7
Pitching Exercises
This chapter brings together the best in experiential learning on pitching. It outlines several exercises—some easy, some bizarre—that entrepreneurs have used to turn their mediocre pitching into confident, powerful, cash-earning pitches. The goal with each of these exercises is to build your pitch muscle, to help you get over yourself, to become more comfortable telling your story, and to identify the style of pitching that resonates for your particular venture and personality.
Be warned, many of these exercises will feel awkward. Embrace the awkwardness. These exercises are what the best of the best use to teach the art of pitching.
Pitching Exercises:
• The Techstars Jedi Mind Trick
• The d.school Pitch Frameworks
• The Dry Run
• The Spy Dry Run
The Techstars Jedi Mind Trick
From Jason Seats, Partner at Techstars
How long does it take? Five minutes
Who do you need? You and one person who doesn’t know anything about your venture
You’ve got twenty words. With those words, can you get someone to ask you the question you want to be asked about your venture?
To play the game, find someone who knows nothing about your venture to play with you. Then, tell the person your elevator pitch. As soon as you are done, ask the person, “What’s the first question that comes to your mind?”
You may be surprised by what you hear. Jason talks about his experience playing this game with Techstars companies:
The entrepreneurs may not know what question they wanted them to ask, but they sure know that wasn’t it. “That question tells me they think we’re in a completely different industry.” It’s about leaving the right holes, leaving an obvious gap for the other participant in the conversation to step into.
In the words of East Coast investor Walt Winshall, “Don’t steal their line.”
Entrepreneur: “I’m going to tell you the elevator pitch of the venture I’m working on, and afterward I want you to ask me the first question that pops into your head. Sound good?”
Listener: “I guess so.”
[Entrepreneur gives pitch.]
[Listener asks the first question that comes to him.]
Afterward, reflect on the following:
1. Was that the question you expected to hear? What did you want to hear?
2. What does that question tell you about what the listener understands about your venture?
3. What changes can you make to your pitch to set up the kind of conversation you want to have?
The d.school Pitch Frameworks
From the LaunchPad, d.school, Stanford University
How long does it take? Thirty minutes
Who do you need? Just you
With the bold claim of being able to take startup founders from idea to revenue in ten weeks, the LaunchPad program at the Institute of Design at Stanford University (known as the d.school) is a perfect place to search for transformative experiences. And when it comes to pitching, the school doesn’t disappoint. One of the key philosophies of the d. school is to use forms of play to overcome fear and unleash creativity. If you are having trouble telling your story in a unique way, or if you get gripped by a sinking feeling whenever you think about giving your pitch, this exercise is for you. Here are eight pitch frameworks, playful ways to tell and retell your pitch.
For each framework, we use the example of Loomis’s venture, TreeHouse, to show you how it works.
1. The One-Word Pitch
If you could only use one word to describe what you want others to know, do, and feel about your venture, what would it be?
Green-building
2. The Pixar Pitch
Originally presented by Pixar storyboard artist Emma Coats, this framework fits every single Pixar movie made and, arguably, every story ever made.
Once upon a time there was __________.
Every day, __________.
One day __________.
Because of that, __________.
Because of that, __________.
Until finally __________.
Once upon a time, there was a thriving industry for do-it-yourself home improvement.
Every day, homeowners and contractors used stores like Home Depot and Lowe’s to renovate and maintain their homes.
One day, people began to become more conscious of their environmental impact.
Because of that, they began to seek out sustainable alternatives for things they were already buying. For food, they went to Whole Foods. For clothes, they shopped at stores like Patagonia.
Because of that, people began to look for sustainable alternatives for home improvement.
Until finally, TreeHouse created the first sustainable home improvement store.
3. The Obituary Pitch
Morbid but powerful. Imagine it’s seventy years from now. You just died. The Wall Street Journal opens your obituary describing your company and its legacy and contribution. What does it say?
When Evan left his job in investment banking, he had no idea that the venture he would help start would change the culture of the home-building industry in America. TreeHouse, the first sustainable home-improvement store, marked a shift in how Americans renovated and maintained their homes—eventually rivaling the big players in the industry, Home Depot and Lowe’s. Today, in large part due to TreeHouse, homeowners are more educated and empowered to build sustainably.
4. The Beaming Review Pitch
A customer just rated your product five stars on the App Store/Amazon/Yelp. What does the fifty-word blurb that she wrote say?
Bar none the best place to buy DIY. If Lowe’s and Whole Foods had a baby, it would be TreeHouse. If you care about the environment, your family, or home improvement then you should consider stopping by. Don’t trust me; come and see for yourself. You won’t be disappointed.
