgeable who are most prone to this mistake.

People who know a lot often think that dishing more facts = providing more value. But facts alone aren't actually meaningful. Facts only become meaningful when you weave them into a compelling story that's relevant for people's lives.

2. Their slides were more crammed than the subway at rush hour

It was stunning to see speaker after speaker cram ten lines of 18-font text into their slides. This would be bad enough with a small crowd and/or a giant screen, but this happened to be a large room with a small screen. 

I took the below picture from near the front, and even from there the slides were tough to discern. So from the back you probably had to be Hawkeye.


What's more, the small screen was made up of four even smaller screens, with their frames visibly running down and across the combined screen, effectively blocking any text that happened to fall on them.

Love the outfit. The screen? Not so much

Love the outfit. The screen? Not so much

With so much information on each slide (and no secondary screen in front of them), many of the speakers couldn't remember what to say without constantly turning around to look at their slides. A few even stayed facing the screen the whole time. 

And this really hurt their connection with the audience. 

No connection = no persuasion.

3. Their slides were unfit for the purpose

Bringing 20 slides for a 4-minute pitch kind of gave this one away: Most of the slide decks were clearly intended for other occasions and other audiences.

One speaker even announced this. He stepped onstage, looked at his slides and seemed confused. Frowning, he said: "Uh... this is actually an old version of the slides." Then he said this a second time, after the next slide also flummoxed him.

Sure, it might've been the assistant who screwed up. But guess what? 

Nobody cares.

It's your job to make sure everything's properly set up BEFORE you get on stage. And if you're already up there when you realize it's the wrong deck? Roll with the punches, don't punch yourself by announcing the screw-up.

If the slide deck is 70%, 80% right, then deliver the right parts.

If it's 0% right? Well... black out the screen and just give it to them straight.


Now that we've seen what NOT to do, how do we avoid these mistakes and deliver a much more effective pitch? Here are three tips.

1. Know your goal (and your audience)

Judging from the way they presented, the investors must've thought the goal was to provide information. And to be fair, the organizers probably asked them to describe several aspects of their funds.

But here's the thing: the goal of a pitch is never to just provide information.

Rather, the goal is to make the audience remember and act. In this instance, it's to get the startups to remember what makes your fund special, and to come and talk with you about potential partnerships.

In order to do this, you have to know your audience. What are they into? (Are you talking IoT to a bunch of biotech startups? What's IoT anyway?) What do they already know about you? What do they want? You have to know them to move them.

A general purpose informative presentation simply won't do the job.

2. Edit mercilessly and focus relentlessly on achieving your goal

Now that we're clear on the goal - to make the audience remember and act - craft your pitch for the singular purpose of making that happen. 

Edit without mercy and focus relentlessly. Anything that does not help you achieve your goal must go.

Think about it: for them to get excited about working with you, do they really need to remember your mission statement, company history, staff biography and more? Probably not, right? Yet speaker after speaker recited these facts robotically.

Truth is, they'll forget these details the moment you step off-stage.

If you want them to remember, don't give them ten things. Give them one key thing that sets you apart from every other competitor (This is crucial even for longer presentations, let alone a 4 minute pitch among 30 others). Edit out anything that's unconnected to this one key thing, and structure the remaining material around it.

If you want them to take action (to approach you about working together), make sure your one key thing is exciting. To find this, rehearse your pitch with a few different audiences. The part that gets the most people to ohhh, ahhh and applaud - that's your one thing.

One wow idea beats 100 meh ones, every time.

One of the best speakers did precisely this. He centered his entire pitch around one thing: the exciting future that technology makes possible.

  • He opened by describing this future in alluring detail
  • Then he said: "Our mission is to make this future happen."
  • Then he described how his fund does this by nurturing breakthrough tech companies

It was focused, compelling, and memorable - and under four minutes.

Naturally, you must extend this ruthless editing and focus to your slides as well. Show only the essential stuff that helps the audience remember and take action. If you're putting your entire eight-sentence mission statement and vision onto the screen, then these better be some memorable and exciting stuff.

Keeping your slides slim and simple has another benefit. An investor who did very well had exactly two slides: the first a title slide, and a second slide with a simple, three-piece graphic that illustrated how the fund operated. And this liberated him: without having to constantly turn around to recall the 100 bullet-points, he was able to face the audience and engage with them the entire time. And he engaged 

3. Scout the venue, prepare for the worst

You might've thought that the conference organizers bore a big part of the responsibility for the speakers' struggles too. They should've set up a bigger screen, installed secondary screens to help the speakers, etc. And you'd be right, the setup could've been better.

But blaming the host does nothing to improve your pitch performance, does it?

The one person most responsible for your performance is you. 

You're the one who must scout the venue - the room, the screen, the lights, etc. - and then choose the most appropriate way to present given the environment.

And if somehow you have no way to learn about the venue, prepare for the worst. 

As Andrew Dlugan of Six Minutes wrote: "Your slides are rarely viewed in optimal conditions. The screens are small. The rooms are large. The projectors always seems to be a little dimmer and a little blurrier than you would like. And someone in your audience was up late last night. Or suffering from allergies..." Design your slides for the worst conditions you can imagine.

Then go one step further: design a version of your pitch where you don't get to use slides at all, where it's just you, your case, the audience and four minutes.

Had the investors done this, they wouldn't have been caught off-guard by the less-than-ideal conditions (or the old slide version). They might have calmly asked the host to turn off the screen, and focused on building a connection with the audience.



In Sum

Pitching is hard. And as this unusual session showed, years of critiquing other people's pitches don't necessarily mean you can do it well yourself.

Pitching well requires that you focus on the right priorities - your goal and your audience - then carefully tailor your content and slides (if any) for them.

To make a big impact in a few minutes requires big work. No way around that.


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