Three Entrepreneurial Books To Read Before You Turn 21

I regularly get asked some variant of “what books would you recommend to an entrepreneur.”  I typically send a quick email answer along with a link to the list of all the books I’ve read in the past few years.

Earlier this week, Fred Wilson forwarded me and Jerry Colonna (his old partner at Flatiron Partners) an email exchange he had with an entrepreneur.  The question in the email was:

“i’m looking for some book recommendation that have made an impact in your life, or books that you would recommend that would benefit me in a beginners life of entrepreneurship.”

Fred’s answer included two of my top three books for entrepreneurs.  My top three, along with a brief reason, follow:

Atlas Shrugged : While I’m not an Ayn Rand fanatic, every entrepreneur (or aspiring entrepreneur) must read this book to better understand the morality of self-interest (which is at the root of Rand’s Objectivism philosophy).  I find the contrast (and conflict) between “producers” / “founders” and “looters” / “moochers” to be a powerful characterization that will meaningfully impact any young entrepreneur.  This is a very long book that should be read slowly and carefully, especially John Galt’s speech near the end.

Zen and the Art of Motorcycle Maintenance: An Inquiry into Values : Robert Pirsig’s first book is a brilliant essay on quality.  I’ve never been particularly good at reading classical philosophy – Zen and the Art was one of the first philosophy books that I actually felt like I grokked (assuming you don’t include Stranger in a Strange Land in the philosophy genre.)  While Zen and the Art isn’t as long as Atlas Shrugged, it should also be read slowly and savored.

The Amazing Adventures of Kavalier & Clay: I didn’t read this until a few years ago and it was the second Michael Chabon book that I read (after The Yiddish Policemen’s Union – also a fantastic book.)  While this book is a fictionalized account of the creation of the comic book industry it really is a treatise to entrepreneur as superhero.  Chabon is an incredible storyteller and he takes the philosophy-fiction genre to a new level.

All three of these books are on my “must read” list for entrepreneurs of any age.  As the dog days of summer wind down, pick one and go for it.  I just inspired myself to go reread all three (five!) of them.

  • Jake

    Thanks, I was just looking for a new book. #1 had a big impact on me when I was in high school. #2 I just purchased on my Kindle. #3 is not available on Kindle so it will have to wait.

  • Eric Willis

    Agreed. Atlas Shrugged should be on the top of the list. I've read it several times… Highly recommended. Going to pick up the other two you've mentioned. Thanks.

  • mark macauley

    I would add Lord of the Flies too. Id, ego, superego all the dynamics of a team, distilled into raw charicatures.

    Totally agree with Atlas Shrugged and Zen…

  • JohnSharp

    "Zen" was a classic. The story behind it should be savored by entrepreneurs as well – Pirsig's book was rejected 121 times before is was finally published.

    Lesson: Never give up. 😉

  • David Ulevitch

    Proud to say I've read all three — Zen a few times, and Atlas Shrugged a few times.

    To add one to the list… Once you've done the entrepreneur thing for a while and decide you want a break before jumping back in, read "Honeymoon with my brother."

    • Brad Feld

      It’s already in my infinite pile of books to read!

  • jason l baptiste

    I'd add Monk and the Riddle by Randy Komisar. I read it at 21 and it most definitely changed my life.

  • Brad Feld

    I read The Monk and The Riddle when it came out.  I liked it, but I wouldn’t put it anywhere near the top of my list.  But – I didn’t read it when I was 21!

  • Jay Levitt

    _Phantoms in the Brain_. It's by a neurologist, in the Oliver Sacks style; it's nominally about amputees with phantom-limb pain, but it's really a magical tour of our brain's capacity for denial, bias, and rationalization. And you need all three of those to build a startup.

    • Brad Feld

      Ordered!  Thanks for the recommendation.

  • Bobby Martyna

    _Think and Grow Rich_ by Napolean Hill. Might seem superficial and even ludicrous from the title, but principles therein were conceived and implemented over 100 years ago by Andrew Carnegie. This book is about the entrepreneur mastering self first — the major theme being that desire for success must be unquenchable.

