I’ve been in my share of trouble.

I was 18, and one day these Mucky Mucks - as my father likes to say :) - were touring the Chicago Park District courses where I worked. They started at one, played a round of golf, then moved onto the next. Their last round was at the course I worked at: Robert A. Black.

Well as the group got ready for their last round, a guy came into the pro-shop and told my boss that he screwed up. He left his car at the first course, and hoped someone could pick it up and drive it to him. Here were the keys to his BMW.

My boss was busy hosting these VIP’s, so he smiled and handed me the keys. He trusted me. He also knew I would love driving this car.

I was driving a 15-year-old Oldsmobile Toronado, a Flying Bull. It had no horn. No air conditioning. No speedometer. Which is really fun on lonely highways when cop cars pull alongside. The real interesting bit was...

I’m insanely excited and honored to be writing a column at Fast Company Labs. It will be a narration of things I’m learning while building Draft.

Two years ago I crashed and burned at Y Combinator’s Demo Day. When I realized what I had done wrong, I endeavored to build Draft, a new way to improve people’s writing, without repeating my mistakes–and I think it’s working. Here’s what I did differently.

I introduce Draft and a process I’m using to try and build something innovative to help people write better, while avoiding more technology for technology’s sake. Also, how I met Ashton Kutcher :)

Here’s the article.

A few Draft updates today:

• Markdown Todos
• WebHooks
• REST API
• Over 75,000 documents

Markdown Todos

There are so many software tools for task/todo lists. But it’s funny how unportable those todos are from system to system.

I really like what Github did.

They created a style of text (Markdown) that can be easily understood as a task/todo list in plaintext, while remaining easily parsed by software. I want this to spread. So Draft now supports Github-style Markdown todos.

Create a todo list like this:

- [ ] Write the documentation
- [ ] Get tickets

And when you’re viewing a document it will look like this:

If you check one of those boxes or labels:

your document’s text will automatically be updated with an ‘x’.

- [x] Write the documentation
- [ ] Get tickets

I keep multiple Draft tabs open now, with one of them being a Draft todo list.

There’s also a...

Just released an API and WebHooks for Draft. TechCrunch covered it and some other publishing features I’ve released recently.

The one-man team of Nathan Kontny has just introduced a new REST API that’ll let any news outfit or other publishing organization connect Draft to the other software it uses. If you’re Buzzfeed or The Huffington Post* or another media company with a big mix of full and part-time writers, you could use the API to let writers and editors work through versions together in Draft then publish straight to your custom content management system.

Eric Eldon, TechCrunch

Twelve years ago I began creating my first software product to sell: TinyDBA, a mobile app to help database administrators. I went to a networking event hoping to find my first customers. I had business cards (really crappy ones). But I didn’t have a single thing to demo. I never had a single thing to demo. After months of talking about this “business” and fooling around with some code on nights and weekends, I never shipped anything.

This is an answer to: What tools do you use at your startup?

Have you ever looked inside a handyman’s toolbox?

My father is super handy. He did a ton around our house growing up. He built a beautiful fence around our yard. And he finished our entire basement. Multiple rooms. One room for homework, another for games like darts and pool.

I helped him with a lot of those projects. Hammering things. Painting. But mostly I did cleanup. Washed the...

I was reviewing an online shoe store the other day. The landing page had this beautiful graphic of all these shoes. Gorgeous looking site. And then I clicked on another link, and saw this photo of food. That’s weird. This shoe store has a dietary help section?

It wasn’t a shoe store.

I finally figured out it was a web designer’s portfolio. These were examples of their photography.

I’ve been helping with a lot of website critiques lately. Here are three mistakes I myself have made and see over and over again.

1. You’ve buried the lede.

Age old wisdom for writers: “Don’t bury the lede”. But web designers ignore it. In my example above, you had to read deep into their page to figure out this was a portfolio, and they’d like you to hire them.

Use a single H1 tag on your landing page to state very clearly what you do. It doesn’t have to be the default ginormousness of an H1 tag, but...

I gave myself a humble but still ambitious revenue goal for Draft. It didn’t look like I was going to make it. But I was inspired by the code editor Sublime Text and how they encourage users to pay.

Here’s how I used the messaging tool Intercom, to mimic what Sublime does, and I ended up meeting my revenue goal 9 days early.

I’ve been given a lot of chances by a lot of people. Some I’ve taken great advantage of. A couple I’ve pissed away.

(This is part of a collaborative answer to: Who took a chance on you?)

I’ve mentioned before how broke I was in college. That was a guiding influence to find a co-op opportunity. A co-op is a job where I could go to school for a semester, and then work for a semester, then go back to school, then back to work, etc. The making money part was very attractive. So was the awesome experience.

As a Freshman, I interviewed for a co-op position with 3M, well known for Scotch Tape and Post-it Notes. To prepare, I read some pamphlets about what 3M does and how innovative they are.

I sat in that interview, inexperienced, naive, using standard cliches like, “I work hard.” And now I’m blabbering on about how important “innovation” is.

The two interviewers got sick of me saying...

A few years ago I had to give a speech about Inkling, the company I co-founded, and what prediction markets were all about. I’ve given talks on stage before, and I practiced this one at home at least two dozen times.

There were other speakers and after our talks we were supposed to stand at these tables, off to the side at this networking event, and answer any follow-up questions people had.

I gave my speech to a hundred or so people and thought it went fine. Then, I went and stood at my table.

No one ever came over.

That sucked. It’s not a pleasant feeling, pouring yourself into something you care very much about, and no one shares any interest.

It didn’t seem like it was because I was generally poor at public speaking. In high-school I was in a public speaking club and even won awards at it. I’m a trained actor too. I’ve gotten some nice compliments from strangers coming up to...

Draft has some neat and useful improvements to announce:

• Audio/video transcription tools
• Comments shown alongside changes
• More social analytics reports
• Set the font color (helpful for dark themes)
• Publish to MailChimp and LinkedIn
• A shortcut using the Draft browser extension

Audio/video transcription tools

I can’t believe how much of a pain it is to transcribe even a short amount of audio. In order to write better, I’ve wanted to start including more transcriptions of podcasts, video presentations, and interviews in my writing, but the tools are in bad shape. I found myself using iTunes for the keyboard shortcuts, but I’d have to flip back and forth to edit the text I was transcribing.

There had to be a better way.

Now Draft can assist you with your transcription. The “New Document” button has a dropdown arrow next to it to start a “New Transcription”.

You can transcribe...