Some humble advice on pitching your startup

[Take one]
Aaron Harris, partner at Y Combinator, recently published a short, powerful list of advice on how to pitch your startup (to investors).
I’d like to complement that and add my humble suggestions.

Hey, wait a minute… Look at the two sentences above. Do they capture your attention? Do they PUSH you to keep reading? Not much.
Let me start again.

[Take two]
Do you need to pitch your startup in 48 hours? Do you suck at pitching? Keep reading, I’ll tell you how to master the art of presenting in public in just a few hours.

[Take three]
I’ve been a public speaker more than 600 times, in front of audiences from a few dozen people to several thousands, across every continent except for Antarctica.
I’d like to share my secret with you.
You can dramatically improve your pitching skills in just a few hours, by following my advice.

[Take four]
Blah blah blah.

There are many ways in which I could have started this article. I’m sure that among these three, you have a favorite. How you start is very important.
And finding the right way to start is not easy. It requires work.

Rule #1: find a hook

If you’re a guy sitting at a bar and want to approach an attractive lady, the first thing you’re going to say is going to make a difference.
If you simply say: “Hi, my name is Simone, what’s yours?”, it might not work. If you ask something unexpected, instead, you will definitively have her attention, at least for a minute or two.
When I go to meetings and meet new people, I give them my business card only at the end (unless I’m in Asia), when they might have a reason to remember me and save my contact details.
When you pitch, you need a hook to make people interested in what you say; use something that forces your audience to pay attention to you. It’s up to you to decide what, and it depends on your personality, your product, and the audience.
If you want to get an idea of a few hooks, just go to a bookstore, pick a dozen books, and read the first page of each book. That’s their hook, and you might be surprised how different they are, and how effective they are.
Or, go online and watch the first 30 seconds of a few TED talks, and try to observe how they “hook” you, or not.

But even before rule #1…

Rule #0: get your story right

I can easily imagine people reading Rule #1, and then opening their Powerpoint or Keynote software, and start writing slides.
Wrong. Slides come last.
First, you need to narrate your story. Still, your story needs Rule #1, or the hook. But then you need to decide what you want to communicate.
Build your story.
Write it down. You can use pen and paper. This is what screenwriters do, before even starting to tape the first scene of a movie.
What’s that thing that you desperately want to tell? I know, it’s about your startup, but what? I know, it’s your great service, but how it affects people? I know, you’re behind it, but what makes you special? What makes your startup a great story?
Or… What makes you terrible? Imagine this.
“We are four founders from Bulgaria. We are decent programmers, but nothing special. We have no idea how to run a startup, since we’ve just graduated from college. We don’t have great ideas, so we’ve decided to build something simple, but powerful.”
Well, at least you’re different. People could still think: “they’re just playing humble”. Heck, if you’re not a GREAT startup, maybe you’re cheap, and in case I can convince the other GREAT startup in which I invested to acqui-hire you for a few dollars.
You never know what’s in the mind of an investor.

Rule #-1: allocate the time, and use it wisely

Even before Rule #0 and #1, the most important rule is to allocate time to work on your pitch. The more time you have, the more you can invest it into learning how to properly pitch.

If you only have a couple of hours before your pitch, there’s very little you can do. No time to read one of the excellent books by Duarte; and in this case Aaron’s list might be the best thing to follow. And, by the way, for an investor you are losing points: you were not able to organize your time wisely, and you disregarded an aspect of your business (preparing the pitch) which has its importance.
If you have some extra time, like 4–5 hours, read my advice here — it’s merged with Aaron’s list down below. This is what most startups do: they spend 1,000 hours on the product, and 4–5 on the pitch, ignoring the fact that 990 hours on the product and 15 hours on the pitch would have produced a better outcome (usually).
If you allocate a lot of time, like 15–20 hours, read some books and do a lot of practice, either in front of a mirror, or a few friends.

