Finding a New Voice

As I prepare my pitch for YC Demo Day I’ve found myself experiencing something that I haven’t felt in a couple years - a lack of clarity around telling the story. I spent the first couple of days frustrated with myself.

“Why is this so hard?”

“I thought I was good at presenting my company.”

But actually, I’m not good at presenting my company yet. I’m good at presenting Twilio. Getting to the point where that was a natural “look Mom no hands” process took a long time, and I need to keep that in mind.

And stop piling on even more pressure to make it perfect.

What Am I Even Talking About?

I’ve been going in circles about my deck and the delivery. Focus on consumer or business? Tell the whole marketplace master plan, or just explain what we’ve built this summer? Interject a lot of my personal story as a marketer or keep it more dry? Talk about about how much our competitors suck, or focus on what we do that no one else does? Use one “up and to the right” graph, or two, or three… or?

Everything that was coming out of my mouth feel so much like a pitch, and so little like me. Buzzwords, bullshit, boring stuff. Bleagh.

I was starting to wonder if I wasn’t going to be able to get my shit together into a script I could deliver without killing my soul, so I sat down with my cofounders to talk it out.

10,000 Hours to Mastery

When we need to have a serious talk one of us yells, “Shed time!” which is the bat signal that we need to grab some beers and head into our converted storage shed in the backyard.

We settled in and I gave them the pitch.

“I know it says what we do, but it has no soul,” I lamented.

Al has a minor in theatre, and he started telling me about creating great improv. Al and Kevin had been watching the movie “Heat” earlier in the day, and Kevin remarked that some of the best Al Pacino lines seemed so natural they must have been improv on the spot.

“No way, those were great because he practiced the fuck out of them,” replied Al. “That’s why he makes millions of dollars and the rest of them are just stock actors.”


I want to be like Al Pacino (on so many levels!) so this advice definitely got my attention. I’m going to have to practice a LOT more. Like, every waking hour between RIGHT NOW and Demo Day. There’s no way I’m going to get to my 10,000 hours but I can make some progress.

Making the Words Your Own

Al didn’t stop there.

“It’s like you’ve been popular on Chicago Second City Improv, and now you’ve been called up to do SNL. You need to take the writer’s lines and make them your own, like you’re saying them for the first time.”

Aha, this!

This is the problem, I am hating the script because it feels like a script. Its just not my style. When I pitch, my preferred style is to sit down and have a conversation with all this rapid back and forth and iteration of a natural human interaction. I’m not saying I’ve perfected the pitch, but I rarely see a blank stare after the first two sentences. And its not the same every time, I’m constantly listening and adjusting depending on many factors.

But you don’t get to do that on stage. Its not a two-way interaction and there is no opportunity to iterate.

The Pitch is Advertising

Mad Men’s Don Draper is a character who has spent 15-20 years of his career pitching to clients. From 1:25 to 2:55 - less than the length of time we will have for Demo Day - he completely re-imagines the Kodak slide projector. Its not an investor pitch by any means, but its still inspiring.

The Goal

Up on stage it is all about lead generation.

Despite what some may think, the true art of marketing is saying the least possible words to convey the most possible information. Its not just about the limited space in an ad, a page or a screen. Its about respecting the limitations of the space in someone’s brain that they’re willing to give up to you. Their attention.

So despite being “a talker” it is not a completely natural thing for me to communicate well.

If I look at how long it took for my presentation of Twilio to get down to something concise that anyone from layman to hardcore hacker could resonate with took YEARS. Years to discover the word “telephony” is the worst jargon imaginable. Years to realize that you can skip saying “API” and just say “developer tool”. Years to cut a word here, a word there.

And then one day, its just natural and you’re not thinking about it anymore and it flows and its beautiful and people smile and you smile and the cash register goes DING!

Until then, it is work.

So I’m working on finding my new voice, and I’m grateful to my cofounders and blogging for helping me work out some of the stress. Back to practicing!


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