How to Prepare for the Stage: Dos and Don’ts on Pitching

Almost exactly two years ago, I was lucky enough to attend this new type of event that a friend told me about, called StartupWeekend. It was a blast. My team was amazing, I got to work on an idea I had been thinking about, and I loved every minute of it… except the pitch.

Our pitch sucked really, really bad.

I left that weekend realizing that it didn’t matter how good the product or team was if nobody bought into it. This was one of those rare moments where you get blindsided with a realization. In 52 hours, I got my first taste of what it was like to tackle not just product, but all elements of a business. Perhaps most important among these was the task of convincing others the idea is amazing.

For the love of god, do not underestimate the pitch.

If you’re at a hackathon, you’re in the clear on this one. The only thing epxected of you is to build something that other hackers think is cool. But if you’re at a StartupWeekend, you had better learn how to convince an audience that an amazing business exists, and that’s no easy task.

It’s something you’ll only get better at with time, but there’s a number of fundamental elements in play that will drastically improve your performance. I had a bunch of notes written up from helping StartupWeekend teams in the past as a mentor, and Zach has been bugging me for a while to publish them for all (sorry Zach!). If you really want to nail your five minute pitch, here’s some things you should really consider…

1. One person pitches, one person drives.

Possibly one of the biggest mistakes teams make is attempting the three ring circus that is a multi-person pitch fest. Don’t do it. There’s no way that everybody can practice to the level they’ll need to in order to not look like an idiot. Teams need one representative for the same reason companies need one CEO: one person always has a true north that can pull everybody through the sticky situations.

The best solution to this comes straight out of Top Gun: One of you is Maverick (the person pitching) and one of you is Goose (the person driving the deck). You know each other’s cues like nobody’s business so that when Maverick forgets a line (and it WILL happen), you know exactly when to advance to the next slide.

2. Maverick writes the pitch.

Speaking is personal. We all have our idiosyncratic gestures and cadences that we’ve learned to time together. We are used to saying things a certain way, and somebody writing your words for you tends to throw a monkey-wrench in the entire delivery.

The simple answer here is to brainstorm on topics to hit and things to talk about as a team, but let the person doing the pitching to write the final copy in their own words. Don’t try and force somebody else’s phrasing, it just won’t sound right.

3. Architect an engaging timeline.

When you’re watching a movie, you’re experiencing a carfeully architected series of visuals and audio effects that are designed to stimulate emotions at exactly the right time. Pitching is no different.

You’ve got the first 45 seconds to grab their attention and keep them from pulling out their phone and checking their email, so if you don’t nail this, you might as well just talk about the weather. I’ll cover pitch structure in another post, but it’s important here that when timing for length, to always shoot for 30 seconds under your limit.

4. Ready your deck.

A nicely built deck can mean the difference between your audience nodding their heads and staring off into space like they’re zeroing in on a magic eye poster.

It’s the slides’ jobs to anchor your words with additional meaning so the audience has an easier time grasping your message. A big step forward is to add short and concise titles to the top of every slide to help hammer home points. Additionally, work to reduce visual clutter by using simple images and graphics, and avoiding complex charts. If you show UI, blur or cut out the unimportant elements and help them find what you REALLY want them to see.

5. Saturday is for structure, Sunday is for practice.

You can always tell the teams that break this rule because they perform the worst. Unless you’re a world class public speaker, you’re already at a disadvantage in the arena of pitching. My advice? On Saturday, there should be two people whose ONLY job is to create the structure of the pitch, so they can lock it down Saturday night, and do nothing but practice it on Sunday.

Spend a solid five hours practicing the pitch in front of a wall, as well as real live humans. Get somebody from another team to listen. Get a random person off the street to listen in exchange for a free Starbucks coffee. Whatever. But pitch for at least five hours, and you’ll be able to do this in your sleep.

6. Have some passion, dangit.

By the time you’re pitching, you have a 48 hour prototype. You’ve bitten off a few features that will simulate a basic idea of what you believe will make an amazing business. 48 hours worth of work is not particularly meaningful in the grand scheme, so don’t forget that what you’re selling is a promise of a future to come, with a simulation of what that future might look like.

It’s your job to recruit a cult with this vision of the future, and you can’t do that if you’re speaking in monotone. Injecting some passion convinces others that there’s a grand idea at play, something worth getting excited about. Moreover, customers and even investors want to invest their time and money in somebody who believes in themselves. Make them believe YOU believe.

7. Slow it down!

When people get nervous, they speak more quickly. The more nervous they are, the faster they speak, and the more they mumble. It’s hard to convince somebody of your idea when they can’t understand you.

The solution to this is simple: slow it down. Find a comfortable speed, and then take it down a notch because from an audience perspective, this should feel like a passionate fire-side chat, not a Busta Rhymes music video.

8. Connect with your audience.

There’s a big difference between talking at people, and talking with people. This may be a five minute non-stop pitch, but you can certainly find ways to engage your audience and break the ice. One of the best ways is to throw in three jokes spaced out throughout the pitch that gets some chuckles. It doesn’t need to be standup comedy that gets you on Comedy Central, but it will loosten you up to hear them laugh, and it will re-engage the people reading their email who suddenly look up and think, “Hey, what did I miss?”

You should also think about how you use the space provided to you. Feel free to walk around, use your arms to gesture. It’s really important that you don’t stare at the screen during the presentation. It’s ok to look at it when you want to emphasize something, or find your place if you miss a beat, but your audience is in FRONT of you, not behind.

9. Prepare for the Q/A

Your pitch isn’t over when you’re done talking for five minutes, because the question and answer portion has just begun. You can anticipate the questions you’ll be asked by pitching other teams in advance, and writing down all their questions. For every question you get asked, you should have an answer.

Some common questions you’ll hear are things like: How do you scale? Where do you get users from? If you were to receive investment, how would you use it? Who is your competition? Why are you better? Who would acquire you? What’s your MVP after today?

You’ll do just fine!

I hope I haven’t made you nervous with this laundry list of dos don’ts. The most important part of the weekend is just embracing the experience having to tackle a new business idea from head to toe, and you’re going to do great.

Good luck!