Rule #2: rehearse

In any of the above cases, rehearsing your pitch at least 3 times, in full, in front of a mirror or your cofounders, will dramatically improve your outcome. It shouldn’t take long.
After the first time or two, try to record your pitch, and watch it afterwards. You will not believe what you see. A smartphone would suffice.
You can even try to do it blindly, and see if you can still remember it.
It would also help you overcome fear of public speaking.
The mirror helps you work on your body language.
The full rehearsal helps you memorize the most important passages.
The blind pitch helps you overcome your fears.

Let’s look at our rules so far (and let me number them properly), and then add a few more.

Rule #1: Allocate the time, and use it wisely
Rule #2: get your story right
Rule #3: find a hook
Rule #4: rehearse

Ok, what else?

Rule #5: Close with a bang

Make sure that your closing is as interesting, captivating, and spectacular as your start. Pick a good movie to get an idea of how it can work.
Most of the things in the middle (the “meat”) are of course important, but they are only if, after you just left, people think: “Wow, I want to talk with this person, and get to know more about their startup.”

Finishing a presentation in Australia, 2011.

Rule #6: Straight, essential, with a mission in mind

Sometimes you can’t do it if you work in a big organization, but if you’re a small team you have all the freedom in the world, and you can build the “meat” of your content (the middle) by being very straight and essential.
Straight means that you should make it easy for your audience to follow your journey. It doesn’t prevent you from using narration tricks, such as flashbacks, etc, as long as they are easy to follow.
Essential, or “to the bone”, means that you should go through your content multiple times, and try to remove anything that doesn’t add much to the message, by having the “mission in mind” at all times.
Ask yourself these questions, when you look at each section of your presentation:
1) What’s the purpose of this part?
2) Is it clear enough?
3) If I could use only half the time, how would I present this?
Rinse and repeat.

Rule #7: respect the audience’s time

When you work on your material, either at the beginning, or when you’re giving the final touch to your beautiful keynote slides, always try to respect the audience’s time. What you say, what you show, should be of interest for them. Don’t waste their time and attention.
Ask yourself if you’re respecting their time, or not.
They’re not there for you. You are there for them, to help them, to teach them, to nurture them. They are giving you THEIR time and attention. Be thankful and respectful.

An example?
I was at a conference in France, the last speaker before lunch. Previous speakers took more time than expected, and one of the big sponsors (telco company, starts with “V”) pretended to have their local CEO speak before me, unplanned, for more than 20 minutes, reading some text for the entire time. READING. No slides, no interpretation.
His message was very boring, very corporate, full of vaporware.
His last words were about how customer-obsessed his company was.
He was using people’s time as he pleased, without even thinking about their needs.
When it was my turn it was already 13:00, and people really wanted to go to lunch. I was in a difficult situation.
I introduced myself, and then told the audience: “My talk was supposed to be 30 minutes long. However we are late, and you are hungry. I’ll cut my talk down to 15 minutes, and then we all go to lunch at 13:15. This is what I call customer obsession.”
Big round of applauses. The crowd was mine.

What would this mean for you?
Well, imagine that twentytwo startups have pitched before you, and it’s now your turn, and it’s almost 7pm, and investors are really tired. What would you do?
Option A: shorten your pitch, but tell them.
Option B: tell them that you are sorry that it’s late, and ask them if they still appreciate the opportunity to hear you pitch; tell them that you worked hard on the pitch, and that it is not a waste of time, and that you would like to pitch.
Option C: come up with an option C, along these lines.

Rule #8: deliver the message

What’s the purpose of your presentation? Do you want them to invest? Do you want them to talk to you more? Do you want to recruit developers? Do you want to get press, since you’ve already got investors covered?
Based on your purpose, make sure that your presentation responds to that goal.
After watching it, will they do what you expect? Will they invest? Or, at least, will they have all the information required to make a decision, such as setting up a follow up meeting? Or, will they simply write you a check if they’re convinced?
There are several things that you should tell an investor:

1. what problem you are solving;
2. how you solve it, and why that’s special;
3. who’s the team, and why it’s special;
4. what did you build so far;
5. what’s your market;
6. how much money are you making already?
7. competition?
8. valuation, ask?
9. strategy?
10. issues to overcome?
11. what are you looking for?

