October 2009 (This essay is derived from a talk at the 2009 Startup School.) I wasn't sure what to talk about at Startup School, so I decided to ask the founders of the startups we'd funded. What hadn't I written about yet? I'm in the unusual position of being able to test the essays I write about startups. I hope the…
February 2009 One of the things I always tell startups is a principle I learned from Paul Buchheit: it's better to make a few people really happy than to make a lot of people semi-happy. I was saying recently to a reporter that if I could only tell startups 10 things, this would be one of them. Then I thought: what…
July 2009 Now that the term "ramen profitable" has become widespread, I ought to explain precisely what the idea entails. Ramen profitable means a startup makes just enough to pay the founders' living expenses. This is a different form of profitability than startups have traditionally aimed for. Traditional…
There are a bunch of basic functional elements to building out a popular Rails app that I've never really seen explained in one place, but we had to learn the hard way while building Posterous....
March 2009 A couple days ago I finally got being a good startup founder down to two words: relentlessly resourceful. Till then the best I'd managed was to get the opposite quality down to one: hapless. Most dictionaries say hapless means unlucky. But the dictionaries are not doing a very good job. A team that outplays…
You're afraid that looking like being a small company means you'll lose sales. It's actually the opposite -- you're alienating your best customers.
Reflecting on selling Smart Bear in 2007, offering insights for entrepreneurs facing similar decisions.
In my 21 years of startups, I had my ideas “stolen” twice. See part one for the first time it happened. This time it was serious. As a reminder, this post is not legal advice, it’s not even advice.…
Super-fantastic-caveat : Despite the title, this post isn’t really about 37signals, in particular. I’ve used them as an example, only. I probably could have called it the “Joel on Software” effect, too. This post is about all of us who aren’t 37signals, or Joel, and the dangers we face when trying to incorporate…
So, in our last installment of the Y Combinator saga, we talked about applying. Since a handful of folks will be gearing up for their interviews shortly, it seems a fine time to move on to the next step in our journey.
I’ve decided to do a mini-series of sorts on our Y Combinator experience. Â Originally I was going to fold everything into one ginormus post, but I think it better to break it up and focus on different aspects.
Modern work can be frustrating and chaotic—if you don’t have the right tools. From context engineering to multimodal search, go behind the scenes and hear how Dropbox engineers are building AI that actually understands you, so you can focus on the work that matters most.
Never mistake motion for action. -Ernest Hemingway One of an entrepreneur’s greatest strengths is their relentless pursuit of a goal. But few realize how this differs from most of the population. W…
I often get asked something along the line of, “If you weren’t leading Automattic, what would you work on?” There’s not a single answer to this question; the answer changes day to day. But I think …
For the next few months I’ll be posting a series of posts on family, startup culture and careers. These vignettes are about how I’ve lived my life trying to make my dent in the universe and trying …
Some of the most important business lessons are learned in the most unlikely ways. At Ardent I learned many of them with a sharp smack on the side of the head from a brilliant but abusive boss. Not…
