The Fine Line Between Love and Hate in Startup

The Startup Show - Episode 6.5


Last week, during what was supposed to be the shoot for The Startup Show's 7-block (episodes 7.1, 7.2, and so on), I instead gathered the talent and crew into the WXYZ lounge at the awesome Aloft Durham Downtown and there we all discussed the future of Teaching Startup.

In short, we discussed whether or not it should have a future.

I was about to throw my hands up. Teaching Startup started as a lark, much like ExitEvent. Only with ExitEvent, I was focused on fixing the "now" of startup, and why it was so awful in places that weren't Silicon Valley. With Teaching Startup, I'm focused on fixing the future, as in "what the heck are my kids going to do with their lives and how do I keep them from being miserable."

Your kids too.

The problem is that ExitEvent became a legitimate business almost immediately, from the first revenue stream I turned on.

On the other hand, Teaching Startup is a business quagmire. It's not working like a traditional business. Let's go ahead and add "yet," because I'm an eternal optimist. I'm only now to the point where I have enough data to measure the success, and the success isn't there. Not where I want it to be anyway.

So I asked everyone if we should continue.

And man, I love this team, the conversation we ended up having in the lounge that day wound up being an extension of this very episode: Entrepreneur Isn't a Job (episode 6.5), and this happened more by serendipity than any causation.

Turns out, we all want to do Teaching Startup for the challenge of seeing it work, however it ends up working, and to exercise our startup muscles outside of our day jobs. In that sense, Teaching Startup and The Startup Show are less like a 2nd job, and more like a rock band or a hobby. It's a serious thing, but not a thing you immediately build a business around.

It's like something you love doing, and wondering if someday you can make money at it.

That pretty much sums up my whole career.

One thing I know for sure is that the content is right. We're saying the right things, just not to enough of the right people via the right delivery mechanism. There's a wall that's going to fall, I'm just not sure where to hammer yet.

So watch this episode and you'll get a sense of where we are right now, and maybe you're there too, and maybe this will give you some inspiration to keep moving forward even when everything looks like hot, smoking failure. Because the alternative is hot, smoking mediocrity.