This was originally posted on in April 2011.

Learning how to pitch an idea effectively is an enormously useful skill that they never really teach you at university or at school. It’s the kind of thing you learn from personal experience. There are many articles providing formulae for pitching or presenting your startup, but few about the principles behind those formulae.

Back when I was still at university, I spent a whole Easter holiday building a prototype for a chemical spot auction site. In this I made many mistakes (among others, I started by building an elaborate user management system rather than focusing on the key dynamics of the auction process), but the real killer came when we pitched it.

I was working with a guy who was just as inexperienced on the business side as I was on the programming side. His father happened to be a top-level executive at a big chemical company, and so through this huge foot in the door we got an entire hour booked to pitch this product to a panel of senior people at this blue-chip company. I remember sitting on my bed and naively thinking of how we would spend the billions of dollars a year we were undoubtedly going to make from this surefire deal.

Golden opportunity

Was this meeting a golden opportunity, or just a formality to please the boss? I don’t know. But what I do know is how much we screwed up on whatever this was.

On the technical side, everything fell apart. This was the day the ILOVEYOU virus hit, and all the corporate networks were down. Our site was unreachable. I had not thought to have it running locally on the laptop so that I could demo it without internet access (über-rookie mistake). When the server finally became reachable again, the meeting was over, with only one sympathetic soul staying behind to have a look at it. I felt mortified. My entire purpose had been to build this prototype for the demo, and that had completely and utterly failed. Two months of work for nothing.

The real killer, though, was our pitch. To my partner’s credit, I must say that he handled the whole thing himself, and certainly did it better than I would have – but it was still a disaster, and unlike me, he had no technical difficulties to blame. As I watched the pitch unfold and observed the audience, I felt my heart sink further.

We had an hour booked. Here’s how my partner structured the pitch: for the first third of the presentation, about 10 minutes, he talked about how startups were changing the world (which was interesting timing, considering we were two months into the dot-bust); the second third focused on how B2B was a growth area and predicted to make many billions of dollars over the next few years; finally, the last third talked about the customer, and repeated things they knew about themselves, and finally maybe one or two slides were about the product we were pitching and what problem it would solve for them.

So, in short, out of about 30 minutes of presentation time, only 2 minutes answered questions that the audience actually cared about.

I can’t remember exactly what sort of questions there were, but if I recall correctly, the “panel” took the excuse that the prototype wasn’t working to leave before the hour was out. At the time, it seemed that they left because the prototype didn’t work, but, in hindsight, I’m pretty sure they left because they hoped to still be able to do something productive with the little bit of time left in that wasted hour slot.

Hindsight 20/20

Fast forward 11 years later, and I still remember this story, I can still bring back to mind the feeling of sitting through that disastrous meeting, and the insights I got from it. I’ve now pitched hundreds of times, various different ideas. I’ve watched our Woobius interns fumble together a pitch with no preparation (they did better than I did back in 2000). I’ve pitched at competitions, during sales meetings, sales calls, networking meetups, and so on. I even spent two weeks cold-calling 20 people a day to pitch them my “voice on the web” startup (I hate cold-calling).

But the most important lesson about pitching, I learned in this very first pitch:

1. You have to tell people what they want to hear.

With this, I don’t mean that you have to make up stuff. What I mean is, out of the vast infinity of facts at your disposal, you need to ruthlessly zoom into the small handful of key points that the people in front of you care about. Back in 2000, our audience didn’t care for startups, B2B, or well-known factoids about their company. In the context of this meeting, they cared about two, maybe three things:

  1. Are these guys pitching something I should care about?
  2. Are they credible?
  3. (probably) Can I get out of here sooner without pissing off the boss?

The whole pitch should have been focused on answering these questions quickly, smoothly, effectively. This could probably have been done in 5 to 15 minutes, with most of the hour left for answering questions and building up our credibility further.

Since then, when pitching anything, I always first try to figure out what the “audience” cares about, what they want to hear. For example, your pitch to a customer and your pitch to a VC must be vastly different. The VC cares about whether you’re building a startup worth investing in. The customer cares about whether you can solve their problems. Your friends care that you’re doing what you like and not heading for disaster. Your parents care that you’re not wasting your life chasing unicorns and rainbows. This brings us to the second most important lesson of pitching:

2. You have to know who your audience is and understand them before you can pitch them effectively.

Any pitch where you don’t know who you’re talking to is a shot in the dark. It might hit something, but who knows what that might be? So, before answering that oft-asked question, “So what do you do?”, make sure you first try and figure out what the other person does.

Finally, there’s a third critical aspect of pitching that we failed at, back in 2000, that I’ve become more aware of as the amount of sales work I do has increased.

A long time ago, Aristotle wrote about rhetoric that it was “the faculty of observing in any given case the available means of persuasion”. Pitches are a minor application of rhetoric. They do not exist in a vacuum. You don’t pitch just for the pleasure of it. To be described as “good” in any way, a pitch must have a purpose, something you’re trying to achieve, and a “good pitch” is one which achieves its purpose.

Let’s say that, against all odds, the chemical company’s executives had liked us and liked our product. What then? They would naturally have asked, “So what are you looking for?” And the reality is that, naive as we were, we hadn’t even thought of that before going into the meeting.

So this is the third most important lesson of pitching:

3. In order to deliver a successful pitch, you have to know what you want to get out of it.

There are many things you can honestly want out of pitching: customers, funding, esteem, friendship, rapport, advice, insight, introductions, and so on. Depending on what you want, your pitch will need to change. You don’t pitch for business in the same way that you pitch for advice or to build a relationship. Thinking about what you want ahead of pitching is not just helpful, it is essential in order to get anything out of it.

In conclusion

Ultimately, there is one great teacher of the art of pitching: practice. This is why entrepreneurs get very good at pitching: they do it all the time. But hopefully, these three principles can help make your practice more deliberate:

  1. Tell people what they want to hear.
  2. Know who you’re pitching so you know what they want to hear.
  3. Know what you want out of your pitch.

Thoughts from 2017

This article has aged perfectly. The principles within it are evergreen – I would argue they were as true a hundred or a thousand years ago as they were today, and so they’re likely to have some lasting power. I now have even more experience of pitching, and of being pitched (as a seed investor) and all of it supports those straightforward points which so many pitches fail at.