5. The Proud Grandparent Pitch
What would your technologically illiterate grandma say if she were bragging about your company? Keep in mind, her bridge friends probably don’t care about the technical details. What do they care about?
The people are so sweet and nice at TreeHouse! Just the most well-mannered and polite bunch of young folks you’ll ever meet in your life.
6. The Three-Act Play in Three Sentences
Write a three-sentence pitch in the style of a three-act play.
ACT I: Introduce hero.
ACT II: Get hero in trouble.
ACT III: Get hero out of trouble.
ACT 1: You care about the environment. You care about your home. And you love DIY.
ACT 2: You just bought an old house. Uh-oh. There’s so much to renovate, but how can you make sure what you buy matches your values?
ACT 3: That’s when you discover TreeHouse, the first sustainable home improvement store. What a life saver!
7. The Haiku Pitch
Pitching your venture
with seventeen syllables
can be fun. Try it.
Green-building made fun
Education, great service
Smart home improvement
8. The Drunk Hemingway Pitch
The d.school team got this idea from the movie Midnight in Paris, in which a nostalgic writer finds himself on the streets of Paris in the twenties and runs into the Lost Generation—Hemingway, Fitzgerald, and a host of the other famous expatriates living in France at the time. In the movie, Hemingway talks about his work:
You liked my book? Yes, it was a good book because it was an honest book. And that’s what war does to men. There’s nothing fine and noble about dying in the mud. Unless you die gracefully. And then it’s not only noble but brave.
(Google it.) Borrow the style for your pitch.
It is a good __________ because it is a ________ _________. There’s nothing _________ and _________ about __________ , unless you __________. And then, it’s not only __________ but __________.
It is a good home improvement store because it is a smart home improvement store. There’s nothing fun and exciting about housework, unless you are building a home you love. And then, it’s not only fun but beautiful.
The Dry Run
How long does it take? Ten to thirty minutes
Who do you need? One to three friendly faces
There is no substitute for simply giving the pitch. No matter how many times you look through and revise your deck or talk through your pitch in your head, you won’t really know how you perform in the field until you get out there and do it. Ask a few people who know and love you to fill in as your audience, and pitch just as you would to an investor. Ask one of them to video record you (just use a phone; no need to get fancy), so you can watch it afterward and debrief how it went. Once you start to pitch, give no prefaces or qualifications; don’t break character. The more lifelike your practice is, the more comfortable you will be during the real thing. You will be surprised how many small details come up during the practice that you never would have thought of otherwise.
Here are a few possible variations on the dry run.
A Formal Pitch Presentation
Give the pitch as you would to a group of partners at a venture capital firm. Start the dry run from the moment you enter the building. Who do you first greet when you walk into the office? What do you say? How do you set up your laptop? Do you make small talk first or launch straight into the presentation? What happens when you are finished?
A Coffee Shop Pitch
Ask a friend to meet you for coffee so you can give her your pitch to play as if she were an angel investor you were meeting for the first time. Again, start the dry run from the moment you walk in the coffee shop. Are you early? How early? Who buys the coffee? What makes this experience different from a more formal pitch?
With the Deck/Without the Deck
You need to be prepared to give your presentation with and without the deck. Baehr once went to pitch a very wealthy man in Colorado; he arrived with his laptop and PDF ready to pitch and found himself sitting on an overstuffed leather couch in a room that resembled a country club. The investor walked in and said, “Tell me what you are working on.” Even if you are meeting a venture capitalist at their office, they may have read the deck already and merely ask for a quick overview.
The Spy Dry Run
How long does it take? Thirty minutes
Who do you need? An angel/high-net-worth individual you know well
This exercise is designed specifically for accelerators and other entrepreneurship training and education organizations. Despite all the practice, it can still be very difficult to know how your entrepreneurs are doing in the real world. To get that kind of data, you’ll need to ask an investor in your network to have a meeting with an entrepreneur solely for the purpose of seeing how he or she behaves. The entrepreneur shouldn’t know that the meeting is a practice run—as far as he or she is concerned, this is as real as it gets. And, to be fair, it should be as real as it gets; the entrepreneur just doesn’t know the investor is going to be debriefing with you afterward. Ask the investor to be as honest as possible in the critique. It is a good idea to do this with more than one investor, so you can overcome bias in any one investor and begin to see patterns.
Questions Investors Should Be Asking Themselves
• What is this person’s body language like?
• Why would I not invest?
• What gets me excited about this opportunity?