Go big or go…

The 3 Types of Startup Pitches That You Will Always & Inevitably Give Venture Capitalists

A long time ago I took a few classes that centered around public speaking — more specifically, homiletics, which is the art and study of preaching. At the time it wasn’t my intent to become a preacher or a pastor but I wanted to seriously level-up my expository skills and my ability to explain and describe a given topic and/or idea.

I needed these classes because, to put it lightly, my communication skills were about as good as a pimply-faced pre-teen asking someone if they wanted to go to the middle school dance (speaking from experience…): My delivery was broken, my thoughts scattered, and I stuttered a great deal, not to mention the fact that my hands could never really find a suitable place to “sit” as I talked. My professor said I was a “gesticulator extraordinaire” — I wasn’t always sure how to interpret that comment.

But ever-so slowly, I improved. I realized that the most helpful coaching, for me, was squarely centered around two distinct things, the first being a physical component and the second being a mental one:

  1. My pacing, which was directly tied to my ability to breathe and to not forget about breathing. I am notorious for getting so excited that I forget to inhale / exhale at a reasonable measure which leaves me winded and then everything goes downhill from there. If I forget to breathe it also means that I forget to swallow which contributes to massive cottonmouth which compounds the problem. You can easily imagine how this growing snowball leaves me pretty debilitated in my execution.
  2. My delivery was predicated 100% on my own sense of identity and the peace that I had about being myself. In other words, the more comfortable that I was in “my own skin” the better I could perform in the unique ways that only I could perform. When you first start out you attempt to copy and model your own speech patterns, styles, and delivery mechanics of people you admire and respect. The goal is to appreciate their distinct communication techniques and then quickly begin to discover and practice your own. This is easier said than done.

And so I was trained, received a ton of tough (but necessary) feedback, and eventually became much better in many of these things. I even worked with a breathing coach at one point in time to help facilitate a better connection between my thoughts and my body.

All of this was bolstered by a ton of practice as that’s really the only true panacea for public speaking and my mentor at the time required me to sign up for as many public speaking events as I could find. I went to them all hoping that I’d eventually become a master.

Naturally, of course, I never did, and that’s because there are a few things that simply never change.


All of them are related, all of them happen at the same time.

Invariably there are 3 types of talks (or speeches, lectures, sermons, and pitches) that you will give to other people. These 3 types of talks, as far as I can tell, never change and there’s nothing you can do about it — sorry.

  1. The Talk (Pitch) that you prepare to deliver.
  2. The Talk (Pitch) that you actually deliver.
  3. The Talk (Pitch) that you wish you had delivered.

If you’ve ever had to do any form of communication then you know exactly what I’m talking about. There’s the talk that you’ve been preparing your butt off to deliver, that you’ve sweated over (and perhaps even bled over), and that has cost you hours of sleep.

Then, when you get there, you give something different than the one that you had so fervently prepared to give — perhaps it was the audience (or one particular audience member) that changed things up (for good or for bad), or perhaps it was a mental hurdle that you couldn’t (or could?) overcome in the last moment, or perhaps it was what you ate for breakfast that threw everything to pot.

And then, after the event, as things have cooled down and as you’ve had a few moments to breathe and a bit of time to reflect on your delivery, you realize that there was a talk that you had really wished that you had given, that may have actually been different than the one that you had prepared for — oh, the irony!

The last one always hits me like a ton of bricks and I may even mutter something aloud as the realization pounces upon me:

“Dang, if I had only _______________!”

(You can fill in the blank based on your own experiences here.)


You know what they say about life and lemons…

I blew it. And, what’s worse, is that I knew it even before they told me that they weren’t interested in what I was building. The intro to this particular VC had been incredibly “warm” from a long-standing relationship that had a ton of relational capital built-upon it.

The institution’s portfolio was right up our alley and there were a ton of principally similar technical companies that almost guaranteed that they’d grok what we were building. They were excited (and I, doubly-so) about our pitch and they even moved a bunch of meetings around so that we could walk in a bit earlier in the week.

But for whatever reason (it could have been the carne asada tacos the night before…) I just wasn’t “firing” on all cylinders and whatever came out of my mouth just didn’t “land” as I had supposed they would. Blank stares and then, the death knell: One of the partners couldn’t help but mentally (and physically) disengage from our pitch and with a clever stretch-like maneuver unlocked his iPhone to check on some updates or email or whatever. Death.

By the way, to be clear, I’m not angry nor am I bitter — in fact, getting a ton of “No’s” is part and parcel of what raising venture capital is all about. I’m used to that and take it on the chin. This is what happens.

You know, sometimes it’s easy and sometimes it’s hard but it’s always stressful and full of anxious-laden nights. But most of that anxiety is generally unfounded as there are circumstances way outside of everyone and any one person’s control and, let’s be honest, sometimes, for whatever reason, someone could just be having a really shitty day.

But it doesn’t stop me from doing the math in my own head as I walk out of the building — what could I have done better, what did I say that could have possibly screwed things up, what could I have done to recover faster (or was recovery even a possibility in that scenario)? It’s all on the table for review.

You see, I inevitably begin to cycle through the pitch that I had prepared to give, the pitch that I had actually given, and the pitch that I wished that I had given instead of whatever “that” pitch was.

And even though I am familiar with this dynamic it still burns me up quite a bit, until I take a moment to pause and remember some very vital coaching advice from one of my business mentors…


This is probably a more realistic depiction of “pitching VCs” than most anything else out there.

One of the most important pieces of advice that was given to me when I first started raising capital for startups was to take every single pitch as a performance in which refinement was the goal, not applause.

In other words, my goal was to learn as much as I possibly could from the previous experience and apply it wisely and strategically to the next. In addition, I was learning to be more comfortable with not only the content of my performance but also the delivery mechanisms that were so important to manage and maintain. I was learning to pace and to become a bit more comfortable in my own skin.

Your pitch (and your pitch deck) is a constant work-in-progress, and it never reaches its “final” form — never is it truly perfected, only on the path towards perfection. Every single time you walk out on that metaphorical stage you have a new opportunity to practice your art, to become better at your pitch, and to learn more about what works and what doesn’t.

In the process you also learn a bit more about yourself — sometimes the first few pitches during a fundraising season (as they call it) is a lesson about self-confidence, self-respect, and courage.

And especially at the early stage, it is oftentimes more about you than your actual product or company.


At TOMO, we’re building the future of work by seeking to automate human capital. This blog post (and the larger publication) is about our journey on doing just that. Follow us on Twitter and subscribe to our email newsletter.

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