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30 books everyone in software business should read (and why)

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I have personally read every book in this list. The enormous value I’ve gotten out of these books is the sole reason I am recommending them. These books helped me to make my Swift To-Do List very successful. There are no affiliate links in this post. If you 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 how easy it is to succumb to hype and to phrases like “anything older than 3 months is irrelevant”, “it’s the age of the app”, “desktop is dead”, and so on. That’s simply not true. Reading these books can be very beneficial for you and for your business. The concepts are still valid, the ideas can be still utilized. Even if the world has fatalistically moved on (and it hasn’t), you can’t catch it up without a strong foundation. Many things are cyclical or ageless. You can re-combine ideas, find patterns, get inspired and most importantly, learn new things. These books are a nourishment for your mind. 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 satisfying 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-ambitiousness and idealism in software. True story about spectacular software failure. 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 Lister) – Are you sure you are not chasing marginal productivity gains while the fundamentals are eluding you? Also, chances are, you are not working alone. If you have not read this yet, then better start whistling and go secretly read it under a blanket with a flash light.
  3. Startups Open Sourced: Stories to inspire and educate (Jared Tame) – Entertaining read. Not immediately actionable, but definitely worthwhile. Even if you have a mature business, the fresh look from the startup perspective can give you some ideas what you might improve upon. Interesting tidbit – reddit founders used to create hundreds of fake user accounts, submissions and comments to get 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 are not only useful, but also fun, and they give you warm fuzzy feeling that your GUI is better. Or is it…? Some of the bloopers reminded me of Interface Hall of Shame.
  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 domain now.)
  6. In Search of Stupidity (Merril R. Chapman) – The subtitle of this book is “Over Twenty Years of High Tech Marketing Disasters”. It’s fun to read because it’s about failures. It will make you feel good, because you are not failing on such a huge scale. But do not be deceived by that false positive feeling – unless you are not failing at least a bit, you are not experimenting enough, which is a failure by itself. Even giants like Google are constantly scraping ambitious projects because they simply didn’t work out.
  7. Do More Faster: TechStars Lessons to Accelerate Your Startup (Brad Feld and David Cohen) – Similar to Startups Open Sourced, basically stories of new startups that were supported by TechStars startup accelerator (which is similar to Paul Graham’s Y-Combinator).
  8. Content Rules (Ann Handley, C.C. Chapman) – A must read. And if you are struggling to grow your businesses to a certain extent, chances are, this book will tell you exactly how to do that.
  9. Code Complete – In case you have not worked in any software company or team, but just on your own, your code will be probably greatly enhanced once you implement the ideas presented in this awesome book. Many developers swear by it; it’s their bible.
  10. Maximum Achievement (Brian Tracy) – There is not much self-help books that I would readily recommend to mISVs. However, Maximum Achievement will help you to live up to your potential, and that has significant impact on your bottom-line.
  11. Founders At Work (Jessica Livingston) – Inspirational and motivational read. Not immediately actionable, but might make you excited again about the fact that you are are in software business.
  12. Blue Ocean Strategy – If you are feeling like innovating, or feel stuck with your current market positioning or product/services portfolio, read this. The subtitle of this book is “How to Create Uncontested Market Space and Make Competition Irrelevant”. It is written by example – lots of cool stories. The stories clearly tell how important is the presentation of your products/services.
  13. Hackers & Painters (Paul Graham) – Really great stuff (that you’ve probably already read). Paul is excellent essayist, and has some refreshing insights. If you don’t know Paul Graham, he is the founder of Y-Combinator. All his essays are also freely available on his website. The book includes only some of them. My favorite 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 pragmatist and software business owner with deep knowledge of Microsoft technologies. This book will bring you loads of ideas to improve your business, and will definitely 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 get enough of this stuff.
  16. Best Software Writing (Joel Spolsky) – That’s right, Joel now occupies 10% of these 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 the book. You’ve probably already read it; if not, you can still pick a thing or two out of it.
  19. Words That Sell (Richard Bayan) – If you do your own copywriting, this book will save you hours of work, help you quickly overcome writer’s blocks, and enable you to create texts that you will finally feel proud about. Just don’t overdo it with the buzz words ;-)
  20. The Pragmatic Programmer (Andrew Hunt and David Thomas) – Another classic 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 success right now, then this book is a must read for you.
  21. The E-Myth Revisited (Michael E. Gerber) – At first, the principles presented in this 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 outdated) classic. Read it, it’s well worth the time only if to gain some structured thinking 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 with your 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 personal 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 that can improve the bottom line of your business.
  27. Head First Design Patterns – If you don’t know what is a “design pattern” in the OOP world, don’t think twice before buying this book. Don’t be discouraged by the fact that the samples are in Java, the sample code is easy to understand even if you don’t know a thing about it.
  28. The Art Of Ignoring (Alwin Hoogerdijk) – This is not really book, but a presentation with slides (and an accompanying video), but reading this stuff is simply not optional. And it’s free!
  29. The Dip (Seth Godin) – Not sure if you should abandon one of your products/services, or not abandon them? Subtitle: “A Little Book That Teaches You When to Quit (and When to Stick)”.
  30. Personal Development for Smart People (Steve Pavlina) – This is probably the best book on conscious self growth ever written. The ageless principles described in this book can be actually implemented into your business, which gives 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.

