30 books everyone in software business should read (andwhy)

I have personally read every book in this list. The enormous value I’ve gotten out ofthese books is the sole reason I am recommending them. These books helped me tomake my Swift To-Do List very successful. There are no affiliate links in this post. Ifyou have suggestions for other books that would benefit people in software business,please post them in comments, and I will update the additional list at the end.

There are both new and old books in this list. For the naysayers: Don’t forget howeasy it is to succumb to hype and to phrases like “anything older than 3 months is ir-relevant”, “it’s the age of the app”, “desktop is dead”, and so on. That’s simply nottrue. Reading these books can be very beneficial for you and for your business. Theconcepts are still valid, the ideas can be still utilized. Even if the world has fatalistical-ly moved on (and it hasn’t), you can’t catch it up without a strong foundation. Manythings are cyclical or ageless. You can re-combine ideas, find patterns, get inspiredand most importantly, learn new things. These books are a nourishment for yourmind. And hey, it can’t hurt to read something different than you are used to read!

The books are ordered randomly; it would be nearly impossible to come with a satis-fying ranking. Apples and pears, you know.

Writing this post took me 5 hours (plus 5 years to find and read the books). Enjoy.

1. Dreaming In Code (Scott Rosenberg) – The definitive lessons about over-ambi-tiousness and idealism in software. True story about spectacular software fail-ure. Dream team, dream budget, and a undreamed-of failure. Reads like a novel.The subtitle of the book is “Two Dozen Programmers, Three Years, 4,732 Bugs,and One Quest for Transcendent Software”.

2. Peopleware: Productive Projects and Teams (Tom DeMarco and Timothy Lis-ter) – Are you sure you are not chasing marginal productivity gains while thefundamentals are eluding you? Also, chances are, you are not working alone. Ifyou have not read this yet, then better start whistling and go secretly read it un-der a blanket with a flash light.

3. Startups Open Sourced: Stories to inspire and educate (Jared Tame) – Enter-taining read. Not immediately actionable, but definitely worthwhile. Even if youhave a mature business, the fresh look from the startup perspective can give yousome ideas what you might improve upon. Interesting tidbit – reddit foundersused to create hundreds of fake user accounts, submissions and comments to gettheir site started. Kindle edition is listed separately.

their site started. Kindle edition is listed separately.4. GUI Bloopers 2.0 (Jeff Johnson PhD) – If you think your GUI design could use

some improvement, read this. It even includes images! ;-) Negative examples arenot only useful, but also fun, and they give you warm fuzzy feeling that yourGUI is better. Or is it…? Some of the bloopers reminded me of Interface Hall ofShame.

5. The Elements of Style – You write a lot of text. This will help you write it better.Your code, writing for web, blog, emails – all that is text. (The book is public do-main now.)

6. In Search of Stupidity (Merril R. Chapman) – The subtitle of this book is “OverTwenty Years of High Tech Marketing Disasters”. It’s fun to read because it’sabout failures. It will make you feel good, because you are not failing on such ahuge scale. But do not be deceived by that false positive feeling – unless you arenot failing at least a bit, you are not experimenting enough, which is a failure byitself. Even giants like Google are constantly scraping ambitious projects be-cause they simply didn’t work out.

7. Do More Faster: TechStars Lessons to Accelerate Your Startup (Brad Feld andDavid Cohen) – Similar to Startups Open Sourced, basically stories of new star-tups that were supported by TechStars startup accelerator (which is similar toPaul Graham’s Y-Combinator).

8. Content Rules (Ann Handley, C.C. Chapman) – A must read. And if you arestruggling to grow your businesses to a certain extent, chances are, this bookwill tell you exactly how to do that.

9. Code Complete – In case you have not worked in any software company orteam, but just on your own, your code will be probably greatly enhanced onceyou implement the ideas presented in this awesome book. Many developersswear by it; it’s their bible.

10. Maximum Achievement (Brian Tracy) – There is not much self-help books that Iwould readily recommend to mISVs. However, Maximum Achievement willhelp you to live up to your potential, and that has significant impact on your bot-tom-line.

11. Founders At Work (Jessica Livingston) – Inspirational and motivational read.Not immediately actionable, but might make you excited again about the factthat you are are in software business.

12. Blue Ocean Strategy – If you are feeling like innovating, or feel stuck with yourcurrent market positioning or product/services portfolio, read this. The subtitleof this book is “How to Create Uncontested Market Space and Make Competi-tion Irrelevant”. It is written by example – lots of cool stories. The stories clearlytell how important is the presentation of your products/services.

13. Hackers & Painters (Paul Graham) – Really great stuff (that you’ve probably al-

ready read). Paul is excellent essayist, and has some refreshing insights. If youdon’t know Paul Graham, he is the founder of Y-Combinator. All his essays arealso freely available on his website. The book includes only some of them. Myfavorite essays are How to Make Wealth and Why Nerds are Unpopular.

14. Joel On Software (Joel Spolsky) – Joel is my hero. Joel is a spectacular pragma-tist and software business owner with deep knowledge of Microsoft technolo-gies. This book will bring you loads of ideas to improve your business, and willdefinitely change your views on many things related to technology, Microsoft,development and software business.

15. More Joel On Software (Joel Spolsky) – Same as above. Really, you can’t getenough of this stuff.

16. Best Software Writing (Joel Spolsky) – That’s right, Joel now occupies 10% ofthese 30 books.

17. Outliers (Malcom Gladwell) – Ever wondered why is Bill Gates so successful?18. Eric Sink On The Business Of Software – This is a classic book from a man

who coined the term “Micro-ISV”. Everyone in the TBoS community knows thebook. You’ve probably already read it; if not, you can still pick a thing or twoout of it.

