I'm a software engineer living vicariously through the Venture Voice podcast and books like Founders at Work. What should I read before I branch out and try to write and sell software on my own?

+7  A: 

Listen to SOF podcast #12 where they go over the FogCreek Software Management Training Program book list and highlight important books in just about every area related to software engineering and management.

Yaakov Ellis
+2  A: 

I found the Business of Software forum to be a great start.

Douglas Tosi
+2  A: 

Bootstrap: Lessons Learned Building a Successful Company from Scratch

Kenneth Hess retraces his steps from starting alone in his home to selling his quite large software company. No grand rewritten history here, but daily struggles and small victories all the way. Mandatory reading. Buy it now.

Christian Lescuyer
+2  A: 

How about taking a three day course? Big Nerd Ranch have great courses.

+3  A: 

Check out the Personal MBA Program. Has a great list 70 books on various subjects (some of which you will not need to read).

+9  A: 

OK, to summarize (in no particular order):

Thanks for your responses!

Dominic Cooney
+1  A: 

It depends on how you plan on starting your company - venture funding or bootstrapped micro isv. If you go the micro isv route, Eric Sink's The Business Of Software is a great read. The book is just a collection of his blog posts, which are all available here.

Shane Arney
+1  A: 

I'm going to branch out from some of the other suggestions, many of which I use myself.

I found The Innovators Solution to be a very interesting read. I recently took the plunge mysekf and became independent and I believe this book helped me see where I can uniquely fit in the market. It is a very academic read, but very well researched. I have actually seen it referenced in other books as well.

The salient point I got out of it is that markets are always moving and if you place your self correctly you can build into markets that other people are leaving (sometimes without knowing it) by keeping a constant, planned cycle of innovation.

Barrett Conrad
+3  A: 

I'd strongly recommend Joel Spolsky's User Interface Design for Programmers. As a software engineer, my passions are mostly enveloped by interesting architectures and neat solutions. Unfortunately, the reality is that your program's GUI is often one of the most important factors in making your software a success - not your algorithms. This book breaks away from the mentality that gui creation is an artistic feat which and lays out an engineering approach to good UI design. When it comes to creating a strong product, I feel that this book is an essential read.

+4  A: 

Getting Real by 37 Signals. Not to shill for them, but they've done very well with a really small team and as a BaseCamp user, their software is good at what it promises to do.

+2  A: 

One important thing to read is the 'terms and conditions' of whatever contract you're working under, to make sure that you won't get your a** sued out of existence if you happen to be successful and your ex employer isn't happy about it.

Leon Bambrick
+2  A: 

For the general business process stuff, I would recommend Michael Gerber's "The E-Myth" (subtitled "Why Most Small Businesses Don't Work and What to Do About It").

Whilst the focus is on businesses that sell to the public, there's a lot to learn about the parts of the business process (customer care, quality, order processing etc) which can be neglected - especially by technical people.

One of the key messages of the book is that ability in a technical field does not mean that you have the skills to run a business that provides those technical services - and the book details a set of strategies to make sure this stuff gets done.

I tried to read Gerber's E-myth book, but I thought it was over-rated, boring and irrelevant to my situation (as a microISV).
Andy Brice