Practical Lessons Learned from a Pitch Coach to Pitch Effectively

Practical Lessons Learned from a Pitch Coach to Pitch Effectively

Like swimming, it’s best to learn from a coach to correct mistakes and advance to the next steps

Practical Lessons Learned from a Pitch Coach to Pitch Effectively
Photo credit to Antenna on Unsplash

You may ask, what does swimming have to do with pitching your company?

The problems are different, but the solutions are similar.

My partner is a natural swimmer. During high school, he was the swimming captain. He taught himself to swim by watching on TV how Mark Spitz swam. He can swim all 4 styles equally well.
I am the opposite. My Dad made sure we had plenty of swimming lessons. I now swim regularly at my health club and love to observe swimmers while I wait for my turn. Many people swim well, yet others swim awkwardly or ineffectively.

Recently, I noticed 2 people swimming freestyle, but they had no momentum despite trying hard. They turned their heads and bodies with too much vigor, and their bodies swung overboard together with their heads rendering their moves ineffective. In addition, they kicked as if they were half-heartedly doing breaststrokes.

I asked my partner for advice on swimming. He said my left hand was weak when entering the water, and I did not “grasp” the water with my fingers to propel myself. I asked him what leg-kicking does in freestyle. “To help us float,” he said. “Kick rhythmically with your legs aligned to keep afloat.”

15 minutes of discussion with my partner and learning those two tricks improved my swimming technique.

Some of us are natural presenters and storytellers, but many are not. Delivering an effective and skillful elevator pitch as a business owner is harder than swimming.

A couple of years ago, we started building our digital investment solution to provide financial advisors and institutions with comprehensive data and tools to invest better. We are an early-stage startup.

As fund managers by background, we have regularly presented to investors to invest in our funds. Since fund managers usually have a track record and established investment process, investors give us their time and are keen to meet us to discover better ways to invest their money.

These presentations are typically over 25 pages long, with plenty of graphs and technical details. Investors allow us to talk for at least 30 minutes, sometimes hours.

Pitching a fund is quite different from pitching a startup. In Silicon Valley fashion, we need to learn to pitch in three minutes or even one minute to attract attention just to get another meeting.

Most founders will agree with me; squeezing your origin story, your mission, your team, how you are different, the product features, and how your opportunity is attractive for the VCs in a few minutes is tough.

In a Brunchwork Zoom meeting, I was lucky to meet Nathan Gold, hailed as the “Elevator Pitch Expert” by the Wall Street Journal. That was one of the best Brunchwork meetings I had. I took up his offer for a follow-up one-on-one session.

When we met Nathan the first time, he gave us 3 minutes to pitch to him, assuming he knew very little about InvestTech (in our case, a Next-Gen Robo Advisors.) This was the first time we prepared an elevator pitch.

We went overtime and finished after 5 minutes. Amongst the mistakes we made, here are a few:

  • We spent 4 1/2 minutes on our unique product features.
  • We did not make clear who our target customers were.
  • We talked about the team in the last 30 seconds, and my founder said little about himself.
  • We did not use any simile or analogy for our product to simplify things for our audience and increase connections to what we do.
  • We did not provide any business status updates even though we had several.

We missed a lot of stuff, and I hope you do not repeat our mistakes. After 2 more coaching sessions, we learned a lot from our “Pitch Coach” about pitching to potential investors.

Generally, the first meeting with investors is about getting to a conversation from a monologue as soon as possible. We need to establish likeability with Angel investors and build trust with them quickly.

There is no right or wrong way to pitch; there is a more persuasive way.

Remember that you are pitching to investors and not customers. Investors do not need to know the full details of your product.

The lessons shared here apply to any elevator pitch to get someone interested to invest in/with you, whether you are pitching as a tech startup, writer, business owner, or bidder of a project.

1. Allocate time properly and leave details to Q&A

First-time pitches (e.g., in pitch competition) rarely exceed 10 minutes. Before you begin, tell people you will do a 10-minute (or 5 or 3) overview and welcome any questions after your presentation. The key is to have a nice dialogue afterward.

