Six Guys, Two Cameras, and a Hurricane

Why Teaching Startup: The Show Will Succeed


Forgive me, and this is a long-tail forgive me, but I'm about to do something stupid.

I want to flush away any preconceived notions of entrepreneur post-exit experimentation, or maybe even mid-life crisis. Hell, this might just be a poorly executed ego trip, the one where my left brain and my right brain finally have it out in the most awkward way possible.

In fact, you know that scene at the end of the series run of The Office, the British one, when David Brent falls into some money and immediately blows it all self-producing (and over-producing) a pop song and accompanying music video -- living the life he always imagined he was destined for in a humiliating end story for the character?

That's keeping me up at night right now. And man, that arc was brilliantly written.

Last weekend, I got five other dudes to show up wicked early on a Sunday morning, which also happened to be the morning after Hurricane Matthew blew through the state. I mean, we didn't get the brunt of it here in the Triangle, lots of power outages and downed trees, one of us had to skip a shower, I had to go to three different places to find coffee. That kind of first-world thing.

Anyway, two of them, Kyle and Sean from Interbrew, were there with a bunch of equipment to guerilla-shoot a few hours of video. Video of what, you're probably not asking, so I'll use a device to get to the point? Video of four of us entrepreneurs at different stages of our careers talking about whatever the hell we felt like talking about.

And it was awesome.

This didn't come about by accident. I first got the idea for Teaching Startup six years ago. I know I wanted a way to get startup into more people's heads and provide a pseudo-educational support system for what I see as the decline of the corporate system forcing more and more people to create their own livelihoods.

I registered on the same day I registered Since then I built ExitEvent into a huge network of entrepreneurs, spitting the Southeast's most trusted and read source of startup-related content, and hosting a monthly event attended by 200-300 of those entrepreneurs (and only entrepreneurs), and I sold ExitEvent about three years ago for a price that would make you swear at me.

In the three years since I sold ExitEvent, I've been working on Teaching Startup. Now, when I say "working" -- keep in mind that over these last three years, I also played my part at Automated Insights, raising a strategic Series B and soon selling the company to a private equity firm for a price that makes the ExitEvent number look like pocket change.

See, this already sounds like classic mid-life crisisery.

But I've also spent a lot of time thinking about Teaching Startup. And a lot of time talking about Teaching Startup -- to anyone who would listen. I've probably talked to over 200 people about Teaching Startup, from massively successful entrepreneurs to VCs to people trying to revolutionize public and private education, to well over a hundred proto-entrepreneurs.

What are proto-entrepreneurs, a question he used as a device again to move the writing forward? Those are all the brilliant folks I've met who are either starting their own company or want to, and have found the startup process, community, language, and clubbiness to leave a bad taste in their mouth.

That's a feeling I've had, perpetually, since I first got involved with my first startup, a little over 20 years ago now.

(mid-life crisis)

During the last three years and hundreds of conversations, Teaching Startup has iterated, re-iterated, evolved, been trashed and rebuilt, and changed its focus and machinery over and over again, each time becoming more and more refined. And with each change the answer got clearer, and with each change it started to look more and more like the thing I really wanted to do with it, and with each change I started to have that dream about David Brent in heavy makeup in an over-produced music video.

Eff it. It is what it is.

I still speak of what I'm trying to do with Teaching Startup using a preamble, a caveat, a pre-emptive "Look, you're probably going to think this is batbleep insane but…"

And every time I lay out where it's headed, people get it, instantly, and want to hop on board.

I mean, they don't even ask or hint at what might be in it for them, because the mission is clear, and I think… I'm pretty sure anyway, I finally have the delivery right.

A bunch of them showed up last Sunday, completely unaware of what was in front of them, with precious little direction from me, under-showered and under-caffeinated, but ready to go all-in on this concept that feels like it's so crazy it just might work.

So you're going to see video from Teaching Startup. And it isn't going to be a series of lessons or how-to or motivational successory-speak. It's not going to be like Khan Academy (an idea I played with for a while). It's not going to be like all those podcasts from entrepreneurs and investors which are everywhere right now.

It's going to be different. We're going to talk about startup without talking about startup. We're going to talk around startup. People aren't going to get it immediately, we'll get laughed at, and no one is going to want to throw time and money at this right out of the gate.

But I think I've got the formula down, and I think we're going to poke holes in startup culture, Don Quixote style, in a new way that all those protos are going to get, instantly, and they're going to stop worrying about the fact that they don't understand cap tables and they think public pitch events might be their worst nightmare come to reality.

We're going to reach them and, honestly, I don't really care what happens after that.