Learning to Pitch, From Rise of the Rest

Portland Maine had a special guest last week as Steve Case rolled his bus into town for the Rise of the Rest tour. It was exciting that our city was chosen based on our growing entrepreneurial community.

His tour included visits to several area businesses, but the highlight was the evening competition where eight locals got to “pitch” their business to see who would be awarded $100,000.

In areas like Silicon Valley, Boston and New York, the startup community is frequently involved with pitch events. They may be actual meetings with Venture Capital (VC) firms as founders try and raise capital, there are also pitch contests such as this one, and there are more opportunities to practice pitching or to try it just for fun.

But in Portland (somewhat)—and definitely in other parts of Maine—the idea of these fast paces pitches is still a bit new. In Rise of the Rest, each business was alloted just four short minutes (followed by 3 minutes of questions and answers) to try and succinctly show what their business does, why it’s so great and to convince the judges that they were the best ones to win the $100,000.

Even if you own a business that will never seek outside investors, the ability to quickly tell your story in a way that is engaging and informational is a valuable skill to have.

So, I’ve broken down several important parts of the Friday’s pitches to show how you can do better yourself.

frame up what you do

Get people who know nothing about your business to quickly understand what you do. This seems so basic, yet it’s harder than you think.

Here are few good ways to start.

Start with a typical user and their pain point. This is the classic way to start. Describe a typical buyer for your product and why they are searching for a solution to a problem they have.

Use a story. A less dry twist on this is to tell a story about a typical user experiencing some struggle and then show why they’d be looking for your product or service.

Use analogy. Sometimes (especially if you have a very technical or specialized product) it can seem to take forever to lay enough groundwork to get someone to understand the specifics of how your product or service works and can help. In this case, figure out an analogy that will make sense to a broader group of people and tell your story that way.

Pitches are fast, there is no time to waste. If you can’t get judges and audience members to quickly comprehend what you’re talking about, the rest of the pitch is a waste. The judges are going to be stuck with questions rolling around in their heads, unable to fully concentrate on what you’re saying next.

At Friday evening’s event, I felt that the winners (Rapport.io) and the other strong competitors each aced framing up their business. Whether you want to call it an elevator speech, USP, or UVP, you need to learn how to quickly tell a story that will resonate with people even if they know nothing about your business from the outset.

During one of the pitches, I heard someone whisper behind me, “I don’t understand what they do.” It wasn’t until the pitch was complete and a judge asked a clarifying question that I then heard, “Oh now I get it.” We should all be getting it in the first 90 seconds.

If you can’t get someone to understand, you’ve hit a roadblock. Try telling your story in different ways. Is it most understandable when you start with an anecdote, or an analogy rather than a typical summary? Does starting with your customer’s pain point hook people first, or just confuse them?

Provide more details

Once you’ve outlined what you do, start to fill in more details. These details come in many varieties, some or all may be relevant to you and your business:

Customer details. You may have a specific buyer or vertical marketing who will use your product, give details about who they are, where they are found, etc.

Features that make you unique. Everyone will tell you to talk about benefits not features, but you do need to give some details about what makes you distinct and this may start with describing a feature and why it provides a benefit.

Why you solve a problem better than anyone else. Nearly every business has some sort of competitors. Be upfront about who they are and why you’re different.

Why clients are going to love you. This is a great add-on to your story telling at the beginning. What is going to be so easy, so beneficial, so amazing about your product or service that people will buy and keep buying?

Describe your business model: AKA How will you make money?

In a pitch event you are seeking funders. This is different than using the skills of pitching during a sales call or networking event. In a pitch event, people want to know how you will be (or are already) making money.

Be specific:

One time vs. recurring sales: Is this a one-time sale, a recurring sale or a subscription model?

Product vs. service: Will you make money from people-based consulting work (service), or is there a product? Is the product off-the-shelf or does it involve any work to get started? Is there a combination such as software with a set-up program or a product with add-on consulting?

How will you make sales: You won’t have time to get into much detail, but explain the basic sales channels and how you will reach key buyers. Do you have a product that will sell through existing retail stores or will you sell only through your own e-commerce site? Will you use telesales, partners or social media to generate and convert leads?

Pricing details. Many times, you’ll need to overtly address the pricing of your product or service. This makes some business people uncomfortable, but that information may be critical to whether the judges think prospects will likely buy.

At the Rise of the Rest event there will several presentations that left the audience and judges confused about the revenue model. Nobody is going to invest in a company when it’s unclear how they’ll make money!

Prepare a strong deck

At nearly every pitch event, it’s the presenter and their slides. That’s not much, so your slides need to be good! As we all know, a great visual can replace 1000 words. So use them effectively.

Use visuals to complement, not duplicate your message. Don’t read your slides! If you like to talk about the big picture and appeal to people emotionally, use the slides to show your numbers. By contrast, if you like to talk in data points, use the imagery of your slides to add in emotion so it’s not all dry.

Create a branded look to your deck. There should be an overall look and feel to your presentation that looks professional and distinct. When your slides don’t look professional, it’s hard to be taken seriously.

On simple slides, just keep it clean. At this pitch event, it was clear that every presentation was required to talk about their team. With slides such as this one, get good photos, crop them all the same size, line them the photos, line up the titles and other type. It’s just basic, good design. Make sure your fonts are going to load correctly during the presentation, or avoid that altogether by using a PDF that eliminates the needs for fonts.

Practice, practice, practice

Like all public speaking, the more you practice the better you will get. Practice to yourself, practice with a video camera (so you can play back and review), practice in front of others.

In-person networking events are a great way to test out different pitches and see how they connect with people.

Some people hate any kind of public speaking and it’s best to understand your weaknesses. If you are uncomfortable getting up in front of others, it’s unlikely you’ll win a pitch contest like this. It can still be helpful but you’ll have to decide if these events even make sense for you.

For most us, we can improve through practice. So take every opportunity to do that, so when the next pitch contest arrives, you’re ready.

Which pitches did you like at the Rise of the Rest event and why?