The StartupYard Big Book of Pitching

Pitching is a mix of storytelling, sales, performance art, and a type of cold reading. So we’re going to begin at the beginning. Here are some pieces we have done on the core skills you need to build and give a great pitch.

Telling a good story is hard to do. That being said, it’s not that complicated either.

In these posts, you’ll find a clear presentation of these simple principles, and why they matter in telling your story:

  • The Hero’s Journey – the world’s favorite story
  • Imperfect Characters – Why everyone loves Iron Man
  • How to Really Change – Why no one loves Mr. Perfect
  • Plot and Setting – Setting up the stakes for your story
  • Conflict – Making people care what happens
  • Arc Building – Why the story matters to you and me

What is Good Storytelling? Part One & Part 2

The Positioning Statement: A Window Into the Mind

Positioning happens before anything else. It’s the bedrock of your pitch. This post gives you a basic grounding in how product positioning works, and why you have to do it first. Learn how to start with this simple tool to build an incredible pitch:


Product Positioning Statement:

(Our Product) is for (target customers):

Who (have the following problem):

Our product is a (describe the product or solution):

That provides (cite the breakthrough capability):

Unlike (reference competition):

Our product/solution (describe the key point of competitive differentiation):

The Details of Pitching

So maybe you know how to tell a good story, and you know how to position your startup. You’re not done. Now we get to the gritty details of how to pitch effectively. Format, speed, tone, volume. Dive into the nuances of the great pitch.

StartupYard workshop leader and mentor Jeanne Trojan gets into the finer details of how to present in front of real, actual people. Here she covers:

  • How to Practice
  • How to Find Allies
  • How to Get Off Script
  • How to be Actually Funny
  • How to Connect with an Audience

These two posts offer pro level tips on how to craft a pitch to fit any moment. In them you will learn:

Creating Consistency – How to make sense in 30 seconds

Accessing the Logical Brain – How to make people think, not react

The Power of Because – How to persuade by explaining

Exclude to Include – How to bring people in and make them listen

Saying your Name – Harder than you think it is

Repetition – Repeating Repetition repetitively is important. Repeat?

Having a Goal in Mind – Bring your audience over to your way of thinking

Beyond the Pitch

Your pitch isn’t a one off. It’s a lifetime habit. Here are some ways to extend your pitching skills into other areas of your work, like public speaking, PR, management, and sales.

Extending your pitch skills to other media is the key to being a better salesperson, a better manager, and a better communicator in general. Here you’ll learn:

  • Picking and Telling a Human Story
  • Complicating Simple Beliefs
  • Simplifying Complicated Ideas
  • Telling the Real Truth
  • Establishing Authority and Trust
  • Asking for Help and Meaning It

Persuasion and sales is not about convincing someone to do something you want. The key to persuasion is to understand what a person wants, and to try and find a way to help them get it.

This post dives into this process with a simple methodology for guessing, then confirming, 4 qualities every person has in every imaginable situation:

  • Goals – What I want
  • Frustrations – What is between me and what I want
  • Fears – What happens if I don’t get it
  • Joy – What happens if I do