Everything I know about startups I learned from writing

Or maybe vice versa. Because everything is everything; work is work; people are people

I’ve worked in startups since 2011 (including one that I built and grew.) I’ve also been writing since, like, 1992 (including this Medium account I started five months ago.)

And I’ve learned that what’s true for one is more or less true for the other. Which makes sense, really, because both of them are about people and people are, for the most part and fundamentally, consistent from one market to the next.

1. Idea vs. Execution

I actually love use “writing” as the metaphor whenever I hear people say, “I just need an idea.”

Bro, it’s not about the idea. You know how many people might’ve had “the idea” for “a wizard-kid who goes to wizard-school” or “a vampire who falls in puppy-love with a broody girl?” I actually don’t know the answer to either of these, but the point is: success is mostly what comes after the idea, and a good idea executed really well is worth more than a great idea executed poorly.

2. No particular skill holds the secret to success

I also use “writing” when people say “I need to learn how to code.”

Sure, learn how to code. It certainly can’t hurt — and yeah, in most industries, it’ll help. Just like learning how to read and write before it was commonplace helped those fledglings back in the day.

But learning how to code won’t magically make you Silicon Valley any more than knowing how to write magically makes you Stephen King.

Don’t hold “expertise” over your own head as an excuse. Either learn what you think you need, or use what you already know.

3. Scratch your own itch first

And write what you know.

The best writers write authentically, from the heart.

I really dig how writer Jessica Semaan put it. On starting her Medium account:

“I just wanted to write somewhere... I wrote for me. And I wrote about things that scared me, intrigued me. I did not censor myself. It was scary to reveal about being single and struggling with it, and burnout, heartbreak, loneliness and more. I wrote authentically. But it turned out I was writing about emotions we all feel, yet we rarely talk about. So people wanted to read about my experience because they related. I wrote like a human. I wrote with vulnerability.”

I can’t tell you how many readers message me to say how grateful they are to find something that isn’t “fluff.” People are incredibly exhausted and fatigued of exposing their real needs only to have them met with paper-thin, half-hearted solutions offered at arm’s length.

The solution is just richer when it’s real. It’s true for writing, and it’s true for everything else.

4. Decide who else it’s for

I write for a very specific audience, and I have two friends that I most often envision when I write (they are, obvs, the same two friends I’m often referencing in stories.) I don’t write for everyone, and neither does any good writer.

My audience is, probably no real coincidence, pretty much the same exact person I worked with as clients when I had my company. I didn’t set out to find this group — I just put something out there, and really looked at the people who found me — looked them in the eye; in the heart. I saw a lot of similarities across their needs and who they were as human beings. I learned a lot about their values, wants, needs, motivations, and fears, and tried to address those.

5. Less is more

Keep it simple, stupid.

If you’re scrambling to impress the girl with bells and whistles during your first fucking conversation, that relationship isn’t going to go very far.

6. Keep it iterative

Damn, this is so important… Several reasons:

Iteration = improvement

By now many of us have heard the study (was it a study?) with pottery students. One group was asked to make as many pots as possible, and the other group was asked to make The Perfect Pot. The first group spent the entire semester churning through pots as quickly as they could, while the second agonized over their single Work Of Art, scrapping each effort and starting over.

At the end of the semester, the group that had been asked to make as many as possible had inadvertently mastered the art of making beautiful pots, and also had a whole slew of near-perfect pots on top of that, while the group that had actually been asked to do so had nothing at all to show for their time.

My writing this year has improved over last year, and last year was a lot better than two years before that. The improvement isn’t linear — I publish a post a day and not all of them are good; some of them outright piss people off. I make mistakes. But overall, over the long run, churning through work has a huge impact on its quality.

Honestly, sometimes I compare this to a healthy sex life. Who’s better off: the person who orgasms regularly, or the person who’s stressing over a single hookup and/or holding themselves back?

Work in progress becomes baggage

I once held a coaching call with blogger and everything-extraordinaire Sarah Kathleen Peck, and when it came to “draft-management” and the keeping and sitting-on of work-in-progress, she said (I paraphrase — it was a phone call like 4 years ago):

“Either publish it or delete it. Don’t keep ‘writing-baggage.’ It becomes emotional baggage.”

I’ll also quote Jessica Semaan, because I still have her piece on growing 10.5K followers and 0.5 million views in 8 months open:

“I wrote with imperfection. Sometimes I re-edited after, but I did not wait for the perfect New Yorker style piece to publish.”

The longer you sit on something, the more likely it is you’ll stay there forever. We all know at least one person who’s “working on their business” but hasn’t made any significant traction in years. That person is doomed — and they need to ship it or scrap it. Like, yesterday.

When you sit on work, you also don’t get any feedback on it.

Get out of the building. You have no idea if your idea has legs if nobody sees it. Even the dog-ugliest MVPs in the world will be received with love if they actually solve a problem. And the sooner you can get something out there, the sooner you can make it better.

When I had my business, I gave myself 3 months to go from “research” to “revenue,” even though I knew absolutely nothing about the industry I’d entered or its production. My initial products were pretty wily, but the market didn’t care. They wanted them. And getting that sooner rather than later meant I had two invaluable things: actionable feedback. And cash.

Don’t spend your life toiling over a single pot nobody wants. That sole, precious pot is garbage. Suppressed work quickly becomes stale.

You have nothing until you know what you have. (In fact, you have less than nothing — you have a vacuum of infinite unknowns.) You don’t know what you have until you ship.

Ship it. You only get good if you ship it. You only know if you ship it.

7. The biggest needs are rarely truly satisfied, and the market always has room for a good solution

Some of the most impactful products entered some of the most established markets. Because there’s always something that could be improved, and some of the biggest players are ignoring them. Now, whether that improvement is motivating enough is another question, but there are almost always unsatisfied needs.

Don’t focus as much on whether or not you’re entering a “crowded” room — writing is one of the most noisy spaces out there. Focus more on the remaining unresolved needs.

Opening yet another hamburger joint is worrisome. And yet Ray Kroc somehow made it work.

8. Do the work

Outlines are not the work. Designing the cover of your book is not the work. Writing your author bio is not the work. ̶D̶a̶y̶d̶r̶e̶a̶m̶i̶n̶g ̶“Planning” is not the work.

White-boarding is not the work. Designing your business cards is not the work. Making Powerpoints is not the work. For the love of all that is good, your mothafucking business plan is definitely not the work. ̶D̶a̶y̶d̶r̶e̶a̶m̶i̶n̶g ̶“Planning” is never the work.

Writing and publishing and hearing from readers is the fucking work. Building and shipping and selling and getting feedback is the fucking work.

Do that. And then keep on doing it. Execute, execute, then listen to feedback. No matter the industry you’re in.

This story is published in The Startup, Medium’s leading publication for entrepreneurs and startups.

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