And possibly a few others.
Make sure you answer all of the above in your pitch.

Rule #9: Work hard

It might seem obvious, right? Let me explain.
Some people think that presenting in public is something that everybody can do.
Some people think that the pitch should only require a few minutes to prepare. It’s the product that counts. Right?
Wrong. Preparing a pitch is a lot of hard work. And by the way, selling requires work and knowledge; marketing requires it; every function that you see in a large company requires knowledge and work.
Pitching requires work. In fact, pitching is a high intensity activity, meaning that in a few minutes, a good pitch can make the difference, or a bad pitch can jeopardize your chances.
Don’t take the pitching part too lightly. When I mentor startups (usually as part of an accelerator program, such as Techstars) I help them on technical stuff related to Cloud Computing, and towards the end of the batch I also help them on pitching. Half of them take it way too lightly — not mentioning that they completely waste my time and dedication.
Not to sound arrogant, but most of the time this lack of respect, alone, is a good indicator of the future (in)success of these startups.
At least, if you’re not going to work hard on your pitch, just tell me and don’t waste my time. ☺

The final list

I could go on for hours — no wonder, as I’ve been “working the stage” for several years now. I should know this stuff!
Let me stop here, merge Aaron’s list with mine, and see if the result is nice enough (I hope that Aaron doesn’t mind).
My additions will be preceded by an [S] (like Simone, my name — see? Now you’ll remember it), and they can either be new items on the list, or expansions to Aaron’s points. I also incorporated some of the comment on Aaron’s blog post directly on the list.
I would also like to cut off a couple of Aaron’s suggestions. I think they are not necessary, or are more appropriately included in other suggestions.

Preparation

1. [S] Allocate the time, and use it wisely
2. [S] Get your story right
3. [S] Open with a hook
4. [S] Close with a bang
5. [S] Straight, essential, with a mission in mind
6. [S] Rehearse
7. [S] Respect the audience’s time
8. [S] Deliver the message
9. [S] Work hard

Speaking

1. Speak slowly and enunciate. [S] Imagine that people in the audience are not native English speakers, but foreigners who have a good understanding of English.
2. Be excited. Your pitch should not sound memorized. Intonation, cadence, and projecting help a lot. [S] Imagine that you’re going to be extremely successful, and you want to bring your best friend on board because you want him to be part of this journey. How excited would you be with him?
3. Be specific and concise. [S] See #5 in Preparation; the same rule applies to what you actually say, not just to the content.
4. Look at the audience. You don’t have to make eye contact with individuals, just with areas of the crowd. People in those areas will think you’ve made eye contact with them. [S] It helps a lot to familiarize with 2–3 people in the audience, before your pitch. It would make you feel relaxed. It also helps if you have practiced your pitch blindly, as it would send away most of your fears.
5. Don’t use generic phrases as transitions (“so…”). [S] This requires a lot of training, see “essential” in #5.
6. Actually explain what you do, and do it quickly. [S] I disagree — quickly is the wrong word. Being essential is more important, avoid unnecessary details, or repeating the same thing twice. Don’t speak quickly, being in “urge” can actually damage your pitch. One of the traits of confidence is actually speaking at a modest pace.
7. If you make a large transition, be very clear about it and explain why. [S] See “straight” at Preparation #5.
8. Don’t be “cute” with your points, be declarative. [S] See Preparation #6.
9. If you make a joke, telegraph it. If you’re not sure the joke will land, cut it. [S] The joke can work only if you have practiced it several times, and your cofounders think that it makes sense. Making jokes is hard. The joke is 10% content, and 90% delivery. Watch Louis CK, then try to make the same joke. It won’t work. ☺
10. Don’t hide the big good things because you are modest, highlight them specifically early on
11. Use natural language and simple sentences, i.e. no sentences with three verbs
12. [removed; redundant with the previous one]
13. If an example is a real person, make it clear that you’re talking about a real person, not a user model [S] Actually, try to use real persons, real customers, as much as possible. Makes everything much more powerful.
14. [S] Make sure that people can understand you and hear you well; sometimes it would be obvious, some others it won’t.
15. [S] If you are a foreign English speaker, fix your worst pronunciation nightmares — every nationality has its own.
    The worst nightmares, in my view, are:
    a) where you put your accent — an Italian would say “manàgement”, and it would sound weird.
    b) how you pronounce certain letters — an Indian would pronounce “we will” as “ve vill”.
    c) wrong intonation — musicians do it in their songs, but they’re great at it and the music helps; without it, it would simply be difficult to be understood.

