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5 Lessons to Learn About Pitching Your Business

9-minute read

Founding a startup is like walking by yourself to the edge of a cliff, and then having to convince others that you know a better way, and to follow you. You start alone, and start to convert small groups of people (co-founders, customers, investors, suppliers, employees) to believe in what you're creating, and to become a part of it.

For this reason, startup culture is obsessed with pitching. A pitch is simply presenting your idea to an audience in hope of influencing them to do what you want (invest, buy, mentor, etc). Initially, I found pitching your business a bit intimidating. In one single statement, or 60 seconds, or 20 minutes, you are supposed to condense your entire business--and businesses are complex. Get your pitch wrong and you’re not inspiring confidence or excitement for your business. With pitching comes a lot of pressure and tremendous opportunity. Just over a year ago, I had never pitched. Here are five lessons I’ve learned so far...

Lesson #1: Tell it, don’t sell it.

What makes your business worth talking about? Start there, that’s your story.

Storytelling makes pitching your business better. It helps the audience understand the problem you are trying to solve. Charts, statistics and numbers have more context when a story provides the narrative.

It’s easy to get caught up in technical-chat about your product, app, tool or website. Demonstrating your ability and talent is important, but a story will captivate your audience to listen. Stories allow those without deep technical background or domain expertise to understand what you’re saying. Storytelling is the most powerful way to share your idea/concept with the world.

At Poppy Barley, our story is quite straightforward, especially for women. The difficulty of finding boots that fit well resonates with most women. Even if women don’t struggle themselves, they have a friend/daughter/sister who does. Our challenge: 90% of the time, we pitch our business to men. And so, we've had to tell different stories to build support for our idea.

Storytelling lets you convey expertise, capabilities and actions without having to speak directly about how awesome you are. If pitching your business is just about “selling” your idea, your company, yourself--it’s likely boring, overly technical and too centric on you. Tell it, don’t sell it.

How To Pitch Your Business: 5 Tips. Poppy Barley is a start up company based in Edmonton providing the masses with custom made boots and shoes for men and women.

Lesson #2: Find Honest People to Rip You Apart

Pitching your business well is the culmination of months of prep, some stress, and lots of mentorship. As a founder, you are too close to your idea. Reach out to others to provide feedback. Is the problem you’re solving clear? Is your pitch articulate? Interesting? Does it cover all the basics? Is it inspiring?

Initially, my co-founder, Justine, and I took turns pitching. The other person took detailed notes: When did the audience look confused? Engaged? Bored? After each pitch, we recorded all the questions asked. If questions were being asked frequently, we knew we needed to adjust our pitch to be clearer. We always ended our practice pitches by asking what we could do better. We listened. We digested the advice. We often incorporated the suggestions. Sometimes we ignored the advice. You have to make that call.

Listening to honest, trustworthy people will make pitching your business way better.

Lesson #3: Pitch Practice on Repeat

Before we launched Poppy Barley, we participated in the Flightpath Startup Accelerator Program at Startup Edmonton. Once a week, we practiced our pitch. Practising pitching so much was exhausting; and occasionally we questioned if it was a bit of a waste of time (we had a company to build!). But honestly, learning to pitch your business was and is one of the most important tools for building a company. We pitch investors. We pitch talented people to join our team. We pitch our customers to buy from a brand they’ve never heard of. We pitch the media. We pitch our suppliers. We pitch everyone.

Pitching your business is key to the success of your company, so make it a priority to be good at pitching. We found it useful to have four types of pitches always updated:

  1. One Phrase Pitch: Poppy Barley: Reinventing shoe shopping. (Check AngelList for great examples.)

  2. Elevator Pitch: Communicate what you do in 60 seconds. The goal is to leave an impression powerful enough that someone wants to continue the conversation. We practiced our elevator pitch relentlessly. I pitched out loud to myself while driving, showering and walking my dog.

  3. Classic Pitch Deck: 10-15 slide pitch deck covering the important information. This "pitch deck" is built to support your verbal narrative, so keep the slides clean, simple and direct. I’m also a big believer in making it pretty and on-brand.

  4. Read it Yourself Pitch Deck: Ideally I always want to be present to pitch my company, but sometimes I just need to email a pitch deck. This version of the pitch deck contains more details. (I usually PDF-it too!).

How To Pitch Your Business: 5 Tips. Poppy Barley is a start up company based in Edmonton providing the masses with custom made boots and shoes for men and women.

Lesson #4: Don’t Pitch Like a Girl. Don’t Pitch Like a Canadian.

During one of our Flightpath pitch practices, we had a guest. He listened to us pitch, asked smart questions and gave us some of the most important feedback we’ve ever received: "You pitch too soft,” he said. We used phrases like “One day we’d like to...”, “We hope to...”, “We think it may be possible…”

I make this comment as both a woman and a Canadian. We are often too humble, too polite and too inclusive. This isn’t about being boastful or taking all the credit, it’s about articulating your vision with confidence. Pitching is about enlisting someone’s support for your goals. Our “soft” language was selling us short. We were not asserting our vision with sufficient confidence. Using “soft” language was likely our way of deflecting the discomfort of self-promotion.

