Embrace the mess

This post first appeared on Medium.com

Startup culture fetishizes simplicity.

In products, business models and founder narratives, points are given for clean lines and beveled edges, and deducted for rough spots, long explanations and run-on sentences.

Blame Steve Jobs, or @ev, for that matter — for creating this beautiful lie. Just don’t let their considerable magicians’ gifts keep you from spotting the machinery underneath.

I get sucked in myself. I’m an early-stage investor in part because I love the purity of a clean slate: just a couple of brilliant founders with a huge idea and no messy baggage to drag along.

But the older I get, the more I’ve come to appreciate a good mess.

Take Mark Suster’s recent (and excellent) series on the critical role of professional services in enterprise software. How many great young companies have failed to achieve meaningful scale because they drank too deeply from the 37signals Kool-Aid jug? How did the fallacy of “self-service” enterprise software become accepted as gospel by so many talented young entrepreneurs?

Managing people is messy. Humans don’t scale.

And yet the Goliaths of enterprise software all achieved dominance via small armies of consultants and “customer success teams”, who made sure that initial decision to buy metastasized into an ever-deeper commitment to the platform.

No, it’s not always pretty. Incentives get misaligned. Bad behavior sometimes follows. But taking humans out of the equation isn’t a solution, it’s a dodge.

Leadership is a solution. Values are a solution. Embrace the mess.

Here’s another example, a little closer to home (for me, at least): running a seed fund. I’ve spent the past five years learning the basics of early-stage investing. Find great founders, write them checks, how hard is that, right?

But every day I peel the onion a little more.

To run money you have to raise money. How do you do that? To find great teams you have to see hundreds — make that thousands — of not-so-great ones. How do you do that? You see more and better deals if you have a stronger local ecosystem. How do you build one of those?

What began as a simple life of founder meetings and startup hustle is now a tangle of tasks and commitments I couldn’t have imagined when I set out. Not just the obvious-in-restrospect stuff like fundraising and LP communications, but many, many more loosely-coupled activities: supporting accelerator programs, speaking and writing, volunteering on industry trade groups and government commissions, mentoring new investors and seeking advice from veterans so I don’t have to make every mistake from scratch.

It’s a mess. I love every minute of it. And — slowly, very slowly — it is making me more effective at the simple task that sits at the center: finding amazing people and helping them win.

Simple isn’t the opposite of complex, it’s just an elegant (and wrenchingly difficult-to-achieve) misdirection that tucks complexity out of sight.

Messy is interesting. Messy is valuable. Embrace the mess.