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.

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A new high

Most people who’ve read this blog know something of my origin story. It even sounds like the beginning of a Spiderman movie.

I used to be a Chemical Engineer in school, but couldn’t stand working at a uranium processing plant during a summer internship. It wasn’t a radioactive spider that bit me, but a broken ankle tied me to a desk and computer for the rest of the summer because management didn’t want my cast to get contaminated. There goes my superhero career.

So I sat there and programmed. And I fell in love with it.

I worked as hard as I could remaking myself into a software developer, and I dreamed of running my own software company. I remember taking a plane in college and someone spotted me with my Entrepreneur magazine. He asked if I had my own company. “Not yet,” I said. “One day, I hope.”

After college, I took a job as a consultant with Accenture and later a job at a...

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Why are some people so much luckier than others?

James Scott Bumgarner, more famous as James Garner, film and TV star, passed away recently at the age of 86. Many people have been writing about how great a guy he was and stories about his life.

A few things caught my attention. Not the least of which was how lucky he seemed. How does a guy without any acting experience and who hates talking in front of people land a well connected Hollywood agent to jump start his career? Luck?

In 1935, Hollywood created their talent scout system. Just like athletic scouts, folks would monitor Broadway plays and radio for talent. But occasionally they’d “discover” someone in public who didn’t have any acting experience - they just looked like a movie star.

Lana Turner, one of the most glamorous and popular female stars of Hollywood during the 40s and 50s (pictured here at the right with James at the 1966 Academy Awards), is a great example.



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Now That I’ve Created Something, How Do I Spread It?

A long time ago, a guy flew a kite in a storm. When lightning struck it, the current traveled down the string of the kite to a key, giving the victim a jolt of electricity. Who was that famous scientist?

Jacques de Romas.

Wait, that’s not right. Wasn’t it Benjamin Franklin?

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What are you drawing, Lily?

I have more than a few friends who keep talking about the businesses they want to start. But every week there’s a new excuse.

They can’t make up their minds about the best credit card processing company, or the best blogging platform, website CMS, or shopping cart, or the best book that will guide them to success.

Of course, most people invent all these obstacles so they never actually have to start and risk failing. Their ideas can remain flawless dreams.

But others see the Ubers, Dropboxes, and Airbnbs, or whatever else is worth a billion dollars this week, and they think they need to create something as big, and as perfect.

Airbnb recently raised $450 million at a valuation of $10 billion. That’s an awfully big company to look up to.

But Airbnb was a mess when they started.

Paul Graham told them their idea was crazy.

And he was right. Airbnb’s idea wasn’t just crazy, it...

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Draft Announcements: a Chrome App, inline calculator, and more…

Hello. Here are a few new handy things in Draft today:

  • Draft Chrome App
  • Inline calculator
  • New document shortcut
  • Comment emails

Draft Chrome App

I really enjoy using web applications, but there are a few things I miss when a web application can’t be launched from your native operating system.

For example, I thought it would be great if I could use Mac OSX’s Spotlight to quickly launch Draft. Turns out you can have the best of both worlds with Chrome Apps.

Screen Shot 2014-07-02 at 11.19.55 AM.png

Now, if you have the Chrome App Launcher and you install the Draft App:

You’ll be able to launch Draft from places like your desktop, Apps folder, even Spotlight.

Inline Calculator

I constantly need quick ways to do things with numbers. For example, I’ll be typing an email and need to sum up some expenses or hours, but I...

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The Art of the Ask: How to Get on the PGA Tour or a Phone Call with Tim Ferriss

A story on getting what you want.

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10 Things I Learned from Paul Graham at Y Combinator

Given that I’ve known Paul now for over 9 years and been through YC twice, there’s a lot I’ve learned from the guy. Here are just a few of them…

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We all have something to say and someone’s attention we want. But our resumes and cover letters, or the websites we create to sell our products, most of it sounds the same as everyone else. No one notices, as we look like out of context dots in a children’s puzzle.

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A relative of mine was in town and I was brainstorming things he might find entertaining in Chicago. I mentioned the Art Institute, a beautiful museum with a famous art collection.

But my relative said, “We went to an art museum some years back, so it’s not something I have to do anytime again soon.”

By “years back”, he actually meant over a decade ago. And in other words: he’s seen one art museum, he’s seen them all. If you’re an art lover, you’re sad, but more than a few people reading this feel the exact same way as my relative.

And many share this point of view about something - some type of event or place that...

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How can I find someone to help me?

I’ve been running my own businesses for over 9 years. I helped start Inkling at the end of 2005 with Y Combinator.

One of my biggest frustrations was simply how little the company spread through blogs and news sites. I echoed the wants of every other entrepreneur. How can I get more press? How can I meet more bloggers who want to write about us? Do I need to hire a PR person?

We had a blips of press when we first started. But for 9 years in business, it’s a minuscule list.

Inkling has been able to stand despite the difficulty spreading the word the way I wanted, but I hated that feeling of being beholden to other people to spread what I was working on.

As I found myself dreaming of what I’d work on next, I was haunted with the struggle of finding people to spread my work.

In the late 80s there was a teenage actor who was doing well finding movie roles. But as quick as his...

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Draft Announcements: Better sorting, duplicate documents, and more…

Hi there. I wanted to let you know of a few new useful things in Draft:

  • Better sorting inside folders
  • Better sorting of folders
  • Duplicate documents
  • Image names
  • Search in more places
  • Import multiple documents - fixed

Better sorting inside folders

I had tried to make sorting inside a folder a little too clever. Originally, Draft would list documents inside a folder in reverse chronological order (by their updated time), but if you wanted more control, you could click a document in a folder and drag it to whatever order you wanted, then, the “manual sort” would automatically kick in.

But that was confusing, and didn’t work well enough.

So now, you can sort your documents in a folder three different ways that you can control explicitly:


The default sort is by time - the most recently updated documents are at the top.

The next sort - the up and down arrows - is your...

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