Entrepreneurship for The Rest of Us: Lessons from Small Town Startupland

The Sort of Prelude I Tend to Have at The Office, Shamelessly, Two-to-Three Times Per Day, Taken With Water, Like it is a Prescription for Something (It Isn’t)

The bounce of the ball is inevitable. Struck hard, it arrives, twirling with topspin, and skips suddenly sideways. The shift is unexpected, and I, the ball’s uncertain partner, stumble, unable to anticipate the creative way it toys with physics.

Then it is across the room, tapping repeatedly against the concrete, between the legs of waist-high stools, a crackling staccato picking up pace. I fumble around for the thing. First three bounces behind. Two. One. Grasping, cursing, and, at last, captured.

The Small Town Whispers

I won’t be telling you the 5 things you need to do to build a startup community from scratch. I definitely won’t be mentioning what unbelievable thing happens next after you start homesteading the startup wilderness. I won’t because I can’t, and I can’t because I’m still in the thick of it, day in and day out, up to my knees in muck that’s one-half time-of-my-life and another half swirling black hole uncertainty. It’s a funny world out there in Startupland: Things move fast but sure do progress slow.

What I do know is school may have brought me to Tallahassee, but startups are what kept me here. Midway through my grad degree, I interviewed an assortment of local entrepreneurs — some young, some old, many ambiguously in-between — pieced together a couple blog posts, and at some point along the way actually started believing what I was writing. Fast forward one year and a Groundhog Dayesque routine is set in motion (ominously, a cascading line of dominoes also comes to mind). I wake up each day in Florida’s panhandle under the mystery of Live Oak trees well outside the boundaries of rational risk-taking (thanks perhaps to southern conscience, there’s no casinos around, so this is as close to gambling as I can get in these parts). I spend my nine-to-five (and then some) down near the railroad in an old warehouse turned startup space, and I hear, like rumbling clockwork, the whistle of old industry pass by, uninterested in delaying its march — not even for a quick hello over coffee — toward a larger market.

Now, I’ve lived in small towns before; the sort of places where, when the Friday night lights dim, capture the flag in a WalMart just off the interstate constitutes the full menu of readily available entertainment (the only other options being for hands far more idle than mine). Those towns, a series of small ponds, helped propel me to the ever-just-roomier pond where I wade now. I can stretch my legs in this one, if not swim full, heart-pounding laps. My hope, though, is that these small towns, with all their tight-knit charm, may someday turn into more than just another stop along the way. I want to believe that the kind of work I’m engaged in down by the railroad will animate the community, expand opportunity, and attract the quirky, the creative, the bold. I want to believe startups will make this the kind of pond that, if it cannot be large, can at least be deep enough for those that don’t mind diving to have room to explore further than ever before.

The problem is, entrepreneurs are improbably ambitious, and their ambition complicates small town life. At their best, they are consumed by constructive discontent — the staunch feeling that things are not as good as they could be, coupled with the incessant doing of things that might make them better. What the small town does, I’ve come to experience, is disarmingly insidious. It erodes at the edges of the sort of Thielian-scale ambition it takes to picture yourself in the wifi-enabled shoes of a technocratic robber baron. The small town whispers and you wonder: am I spending my ambition in the right place? Should I pack it all up, buy everybody a round of drinks, and take the I-10 west to the land of Series-A and destiny?

Alas, the truth is, even if I could afford to buy everybody a round, doubt knows no boundaries. It is not stuck to certain places like pins on a map. Instead, it is threaded through the fabric of every human being, everywhere, the poor suckers. Once an entrepreneur understands that, they are liberated, especially those who hang out under Live Oaks. You can still build the future from a small town. Hell, you might even end up building a better one, something more human, more constrained, and more, god-forbid, useful.

Some places that others call home have their advantages — that’s undeniable. But time spent worrying about those advantages only amplifies disadvantage. What’s more entrepreneurial than building a strong company in spite of where you live, all the while hoping that doing so will improve that very place? The danger, of course, is wearing a chip on your shoulder like it’s fashionable and slipping from constructive discontent into old fashioned stubbornness. No one I’ve read has captured that danger better than Matt Carroll’s retrospective look at startup life in central Florida. In Gainesville: A Post-Mortem, he delivers a heavy blow: “I let the dream of becoming a successful entrepreneur in Gainesville distract me from the reality of what it takes to become a successful entrepreneur anywhere.” Somewhere in there is just the right balance. If you’re ever lucky enough to find it, send me directions, and I’ll see what I can do about meeting you there.

This is what I’ve realized: doubt is a siren song. You can spin and dance and merry-go-round all damn day and all damn night, growing dizzy, overlooking the beauty of a sunlit day, wasting home-cooked meals discussing what comes next and which major metropolitan city it’ll all happen in, those dream jobs, those bastard bastions of progressive politics and ride-sharing and jazz in the park where millions of lucky folks live like they’ve won the lottery if there were a lottery for upwardly mobile, dual-income young professionals. Forget the misgivings of internal monologues — they’re futile (and wordy).

At the end of the day, you have two options: Move to the kind of city you want, or stay, dig in, and build it. For whatever reason, perhaps the curse of constructive discontent, I have decided to do the latter. Along the way, a clear truth has emerged: in small towns, entrepreneurs do not build because they can. They build because they must. And, if there’s time worth wasting, it is on ping-pong, love, and local brews, not on quivering, not on doubt, and surely not on living with your feet in one place and your heart in another.