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  • Scott Yu

    Or you could just stop fantasizing about running a business by reading books, and just do it.

    Sometimes you’ve just got to start something, rather than wasting your time lining up the ducks.

    • http://www.dextronet.com Jiri Novotny

      Hi Scott,

      Actually, I’m a huge pragmatist. 1 second of action outweighs 100 years of theory, and all that. In fact, I’m working about 8-12 hours a day and I read the books (or listen to audiobooks) mainly on my way to/from the office, while eating lunch, etc. This would be dead time otherwise. I had many deep insights thanks to the things I read. Sure, I still get many insights and great ideas “on my own”, but the books are a great raw material for my mind (and sub conscious mind) to work with, so it’s hard to separate the two.

      • Scott Yu

        Oh, I agree that it’s good to filll “dead time” with something constructive. You could do worse things than read these books.

        I’m just envisaging people forcing themselves to read all 30 books before they actually do anything that actually advances their cause. Because in all 30 books, there’s probably enough real, useful advice to fill just one. But everybody gets benefits from different parts of each book, and you can’t know what’s useful until you’ve read it.

        The problem with a lot of “business” books is that they are like “self-help” books – they are a lazy man’s replacement for self-awareness, or more specifically to mISVs, experience and domain knowledge. But the dreamers just lap them up.

        If you find yourself reading any of these books and you go “wow, I never thought of that!” more than about 5 times in each book, you probably don’t have the aptitude for this business. These books are not instruction manuals. They confirm what you should already know or be able to work out. If you do have the aptitude, they stroke your ego by confirming your hunches.

        Try reading The Art Of War and apply it to sales and marketing techniques against competitors. It’s almost like it was written specifically about software companies. But it’s actually about killing people. Go figure.

        • Alderaan

          “Business is war” – Jack Tramiel

          • Mr Mister

            American Psycho

          • http://www.dextronet.com Jiri Novotny

            Umm… how that relates to software business? :-)

      • Dave

        If you work 8-12 hours a day (work as opposed to being productive) & see lunch as “dead time” you should definitely absolutely add ‘Slack: Getting Past Burn-out, Busywork, and the Myth of Total Efficiency, by Tom DeMarco’ to your reading list.

        I have only a few books that I consider essential reading, the rest I learn from the internet (which is the greatest tool for informational exchange in human history, bar maybe writing itself).

        • http://www.dextronet.com Jiri Novotny

          Hi Dave, thanks for the suggestion. I will read Slack.

          Just to clarify – I am having a total blast doing what I love. Lunch is not a really dead time for me, but transit to/from office definitely is. When I relax, I want to do it fully, so I have a dedicated time for that as well.

          • Dave

            Cool – it’s a short book & potential game-changer for the creative environment in which you write code & for deciding which code to write.

    • Patrick Cummings

      Number one on the list ought to be Appendix B in “the Unix Hater’s Handbook”. Very enlightening

  • http://www.runin.to Petr

    Regarding the Elements of Style… I suggest you have a look at this http://chronicle.com/article/50-Years-of-Stupid-Grammar/25497

    • http://www.dextronet.com Jiri Novotny

      Hi Petr,

      Great article, thanks for sharing. Have you run into any other grammar/writing books that you would recommend instead of ELOS?

      The emphasis on clear writing and the advice on omitting of needless words, were both beneficial to me. Perhaps this advice could be considered the main merit of the book.

      • http://www.copyhackers.com Joanna Wiebe

        I’ve never heard of someone hatin’ on “Elements of Style”, Petr. It’s such a foundational text. But I guess there are always flaws with any book.

