Lispian Random meanderings on whatever catches my fancy

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Books Entrepreneurs Should Read

Over at Seedcamp there’s an article on 30 books every young entrepreneur should read. As with any list you can take it or leave it. But it is a very good list. I’m also assuming they’re not in any particular order.

Although I don’t agree that those are the top 30 I’ve never really thought about a top 30 list. I do know certain books I’d put up on any list. Since I’ve been asked before which books I’ve read with an entrepreneurial slant I’ll list them now. They’re not in any particular order.


1.High-Tech Ventures: The Guide for Entrepreneurial Success. In my opinion, the best book on entrepreneurship I’ve ever read. It’s immaterial how old the book is, the book is something everyone should read.
2.The Art of Ware. A book long out of print but now available at Bruce Henderson’s blog site. Quite simply it’s the Art of War interpreted for running a software business. An excellent book. Well worth the read.
3.The Art of the Start. An excellent book describing the actual art of starting up a company. It’s much more complex than most people think. Here Guy outlines things in an elegant fashion for everyone to see and appreciate.
4.Rules for Revolutionaries. In a way this appears to be a description of what Apple does. And you can’t really go too wrong trying to emulate Apple’s fanatical desire to please the customer.
5.Computer Wars. One of the best books to comprehend the computer industry ever written. A great history lesson on how Microsoft became ascendant.
6.Accidental Empires. Still my favourite history of the high tech industry, especially of the early Silicon Valley. Read it to comprehend the characters that shaped the industry into what it is today.
7.Startup: A Silicon Valley Adventure Story. Read it and weep. Find out how having the best doesn’t always matter. And why “good enough” usually is plenty good for most people.
8.How the Web Was Won. Watch as Microsoft takes apart Netscape. This book documents why so many companies fear Microsoft. It also explains why so many VCs ask: “What’s Microsoft doing in this space?” or the more dangerous, “What will happen to this space once Microsoft enters it?”
9.Almost Perfect. This book is the history of WordPerfect as told by Pete Peterson. The book is long out of print but Peterson has put the book online for those who wish to read it. The book is a great read into the minds of WordPerfect corporation. I still highly recommend it to many friends starting out. It shows a company well ahead of everyone and the horror of watching Microsoft catch up and crush them. And while reading the book you quickly realize that it was more than Microsoft’s business acumen that helped them succeed. Some of the errors Peterson points out in hindsight are brutal and should act as a cautionary tale to those who figure their positions are unassailable.
10.The Mythical Man Month. The classic software engineering text. Everyone in the computer business should be forced to read this text.
11.Slack. More in tune with large companies or startups that have passed the 100 person marker, this book explains the pitfalls awaiting those that are driven to succeed in today’s world. It explains how slack — in schedules, life, etc. — are necessary. An obvious sentiment, all too often ignored.
12.High Stakes, No Prisoners. This is a classic “grab the bull by the horns” type of tale. Ferguson, who founded what would become FrontPage, documents the path taken by him and his team to develop one of the first web page editors. It’s truly a roller-coaster of tale, even if you do know the outcome. Entrepreneurs, successful and otherwise, will be nodding throughout the book as they see their own lives echoed in what Ferguson lived.
13.Crossing the Chasm. Another classic text that everyone who either runs or works in a company should read just to understand what it’s like trying to get a new product out the door and into customers’ hands. The follow-on, Inside the Tornado, explains what happens once customers figure they truly need what you’re selling.
14.Peopleware. Another classic tome on running a business. All too often this book is ignored or unheard of. And yet it lays out the particulars of what’s necessary to have a successful team, most of which means actually caring about the team itself. Find a used copy and read it. DeMarco’s best.
15.Where Wizards Stay Up Late. We take it for granted now, but read about the early history of the Internet. When you realize what they had to work with it’s amazing what they got accomplished. It’s also sad to realize how little has changed.
16.Fire in the Valley. Another history book on the Valley. Long, at 560 pages, but well worth reading to get an insight into what it was like way back when. Although published in 2000 it seems like it was written much further back. It highlights how much has changed since 1999.
17.Fumbling the Future. Xerox had it all. Why didn’t they come to rule the computer age. This book will explain that. But it’ll also leave you wondering why haven’t we really progressed much since this was written. For that matter, why do we have little new today when you realize the work that was done by Xerox and others in the 60s and 70s when there was a burst of innovation and then a near complete halt.
18.Gates. The history of Microsoft and Bill Gates. They’re inseparable, especially early on. And here we can see not only how Microsoft grew but also the culture that infuses Microsoft and where it came from.
19.Hard Drive. Another biography of Microsoft and Bill Gates. Again, fascinating as you realize that what is Microsoft was formed through the years from the small startup to the behemoth it is today.
20.Show-Stopper. The tale of Windows NT. Hard to find but so worth it. The culture clashes alone are worth the read, especially as Dave Cutler discovers Microsoft’s love for Hungarian Notation.
21.The Innovator’s Dilemma. A classic on why some companies can’t innovate once they have a successful product. The follow-on, The Innovator’s Solution, provides some possible avenues out of the dilemma.
22.The Tipping Point. In clear form provides the reader with information explaining how some products seem to just suddenly become mega-popular. It truly explains some of what we see with the internet and how certain sites simply explode on our consciousness.
23.Made to Stick. What makes some products “sticky”. Or, put another way, why do we remember some things and not others. This book attempts to distill the real reasons why we remember some things and not others. Well worth it. Lifehack.org has an ongoing workshop series on the book that is worth checking out.
24.Starving to Death on $200 Million a Year. This was my favourite Dot Com Era publication. This is the sad story of its demise.
25.About Face 3. If you’re planning on writing software that has to interact with a user you should read this book.
26.The Inmates Are Running the Asylum. And if you want to know why software is the mess it is, and why it’s so hard to use, and why the folks who write some software seem out of touch with their client base, then read this book. It’ll make you laugh so hard you’ll cry. And then you’ll cry because you’ll know what he’s saying is too true.

There are other books that I can quickly think of, too. Such as Prophets in the Dark or Nerds 2.0.1 or the The Ingenuity Gap. The number of books attempting to provide useful information to entrepreneurs has never been greater. And I do find that a good number are quite good. But browse your local bookstore, talk to local entrepreneurs, and I’m sure they’ll point you at other gems.

If I have the time I’ll update this in the future.

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September 2007
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