Recommended Reading and Viewing List for New and Aspiring VCs – Info Entrepreneurship

I’m often asked by new and aspiring VC’s, “What are the best resources to learn about being a VC?” I find this is actually a trick question, because VC is a “learn by doing” business. The best way to learn is to actually make investments, ideally alongside experienced, knowledgeable investors who can show you the ropes.

But given how difficult it is to get into the industry, there are many resources that can shed light on how this mysterious industry really works. Below is a rough list that I have accumulated over my fifteen years as a venture investor, in no particular order. All of these books can be purchased relatively cheaply on Amazon. I’ve included Amazon links so that you can easily click through and buy them. I’ve also listed several videos and podcasts that I’ve found valuable over the years. All of the videos and podcasts can be accessed for free, and I’ve included the links below as well.

I hope these are helpful to you. And I’d love to hear additions, comments and criticisms.

“Done Deals: Venture Capitalists Tell their Stories” (Udayan Gupta): I first picked up this book when I was a college senior at Harvard, aspiring to enter the venture industry. Published in 2000, this book remains a treasure almost twenty years later. It is a set of essays written by prominent VCs. What’s most compelling is the quality of the VCs who are profiled, and how the the profiles bridge multiple generations of successful VCs. VCs from the first generation include pioneers such as Arthur Rock, early investor in Apple and Intel and perhaps the first VC to make the cover of Time Magazine; and Eugene Kleiner, Co-Founder of Kleiner Perkins. VCs from the next generation include Don Valentine, Founder of Sequoia Capital; and Dick Kramlich, Founder of NEA. The book concludes with essays from the VC pioneers of the time when the book was published, including John Doerr of Kleiner Perkins, investor in Amazon and Google; and Jim Breyer of Accel, who invested in Facebook. The book enables you to go inside the minds of these VCs and understand how they size up entrepreneurs, products and markets. This book is a gem and is as valuable today as when it was first written, almost twenty years ago.

“Break Into VC: How to Break Into Venture Capital and Think Like an Investor Whether You’re a Student, Entrepreneur or Working Professional” (Bradley Miles): Young professional Bradley Miles wrote a very valuable primer on how to break into the venture capital industry. This is the best book I’ve seen that breaks down the mysteries of the industry and provides approachable advice on not just how to enter the industry, but to succeed in it. Topics covered include the various stages of venture investing; company performance metrics; accounting fundamentals; returns and valuation; and case studies on young VCs. This book is a valuable addition to any new or aspiring VCs library.

“EBoys, The First Inside Account of Venture Capitalists at Work” (Randall Stross): I love this book because it provides a very rare inside view into a venture firm. But not just any venture firm: Benchmark Capital in the middle of the Internet wave. The book profiles the upstart VC firm as it invests in multiple industry-shaping companies, including spectacular successes such as EBay, Juniper, and Priceline, as well as spectacular failures such as Webvan. You get a great sense of how these investors think, and how they make decisions. You also get an inside view on how a venture capital firm is built. Given the quality of the firm and the time when this book is written, the best analogy might be having an inside view of the Golden State Warriors in the middle of their championship run. For VCs who are building new firms, this book is also valuable in explaining how Benchmark built its organizational culture and team dynamic.

“The Monk and The Riddle” (Randy Komisar): I was first introduced to this book by David Hornik of August Capital, when David was teaching a class at Harvard Law on venture capital. Reading this book was a course requirement for David’s class. I first found the book a bit non-conventional, but as I read more found it quite endearing. The book combines the author’s personal narrative with fictional interactions with entrepreneurs, structured in a way to emphasize the critical aspects of entrepreneurship. Komisar emphasizes that meaningful entrepreneurship must encompass passion and purpose, and he lays bare what great entrepreneurship looks like in its purest form form. Any VC who seeks to form meaningful partnerships with the right entrepreneurs, and understand what they go through, should read this book.

