3 Tips for Perfecting Your Early-stage Pitch

Posted by: Team Outlander

Posted on 11/10/2021

3 Tips for Perfecting Your Early-stage Pitch

As an investor, I’ve seen a lot of startup pitches—the good, the bad, and the ugly. And as a former founder, I feel for them. I know how daunting it can be to take the vision in your head, condense it into a clear explanation, and get others to quickly believe in it too. Early on, I also struggled to succinctly communicate the vision I had for my company. 

At Outlander VC, I combine my experiences as a founder and investor to help our portfolio companies perfect their pitches. These are some of the best tips and tricks I’ve learned along the way to prepare, perfect, and present your pitch so that investors want to hear it. 

#1: PREPARE to showcase the founding team’s intelligence, vision, character, and ability to execute

When you’re raising capital in the early stages, there isn’t much of a company to pitch yet. It’s just a few folks, an idea, and maybe an MVP. You probably don’t have customers, users, or meaningful quantitative data to inform the investment decision.

Early-stage investing decisions come down to evaluating how the founders answer the following questions, based on Outlander’s Founder Framework model:

  • Intelligent narrative: What series of events did the founders experience or observe that led them to a problem or unique insight that others don’t see?
  • Visionary storytelling: How well do the founders communicate how they view the problem, how they want to solve it, and the impact their solution will have?
  • Team characteristics: How strong is the team? Do they have what it takes to solve the problem? Will they sustain the motivation and passion needed to weather the ups and downs of the journey to the solution?
  • Quick, deliberate execution: How long has the team been working to solve this problem? Did its members fall into the founding team, or were they chosen purposefully?

Ultimately, early-stage investors are looking for a founding team worth betting on. Early-stage founders with compelling answers to the above questions demonstrate they have the intelligence, vision, character, and ability to execute necessary to build on their thesis and scale it into an industry-disrupting powerhouse.

#2: PERFECT by hitting “record” first; then practice, practice, practice

Helping early-stage founders perfect their pitches, I’ve noticed a common disconnect: passionate founders who eat, sleep, and breathe their startup perceive the cadence of their pitch as clear, confident, and compelling—but investors often hear it differently.

For example, I was recently working with a founder on his pitch. He has the big vision and passion necessary to convince investors, but his delivery needed fine-tuning. Seeing is believing, so I suggested he record his next pitch and send me the recording.

The next time we spoke, he told me that he’d realized, watching the recording, that he’d had no idea how his pitch sounded. With the recording, he could self-critique and correct every part of his delivery he didn’t like. He could sit on the other side of the pitch deck and, for the first time, see exactly what his potential investors would see.

We decided to take this exercise a step further. Instead of booking time with peers to get their feedback, he sent them links to his recorded pitch. Recording his pitch practice worked well for several reasons:

  • Self-correction: First of all, it forced him to put his best self forward. Who doesn’t watch a video of oneself before sending it to other people? No one. He watched himself pitching, redid the parts he didn’t like, and continued self-correcting until it sounded exactly right before tapping “send.”
  • Asynchronous feedback: The recipients could watch the pitch and send detailed, time-stamped feedback whenever convenient. He began receiving more thorough, thoughtful feedback from his peers.
  • Efficiency: This method saved time. He was able to share his pitch with more people and get more feedback.

Recording yourself isn’t novel—it’s a time-tested tool, and it’s still highly effective. Plus, with new WFH tools like Loom’s simultaneous camera, microphone, and desktop recording technology, sharing a virtual pitch has never been easier. If you want to perfect your pitch, consider tapping “record” first!

#3: PITCH starting with these three questions

As I said, I’ve watched a lot of pitches. The most painful to watch are those where the investor struggles to understand what the founder is trying to communicate. But I’ve helped founders whose pitch crashed and burned in the morning regroup, adjust their approach, and nail the same pitch a few hours later.

The difference? At the beginning of the second meeting, the founders sought to understand their audience by asking a few simple questions, which allowed them to deliver the pitch in the way the audience preferred. The change was small but powerful.

Here are a few questions founders can ask to understand their audience:

  • Have you had a chance to review any of our materials? Founders often assume investors have reviewed their pitch deck, one-pager, product demo video, etc. But sometimes, investors haven’t received the materials or haven’t had an opportunity to look at them. They’re human; they miss things. Some are just busy and run out of time. Understanding what they know about your company (if anything) is essential. Filling in gaps is different from starting with a blank canvas.
  • Where would it be most beneficial for me to start? Some investors want to dive straight into the solution you’ve built and the business. Others want to understand the founders and their journey that led to founding a company. Beginning the conversation with what matters most to the audience dramatically increases the likelihood that they’ll clearly understand what you’re trying to do.
  • Would it be more helpful to stay high-level or to explain the details? For technical founders who live in the weeds of their technology, this is a critical question to ask. Some investors love the technical details, while others love the big picture. It’s essential to understand this and deliver your pitch at a level that interests them. Miss the mark and the conversation could spiral downhill fast.

Understanding the audience goes a long way toward helping founders communicate effectively and gain support. The questions above will help accomplish that, but it’s by no means an exhaustive list. Plenty of other questions would also work. Regardless of what you ask, I’d limit it to two or three questions.

Test your perfected pitch at OutPitch 2.0

Now that you’ve perfected your pitch, we want to see it! Here’s what you need to know:

Outlander VC is inviting the most innovative early-stage tech startups in the United States to out-vision, outsmart, and outpitch the competition at OutPitch 2.0! Apply now to compete for $100,000 investment from Outlander VC during the live event on December 7, 2021.

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

Team Outlander

Jermaine Brown, Investor + Startup Advisor



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