        …If you’re looking for a great book about grammar + writing well, I highly recommend the out-of-print, hard-to-find “Grammar As Style”. It’s written by Virginia Tufte… who just so happens to be the mom of data visualization guru Edward Tufte.

        BTW, thanks for including “Copy Hackers” on your list, Jiri. Feels awesome to know my little books are getting recognized and helping! :)

        • http://www.dextronet.com Jiri Novotny

          Hope you get some sales out of the mention Joanna. Keep up the great work! Cheers

  • John Stevens

    The list lost all credibility when you recommended Sebastian Marshall as a must-read book. You might as well slap the “4-hour body” by Ferriss on that list.

    • http://www.dextronet.com Jiri Novotny

      John, could you please explain me what do Tim Ferris and Sebastian Marshall have in common? No such similarities have ever occurred to me.

  • http://pcchip.hr Boris Plavljanic

    I can’t believe that you didn’t recommend The Art of Computer Programming by D.Knuth. Ok, it is not “business” book, but it is something that every good programmer must read. At least, this is my opinion…

    • http://www.dextronet.com Jiri Novotny

      Hi Boris,

      Thanks for pointing that out. I’ve added it to the appended list. If I were to create list of 30 books for programmers, it would be definitely there, but this list is more general.

    • Paula B Green

      Wow, Boris, I haven’t thought about Knuth in years… Thank you for a blast from the past.

      • http://pcchip.hr Boris P

        No problems =)… Knuth is my #1! The art of Computer Programming + Concrete Mathematics: A Foundation for Computer Science is something that every CS student or programmer must read!

  • Sebastian

    @ Boris Plavljanic, second that. Absolutely worth checking out: http://amzn.to/xYovXl

  • http://Disruptivegeo.com Joshua Campbell

    The Innovator’s Solution by Clayton Christensen has been an incredible resource for me.

    http:/www.amazon.com/gp/aw/d/1578518520

    • http://www.dextronet.com Jiri Novotny

      Looks really great Joshua. Thanks so much for sharing! I’ve added it to the appended list.

  • Stefano Guandalini

    What about “the mythical man month”?

    • http://www.dextronet.com Jiri Novotny

      It’s there, just not in the 30 books. I wanted to bring attention to some less known books as well.

  • http://dodgycoder.net dodgy_coder

    I put together a compilation of responses from a question on stack overflow that I believe has some greatest titles ever written about programming – this post lists the top 30 … enjoy!

    http://www.internetsecuritydb.com/2011/09/top-ten-most-influential-programming.html

    FYI, top 5 are:
    1. Code Complete (Steve McConnell),
    2. The Pragmatic Programmer (Andy Hunt & Dave Thomas),
    3. Structure and Interpretation of Computer Programs, Second Edition (H. Abelson, G.J. Sussman and J.Sussman),
    4. The C Programming Language (2nd Edition) (B.W.Kernighan & D.Ritchie),
    5. Introduction to Algorithms (Thomas H. Cormen, Charles E. Leiserson, Ronald L. Rivest and Clifford Stein).

  • http://www.itoctopus.com itoctopus

    The only books really worth reading are those written by Paul Graham.

    There are also other basic programming books that I think everyone should read:

    - C: How to Program
    - LISP: A Gentle Introduction to Symbolic Computation

    Learning LISP will make any programmer think outside the box. It’s probably the most “free” language out there, but the world is still not ready for it.

  • http://www.twitter.com/andrewferk Andrew Ferk

    Sorry, I have not read many of these books on this list (but I would like to read the majority of them when I have time). Do any of these books cover quality and process management, or even at a finer level, metrics? “Managing the Software Process” by Watts S. Humphrey is a good example (http://www.amazon.com/Managing-Software-Process-Watts-Humphrey/dp/0201180952/ref=sr_1_1?s=books&ie=UTF8&qid=1327285391&sr=1-1).

    • http://www.dextronet.com Jiri Novotny

      Thanks for the tip Andrew! The book is from 1989, but it looks like it’s still sound.

  • http://www.youtube.com A Cheap Tart in a Pond

    Good list. As for those who don’t think reading is important, why did they read this & then comment? Kill your tv, rftb!

  • http://wileyindia.com V S

    my top 3 are

    Web Design Digital Classroom by John Wiley and Sons
    Microsoft Mobile Development Handbook by Andy Wigley
    Cloud Computing Bible by Barrie Sosinsky

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