2. Use a good simile, analogy, or metaphor

If the product you are building is complex and you use lots of jargon in your industry, people will struggle to understand what you are doing. It saves time to use an analogy to explain to an audience who does not have similar expertise.

If I ask you to take a bite at a funny-looking piece of meat, the first thing you may ask is “what does it taste like?” “Chicken,” I respond, and the audience immediately connects.

3. Spell out who your target customers are and bring in early proofs

Your target customers are those who get value from your product. They are your primary users. If you can give investors more data about who will or has already used your products, you can build a better case for investors to spend more time with you.

There are only 3 outcomes when pitching to investors:

  • Investors agree to a next meeting.
  • Investors refer others who may be interested to learn more about your business.
  • Investors say no.

The first meeting is never about asking for a cheque. Instead, show more proof points, so investors want to listen to you more.

4. Talk about 1 or 3 things you do that your competitors don’t do as well

If you have one massive difference, talk about that. Otherwise, talk about the 3 main things you do for your target customers.

You can say something like: we are the first in the world who can do _______.

If you don’t say the 1 or 3 main things to the investors, you are just another person or another product.

5. Use a humble brag

Pitching is about building a relationship with your potential investor. Let’s say you talk about big changes in your market, and you cite several ways of transformation. In our case, we talk about how active stock-picking no longer provides a sure way to make money. The traditional 60% equity and 40% bonds portfolio does not work, but a comprehensive asset allocation strategy does.

After you talk about your market, you tell the investors: how do we know that?

This is the right time to tell people the founder’s story, your background, your experiences, and the team’s expertise. Be purposeful. Be educational. In our case, let people in a bit of finance history. They will remember they learn this “new thing” from you. Show people why you are the right one to build this product.

Better still, start with real people stories to illustrate your credibility. For example, if you showed your product to a customer, and they told you it was a dream come true for them, tell that delightful story of how you shifted the customer’s thinking or prompted her behavior change.

Bringing it Together

Nathan shared a story at the end of our sessions:

You and your 5 kids are on a lifeboat at sea. Unfortunately, one of you has to get off the lifeboat or the boat will sink. You can’t get off because you are the helmsman. So who do you get rid of?

Founders must carefully weigh what to include in an effective elevator pitch.

Our elevator pitch takes the following format:

  • Describe the seismic changes in our market/industry. Share a real user story.
  • Our product has what the customers need. Describe what we do. A good formula to use is to say: we help X to do Y by doing Z.
  • We provide a simile of what our solution does.
  • How we distinguish — name the 1, 2, 3 things.
  • Where we are at our business — when we will finish building our Minimum Viable Product (MVP) and how many beta users we will have.
  • Talk about our distinguished team. Our founder sprinkles in bits of his experience throughout the pitch.


As I learn from a coach how to swim effectively, I also learn from a coach how to deliver a compelling pitch.

Don’t do pitching alone; learn from a teacher.

Summarizing what we have learned in pitching:

  1. Allocate time properly to different areas of your pitch and leave details in the Q&A.
  2. Find a good simile or analogy as your figure of speech to make it easier for your audience to understand what it is you are creating.
  3. Be clear who your target customers are and bring in early proof points to establish credibility.
  4. Show how you are different from your competitors by naming either 1 massive difference or 3 main things that you do.
  5. Talk about yourself (humbly) and show you are believable and worthy of respect/being listened to. Use real person stories if you don’t want to talk about yourself directly.

Practice, practice, practice. Do that with your colleagues, family and friends, other founders, and friendly investor contacts.

Ask your coach, friends, and colleagues for permission to tape the session. Rewatch and learn.

We are grateful for Nathan’s help to hone our story and proceed to receive Angel investments.

Thank you for reading. If you are interested to follow my firm and journey, please visit here.

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Entrepreneur's Handbook – Medium

Author: Marianne O