Best Books, Blogs, Podcasts, and Resources for Venture Capitalists — 2021 Edition

One of the most interesting aspects of the growth of the venture industry over the past few years has been the proliferation of resources for investors. The growth of VC blogs, podcasts, and books, combined with VC Twitter, has created a seemingly endless stream of information, and it’s not always easy to sift through the noise. At the same time, several industry participants have created truly valuable resources for aspiring and experienced venture investors alike.

I’ve created a completely new list of the best resources for venture capitalists, which follows the first list that I published back in 2018. Several of the resources on the new list were created or launched since I put my last list together, evidencing the impressive pace of thought creation happening in our industry. The list is not in a particular order, it may be updated periodically.

Thank you to everyone who suggested resources for the new list. There are links to all of the resources, and for the books, there are Amazon links so that you can purchase them easily.

For this list, I focused less on the basic fundamentals of VC, which was the focus of the first list, and more on resources that provide a broader range of perspectives, as well as provide deeper insights into the finer points of the craft. I also included several more resources created by female and minority authors. One of the most exciting aspects of the industry’s growth is the diversification of its voices, in particular industry participants who bring a new and fresh perspective.

  1. VC: An American History (Tom Nicholas, 2019): Nicholas’ text is the most comprehensive history of the venture capital industry that has been written in recent years. For students of the game who want to understand how the industry evolved, VC is a great book to read. The book begins with the origin of the industry in early whaling ventures and traces the creation of the limited partnership structure, the role of government, the evolution of Silicon Valley, the dotcom boom and bust, and the industry at present. It also provides valuable statistics and data to explain how the industry has expanded. For anyone who wants to understand why the industry is structured the way it is, this is the book to read. Although it is dense and a bit dry at times, this is a great historical primer for VCs to have on their bookshelves and refer back to.

2. The First Round Review: The First Round Review is the best content library for seed-stage entrepreneurs and investors. Comprised of articles, digital magazines, and even a book on the Essentials of Management, the Review is a great resource for founders and investors focused on the earliest stages of company development. The content is very approachable and easy to digest and is written by experts. It also focuses on highly specific tactics of company building, with valuable tools for founders. As an example, when one of our portfolio founders was looking for best practices for employee reviews, he used the First Round Performance Review System, which includes employee review templates.

3. Technology Revolutions and Financial Capital, the Dynamics of Bubbles and Golden Ages (Carlota Perez, 2003): The venture capital industry is prone to dramatic fluctuations. To succeed as a venture capital investor in a boom or bust period, you need to understand the drivers that influence what is happening, and why. Carlota Perez’s seminal book is one of the best at providing that context, explaining why technology markets are highly cyclical. In Technology Revolutions, Perez analyzes the major industrial ages that have occurred in history, beginning with the Industrial Revolution and ending with the Information Age. She argues that every industrial age can be separated into four phases. Between those phases, a crash typically occurs due to an excess of financial capital, followed by a deployment phase where technology innovations take hold. Her book is widely read and cited by legendary VCs including Marc Andreessen, Bill Gurley, and Fred Wilson, who concisely describes the merits of her framework here.

4. Women Who Venture: You Can’t Be What You Can’t See (Renata George, 2019): This book is a wonderful resource, comprising over 100 interviews with female VCs. Interviewees include industry heavyweights such as Kirsten Green of Forerunner and Aileen Lee of Cowboy Ventures, as well as the next generation of up-and-coming VCs. What is so unique about this book is the broad range of perspectives that George was able to incorporate, and the candid lessons and stories that these investors can convey. The book also provides a valuable perspective on the unique challenges that female investors have to navigate in the industry and the structural biases and obstacles that must be removed for VC to be truly inclusive. This is a valuable read for all venture investors, regardless of gender.

5. Alpha Girls: The Women Upstarts Who Took On Silicon Valley’s Male Culture and Made the Deals of a Lifetime (Julian Guthrie, 2019): Alpha Girls profiles four amazing women who broke barriers in the venture capital business. These women are MJ Elmore, one of the first women to become a partner at a U.S. VC firm; Theresia Gouw, a top investor at Accel and then founder of Aspect Ventures and ACrew; Magdalena Yesil, the first investor in Salesforce; and Sonja Perkins, a prolific investor in Internet infrastructure companies. This book tells each of their unique stories and provides a personal perspective on how highly successful women have navigated careers in VC.

