300 pitches later, GIFT founder offers a cheat sheet for selling your vision (hint: it starts with the pitch deck)

September 14, 2026  |  Brandon Calloway, The Equity Advocate, Generating Income For Tomorrow (G.I.F.T.)

Brandon Calloway, Kansas City Generating Income For Tomorrow (G.I.F.T.); courtesy image

Brandon Calloway, Kansas City Generating Income For Tomorrow (G.I.F.T.); courtesy image

Editor’s note: The perspectives expressed in this commentary are the author’s alone. Brandon Calloway is CEO and Co-Founder of Generating Income For Tomorrow (G.I.F.T.).

Over the past 6-plus years with Kansas City G.I.F.T., I have had the privilege of listening to more than 300 business pitches, to evaluate their readiness for funding from our organization. Based on those pitches, I must then give recommendations regarding whether or not each business should be funded.

These were not small decisions either.

My votes, along with the rest of the KC G.I.F.T. board of directors, have played a role in granting more than $2 million directly to local Black-owned businesses.

I’ve learned that having a well-rounded and thorough pitch usually means that you have a solid understanding of your business, the market you operate in, and your path to growth.

If you are a business owner, it’s critical to develop a pitch deck.

You don’t have to apply for any competitions or even try to use it to get funding, you need to do it because you need to answer the questions a pitch deck will ask of you. This will become your business plan in visual form, that you can present to anyone.

But if you’re going to pitch for money, then you need to know how to do it. You need to know what questions to answer and what not to spend too much time on. Based on the plethora of pitches that I have both seen, and done myself, I want to share my recommendations through this open letter to Kansas City entrepreneurs.

Make sure your offer is clearly understood: (Spend little time here)

This one is simple. As someone making a snap judgment about your business, I need to quickly understand what it offers. What does your business do? Tell me directly, clearly, and avoid unnecessary fluff.

People often spend way too much time here. They are moved by the passion of the business and/or the complexity of their market, and that makes them want to give all the details of their business, but you often just waste time telling us what the business does when we have already got it. Even worse, sometimes I will get all the way through a pitch without really understanding what the business is because they never clearly state what the business does.

Demonstrate credibility/market understanding: (Spend more time here)

Credibility is another one that should be short and clear. If you are operating a business in the pet industry, it helps to know that you are a veterinarian or that you have worked in pet rescue for 10 years. But once you have told me that, you do not have to keep proving it to me; I believe you.

Demonstrating market understanding by including data like Total Addressable Market (TAM), Compound Annual Growth Rate (CAGR), customer segment trends, competitive analysis, and data on related markets, are all hints that you understand your market. This is always impressive, but this still should not be where you spend most of your time when pitching.

Show traction and financials: (Spend even more time here)

Traction is one of the most important, if not the most important, datapoints to show. I need to see that you have traction in your market, and that people are willing to buy what your business offers. Show me that you have gone from selling two cookies a day to 10 cookies a day. Show me that you have 100-plus new five-star reviews this year. Show me that attendance at your events keeps increasing by 10% with every new event. This is important because at the end of the day, it matters what the market is showing.

Financials are non-negotiable when pitching. Here I want to know how much money you’re making and how much you’re spending, for each revenue stream, and overall. Business success boils down to financial data and at a bare minimum, I must see that you can talk about it. It also helps to show off your bookkeeping system by having a Profit & Loss summary. This whole section should be one of the places you spend most time in.

What are you asking for? How much and to do what? (Spend the most time here)

How Much: If you are asking for money to invest in your business, then I would expect you to know specifically how much you need and be able to defend your stated need.

For What: How are you going to use this money to implement a plan that will grow your business? You need to be as specific as possible. You can’t just say, “I have a restaurant and I need to have more seating and get more customers,” or, “I have a moving company, and I need more trucks to do more moves.” These are not plans.

You need to show where those new customers are coming from. Do you already have the demand? Can you articulate the plan for how you will identify leads that will turn into customers? What is your process for identifying a lead, and turning that lead into a customer?

The more specific you get, the greater your chances are of receiving what you are asking for. That’s the most important part of the pitch. This is where a judge gets the information that they need in order to make a decision. Give this section all the time it needs.

The Outcome: After you implement this detailed plan, what impact will it have on your business? What’s the impact on future revenue? Will it allow you to expand the business offering? I need to know why the plan is worth the risk.

Additional advice

  • Leave space for Q&A: This can be your cheat code. Be sure to get all the necessary information into the pitch deck, but always leave space for Q&A. The judges take this opportunity to get any additional info they need. The judges are directly telling you what information will influence their decision. If you ramble or overtalk the judge, you are shooting yourself in the foot. There have been numerous times that I couldn’t ask a question that I needed to ask, because the person wouldn’t let me ask the question.
  • Practice: Your first draft is never good. I say that from personal experience. Anytime I draft a pitch deck, I ask the people I trust to rip it apart. I know they will see things that I didn’t and the deck always gets better. A pitch deck needs to be looked at from multiple perspectives, just like the business will be.
  • Watch other pitches: Watch episodes of “Shark Tank,” YouTube, and any other pitches that you can find. Take notes on what questions the judges are asking, and on what information the winning pitches were able to communicate.

This is just my advice, based on my personal experiences. Different judges/investors will value different things in your pitch, but they will all need the same information to make their decision.

Brandon Calloway is CEO and Co-Founder of Generating Income For Tomorrow (G.I.F.T.). Email him at contact@kansascitygift.org

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