Someone asked me the other day if he should get a job to help acquire the skills needed to run his own business or just jump in and start.

I’ve written before about getting crappy jobs to help learn more about specific industries and problems people have. For example, if you want to create a photography website - some kind of Flickr competitor - it would behoove you to work as an assistant to a wedding photographer even if it didn’t pay well. Learn how he or she does their job. How they take good photographs. How they deal with emergencies when a camera doesn’t work. How they make a couple happy on such an important day. Those are examples full of potential insight to build a business for photographers.

But many of us think we need corporate jobs to learn how to scale servers, charge customers, or make things look “professional” before we can start our own business.

That’s not how...

Happy Halloween!

I’ve got some fun Draft things to announce. Two big areas of focus were improving collaboration and providing more tools to help people use folders, especially for National Novel Writing Month (NaNoWriMo, which starts tomorrow). Here we go:

• Team Folders
• Import Multiple Files
• Export Folders
• Beeminder Integration
• Firefox on Windows

Team Folders

You can now share an entire folder with collaborators. Just look for the share buttons next to your folders:

Share a folder with a list of email addresses or grab a link to send to whomever you want.

What’s great about these Team Folders is that you don’t have to send around Share links anymore to the documents inside. Your collaborators sharing a folder will automatically get updates of your documents or any new documents you create. You’ll get their new documents as well. Any edits they make to your documents...

Last week I wrote about not going to an Ivy League school, and not having any money, and definitely not having any connections.

Some people mistook my post as advice to be the loudest one in the room. But that couldn’t be further from a description of me and what I’ve done to get people to listen.

I don’t like cold-calling. I’m shy. I’m introverted.

What I wrote last week was to remind us of the people who are eager to help; you just need to ask.

I’m also reminded of something else that’s helped me make connections when I wasn’t even trying to make them.

We didn’t work on the Obama re-election campaign for the pay. Many folks working there could have easily gotten paid twice as much working somewhere else. And, we definitely didn’t do it for the long hours or the 7-day-a-week work schedules or the poorly maintained bathrooms or the malfunctioning air-conditioning.

But one of...

I picked up a book recently with an overwhelming majority of positive reviews, but a few negative ones like this:

It’s great to be presented with new ideas for raising capital and meeting contacts, but as an Ivy League graduate, and a former wall-street analyst I think it’s fair to say the author’s contact book and access to resources is a little different than ‘most people’.

I can relate to the reviewer. When I got out of college, I had a lot of ambition, and wanted to start a software company, but… I didn’t come from money or go to an Ivy League school. I didn’t even know how to make software. And I sure as hell didn’t have any connections.

I suck at networking. “Never eat lunch alone,” the book says. I always eat lunch alone. I love it.

When I went to the first Startup School hosted my Y Combinator, all these brilliant kids from Stanford and MIT were in the crowd. Great people...

Hello! Here’s another round of some cool new things in Draft:

• The Draft Job Board
• Draft Sites
• Editor Flow
• Import public urls
• Autocomplete names
• PDF exports
• Count selected text

The Draft Job Board

Two of the proudest moments of my life were helping a couple friends find new jobs. Work is obviously important to us, and to be a tiny part of helping people with that process was incredibly rewarding. I want that to continue.

So today I’m launching the Draft Job Board.

It’s simple. If you are looking for a great writer or editor, the community using Draft is full of them and the job board would be a great place to connect. If you’re a writer/editor looking for work, I’m really hoping this is a handy resource.

One problem I have when using job boards to post jobs is the upfront cost of the post. It might cost me $400 to post a job on a developer job board, but even if I don’t...

With theampm, write Time like this in Ruby:

1.am
=> 2013-10-08 01:00:00 -0500

130.am
=> 2013-10-08 01:30:00 -0500

4.pm
=> 2013-10-08 16:00:00 -0500

925.pm
=> 2013-10-08 21:25:00 -0500

 There's also a to_time method
1515.to_time
=> 2013-10-08 15:15:00 -0500

This code is so simple I debated even creating a gem for it, but I find myself using it repeatedly for new projects, and now again for Draft, an app to help people write better.

Installation

1. Add gem 'theampm' to your Gemfile.
2. Run bundle install.
3. Restart your server

Feedback

Source code available on Github. Feedback and pull requests are greatly appreciated. Let me know if I can improve this.

P.S. I’d love to meet you on Twitter: here.

I make writing software. You might love and rely on products like Draft (hopefully), but 99.9% of the people reading this have used Google Docs or Microsoft Word. Their products are ubiquitous.

My competitors are giants.

I loved Outliers by Malcolm Gladwell. It inspired people to be persistent. And now, Malcom’s new book David and Goliath: Underdogs, Misfits, and the Art of Battling Giants, which comes out today, will inspire a lot of Davids to take on their own Goliaths (I was sent a preview copy).

In the biblical story, David outsmarted the giant using a slingshot to strike Goliath where he was weakest. David was an unlikely hero. He got lucky.

But in Malcolm’s retelling, David’s chances were actually much better than I thought. Goliath was the underdog.

Why then did weak teams play in a way that made it easy for good teams to do the very things that they were so good at?

...

This time 2 years ago, Cityposh, my branded games company, wasn’t working out.

Our original vision was to help small businesses market themselves through a captive audience playing our games. Instead of having to pay for that privilege with thousands of 50% off coupons, they’d put up a few prizes.

One Cityposh customer I was most interested in was a solo-entrepreneur-run, teenage-focused online store - jewelry, clothes, stuff teenagers like.

After our promotion ran, I was eager for her feedback. I thought we did a decent job getting traffic and followers. She wasn’t impressed.

I wasn’t sure if she didn’t understand the future impact our “brand advertising” and new Facebook/Twitter followers might have, or if I was naive of the problems her business actually had. I suspected it was me.

My wife and I once took a bus tour around the island of Maui, Hawaii. We saw black-sand...

There’s a company I rely on. Sometimes something goes wrong; I create a support ticket. Often the response is: “I’ll forward this to an engineer.”

Days or weeks go by. No reply. Then I get an automated message saying: “We’ve closed the ticket because there isn’t any activity. If you want to re-open it, you can’t. If you still want help, create a new ticket.”

This company tries to use automation to keep things more efficient for their support agents. They hope the efficiency trickles down to their customers - the fewer inactive open tickets, the more tickets they can actually spend time fixing. They’re trying to be helpful. But they’ve let automation screw this conversation up.

One thing I was taught to do as a young employee was to end all my emails with: “Please let me know if you have any questions or concerns.”

Which seemed funny. It was used by everyone, like an automated...

One thing that holds many of us back as creators, inventors, and entrepreneurs is simply our inability to repeat ourselves. Two people who do a great job repeating themselves are Brian Chesky (CEO of Airbnb) and James Altucher (author and entrepreneur).

My latest article at FastCompany. Read more…