    I like this one — Think and Grow Rich!: The Original Version, Restored and Revised (ISBN-10: 1593302002) — the historical footnotes are illuminating.

  • cmadler

    Personally, I’ve always preferred The Fountainhead to Atlas Shrugged. Both have their strong points, but I find the former better both as a novel (better plot, more character development, better prose) and as an exposition of Rand’s Objectivist ideas.

  • cmadler

    That said, if I were to add one book to this list, it would probably be Pearl Buck’s The Good Earth.

  • MattCope

    I saw the post title and thought, "Atlas Shrugged better be up there…"
    And, Lo!

    Now…..about the Feld bar…..who made it? Had any feedback? Plans to roll it out further?

    • Brad Feld

      Wibiya.  Maybe more coming soon.

  • Peter

    Add: "The Little Prince"

  • Steve

    "Atlas Shrugged : While I’m not an Ayn Rand fanatic, every entrepreneur (or aspiring entrepreneur) must read this book to better understand the morality of self-interest (which is at the root of Rand’s Objectivism philosophy)."

    Please please ignore this. Or, read Atlas Shrugged for the entertainment value (it's entertaining!) but approach Rand's morality with extreme skepticism. You can be a successful entrepreneur, and a good person, but don't conflate the two. There is no causal relationship. Do not try to find meaning in profit, it's a waste of time.

    People who look to Rand for direction are, in my experience, pretty insecure and one-dimensional. It's Stuart Smiley for businesspeople (and the whole idea of Going alt – taking that seriously – is pompous and transparently self-serving). If anything it's important to read from a kind of anthropological point of view because there are very earnest Rand nuts you'll encounter in the business world, who talk with earnest reverence about John Galt like this blogger (similarly, The Selfish Gene is a brilliant book completely misused by business people – Rand and The Selfish Gene were what everyone at Enron was reading).

    My #1 recommendation to a 21-year old would be Letters to a Young Contrarian by Hitchens (it's a quick, entertaining read). After that, Arendt's "Eichmann in Jerusalem", Neiman's "Moral Clarity", Hirsi Ali's "Infidel", Haley's "Malcolm X", and Pirsig. If you want to start developing a moral center, intellectual self-assuredness, and good judgement – I'd start with those and enjoy Rand for the pulp/kitsch that it is.

    • Brad Feld

      Excellent – I was hoping that I would get a “hey – Atlas Shrugged is a bad thing” comment within the first 24 hours of writing this.

      Your experience that “people who look to Rand for direction are, in my experience, pretty insecure and one-dimensional” is incongruous with my experience.  Of course, some people who follow Rand’s philosophy fit this, but the broad generalization is one-dimensional in and of itself, which is deliciously self-referential.  I know many secure, multi-dimensional people who think Atlas Shrugged is an important book.

      That said, each to his own.  And – thanks for the other suggestions!

      • Satish

        My 2 cents: I read Atlas Shrugged and Fountainhead when i was 21. :) When i read those books, I felt each of those characters were qualities each of has in different proportions. I started to introspect to see what ratio i had each of those qualities. I started to look at different people around me and try to identify the same. A lot of people take the books literally and see themselves as heroes and look down upon others etc. But most normal people get a better understanding of themselves by reading those two books. And for most people it helps crystallize the qualities that they want to work on and the person they want to become. And for an entrepreneur it lights a fire inside to create something worthwhile. :)

        • Brad Feld

          Great comment – you definitely grokked the essence of the book.

      • Steve

        "Excellent – I was hoping that I would get a “hey – Atlas Shrugged is a bad thing” comment within the first 24 hours of writing this."

        I'm happy to play into your plan!

        " I know many secure, multi-dimensional people who think Atlas Shrugged is an important book."

        Me too, we probably differ in what we mean by "important". It was a good read and certainly presents a point of view and certain mental models that I would encourage everyone to be aware of. It would be bad for a prospective entrepreneur to get caught up in the idea that there is a good "us" and a "moocher" "them" – the gubmint or the proles or whatever – and that entrepreneurs deserve any kind of moral credit or higher social standing for simply being successful at business – the view put forward in the book. Or develop a siege mentality wherein the vast sea of others/moochers want to tear down the poor capitalists – where you're the poor Galt-like Romans defending civilization against the Visigoths at the gate. Some Rand enthusiasts seriously believe that kind of thing (Rand and her followers did, obviously).