“Founders at Work” (Jessica Livingston): Livingston, Co-Founder of Y-Combinator, compiled an illuminating set of interviews with startup founders. Most compelling about this text is how Livingstone was able to convince extraordinary founders such as Steve Wozniak (Apple), Evan Williams (Twitter), and Max Levchin (PayPal) to be very honest and candid about the earliest days of their startups. You feel how they felt when they were just starting out, and their futures were uncertain. The book is inspiring in that it enables new founders to put themselves in the shoes of the best in the business.

“Venture Capitalists at Work: How VCs Identify and Build Billion-Dollar Successes” (Tarang Shah and Shital Shah): This book is a good companion to “Done Deals”. Published in 2011, this set of interviews includes prominent VCs from the current generation, including Jim Goetz and Alfred Lin of Sequoia and Rich Wong of Accel; as well as seasoned professionals such as Ann Winblad of Hummer Winblad and David Cowan of Bessemer. The interviews probe each investor’s rationale behind their most successful deals. Being able to understand how Roelof Botha of Sequoia, for example, identified that the prevalence of broadband connections combined with innovations in broadband technology created an opportunity for YouTube, is highly instructive for the new VC.

AVC (Fred Wilson): Fred Wilson’s blog is perhaps the most popular venture blog, and for good reason. There is perhaps no one better at explaining key concepts, trends, and phenomena in the venture business than Fred Wilson. He has an ability to take complex topics and make them approachable and understandable by the average entrepreneur. He also writes in an honest, straightforward manner and it is always clear that his first priority is what is best for the entrepreneur. His perspectives on the role of venture capitalists and how they should do their job should be required reading for any new VC. He is also far ahead of the curve, and his explanations for USV’s investments are often prophetic. Consider his blogpost on why USV invested in Twitter back in 2007.

“Venture Deals: Be Smarter than Your Lawyer and Venture Capitalist” (Brad Feld and Jason Mendelson): Brad Feld, Jason Mendelson, and the Foundry Group team are known as some of the most helpful and founder-friendly investors in the business. Feld is one of the highest-regarded writers in the venture capital industry, and his blog “Feld Thoughts” has been invaluable to countless entrepreneurs. “Venture Deals” is a comprehensive guide for entrepreneurs on the key aspects of a venture capital investment, and how venture deals are put together. It is a great companion to Wilmerding’s “Term Sheets and Valuations”.

Sarah Lacy Fireside Chats: Sarah Lacy was on a roll from 2012 to 2015 where she basically interviewed everyone who really mattered in the technology world. This interview series includes many great ones with legendary technology founders, including Elon Musk, Drew Houston, and Brian Chesky. Her interviews with top VCs and angel investors are also excellent; interviewees include Peter Thiel, John Doerr, Chris Sacca, and Marc Andreessen. Sarah doesn’t pull any punches, and the candor of many of the interviews is illuminating.

“Term Sheets and Valuations” (Alex Wilmerding): This book was written many years ago but Alex Wilmerding. I picked it up as an analyst in my first VC job at Insight Venture Partners, and it was a wonderful primer as I got up to speed on how venture deals work. There is a companion book by Wilmerding called Deal Terms, which is also very good. These books will help you understand the nitty gritty of venture deals, including terms types of preferred stock, governance rights, and different wants to value an early-stage company.

“Creative Capital: George Doriot and the Birth of Venture Capital” (Spencer Ante): George Doriot is considered the father of the venture capital business. Nicknamed the “General”, Doriot founded American Research and Development Corporation, the first venture capital firm, in addition to founding INSEAD. This book traces Doriot’s life and career, and provides insights into how the venture capital industry was created. It’s an excellent primer for students who seek to understand the beginnings of this once cottage industry, and how it evolved to what it is today.

“Zero to One” (Peter Thiel): I consider “Zero to One” perhaps the seminal book on technology entrepreneurship over the past decade. Thiel is able to brilliantly elucidate concepts which may initially appear to be contrarian, but which explain many of the phenomena that drive the technology economy. Thiel argues that many commonly-accepted concepts, such that technology market leaders are competitive and non-monopolistic, are actually not true. He argues instead that the best companies avoid competition, and are able to capitalize on moats that enable them to create monopolies. He also explains why most venture firms do not make money. This book is a must-read for the new VC.

