Ninjas and Robots

CEO of Highrise. Also founder of two YC companies. Engineer for President Obama’s re-election campaign. Makes the awesome writing software Draft.

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Pricing a new product

“What price do we charge?” That question brings up endless debate. If you have a business partner, you probably argue about it. I know we did at Inkling.


This is an answer to: How did you choose your pricing model?


There’s a lot of great advice. Things like using split testing to experiment with different prices. Or an interesting psychological principle called anchoring that can occur when you have multiple price points. But here are a few thoughts on pricing that have been helpful to me.

 1. Pay for your own product.

This is the most important. It’s simply to take dogfooding to the next level. Dogfooding is the act of using your own product. So I don’t just use the product I create. I also take out my credit card and pay for it like everyone else.

You might think that’s a trivial detail. It might even seem silly, since I have to pay credit card processing fees just to charge...

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The Zeigarnik Effect

It’s hard for me to eat right. To find the time to workout. To keep up on literature. To get all the features done for Draft.


When I was young, my parents remodeled the downstairs of our house. My sister and I got this awesome new homework area and our own desks. But I remember being a brat when my father said it was ready for us. My desk didn’t have a desk pad calendar:

Which I wanted for a soft writing surface.

A naive, impatient kid. But what’s interesting is how this childlike attitude manifests itself in adults in a much more destructive way.

We hate things that aren’t finished.

Like the times we go out for dinner and lament we ate too much. We regret finishing the entire plate of food. Now we feel terrible and don’t want to see the movie we were planning afterwards.

Or we can’t find the time to workout. We’ve tried DVDs at home, like the popular P90X, but the...

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My new BMW

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...

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Is success or failure brought by chance or through one’s own actions? How I learned to build products people care about.

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.

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Draft Announcements: Github-style Markdown Todos, WebHooks, REST API

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...

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In Writing Platform Push, Draft Lets You Collaborate Then Publish Anywhere

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

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A Handyman’s Toolbox

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...

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Three mistakes I see web designers make over and over again

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...

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How Draft Grew Paying Customers by 200%

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.

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Innovation

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...

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