Ninjas and Robots

Makes stuff. Previous: Founder of writing software Draft, CEO of Highrise. Also founder of two YC companies. Engineer for President Obama’s re-election campaign.

Page 8


Stuck

Last week when I wrote Downward, I looked back on my life and found quite a few places where I felt stuck.

This post is inspired by Startup Edition’s question: “What advice would you give young entrepreneurs?”

I was stuck in a job after college. I was trained to be a Chemical Engineer, but really wanted to be a software developer. When I graduated, I got a non-developer position at an information technology consulting company, Accenture, recording meeting minutes and documenting requirements. I hated it.

What’s interesting about ruts in my life is how often writing got me through them.

I was bored with my job, so I’d email tons of Accenture partners ways to improve business or ideas for clients. I worried a little bit about looking stupid. I’m 21. A complete newbie. I kept doing it anyways.

Most people ignored me. But, eventually, some didn’t. And I got promoted to a position...

Continue reading →


Downward

I saw a chart of Scribd’s website traffic the other day.

Ouch. Scribd has been a hot company. Looks like a rough six months.


I was talking with someone about a recent setback in their business. The loss of confidence was all too familiar.

My startup career over the last 15 years has had its own setbacks. I can definitively count more losses than wins.

There was the mobile database administration tool, TinyDBA, I was creating. It was supposed to be my first real business. I even spent the money creating a Limited Liability Company for it. Of course I needed the limited liability to protect myself from potential lawsuits. LOL. I never shipped anything. No one ever saw it. No one ever used it.

Things weren’t that much better in my next venture. I joined a friend to build an eBay-like auction site for industrial equipment. Spent months building out an entire platform for this...

Continue reading →


Draft Announcements: Folders, Daily Word Count Report, Reject Changes, Wordpress Drafts, and more.

Quite a few Draft announcements:

  • Folders!
  • Daily Word Count Report
  • Accept AND Reject Changes
  • Wordpress Drafts
  • Evernote Sync Bug
  • Tweet Images

Folders

A super popular request. Now it’s easy to organize your Draft documents with folders. I have folders for all sorts of use cases: managing chapters of a book, archiving published work, pending ideas, etc.

Just look for the Folders link on the left side of your main list of documents:

That will pull up your list of folders.

If you want to change their order, it’s simple. Just click and drag a folder to the right location.

To add existing documents to your folders, look for the “Move” buttons and links.

Which will give you a window like this:

Pick the folder you want to move this document to. Or create a new folder from this window as well.

When you click a folder name, you’ll see its documents.

You...

Continue reading →


How to become a better writer? Fail like a comedian.

The best comedians are often not that funny. The reason you see Chris Rock and Aziz Ansari perform hilarious routines with audiences laughing for an hour or more is because that routine is practiced and polished. You never see the duds.

Friends of mine are big fans of Aziz and they’ve seen him perform a handful of times. Once, they caught him in a really small club where he was testing jokes from his cell phone. He was on stage, literally reading jokes from his phone that he had typed out earlier.

Chris Rock does this too.

In gearing up for his latest global tour, he made between forty and fifty appearances at a small comedy club, called Stress Factory, in New Brunswick, New Jersey, not far from where he lives. In front of audiences of, say, fifty people, he will show up unannounced, carrying a yellow legal note pad with ideas scribbled on it.

…he will talk with the audience in an...

Continue reading →


Stay in the building.

I sit at my hotel at night, I think of something that’s funny, then I go get a pen and I write it down. Or if the pen’s too far away, I have to convince myself that what I thought of ain’t funny.

Mitch Hedberg

This post is inspired by Startup Edition, in response to the question, “How do you discover what people really want?”


“Why am I talking so fast?” I thought as I sat across the table from Martin, an owner of a restaurant in my neighborhood. I cold emailed the guy to get a meeting to chat about his business. I was hoping I’d discover a problem I could create a new product around.

If you’ve read any of the dozens of books about running a Lean Startup (I’ve read them all), you’d probably call this “getting out of the building”.

I got my nerves to calm down, and I sat with Martin for quite awhile listening to how he runs his business. I asked all the advised questions, “If...

Continue reading →


ProgrammableWeb Interview: Nathan Kontny’s Draft Takes on Google, Microsoft, Apple.

I did a three part interview with ProgrammableWeb. We talked about writing, being an underdog in a fight against Google and Microsoft, innovation, and what’s maybe next for Draft.

  • Part 1
  • Part 2
  • Part 3

View →


Thank you, John. Thank you, everyone.

There’s this cafe near my home. An Argo Tea. My wife and I go by it frequently at night walking our dog, Bailey. Even at 10:30PM, there’s always at least a couple people typing away at documents. Peering in the window, you see the glow of Word or Google Docs.

I tell my wife that it’s a goal of mine to walk by the Argo Tea window one day and see a complete stranger using Draft to type that document. It would be so neat to spot someone I don’t know, obviously working on something important to them to be in this cafe at night, using something I made only feet away from where they’re sitting.


I’m a big Tim Ferriss fan since randomly coming across 4-Hour Workweek in a Borders Bookstore many years ago. And now I give his books away as presents to my friends. I’m a frequent visitor to his blog and yesterday I was checking out his most recent post. I spotted this in the comments.

I...

Continue reading →


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...

Continue reading →


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...

Continue reading →


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...

Continue reading →