“Dare to Do Legendary Things” (Mike Maples): In a speech to Stanford Students, Mike Maples masterfully breaks down the key elements of exceptional technology companies. In under one hour, Maples manages to distill down the formational concepts of what makes the technology industry so unique, and why certain companies become exceptional. He provides sage advice on how young people should strategically think through their careers in the technology industry, so that they can “do legendary things”. Maples’ presentation and tone is highly approachable, and his insights are brilliant. I personally think Maples is long overdue to write a book on his investment philosophy, and I hope he writes one.

“Angel” (Jason Calacanis): Although intended for angel investors, Calacanis’ candid, honest assessments on how to evaluate entrepreneurs, build deaflow, build a calling card as an investor, and avoid investing mistakes are highly applicable to VCs as well. Calacanis is highly candid about his angel investing wins, including his investment in Uber, as well as his investing mistakes, notably passing on Twitter, which he describes as a “$50 million mistake”. Calacanis’ recommended investment process and framework for angel investors is exceptional; I wish I had followed it when I began angel investing. Individuals who begin investing as angels before entering the venture world would be wise to read this book.

“Don Valentine, Sequoia Capital: Target Big Markets”: An eternal debate amongst VCs is which element of an early-stage company is most important: team, product, or market. Don Valentine, founder of Sequoia Capital, is decidedly a market guy. In this video lecture, given at Stanford GSB, Valentine describes how Sequoia made some of its best-known investments, and how the firm has used the strategy of targeting big markets to identify these deals. Valentine’s dry humor spices up this talk, and new students of VC can learn a lot from Valentine’s long and distinguished career.

The Twenty Minute VC (Harry Stebbings): This set of podcasts has been an awesome addition to the venture capital canon over the past few years. What is incredible about this podcast series is the breadth of the coverage. Stebbings has managed to interview a who’s who of investors and entrepreneurs since starting the podcast in late 2014, doing two podcasts per week. When does the man sleep?

“A Dozen Lessons for Entrepreneurs” (Tren Griffin): What I like most about this collection of insights from investors and “founder coaches” is how is how it focuses on fundamental principles of startup success, in a much more thesis-driven approach than most venture capital texts. The investor interviews are categorized by concept: key concepts include moats, humility and hubris, luck, missionary, and power law. The book also has better gender balance than many of the resources on this list, with insights from top female investors such as Kirsten Green from Forerunner, Mary Meeker from Kleiner Perkins, and Jenny Lee from GGV. This book is excellent for the aspiring VCs who want to develop investment frameworks for identifying exceptional companies.

“Mastering the VC Game” (Jeffrey Bussgang): Jeff Bussgang writes from experience. He is a co-founder of Flybridge, an early-stage venture firm managing $600 million; a lecturer in entrepreneurship at Harvard Business School; and was previously a co-founder of Upromise, a loyalty marketing company acquired by Sallie Mae. In “Mastering the VC Game”, Bussgang explains in detail how entrepreneurs can successfully navigate the startup path. He provides profiles of successful entrepreneurs, and personalizes their stories, explaining the obstacles they encountered along the way. Bussgang also interviews successful VCs and provides a valuable perspective on how they think. This book is a great one for the new VC who is interested in understanding how the game works both from the entrepreneur and the VC perspective.

“Play Bigger: How Pirates, Dreamers and Innovators Create and Dominate Markets” (Al Ramadan, Dave Peterson, Christopher Lochhead, Kevin Maney): Venture capitalists understand that the technology markets follow a power law distribution, where a handful of companies each year capture the vast majority of the market share of the industry. More difficult to understand, however, is what unique traits those “category kings” have, and what sets them apart from their competitors. “Play Bigger” is an outstanding primer on the characteristics that define exceptionalism in entrepreneurial companies, and why these companies capture 80%+ share in their markets. This book is a valuable guide for VCs on how they can evaluate category king potential in entrepreneurs, companies, and markets.

Note: After receiving several requests for additions to the list, I’ve decided to add new ones as they are recommended to me:

“Something Ventured”: Documentary that focuses on the the growth of the venture capital industry in Silicon Valley, and the early pioneering VCs who funded companies such as Apple, Cisco, Atari and Genentech.