6. + 7. This Week in Startups and Angel (Jason Calacanis, podcast created in 2009 and book written in 2017): Jason Calacanis has been in the entrepreneurship and angel game a long time, and he isn’t shy about voicing his opinion. His podcast This Week in Startups has been running for more than a decade and has featured many of the best in the business across more than 1,000 episodes. One of Calacanis’ greatest strengths is that although he is a successful founder and investor in his own right, he’s not afraid to ask tough questions. He’s also able to engage his guests on a deeper level than many interviewers.

Calacanis also distilled the key elements of angel investing in his book Angel, written in 2017. As an angel investor in Uber, in addition to many other companies that have reached large scale, Calcanis offers unfiltered advice from experience on how anyone can become an angel investor. Because VCs often co-invest with angels, and also because many top VCs began as angels, this book is highly recommended.

8. Starting Greatness (Mike Maples, launched in 2020): Maples’ podcast is a new entry into the lexicon, and it distinguishes itself by its sharp focus on defining and explaining the elements of exceptional entrepreneurship. In Maples’ view, there is a science behind building a breakthrough that is very different and sometimes in sharp contrast to traditional investing frameworks, and this podcast is his attempt to explain that science. Starting Greatness is not intended for the average entrepreneur or investor. Maples focuses on “super-performers”, individuals who have built industry-defining companies (for example, Bob Metcalfe of 3Com and Marc Andreesen of Netscape), as well as individuals who have created some of the foundational frameworks governing tech entrepreneurship and company building (for example, Geoffery Moore, author of Crossing the Chasm). Maples distills the key learnings from each episode into short, 5 to 6-minute summaries that are easy to consume. This podcast is an excellent complement to Paul Graham’s essays. The two resources share an ability to illuminate the often counterintuitive characteristics of exceptional entrepreneurship.

9. Secrets of Sand Hill Road: Venture Capital and How to Get It (Scott Kupor, published in 2019): Scott Kupor, Managing Partner of a16z, describes the inner-workings of the venture capital industry in this valuable text. Although the book is primarily addressed to founders, it is a valuable resource for new VCs who want to understand how VC firms are structured, where their capital comes from, and how decisions are made. These are topics that surprisingly haven’t been covered in detail in many of the traditional venture texts. Kupor also provides valuable technical insights in his book, on topics ranging from term sheets to structuring exits. As someone with deep operational and venture experience, Kupor is nevertheless able to explain concepts in an easy to understand, straightforward manner.

10. Masters of Scale (Reid Hoffman, launched in 2017): Reid Hoffman’s Masters of Scale podcast is special for several reasons. Each episode has a theme and draws from a broad range of disciplines (art, sports, science, history) that connect back to the central theme. There are typically multiple interviewees per episode, rather than just one, and each interviewee has a unique perspective on the main theme. Masters of Scale was also one of the first to commit to 50/50 gender balance, featuring interviews with many highly successful female founders, including Diane Greene (VMWare), Julia Hartz (Eventbrite), and Sara Blakely (Spanx). Finally, each episode has concrete learnings and takeaways for founders (and investors) who are involved in building and investing in startups. I listen to it regularly and always learn something new.

11. Bessemer Ventures: Atlas: Originally founded in 1911 as a family office and formalized as a VC firm in 1974, Bessemer is one of the oldest and most successful VC firms in the country. Bessemer has been creating valuable content for VCs and founders since before most VC firms were started. Their contributions over the years have included the State of the Cloud, 10 Laws of Cloud Computing, and their Anti-Portfolio, where they confess to all of the huge companies they missed. What’s most valuable about Bessemer’s content is how well-researched and comprehensive it is. Bessemer’s frameworks and Roadmaps are a must-read for new VC’s. Bessemer also just released Memos, the deal memos for several of their best investments, which provides tremendous insight into what billion-dollar companies actually look like in their earliest stages.

12. Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts (Annie Duke, published in 2018): Annie Duke’s book has become a must-read for all types of investors. What is most unique about this book is how Duke can cogently explain why our traditional frameworks for evaluating the decisions we make are often wrong. She explains the concept of “resulting”, where we use the result of an action (or inaction) to justify whether it was the right decision, rather than evaluating whether our decision was correct given the probabilities. Duke also discusses the myriad of additional biases that shape our decision-making, and how we can avoid them. Annie’s background as a Ph.D. candidate in psychology, turned world champion poker player, gives her credibility. Although not a book specifically about venture capital, this book is highly valuable in providing frameworks for making better investing decisions, which is critical as a venture investor.

