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How I Pitched My First Startup

Hi there, I’m Ryan. I’m the nerd that delivered Keen’s Demo Day pitch for TechStars and our winning presentation at Structure.


Before TechStars, I’d never pitched a company before — in fact, I shied away from it. This is my story of how I tried to transform myself into the best pitch person I could be. I’m not saying this is the only way or the best way, but it definitely worked for me! Hopefully, this helps other first time founders, first time pitchers, or anyone with a daunting public speaking event in their future.

As mentioned in a previous post, TechStars has their companies start pitch practice on week one of their three month program. In the beginning, we didn’t bother with getting good at delivery because we knew our content was still being developed. After week six, we still hadn’t solidified who was going to deliver the pitch. Kyle, Dan, and I all took cracks delivering various pitches at our weekly pitch practices — all of which were complete garbage. Without any of us being the obvious pitch-person, we simply had to bite the bullet and make a decision because we were running out of time.

Our pitching coach and TechStars director Nicole Glaros strongly advised that the CEO should give the pitch. But, I’m not the CEO, Kyle is. So, how did I end up with the most nerve-racking task of my entire life? Well, TechStars taught us not to treat advice as gospel. We looked at our team — our strengths, interests, and availability and ended up deciding that I should do the pitch. Here was our reasoning:

1.) I had the time to do it. Kyle was obviously going to be our main fundraiser — connecting with VCs on a personal level is not my strongest suit. Dan was obviously going to be our main developer — I consider myself a “meh” developer at best. That left me with some “free” time between web development, customer development, building alcohol tolerance, and a hundred other little things.

2.) I had *some* experience talking to crowds. I delivered a rousing 8th grade valedictorian speech to 50 fellow classmates in bumblefuck Illinois. But more recently, I had done a number of lectures at Dreamforce during my time at Salesforce. You can find them on Youtube if you really try, but they’re… just awful.

3.) I was capable of memorizing the content. Our TechStars pitch was 6 minutes. I did a word-count in the days before the event and our pitch content was 1,000 words on the dot. Not everyone can memorize something of that size in the amount of time we had. I felt I could — and not just the content, but the intonation, hand gestures, and delivery tactics needed to keep an audience engaged.

But I did have some things working against me. Analyzing my personality honestly, the team and I agreed that we would need to work around these factors to have an awesome pitch:

1.) I’m not funny. Okay, don’t listen to that. I’m funny, but in a dry, profane, self-deprecating kind of way. Nothing that should be in a pitch. I can’t deliver a pre-planned pun confidently. We’d have to avoid using humor.

2.) I don’t show excitement. This doesn’t mean I’m deadpan. I’m just saying that my emotions aren’t contagious or obvious. The entire pitch — including the enthusiasm, confidence, and vigor — was going to have to be “acted out” because my natural personality isn’t great at conveying it. Luckily, I’m pretty good at pretending. Which is the nice way to say “lying”.

So it was decided. I’d be the one pitching. We’d have to avoid humor and I’d have to rehearse it until it could be delivered with mechanical precision instead of natural charisma, but oh well, play the cards you’re dealt.

So what did I focus on when practicing?

I won’t say much about content since this post is about delivery, but I wanted to point out one thing. Contrary to what a lot of people think, I did not write the pitches that I delivered. Yes, I was in the room helping, but the majority of the writing came from the members of my team that are actually good at writing (see: Kyle and Dan). Having the same person create and deliver the presentation seems to be common, but if you’re like me and not a great writer, then get some help from your teammates who are. It’s important to get everyone involved anyway so that the presentation is something the entire team can get behind and be proud of. Play to your strengths.

It’s a Performance, Not a Talk
I had to really force myself to make dynamic movements with my arms. For example, If you’re saying something is a “huge opportunity”, then show it by stretching your arms out wide. If something is “frustrating your target market”, then show their ire by shaking your fist at the world. It was really awkward for me at first — talking with my hands, wrists, elbows, AND shoulders. But, as the motions got more and more rehearsed and in sync with the concepts I was talking about, it took my presentation to the next level.

