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...

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...