Best Books on Startups & VC

Until recently, there have been astonishingly few good books by and for people who are building (or investing in) high-growth startup companies.   Fortunately that has changed:  after digesting far too many (burp), here are my picks of the most actionable and readable.  Unlike the many “textbook” treatments, these are written engagingly by successful principals who have “been there done that”, share their real-name stories, and know what you’re facing.   For fun there are couple of books in the “how to spend it” department by successful VCs (Tom Perkins) and entrepreneurs (Larry Ellison.)

Andrew Roman’s Entrepreneurial Bible  < (Click to buy from Amazon)Andrew Roman's Entrepreneurial Bible My pick for the best, most complete, and most applicable CEO / founder oriented startup book in print.   Mr. Romans has extensive experience in venture capital and has been an entrepreneur, so he writes from the useful perspective of one who has been on both sides of the table.   (Some of us think such experience makes the best VCs because we who have been entrepreneurs understand what it takes.)

The book’s real stars are the domain-expert guest authors who have written many valuable chapters.  These range from well-known attorneys like Elton Satusky of famed Silicon Valley law firm Wilson-Sonsini, to legendary founders of venture funds including Pitch Johnson (Asset Management) and Tim Draper (DFJ), and successful CEOs.  The chapters are self-contained bite-size sections and the examples are real,  which makes for a fun read whether cover to cover, or in an a la carte open-it-anywhere style.

It focuses mainly on consumer-oriented companies (as do most of these books) so it lacks some depth in IP and other aspects of “hard technology”, B2B or enterprise-oriented startups, but everything in it is applicable to almost any startup.   The one flaw is that it has a few too many personal chest-pounding stories which most entrepreneurs may neither identify with or profit from.  For example, of course it’s easy to attract top-tier venture capital in a couple of meetings if your entire team is 3X successful founders with IPOs aplenty.   Read it anyway.

513Krp4qLkL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_The close runner up (I recommend reading both) is Jeff Bussgang’s Mastering the VC Game   Written from the perspective of a General Partner at Flybridge Capital  If you’ve ever wondered what it is really like being a VC (there are only a few thousand worldwide) this is the real deal.

More practically, it  gives entrepreneurs real insight into what VCs really think about, and why they do what they do.  It’s reallyimportant to understand how the guy on the opposite side of the table thinks when you are seeking funding.  It’s unique in giving entrepreneurs insight into how to choose investors, what questions to ask prospective investors, and how to work with VCs and angels once they have invested.

It is also one of the only books that present an excellent discussion of what happens when companies don’t evolve according to plan and how to work with partners, employees and financiers in this situation.   We have all been there – some of us from both sides of the table.   Notice to entrepreneurs, you will, at some point, face such a situation whether it is with a VC or friends & family.  It happens to us all.  Forewarned is forearmed.

Venture Deals:  Be Smarter Than Your Lawyer and Venture Capitalist 51p0oeLn-PL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_ by prolific Brad Feld and Jason Mendelson of Foundry Group .     If you are planning to do a financing whether it’s a $100,000 bridge note, or a $5M Series A deal, read this book first.  It will save you far more in legal bills than the cost of the book, and, more importantly, it will arm you with the knowledge to negotiate smartly vs. messing about with legal terms you don’t understand that are likely to (a) piss off a VC (b) run up your legal bills (c) not get the results you want.

My Termsheets:  The Good, The Bad & The Ugly (free) may be the most popular appetizer in this dept. , but Brad and Jason deliver the whole meal.  It’s best digested this in tasty book form (which you can also refer to later) instead of spoon-fed at $500 per hour from your lawyers.  PS – this doesn’t mean you won’t need a lawyer.

TOPICAL BOOKS (in no particular order – both are best in class on their topics.)

Hooked:  How to build Habit-Forming Products by Nir Eyal     41AWSTOJiqL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_  If you are building a consumer service and seek real community growth and habit-forming repeat engagement, Nir Eyal (Stanford) is THE MAN.   We sponsored Nir to visit Honolulu a couple of years ago and it was a game-changing moment for me.  He has cracked the code of consumer engagement and broken it down into a design language you can immediately use team collaboration tools.  It is no surprise this is among the highest rated of all books on Amazon.


The Lean Startup by Eric Ries    There is a reason why this detailed “recipe book” on building (mostly consumer) startups is a best seller and has developed its own language around concepts like “minimum viable product” or MVP.   Its core thesis is fast development cycles and active A/B customer testing as soon as an MVP can be launched is faster, better and cheaper than traditional long internal development cycles without customer feedback.   It’s far more than that, including great detail on how to actually run development “pulled” by customers vs. “pushed” by internal teams, but this is the core and why it is worth reading.  Downside:   Chapters are wordy which makes for a long read.

BOOKS BY VC LEGENDS:  Useful, amusing and occasionally revisionist history. 

51O3UjOp+LL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_Valley Boy:  The Education of Tom Perkins  Written the “P” in KPCB.  This is the red Ferrari of VC books, faster and funner in all ways. Tom Perkins arguably did more to invent modern venture capital (including the investment terms that are still used today with both LPs and startups) and presciently kickstarted the semiconductor , PC (Compaq) and biotech. (Genentech) revolutions.   Tom is an excellent and very human writer (and plenty brash), and offsets the stories with copious doses of humor, surprising humility and side stories.


The Startup Game:  Inside the Partnership Between VCs and Entrepreneurs by Bill Draper  41cFH4Zp7TL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_(cofounder of Draper-Johnson, the first West Coast venture fund and father to Tim Draper of DFJ) is ponderous vs. Tom Perkins writing (it feels dictated), but includes much direct practical advice in the second half of the book.



BOOKS ON HOW TO SPEND IT:  going on vacation and dreaming of what to do once you get your first billion $ exit?  Start here.


Mine’s Bigger by David A. Kaplan  515SRN7GtnL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_on how Tom Perkins (the Perkins in KPCB) conceived, designed, and built Maltese Falcon, the world’s largest and most innovative sailing yacht and ultimately sold it for a $100M profit.



51tn9bvI9EL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_The Billionaire and the Mechanic  by Julian Guthrie   on how Larry Ellison pursued and won the America’s Cup.  An insightful read on organizational development with direct input from Larry Ellison.  An excellent story of the auto mechanic who headed the unglamorous Golden Gate Yacht Club and Larry Ellison who rose from a Chicago orphan to tech. titan and Americas Cup winner.   Strays a bit into “puff piece” territory but even this, in a way, is a rare insight to an otherwise intensely private entrepreneur.

If you know of a book that is worthy of addition, add it to the comments.  Now, back to work.