Movement on stage keeps people’s attention. And believe me, you’re competing for it even at events where people are paying to see you. As soon as someone takes out their cell phone, you’ve lost them, so I tried to keep them visually stimulated with my movements as well as my words.

How to Talk
I tried to let the tone of my voice reflect the feelings I was trying to convey to my audience. If you’re trying to tell them how difficult things are for your target market now, let your voice show the concern, worry, and frustration. When you’re talking about how your startup is going to solve all of their problems, sound excited, triumphant, and eager. Changes in tone of voice also bring people back to your presentation if you’ve lost them, so it’s a great way to keep your audience engaged.

I tried to use word emphasis and intentionally elongated pauses to make it seem like a person was delivering the presentation and not a robot. However for me, all that intonation needed to be planned, rehearsed, and intentional. Doing it on the fly would have just been too much for my brain to handle while it was screaming for me to get the hell off the stage because I was going to puke.

I needed the pitch to be 100% scripted. Unless you have massive amounts of improv, public speaking, and stage experience, I highly recommend scripting the entire thing. I spent a lot of time on this. Shit loads of it. In order to get all of the emphasis, pauses, and transitions right, I had to practice for at least four hours per day outloud — basically until my voice hurt.

Practicing out loud helped me deliver my content conversationally and with personality. We wrote the drafts of our pitch with perfect grammar and precision vocabulary. The problem is, no one talks like that, or more importantly, no one wants to hear a talk like that. Hearing yourself give the presentation will help you find the areas that don’t flow, make no sense, or are difficult for you to say out loud. Don’t give yourself a tongue twister!

Finally, I used a mirror when I practiced as much as possible. This helped me get comfortable moving my arms and finding out which arm motions looked natural and which ones looked forced. Linking together my motions and my words really helped with keeping my speed controlled. I would start to notice when I sped up because my hand motions started getting faster.

Get Feedback
Luckily, at TechStars, feedback on your pitch was easy to come by. We truly had masters of the art of pitching at our disposal. Pitch practices with that group of people not only got me over my fear of crowds, but also got us valuable feedback about what was working in the pitch and what was falling flat. I know not everyone will have an opportunity to pitch to the same amazing group of people we did, but the point is to make sure you’re not just practicing in isolation. Pitch in front of as many people as possible, and get their feedback!

On Memorizing
Memorizing every aspect of a presentation like this can be an intimidating task to start. While there’s no silver bullet for memorization because everyone’s brain works a little differently, I can tell you what worked for me. I worked from start to finish, one slide at a time. Each time I added a new slide (this includes emphasis and gestures), I’d force myself to start from the beginning and make it all the way to the new slide. This turned the pitch into one single item in my brain. I couldn’t start the pitch from any point other than the beginning. Taking this approach meant that the beginning of the pitch was the part that I had the best memorized.

Also, sleep! I’d follow up a few hour long practice session with a solid hour long nap. Not only did it help keep my voice from dying completely, but it refreshed my mind and I felt like I better retained what I had just memorized.

The Payoff
The day of the pitch was like nothing I’d ever experienced before. I was so jacked on adrenaline and stress hormones that I don’t remember any of my time on stage. But it was fine. I didn’t need to be conscious for it; after 3 weeks of nonstop rehearsal, the pitch was burned into my very being. Somehow I remember messing up my intonation once (3:03) and stumbling over my words once (3:41), but I knew those were minor mistakes. Once I got off stage, I jumped into Dirk Elmendorf’s arms and gave Dan a huge hug and an NFL style chest bump that may have bruised a rib or two.

Overall, pitching was an amazing experience. Actually going through the motions, putting in the time, and ending up with a good pitch was one of the most rewarding things I’ve done. If there’s any way I could help a new or aspiring entrepreneur with their pitch delivery, I’d love to help out in any capacity — even if just moral support. Feel free to reach out to me at ryan@keen.io, I’d love to hear your thoughts, comments, or stories.

– Ryan (@spritz)

PS: Dan wrote more about what Demo Day was like in this blog post. It also includes a video of one of our early pitch practices, for contrast. Here’s our final pitch:

Our Demo Day Pitch