Milestone One

The tough love and practical advice you need to get an actual business off the ground

JD Graffam
Mar 6, 2017 · 10 min read
Original illustrations by Travis Knight from Simple Focus.

Grammar Lesson: Startup Is A Verb

Every city’s got a startup scene, especially the smaller ones, the underdogs. I love my city, and yeah, we’ve got one, too. Good ol’ Memphis, Tennessee. Swap out the details and this will sound a lot like your own city.

“We’ll see to it that you’re well-fed while we brag about our thriving high-tech startup scene.”

So what is the missing piece? What is the thing I’m suggesting that will give you a better chance at succeeding with your business idea?

Fig. 1: Bronze-cast Unicorn

Fail Easy, Fail More Often: the Gap Year for Entrepreneurs

These cities all have some sort of egg hatching metaphor for these things. The idea is that the programs keep little eggs warm and nurture them while they’re fragile. It’s a nice thought, it really is, but people who start successful businesses aren’t delicate little eggs, they’re triple-tempered steel. I have a different phrase I use when talking about these hatcheries — I call them gap years for entrepreneurs.

“People who start successful businesses aren’t delicate little eggs, they’re triple-tempered steel.”

I asked my wife what she thought of gap years. She said, “I think they’re dumb.” Then, she paused and reflected. “But maybe,” she decided, “they’re okay and I’m just jealous that I didn’t have one.”

“A gap year is what people do when they want a break from the slog and want to get experiences.”

To be certain, I have strong relationships with the folks in my city, and cities all over, trying to make a real go of their startup scenes. It’s a good battle to be fighting, but in Memphis and in your city, it doesn’t do any good for us to fool ourselves into thinking startup hatcheries are the formula for building a better local economy.

Fig. 2: Over-eager Mayor

“We build better local economies when businesses succeed.”

But it should be hard. It should be scary. You do have to sacrifice. Tough choices force you to act on difficult decisions, to put up or shut up. These programs drive entrepreneurs hard, very hard. I’ve got no problem with that.

Move To Our City: the Play Pretend Startup Life

Most of these startup programs have partners in place to incentivize founders to apply to their cohorts and move to their fair city. “We have it going on, you know. We were written up in Newsweek, you know. We’re a Top Eight Place to start up, you know. We have insanely low cost of living, you know, it’s basically free here and we have an emerging creative class. Seriously. Please. Move here, we’ll make it easy. Promise.”

“When their startups fail it’s relatively painless to move on to the next thing.”

The fact is, every city is doing it, so your city needs to do it, too. Local angels want the warm and fuzzy feeling that comes with helping the city become attractive to millennials, and city leaders need to make investments in these things. Local papers eat this stuff up.

Fig. 3: Shared-office Espresso Maker

Take Failure Off The Table

Our investors and startup programs need to help entrepreneurs succeed in business by taking failure off the table as an option.

The Thirty Year Business Plan

I think it’s ridiculous to let startup founders who’ve never built a real digital product try and build one in six months using other people’s money while learning to code — that sounds like a scholarship to me, an opportunity to “find yourself and gain real world experience.” Except it’s not really the real world.

“Today, I own several multi-million dollar businesses. But seven years ago, this wasn’t my plan. My plan was to sell another $1,500 website.”

I think of myself in this way because I am focused on building generational businesses that I’m able to live off of for thirty years, not eighteen months. And that means starting with Milestone One.

So, what is Milestone One?

Milestone One is the first thing your business needs to accomplish, which is providing enough cashflow to put a roof over your head. Everything else is a distraction.

“When you look at small businesses that succeed, you see a common thread: the owners are committed to the long game.”

Before you worry about anything else, work towards Milestone One tirelessly, and don’t let anything else distract you from it.

JD Graffam

Written by

I own two agencies and six software businesses that employ about 30 people. My household goes through as many diapers each day. I’ll be me; you be you.