I make writing software. You might love and rely on products like Draft (hopefully), but 99.9% of the people reading this have used Google Docs or Microsoft Word. Their products are ubiquitous.

My competitors are giants.

I loved Outliers by Malcolm Gladwell. It inspired people to be persistent. And now, Malcom’s new book David and Goliath: Underdogs, Misfits, and the Art of Battling Giants, which comes out today, will inspire a lot of Davids to take on their own Goliaths (I was sent a preview copy).

In the biblical story, David outsmarted the giant using a slingshot to strike Goliath where he was weakest. David was an unlikely hero. He got lucky.

But in Malcolm’s retelling, David’s chances were actually much better than I thought. Goliath was the underdog.

Why then did weak teams play in a way that made it easy for good teams to do the very things that they were so good at?

...

This time 2 years ago, Cityposh, my branded games company, wasn’t working out.

Our original vision was to help small businesses market themselves through a captive audience playing our games. Instead of having to pay for that privilege with thousands of 50% off coupons, they’d put up a few prizes.

One Cityposh customer I was most interested in was a solo-entrepreneur-run, teenage-focused online store - jewelry, clothes, stuff teenagers like.

After our promotion ran, I was eager for her feedback. I thought we did a decent job getting traffic and followers. She wasn’t impressed.

I wasn’t sure if she didn’t understand the future impact our “brand advertising” and new Facebook/Twitter followers might have, or if I was naive of the problems her business actually had. I suspected it was me.

My wife and I once took a bus tour around the island of Maui, Hawaii. We saw black-sand...

There’s a company I rely on. Sometimes something goes wrong; I create a support ticket. Often the response is: “I’ll forward this to an engineer.”

Days or weeks go by. No reply. Then I get an automated message saying: “We’ve closed the ticket because there isn’t any activity. If you want to re-open it, you can’t. If you still want help, create a new ticket.”

This company tries to use automation to keep things more efficient for their support agents. They hope the efficiency trickles down to their customers - the fewer inactive open tickets, the more tickets they can actually spend time fixing. They’re trying to be helpful. But they’ve let automation screw this conversation up.

One thing I was taught to do as a young employee was to end all my emails with: “Please let me know if you have any questions or concerns.”

Which seemed funny. It was used by everyone, like an automated...

One thing that holds many of us back as creators, inventors, and entrepreneurs is simply our inability to repeat ourselves. Two people who do a great job repeating themselves are Brian Chesky (CEO of Airbnb) and James Altucher (author and entrepreneur).

My latest article at FastCompany. Read more…

Some new things in Draft I think you’ll like:

• Hemingway Mode
• Word/Google Docs support
• Export to your Kindle
• Hourly report
• Daily quota
• iDoneThis
• This Week in Google

Hemingway Mode

The best advice about creativity I’ve ever received is: “Write drunk; edit sober” - often attributed to Ernest Hemingway. I don’t take the advice literally. But it points to the fact that writing and editing are two very different functions. One shouldn’t pollute the other. It’s difficult to write if you’re in an editing mindset and removing more words than you’re putting on the page.

So I’ve added Hemingway Mode to help.

To turn it on, when writing a document, use the keyboard shortcut SHIFT+CTRL+ALT+RightArrow.

Draft will turn off your ability to delete anything in your document. You can only write at the end of what you’ve already written. You can’t go back; only forward. To return to...

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

• “How do I make a cheap landing page to validate today’s business idea?”
• “How can I get traffic to this ‘business’ I started last week? I’m considering buying an expensive banner ad.”
• “I’ve been trying Twitter and Facebook for 2 weeks to get traffic to my new business. It’s not working!”

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...

litmus test

• A test that uses a single indicator to prompt a decision

Every few days I get an email for feedback on whether someone’s startup idea is worth doing, or for help figuring out how to pick just one idea and focus on it.

It’s tough making these decisions. We waste too much time working on the wrong things. So how do we improve our chances of picking the best idea?

This post is inspired by Startup Edition, in response to the question, “How do you turn your idea into a startup?”

Folks like Tim Ferriss and Eric Ries have championed the idea of a “smoke test”: simply make a landing page selling a product that you pretend you’ve already made and then use things like Google Ads to drive traffic to those pages. If you measure enough interest (clicks, signups, etc.), make the product.

It’s a valid method for testing some ideas. I’ve even used it myself. But here’s another...

Opportunity looks a lot like hard work.

Ashton Kutcher

To which some added: That’s funny, considering Ashton was discovered by a modeling agent while drinking at a bar.

Ashton Kutcher recently won an MTV Teen Choice award. Instead of a traditional thank you speech, Ashton shared:

1. Opportunity looks a lot like hard work. No job is beneath you. And they are all stepping stones to the next thing you want to accomplish.
2. Being smart is the sexiest thing you can do.
3. All the things in life have been made by people no smarter than you. So don’t just live life; go build it.

An inspiring speech, especially for teenagers, but some were quick to point out Ashton’s lecturing about hard work, when his own career luckily began after a modeling agency discovered him drinking in a bar.

I mentioned the speech and the replies about “luck” to my wife, who wisely pointed out, “But what were...

I did a fun interview this morning with Tom and Tony of tastytrade.

“Is this a joke?” was feedback on a cartoon I drew a few years ago. Someone else commented, “Not working.”

I’ve never been good at art, composition, drawing, or even color schemes. As a kid I wore a purple sweatshirt and orange Zubaz.

To make the software I’ve been making for so many years, I’ve relied on other people designing things for me. At the first company I founded, I had a talented partner who did the things I couldn’t do or do well, like design. But in 2011, I found myself trying to start a new project. This time, alone.

Read more of my latest article at FastCompany.