Charts/metrics

1. Charts should be easy to understand — make one point with any graphic or chart. Don’t make people read charts — they’ll stop listening to you.
2. If you put up a graph that confuses people, they will feel stupid and stop listening
3. Line graphs are better than bar graphs when showing growth
4. Label your axes and use real numbers — even if they are small. The shape of the graph matters, not the absolute numbers
5. Explain anomalies [S] A good way to keep the audience engaged is to ask if they notice any anomaly, and then if they point it out, you can explain it.
6. If you should be generating revenue and then show a different metric, investors will be suspicious [S] Well, this is true in general: be consistent.
7. TAM (Total Addressable Market) should be bottom up, not top down. If you just throw a huge number on a screen: “Ecommerce is a $2 Trillion market,” people will ignore you. It’s big enough and detached enough to be meaningless. It’s better to show how a business builds such that the endpoint is truly huge. By grounding it, you make it more interesting.

Slides

1. Titles should describe the slide [S] Titles should be such that, if you remove everything else, the slide would still make sense.
2. Slides should be reentrant — each should make sense and make your case individually [S] For each slide, ask yourself if it can be killed without subtracting anything from the story.
3. Remember that minds wander, and people check phones. When they look up, they should immediately be able to pick up the thread [S] you can actually ask for their full attention in a particular section of your preso, if that’s what you want. You can even explicitly say that you’d like them to put down their phones for a few minutes.
4. Don’t use pretty, but thin, fonts. This isn’t a time for subtlety, make sure your slides are legible from far away [S] A font can make a huge difference. The purpose of a font is not to show them that you’re a designer, but to make it easy to read things.
5. Coolness and legibility are not orthogonal, they’re diametrically opposed[1] [S] No. You can achieve both, but it’s very difficult.
6. Screenshot slides are typically bad. In most situations, screenshots are hugely distracting. They force your audience to focus all their attention on details of your slide, rather than the things that you’re saying.[S] Most of the time, it works to highlight the important part of the screenshot, and perhaps grey out other parts of the screen.
7. [S] Don’t look at the screen where slides are projected. If you can, make sure that you can look at the audience, and at your laptop, without turning your head in the opposite direction.
8. [S] If possible, remove obstacles between you and the audience. Sometimes putting the laptop on a chair helps, because it clears the space between you and the audience and helps you connect with them better.
9. [S] Be prepared for disaster. Your laptop might not show the slides; the resolution might be wrong; there might be several reasons why it won’t work. Print 5–6 copies of your slides to pass them around if needed — you can keep one copy while you present, if it helps.
10. [S] Colors should go nicely together. You don’t need to learn the theory, just pick a color scheme and stick to it. Make also sure that the color scheme allows for very readable slides.
11. [S] Slides can be used as a guide and a reference, but you should know your story well. Don’t let the slides be your guide. Use them simply as support.
    Can you tell the story if, say, the projector fails?
    Well, I did twice. First time was in London in 2009. I did well, despite the lack of slides. Former Channel4's CTO Bob Harris still remembers it (I was at Amazon Web Services when we met, and when I tweeted this):

Bob remembers!!

Final words

Well, I hope that this is useful. Based on your feedback, I might work on it again and improve the list.
What do you think?