Here’s the reality: you pitch because you’re asking someone for resources to make your idea happen by convincing people that it’s in their best interest to support you. There is no room for “soft” language (or, as we like to remind each other “Don’t pitch like a girl,or a Canadian!”). Be confident, use action-phrases like “We are…”, “We’re making it happen by…” etc.

Justine and I spent A LOT of time correcting our language. We weren’t aware how often we took credit away from ourselves by simple language choices. Once we changed our language, it was clear our ambitions were to build a scalable company, not a lifestyle business. This changed everything for us when it came time to raise money.

(If you’re still struggling with self-promotion, re-visit Lesson #1: Tell it, Don’t Sell it).

Lesson #5: Know Your Audience

Who are you pitching your business to? Investors? Media? Employees? Partners? Customers? Make your pitch relevant to your audience.

For example, Poppy Barley had a last minute opportunity to pitch in the PR Dragon’s Den at AccelerateAB. Here’s how it worked: Four Alberta entrepreneurs went up on stage and did a 4-minute pitch to a panel of media dragons (and 350 other people in the room!). These dragons were senior leaders from major publications (National Post, TechVibes, Metro, NEWAD and RSquared Communications) that committed to investing directly in the best PR pitch by guaranteeing them major coverage in their next available media cycle.

Poppy Barley swept the whole competition winning coverage from all five judges. The companies we pitched against are all outstanding. The reason we won: we adapted our pitch to be specific to media. Instead of pitching the details of Poppy Barley, we pitched stories they could write about. It made it way easier for the journalists to see how our company fit within their publications.

A Final Word on Pitching Your Business: Keep it Fresh!

When we created our first pitch deck, we had very little to communicate beyond an idea. As our business expands and changes, our pitch changes with it. A pitch is never really complete, just evolving. Keep it fresh.

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The Harley Heeled Sandal Ankle Size Guide

How To Measure:
The Harley Heeled Sandal: Take a tape measure and wrap it around your foot, right below your ankle bone as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 26 cm
5.5 26.5 cm
6 27 cm
6.5 27 cm
7 27.5 cm
7.5 27.5 cm
8 28 cm
8.5 28 cm
9 28 cm
9.5 28.5 cm
10 28.5 cm
10.5 29 cm
11 29 cm
11.5 30 cm
12 30 cm

The Esther Heeled Sandal Ankle Size Guide

How to Measure:
The Esther Heeled Sandal: take a tape measure and wrap it around your ankle, above the ankle bone, as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 23 cm
5.5 23 cm
6 23 cm
6.5 23 cm
7 24 cm
7.5 24 cm
8 24.5 cm
8.5 24.5 cm
9 24.5 cm
9.5 25 cm
10 25 cm
10.5 25.5 cm
11 26 cm
11.5 26 cm
12 26 cm

Belt Sizes

Natural Waist Measurement Typical Jean Size Belt Size for High‑rise Pant Belt Size for Mid‑rise Pant Infinite Belt Size
23-25" 23/24 26" 28" 1
25-26" 25 28" 30" 1
26-27" 26 30" 32" 1
27-28" 27 30" 32" 1
28-29" 28 32" 34" 2
29-30" 29 32" 34" 2
30-31" 30 34" 36" 2
31-32" 31 34" 36" 2
32-33" 32 36" 38" 3
33-34" 33 36" 38" 3
34-35" 34 38” 40" 3
36-37" 36 38" 40" 3
38-39" 38 40" 42" 4
40-41" 40 40" 42" 4
42-43" 42 44" 46" 4
43-44" 43 44" 46" 5
44-45" 44 46" - 5

Sizing Note: For the most accurate fit, measure around your body where you plan to wear the belt. Choose the closest belt size to that measurement.

Belt Diagram Accent Belt and Complement BeltThe Accent Belt, The Polished Belt and The Complement Belt size measurements start from the beginning of the leather to the middle hole.

Belt Diagram Infinite BeltThe Infinite Belt size measurements cover the entire length of the leather.

Belt Measuring Guide

Belt Measuring Guide

A - High-rise style:

If you plan to wear your belt around your natural waistline, wrap a measuring tape around the narrowest part of your midsection. Then, add 3” to determine your high-rise belt size.

B - Mid-rise style:

If you plan to wear your belt lower than your natural waistline, you will require a dierent size. If you have a particular pair of bottoms you intend to wear your belt with, wrap a measuring tape through the belt loops while in a relaxed position.

When wearing your belt in your preferred style, it should fasten in the middle hole. The belt will relax with wear allowing you to cinch it tighter, as needed.

If you plan to wear the belt in both the high and mid-rise styles, you have two options:

  1. Select your high-rise style and fasten it more loosely when worn in the mid-rise style.
  2. Select your mid-rise style and fasten it more tightly when worn in the high-rise style.