13. It’s About Damn Time: How to Turn Being Underestimated into Your Greatest Advantage (Arlan Hamilton, published in 2020): Arlan Hamilton’s inspirational story provides an alternative perspective on the technology and venture capital industries, illuminating why they are not the open meritocracies that they claim to be. As a black, female, gay VC, Hamilton breaks the stereotypes of what a tech investor should look like. Her story of how she went from sleeping on the floor of the SF airport to launching Backstage Capital, a VC firm focusing on underrepresented founders, is a refreshing and eye-opening account. Hamilton’s book provides a compelling outsider’s account and also illuminates how and why the VC industry must change to become more inclusive.

14. How I Built This (Guy Raz, launched in 2016): Through its first-person interviews with entrepreneurial legends, the “How I Built This” podcast does a great job of describing how improbable successful entrepreneurship really is. Host Guy Raz takes listeners back to the very early days of each entrepreneur’s journey when the original idea for the founder’s business usually sounds outlandish and even downright crazy. Raz has the ability to get successful founders to open up and place themselves back to the time when they were just starting out. One of my favorite episodes is his interview with Sara Blakely, founder of Spanx, who is remarkably candid about her improbable journey in building the company, and the many mistakes she made along the way to building a billion-dollar business. Although not specifically focused on venture capital, the podcast profiles many venture-backed companies and discusses how the companies raised their first funding rounds.

15. Haystack/Semil Shah Blog: Semil Shah’s blog is a unique window into some of the finer points of VC decision-making, firm building, and how to approach venture markets. What Semil does really well is make these topics approachable for the new investor, and also provide transparency on how he makes decisions at his firm, Haystack. Semil’s blog is a must-read for VCs who are starting new firms because he provides excellent recommendations on fundraising, fund management, and portfolio construction.

16. Andreessen Horowitz: Content (launched in 2009): The a16z content library is a treasure trove for aspiring investors, including podcasts, articles, videos, and more. What makes a16z’s content impressive is its combination of depth and breadth. Many of the podcasts and articles dive deeply into technical areas, such as autonomous vehicles, crypto, or bioengineering. They cover all aspects of company building and also include a16z’s description and rationale for every investment they make. As a new or aspiring VC, it’s valuable to understand the investment rationale of a top VC firm, and how they break down a deal. New VC’s can learn a great deal from the a16z content site. In my view, this is the best resource library of any VC firm.

17. Paul Graham’s Essays: Paul Graham, Co-Founder of Y-Combinator, offers a unique perspective on entrepreneurship. His style is no-nonsense, and he thrives on being a contrarian. He often writes from the perspective of a “maker”, providing insights into how technical founders view the world, which is a welcome departure from the managerial, finance-oriented approach of many VC bloggers. Graham’s essays are most instructive in explaining the fundamental laws of technology entrepreneurship, which are often counterintuitive and contrarian. For example, in his blog post, “Black Swan Farming,” he explains how Y-Combinator approaches investing in startups, and why traditional thinking around entrepreneurship is wrongheaded when it comes to grasping the power-law distribution of entrepreneurship.

A Visualization of Paul Graham’s Essays (Source: Solipsys)

18. Acquired Podcast (launched in 2015): This podcast, created by Ben Gilbert and David Rosenthal, takes a unique approach to tell the stories of great tech founders and investors. Instead of the typical broad-ranging focus of VC podcasts, Gilbert and Rosenthal often focus on a specific company success story, drawing out valuable details to describe the story arc. For example, to tell the story of Zoom and its IPO, the hosts interviewed Santi Subotovsky, an early investor in Zoom from Emergence Capital, who described in detail what Zoom looked like when they first invested. This approach is also differentiated because it focuses on exits, providing insight into how and why technology companies reach large liquidity events. Acquired also has an “LP” subscription, which includes premium content, a book club, and monthly Zoom calls with Ben and David. This is one of the most thoughtful podcasts out there.

19. Stanford eCorner: Stanford’s eCorner is a long-running hub of videos, podcasts, articles and events, focused on all aspects of technology entrepreneurship, company building, and investing. Since 2001, Stanford has been inviting the most successful founders and investors to speak as part of their Entrepreneurial Thought Leaders Series. Some of my favorite eCorner talks include those by Jensen Huang, Mike Maples, Doug Leone and Tracy Young, and Elon Musk. The discussions are interactive and feature Q&A from the student audience.

Co-Founder/Managing Partner of 645 Ventures; Focused on investing in the world’s best technology startups