The Ballad Of the Company Man

Startup Is For Everyone, So Why Doesn't Everyone Think So

9.15.15

Last Wednesday, I was at the outdoor patio of a local bar in the middle of our area's startup hub, enjoying a few beers with an entrepreneur I'm advising. Kind of ground zero for startup talk.

We were preparing for his second fundraising cycle, so we were slinging around startupy terms, but after a couple beers and playing off the excitement we were both feeling around what he was building, the conversation became less numeric and more fun.

That's when the dude two stools over spoke up.

“Hey, I don't mean to be eavesdropping on your conversation, but I just want to say the way you guys are talking is pretty cool. I wish I was a part of something like that.”

Or it was something close to that (beers). My first reaction was kind of a warm glow -- that guy just made my day. Then my annoying side kicked in and I responded.

“So… Why aren't you a part of something like that?”

This turned into a longer conversation over another round. I'm going to call this guy Ernie, because that's nothing like his name.

Ernie is a family man and holds down a very respectable, important job in the public sector, one that takes a long time to achieve in both education and time served, and it's a job that if you told your mother you just landed, she'd pick up the phone and start calling her friends.

He's also very active in his industry and his community. He teaches his craft, and he's on boards of nonprofits.

Ernie is happy, but he isn't happy. He's got ideas. And he has no idea where to go with them.

His ideas, from the two-minute pitch I got, are OK. I can't speak to whether or not he's going to change the world, but I do know that said ideas aren't far enough along to where I can make an assessment and tell him what to do next.

Ernie is at that wait-a-minute point. That moment where he's amassed strong credentials and a solid career and he's probably the envy of a bunch of his friends and colleagues, but he's got that itch, that little voice inside his head casting doubt.

He got into his career to help people, and he's doing that. But he feels like he can do more, and it's likely the very structure that he's fought so hard to get into and advance through that's holding him back.

Startup, or in fact anything other than the bureaucracy in which he finds himself at this point in his career, would be “liberating.”

But it's also something else.

“Terrifying.”

The reason why it seems that most entrepreneurs come right out of college or even drop out of college and get into startup at a young age isn't because they're naturally more equipped or are better at entrepreneurism than their more seasoned and experienced peers (elders).

It's because they have nothing to lose. If you're going to dine on Ramen every day and stare down the barrel of student debt, you might as well take a chance on your own thing.

But there's another reason startup seems like a kid's game, and that's because those kids haven't been programmed yet.

Much like a musician or a writer or an artist, as an entrepreneur you've got to be ALL IN on what you're doing, and you've got to come to grips with the fact that those established tokens of success -- the right house, the expensive car, the eff-you money -- might not happen for you. There's also no roadmap, no career ladder, and -- even despite all the interest around startup these days -- still very little in terms of support or education.

However, unlike rock stars and running backs, the life expectancy of an entrepreneur doesn't end at 30. There's no ticking clock other than the one in your head. But those ticks get amplified when you see people achieve all those success tokens -- the corner office, the sales trips to Vegas, the tailored suits -- whatever it may be.

Ernie put it best: “I'm probably, at this point, a company man.”

No, Ernie. No you're not.

There's no one single path to startup, just like there's no one single path to being successful once you get there.

Startup doesn't require that you ditch and unlearn everything you've fought so hard for. You don't need to quit your job this minute in some zen-like moment of self-discovery. That would indeed be terrifying. You don't have to blow the kids' education fund on offshore development of your app. You don't even have to spend the couple hundred dollars to incorporate.

Yet.

Startup is not about risking everything on one roll of the dice. It isn't about your job at all. It's about that wait-a-minute feeling that my buddy Ernie is having right now, and doing something, anything, every single day to bring that idea a little closer to reality. It's about confronting that voice of doubt and living your life doing what you truly want to do, not trying to be what you think you should be.

Frustration and fear kill way more entrepreneurial careers than running out of money does.

In that sense, when done right, startup can actually be kinda boring. Maybe even maddening. But it's also something you can be a part of. Yes you. Right now.
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