3 Reasons why entrepreneurs struggle with their pitch

Will Greenblatt

February 21, 2022

Entrepreneurs: does this sound familiar?

You spend an INSANE amount of time creating, designing, honing, and tweaking your product/service, lovingly and obsessively planning and executing to make your business operate as smoothly as possible and solve problems as best you can for your customers. Then, someone asks you “so what do you do?” in an unfamiliar situation, and you go “Uhhhhh…”

All the thoughts, facts, numbers, and minutia of your company swirl around in your head, unformed and disjointed ideas vying for attention in your brain, so that nothing comes out of your mouth except clichés and jargon. You see the other person nodding politely, but you know you missed another opportunity to get someone EXCITED about what you do. This experience is all too common; I hear a version of this problem pretty much weekly from clients, prospects and other business owners.

I started my company to make sure no entrepreneur has to deal with this alone, so here are 3 reasons why you might be struggling to pitch (which, like it or not, is always what you’re doing when you answer the question “What do you do?”), and how to approach these issues:

1.     You don’t have a reliable opener

2.     Your mind is working TOO hard and fast

3.     You’re not appealing to your listener’s emotions

 Let’s look at them one by one :

1.  You don’t have a reliable opener

The importance of this simple practical technique can’t be overstated. As a performing musician who’s suffered from stage fright all my life, I always find the first 2-3 songs excruciatingly nerve-wracking, and then I find the groove and start enjoying myself. Similarly, most people I speak with have the most trouble with the beginning of their pitch, presentation or speech. The strangeness of public speaking seems most acute in this moment, where we feel like we need to perform and be impressive, and the desire to not sound foolish takes the place of the ability to communicate clearly, warmly and passionately.

A way to minimize this is to practice our OPENER: 1-3 sentences that we spend time writing, editing and rehearsing so that we can do it at the drop of a hat, perfectly, on command. Because of connection mnemonics and the benefits of repetitive rehearsal, this practiced opener will get us through those awkward few moments where we find ourselves caught off guard; the time we spend training this opener into our brains and bodies (as Kristin Linklater said, speaking is a physical act) pay off when the pressure is on, just like military, athletic or music training. Here’s my opener:

“I run a business training company called OutLoud Speakers School. We’re actors helping entrepreneurs develop a Powerful Pitch, through public speaking, communication skills and storytelling.”

I can trot this out in my sleep because of the number of times I’ve practiced it, and the fact that I’m always working on it and I recognize its importance.

Do the same, write yours out, make sure you say what industry you’re in, who your customers are and what exactly you do, and you’ll notice a HUGE difference in your confidence and others’ reactions.

2. Your mind is working too hard and fast

As I said, many entrepreneurs tell me they have too many things they want to say, so that they end up not being able to say much of anything at all. All the details of their business, which are SO important to them given how much effort they have put into solving the problems of each moving piece, seem almost equally important to one another, leading to hyper-activity in the brain, which hurts rather than helps the public speaking process.

The best thing to do for your pitch, which may seem counterintuitive, is to SLOW the nervous system down, which can calm brain activity and allow you to choose your words and ideas with greater specificity and care. The best way to do THAT is mindfulness meditation. Getting better at this practice and dedicating a least ten minutes a day (when I can) to breathing and paying attention to my body and mind is probably the most important thing I’ve ever done, no exaggeration. Putting aside the incredible physical and mental health benefits, the ability to slow myself down and choose my words carefully makes me a better public speaker, business leader, as well as a husband, family member and friend.

Find an app like Calm, Headspace or 10% Happier, or subscribe to this wonderful guided meditation channel on YouTube which has fantastic 10 minute videos, and set aside 10 minutes in the morning to sit and follow along to these recordings. This will help you in more ways than you can imagine, but especially during your pitch.

 3.  You’re not appealing to your listener’s emotions

Nobody cares what you do, they care about what’s interesting to them. Simply describing the work that your company does is NOT an effective pitch, unless you happen to stumble across a person who needs exactly what you offer and doesn’t know where else to look.

What really moves an audience, whether in a film, story or pitch, is something that speaks to their emotions. Emotions have an essential evolutionary reason for existing; they reinforce useful information whether positive (like finding a new source of food leading to release of serotonin a.k.a. happiness) or negative (reacting quickly to danger sounds, releasing cortisol a.k.a. fear to help us run away from predators) so that our brains record this information and store it.

Our brains, being the efficient machines they are, are constantly trying to conserve energy; most of us don’t really pay attention until we need to. Evolutionarily speaking, our emotions are indicators to us that we should pay attention to something, and if you don’t engage the listener’s emotions, you’ll NEVER have their full attention. Consider the following two examples:

“My company provides quality security and monitoring systems for large-scale industrial sites…” (*listener tries not to yawn*)


“Not sure if you know this, but every year there are over FIFTEEN melt-down scares across North America. Bad monitoring systems can cause explosions, leading engineers to lose their lives, and companies lose billions. Our systems fix that.”

Which one gets your attention? Why? Obviously the second one, for numerous reasons: it’s more specific (number of accidents, geographic location named), more descriptive (reads like a Michael Bay scene with engineer characters in dangerous situations) more direct, informal language which affects us more quickly (scare, explosion, bad, lose lives, lose billions) and it deals with emotional themes like physical safety and huge sums of money.

Also, it flips it from POSITIVE (“my company PROVIDES…”) to NEGATIVE (“this is a HUGE problem we solve”). Negative emotions tend to get our attention faster than positive ones, and setting aside the social dilemma of that fact, slightly tweaking your pitch to START WITH A PROBLEM will do wonders for it, and activate the emotions of your audience.

These 3 things you can start doing today (one practical technique, one practice to start getting into and one higher level principle) will have a MASSIVE benefit to how you construct, deliver and get results from your pitch.

Please let me know: what are the best pitch techniques you’ve ever learned, and share this with anyone who needs it! 

P.S. If you want to improve your pitch fast, check out my Powerful Pitch Bootcamp here!