19. Words That Sell (Richard Bayan) – If you do your own copywriting, this bookwill save you hours of work, help you quickly overcome writer’s blocks, and en-able you to create texts that you will finally feel proud about. Just don’t overdoit with the buzz words ;-)

20. The Pragmatic Programmer (Andrew Hunt and David Thomas) – Another clas-sic full of great guidelines and principles related to programming. For example,if it has never occurred to you that it is fairly easy to write code that writes code,and you could probably utilize that in your own projects with great successright now, then this book is a must read for you.

21. The E-Myth Revisited (Michael E. Gerber) – At first, the principles presented inthis book might seem not much applicable to mISVs, but if you switch the word“employee” for “script”, the book gets whole new (and useful) perspective.

22. The Business Of Software (Michael. A Cusumano) – Another (perhaps outdat-ed) classic. Read it, it’s well worth the time only if to gain some structured think-ing about (your) software business.

23. Anything You Want (Derek Sivers) – Useful for gaining high-level perspective.Reminder that there is more than money in business (and life).

24. Permission Marketing (Seth Godin) – If your email marketing is underutilized,this book will give you the basics for successfully building relationships withyour customers via email.

25. Ikigai (Sebastian Marshall) – This book presents sharp unique thinking related

to many areas of life. It is not directly related to software business, but to per-sonal achievement, individualism, productivity, negotiation, and similar things.Both enlightening and entertaining read. For Kindle only.

26. Copy Hackers (Joanna Wiebe) – If you write text for web, you are a copywriter.In such case, definitely read these 4 short e-books. Highly actionable advice thatcan improve the bottom line of your business.

27. Head First Design Patterns – If you don’t know what is a “design pattern” inthe OOP world, don’t think twice before buying this book. Don’t be discouragedby the fact that the samples are in Java, the sample code is easy to understandeven if you don’t know a thing about it.

28. The Art Of Ignoring (Alwin Hoogerdijk) – This is not really book, but a presen-tation with slides (and an accompanying video), but reading this stuff is simplynot optional. And it’s free!

29. The Dip (Seth Godin) – Not sure if you should abandon one of yourproducts/services, or not abandon them? Subtitle: “A Little Book That TeachesYou When to Quit (and When to Stick)”.

30. Personal Development for Smart People (Steve Pavlina) – This is probably thebest book on conscious self growth ever written. The ageless principles de-scribed in this book can be actually implemented into your business, whichgives this book a whole new perspective.

Books that didn’t made it into the list

These books were a bit disappointing to me, but they might be awesome for you.

Micro ISV: From Vision to Reality (Bob Walsh) – While excellent for beginners,if you are already running a successful business, this book can’t help you. It’stoo basic, unfortunately. That being said, it could give you some inspiration, asit includes a couple of interviews with mISVs, too.Coders At Work (Peter Siebel) – Overly technical and sometimes academical,not actionable. However, it gives you inside look into many brilliant minds.The Art Of The Start (Guy Kawasaki) – Unless you want to pitch venture capi-talists, or are from the venture startup/Mac world, this book is probably not foryou. Sorry, I am a Windows guy.Reality Check (Guy Kawasaki) – Same as above.Microsoft Secrets (Michael A. Cusumano) – While interesting to some (it wasfor me), it is not really relevant to independent software vendors. And the factit’s from 1995 doesn’t help much either.Bootstrap (Kenneth L. Hess) – If it wasn’t 11 years old, it would’ve been awe-some. Don’t get me wrong, it’s a great story and excellent material for bedtime

some. Don’t get me wrong, it’s a great story and excellent material for bedtimereading, but you won’t get much value out of it other than nostalgic feelings.The Marketing Gurus (Chris Murray) – Mainly irrelevant to mISVs; outdated.Content Rich (Jon Wuebben) – Get “Content Rules” instead. This one is very ba-sic and not written for computer rock stars like we all are ;-)

Other possibly interesting books:

MicroISV Sites that Sell! (Bob Walsh)The Web Startup Success Guide (Bob Walsh)The Twitter Survival Guide (Bob Walsh)The Best of Guerrilla MarketingGuerrilla Marketing on the InternetGuerrilla Social Media MarketingDesign Patterns: Elements of Reusable Object-Oriented SoftwareStart Small, Stay Small (Rob Walling and Mike Taber)From Program to Product (Rocky Smolin)Software That Sells (Edward Hasted)This Little Program Went to MarketThe Mythical Man Month (Frederick P. Brooks) – Another classic.Slack: Getting Past Burnout, Busywork, and the Myth of Total Effi-ciency (Tom DeMarco)Death March (Edward Yourdon)The Secrets of Consulting (Gerald M. Weinberg)User Interface Design for Programmers (Joel Spolsky)Don’t Just Roll The Dice (Neil Davidscon) – “a usefully short guideto software pricing”. Available as free ebook, or as paperback on Ama-zon.Showstopper! The Breakneck Race to Create Windows NT and theNext Generation at Microsoft (Pascal G. Zachary) – A tip by NicolasKassis, who says: “I can’t recommend the book enough. I’ve read it afew times already.”The PayPal Wars (Eric M. Jackson) – A tip by Akash Garg. Subtitle ofthe book is “Battles with eBay, the Media, the Mafia, and the Rest ofPlanet Earth”.The Art of Computer Programming (Donald E. Knuth) – True classic.The Innovator’s Solution (Clayton M. Christensen) – “Creating andSustaining Successful Growth”.