I was broke in college. I remember giving a friend a ride once to Chicago because we both had internship interviews there, and I had a car. It’s a 2.5 hour trip, and I was on empty, so we stopped to get gas. When I went to pay, I found my credit card maxed out. The ATM was useless. I had $3 in my checking account.

F me.

So you’ll understand, when I applied to be a Chemistry teaching assistant (TA) my Senior year, it wasn’t for the love of teaching. It wasn’t for the love of Chemistry. I just wanted the free tuition and stipend it paid.

And I thought, “It won’t be too hard. I have to teach once a week, and hold a couple office hours, where usually no one shows up and I can get some work done? Nice.”

I got picked for an experimental program to teach Chemistry 101 at the University of Illinois. Typically, students attend a professor’s lecture with 300 other kids 2 or 3 times a week...

Someone wrote to tell me they really wanted to pay for Draft (I recently turned on paid subscriptions), but they were underemployed and short on cash. However, they were using Draft this very second to write a cover letter for a job application.

I wrote back to thank them for the nice things they had to say, and offered to look over their writing, if they wanted.

It was ok. It was like a lot of other cover letters. It probably looked identical to one I wrote 12-15 years ago. But I’ve learned a lot since then about writing, and finding jobs, and hiring people, and getting people’s attention. Here’s some advice I gave.

The first thing I noticed in this cover letter was how much language was boilerplate. I’m a team player. I work very hard. I know these software packages: X, Y, Z.

Great copy doesn’t remind people what they already know and expect about your product, it tells them...

A friend of mine had an idea for an iPad app to help kids with autism. It seemed like a pretty good idea, but he was in a place many others find themselves in.

He didn’t have any money. He didn’t have any resources. And he sure as hell didn’t know how to make an iPad app. Or software of any kind.

He’s just a guy with an idea and no way to see it through.

Seven years ago, Kyle MacDonald, took a single red paperclip and bartered that paperclip into a house.

It didn’t happen overnight. It took 14 transactions over a year. But he plodded along, trying his hardest to trade up, and eventually he got his house.

That’s how a paperclip turned into a pen. That pen turned into a doorknob. That doorknob turned into a camping stove. And on and on. Eventually it turned into a KISS snow globe, which was valuable to one of the largest snow globe collectors in the world, Corbin Bernsen, the...

What if you wanted to start a business with too much competition? What if the competition was as popular as Starbucks?

There’s a countless number of eyeglass shops in Chicago. It reminds me of The Simpsons episode where Homer is walking through the mall and passes by Starbucks after Starbucks after Starbucks.

On my block alone there are two eyeglass shops. There was a third a couple years ago. Unsurprisingly, it shutdown.

It was interesting to spot the story of LabRabbit Optics, named “Best Eyewear Shop in Chicago” by the Chicago Reader, a popular independent newspaper here.

The first iteration of my business was run out of my apartment. And it started out with me cutting lenses in my bedroom. I started carrying some frames. That took up a small portion of my living room. I got more frames. That took up the entire living room. Eventually it spilled over into my dining room as...

A long time follower told me the other day, “You’re a good writer, but you shouldn’t use profanity. You don’t need that. It ruins your writing.”

I want to show you something.

This is a chart from Draft’s social analytics, showing traffic to this blog going back to its beginning: April 5, 2012. As you’d expect, as I started ninjasandrobots.com traffic was low. But soon, I started getting spikes from my posts every 2-3 weeks. Then there is a long lull from the beginning of July until November 15, 2012. What happened?

The Obama re-election campaign.

No one told me that I had to stop blogging. No one told me what I could write about.

So when I joined the campaign in May, I didn’t stop. I kept writing. At least once a week. You even see the spike in a post I wrote on June 6, 2012 that made it into Lifehacker.

Some people in the campaign office saw that June 6 post and...

Without great solitude no serious work is possible.

Picasso

This essay is part of a collaborative blogging project to answer the question: ‘How do you invest in yourself?’

I invest in myself in all the usual ways. I try to work out a lot and eat right. You can read more about that effort in: [Fragile](ninjasandrobots.com/fragile). And I read a ton.

But I want to share a couple anecdotes about one way I invest in myself that’s underappreciated.

I spend a lot of time trying to be alone.

Regardless of your politics, a presidential campaign is both crazy and incredibly enlightening. I was asked to help the tech team of the Obama re-election campaign last May. I was in the middle of figuring out life after my third company failed. So I thought it would be a good change.

It was impossible to be alone.

What happens if you stick someone, who’s worked at home by themselves...

Some helpful Draft improvements today.

• Bidirectional sync with cloud services (Dropbox, Evernote, Drive, etc.)
• Blogger publishing
• Printing
• Sticky position when toggling between View/Edit modes
• Improved merging algorithm
• New features page

Help Support Draft - Upgrade Your Account

You can now upgrade your Draft account with a paid subscription. You’ll get extras like the ability to beta test new features, and a discount on our Ask a Pro service.

Most importantly, your subscription helps me to keep supporting Draft. If it’s something you find handy, please consider signing up for a subscription today: here.

Bidirectional sync with the cloud

Since Draft launched, you could export to or import from the cloud (Dropbox, Evernote, Box, Drive, etc.) and any changes you made in Draft would automatically sync back to their cloud location.

Now, Draft will also sync changes the other...

One of my favorite books is Different: Escaping the Competitive Herd. Youngme Moon, a professor at Harvard Business School, explores how some companies break through the noise of competition.

The photo above is an exercise from her class where students came up with ideas for a new loyalty program. Loyalty programs are drowning in competition. What company doesn’t have one? I have hundreds of plastic cards collecting from everywhere. And I don’t think a single one has made me more loyal to anything.

What you’ll notice in the image is a constant theme of the book. Companies that escape the herd often do the opposite of whatever everyone else expects.

By definition, for most of us, a loyalty program makes it harder for a customer to quit. But what happens if you throw away the basic premise of a loyalty card and try the opposite. Make it easier for customers to walk away.

Isn’t...

I don’t have enough time. I don’t have enough experience. I don’t have enough resources. I sure as hell don’t have enough money.

In 2006, I started my first company with Y Combinator, Inkling. Three of us moved in together and rented a house that doubled as our office space.

One of my favorite memories was cooking. I didn’t want to spend a lot of time cooking, when I could be spending time building features or talking to users, so I brought this cookbook with me: The Best 1001 Short, Easy Recipes.

It’s amazing what you can do with chicken and a can of soda. I love cookbooks like these. What can I do with the fewest resources possible?

The constraint of cooking is the perfect playground to practice resourcefullness. There are so many ways to substitute things you have on hand for what a recipe actually calls for: ingredients, methods of cooking, even cookware.

Why can’t a...

Ambition is a dangerous tool. I still don’t know how to wield it properly. Somedays it helps me create really cool things, and other times it feels like I’m stabbing myself with it.

The other day I heard an interview with Mandy Patinkin on National Public Radio. Mandy is the actor who plays Saul on Homeland, a current TV series that’s been successful. He’s also very well known for his role in The Princess Bride.

Hello, my name is Inigo Montoya. You killed my father. Prepare to die.

Mandy has gone through his share of setbacks.

Patinkin suffered from keratoconus, a degenerative eye disease, in the mid-1990s. This led to two corneal transplants, his right cornea in 1997 and his left in 1998. He also was diagnosed with and treated for prostate cancer in 2004.

Wikipedia

I enjoyed his perspective on ambition.

When I’m on the Homeland set, and I’m the oldest guy there. I’m so...