Go Long

One of our most common mistakes as entrepreneurs is short-term thinking:


This post is inspired by Startup Edition, in response to the question, “How did you make your first dollar online?”


There’s a great scene in Netflix’s series Orange is the New Black, a dark comedy about inmates of a women’s prison. Two of the main characters, Piper and Alex, discuss their enemy, Tiffany, who has broken Alex’s glasses, stolen her mattress, and locked her in a clothes dryer. But as Piper stresses out about how to exact quick revenge on Tiffany, Alex calmly reminds her:

You gotta have a long game.

In August 2011, I had spent 6 months building “Cityposh” to help companies do brand advertising through online games. I had over 10,000 users, it was growing 10% a week, and started making thousands of dollars in revenue.

Not a bad start. But typical struggles of running a business came up, and I didn’t have the motivation to tough through this type of business for the next 7 years or even the next 6 months. So I moved on to other projects and eventually arrived at Draft.

But, where did all those Cityposh users go? How many of those 10k+ players and paying clients are using Draft?

0.1% - What a waste.


I’ve been working full-time as an entrepreneur for 8 years. Before that, I’ve worked on entrepreneurial side projects almost my whole life.

My first dollar as a “business owner” was selling lemonade as a kid outside our house. And, when I was 8 or 9 in the 80’s, I made a little dough selling greeting cards to family members. It was one of those marketing gimmicks in the back of comic books. Make a commission on your sales or get prizes.

When I wanted to buy my first Walkman, I shoveled some snowy sidewalks in Chicago. After college I set up an LLC to bill a friend for moonlighting work he needed done. And then there was the money I made running an affiliate site selling other people’s software like Norton AntiVirus.

It’s funny how I had to start all these projects from scratch: How was I going to get my first customers to this new business, now?

Even after running Inkling successfully for over 5 years, it felt like we barely had any leverageable assets to start Cityposh - the businesses were so different. We immediately scrambled to find our first users and paying clients. Friends and family got things moving early on. But the growth quickly stopped. So we bought Facebook and Google ads to bring in new users. It worked!

And, I too considered buying an expensive banner ad for $30k at a popular website. I’m thrilled I didn’t. New users would have vanished like everyone else.


You don’t have to look far to see that some of the most admired and successful people in the software industry have spent their entire lives chasing the same few ideas (and in some cases literally building the same product ad infinitum).

Dan Grover, Code and Creative Destruction

Steve Jobs focused on making the best computer for so many years. Fired from Apple, he just started another computer company. Ev Williams is another great example, obsessed with online publishing for over a decade with: Blogger, then Odeo, then Twitter, and now Medium.


Since closing Cityposh’s games business, I’ve been doing things differently. I’m solving problems that have been nagging me for years. I’ve focused on building an audience who doesn’t just care about my most recent software project, but who cares about: writing better, design, software development, entrepreneurship - topics I’ve enjoyed teaching for 10 years, and anticipate enjoying for many more.

The results are quite different from Cityposh. I get emails from people who started beta-testing Draft almost a year ago, still use it today, and are even more excited about it now. Revenue and usage are growing without spending a dime on advertising. And please forbid anything bad happening to Draft and my ability to work on it for many years, but from all indications, I have a great group of users and readers who would follow me to the next project that helps us all write better.

And of course, I have the motivation to see Draft through its obstacles.

The reason that most of us are unhappy most of the time is that we set our goals not for the person we’re going to be when we reach them. We set our goals for the person we are when we set them.

Jim Coudal, Creative Mornings

Making your first dollar is relatively easy - grab a shovel; find some snow. But if we want lasting success, we need to find people who care enough to come back to us as customers a second time. Even more importantly, we need to work on ideas WE’d be willing to come back to a second time. We need a long game.

P.S. I’d love to meet you on Twitter: here.

Or read other perspectives on this topic from an awesome group of entrepreneurs at Startup Edition.

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