Startup Pitch Wars: How I Won 5 Pitch Battles
I love winning. If you know about my background (Junior tennis champion, West Point grad, decorated combat Army veteran, successful entrepreneur), you would rightly assume that I’m competitive AF. However, when the task of entering a pitch competition was presented to me six years ago in New York City I found myself way out of my comfort zone. To be honest, I wasn’t in it to win, I was only in it to survive.
So why would you enter your startup in a pitch competition? Win or lose — pitch competitions are a great way to get exposure for your startup and gather feedback from others. Even if you are not selected to advance, the exposure is worth it. You will learn a lot from pitching your idea or company and be able to improve for future pitches! Not only that but if you win, you sometimes get an awesome prize which can really help take your startup forward. Over the years, I’ve overcome the fear of pitch competitions and now have a garage collection of life-size checks with five victories under my belt so I thought I’d share my process with other founders.
Step 1: Determine the audience and requirements. This is a big one to know upfront because that will determine how you structure your pitch. For an investor crowd, you want to explain the go-to-market strategy and financial projections while a crowd full of customers care about how your product helps them. Also, how long do you have? I’ve participated in ones anywhere between 2.5 minutes — 10 minutes. This makes a BIG difference and I’ll tell you the shorter ones are so much harder.
Step 2: Develop outline and script. The shorter the time requirement, the more I stick to a script rather than an outline because every word matters. Developing the script helps to reduce the number of words in my head and gives me direction. It also ensures that I hit all the important points. One of the biggest factors for my success is my ability to craft my pitch into a story. The outline I typically go by for investors is: 1) attention-grabbing intro 2) problem 3) solution 4) how it works 5) competition 7)go-to-market/scale strategy 8) financial projections 9) team 10) Big close. For overall product pitches I don’t include financial projections and it’s tailored to the audience’s perspective of the problem and how we are solving it for them.
Step 3: Create slides. This is where I take my script/outline and translate it into pictures/graphs to slides for the presentation. The fewer words the BETTER — people are visual and you don’t want them reading slides when they should be listening to you. We use Slidebean for design (which is so worth it and way cheaper than hiring a designer). If animations are allowed I always include them by timing images appearing with my script. I’ll get into why in the next steps. Get Backed is a book of successful slide decks and a great resource to give you an idea of how other entrepreneurs pitched their ideas.
Step #4: Finalize timing and execution. This is where your presentation skills come into play. A mentor recently told me that pitch competitions are a lot like standup comedy — timing is EVERYTHING. I personally feel like an actor at this point ensuring my script/talking points and slide animations are in sync. One of the ways I finalize all of this is doing a video of myself doing various versions of executing the pitch until I find the one that sticks. I always want to make sure I come across as confident and genuine in my presentation style.
Step #5: Rehearse, rehearse, rehearse. Here is the most important part — rehearsing the finalized pitch over and over again. I usually give myself at least a week to practice over and over. I recite it while I’m driving, cleaning, walking my dog. My wife can pretty much present for me by the end of the week. I want my lines to be second nature where I can do it in my sleep. Why? Because I inevitably mess up or get distracted EVERY time I go on stage and the practice helps me bounce back in a way that nobody even notices (but maybe my business partner who practices a good amount with me as well).
Step #6: Visualization. 30 minutes to one hour before I go on stage I lock myself in a bathroom stall, close my eyes, and visualize myself going through my pitch. I learned this technique from my sports psychologist coach in college when I played Division I tennis. Visualizing makes me feel like I’ve already successfully done it once and by the time I get on stage it’s like the second time and makes me feel a little more relaxed.
Step #7: BREATH and have fun! Right before I step on stage I do some breathing exercises to calm my nervous system and remind myself that the jitters are excitement, NOT fear. Confidence and authenticity are mandatory. I tell myself I’m a badass and I’m about to make a valuable connection between my company and the audience. I let go and step on — I inevitably mess up or get distracted, but I always recover and finish strong.
Questions may be part of the competition after the presentation. Preparing for these is important not only for the competition but also for pitching in real life to investors. My co-founders and I always challenge our ideas more than anyone so I simply take those challenges and craft responses to them. I think of a question that may be asked and write down my answer. This way, if the question is posed to me, I’m ready with an intelligent response instead of pausing or rambling about something else.