        • Brad Feld

          There is no doubt that there are some crazy Randian nutbags in the world.  Someone told me recently that Rush Limbaugh is suddenly a Rand disciple.  Oops.

          I disagree with your assertion that “it would be bad for a prospective entrepreneur to get caught up in the idea that there is a good us and a moocher them”.  I think it’s important for a prospective entrepreneur – and any sentient being – to contemplate stuff like this early as a part of developing THEIR OWN moral code and perspective.  Atlas Shrugged is merely an input – not “the answer.”

          • Steve

            We clearly agree on a lot (and have some healthy disagreements, probably on various matters of degree and emphasis).

            I regret my original tone, I blame the internet 😉

          • Steve

            I saw this post


            and thought of this thread. Freddie's analysis is pitch-perfect,in particular:

            "And it's this, ultimately, that makes Rand so corrosive, so deadening to the heart of the intellectual project. People far abler than I have prosecuted the case against Rand, and I don't intend to rehash it here. But this tendency of her writings and her philosophy to compel people to slap concrete on the foundation of their own ideas, to build a moat around their intellectual life, to categorize the whole world into the tiny fraction who are worthy and the great horrid mass that are simply not to be listened to in any circumstance… this is the greatest failing of the woman and her teachings. There are a worse things to inspire people towards– genocide, war, ethnic cleansing– but still, a philosopher whose greatest contribution is a vast incuriosity is a dismal thing."

  • Steve

    Whoops! I meant Stuart *Smalley* for businesspeople. Sorry Stuart.

  • Durst Hineybuck

    Marketing Warfare by Ries & Trout

  • Justyn Howard

    I enjoy hearing about books that weren't intended to be entrepreneurial, but have great lessons. That said, I really wish there were more great books intended for this audience! Every few weeks I return to Amazon or Borders hoping to see something under-the-radar read from the trenches. Brad Feld, Ron Conway, Jason Calacanis. The information possessed by the leaders in our space is pure gold (This Week in Startups is a great example).

    Unfortunately world-domination takes a lot of work and I'm guessing sitting in front of a word processor for a few months isn't high on the priority list.

    Thanks for the recommendations! Needed more to read.

  • day_dree

    If you're boot strapping something or are in the early days, you may find Pour Your Heart Into It by Howard Schultz interesting … It's probably 10 years old but has more than a few inspiring sections for the dog days of getting something launched.

    2 more 10 year old books worth the read are Geoffrey Moore's Crossing the Chasm and Inside the Tornado if you're launched but anywhere short of the market domination. Some people may find Business Lessons from the Edge, a new book on intelligent risk taking from Jim McCormick, useful in defining personal limits and approaches. It pulls lessons from tough athletic pursuits.

    If you've got a staff of strong VPs in place, good time to pick up Peter Drucker on management again — especially if you're a founder.

    Launching/growing a business can be lonely, even isolating … the difference between driver's seat and passenger seat is vast, starting with the inability to talk completely openly with the other passengers. A good book can help.


  • Lincoln Nguyen

    Letters from a Stoic – Seneca

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  • John Dean

    I have some moral qualms with Ayn Rand but I do remember loving that book (and the Fountainhead) back in college. Looking for something under the radar? I really liked "The Mouse Driver Chronicles"-about two guys who decided to start a business right after getting their MBAs (instead of working for a company). They made a mouse shaped like a golf club (hence the name). Just a nice account of the ups and downs of figuring out how to make a go of it.

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  • kyjenkyle

    I'd sugest these classics: 22 Immutable Laws of Mareting, The E Myth, Word Of Mouth Marketing.

  • Brad Feld

    E Myth is a great book – thanks for the suggestions.

  • Matt S.

    As the Crow Flies by Jeffrey Archer…entertaining fiction about the entrepreneurial spirit

  • Brad Feld

    Thanks – I haven’t read that one yet.  Grabbing in on Amazon right now.

  • Paramendra Kumar Bhagat

    How can "all three" become "five of them?"

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