Venture capitalist Sarah Downey explained in a 2018 article on Medium that "the day-to-day reality of being a VC is that we spend about 99% of our time saying 'no.'"
Whether you're a VC delivering a rejection to a startup or a founder receiving bad news, it can help to have support — in the form of apropos books, podcasts, and other go-to resources — to keep you going in this tough business.
Business Insider picked the brains of six VC experts to learn what their favorite reads are. The books that they chose offer equal doses of information, innovation, and inspiration for those in the VC space.
1. "Give and Take: Why Helping Others Drives Our Success" by Adam Grant
Kenn So, an associate at Nest-investor Shasta Ventures, recommended this classic read by Wharton professor and business thought leader Adam Grant.
"This book says a lot about how the most successful people are 'givers,' while also underlining where to draw the line to not get taken advantage of," So said. "It parallels a lot with how the most successful VCs are those who really give and support their companies — picking up the phone at 3 a.m. without batting an eye ... to being the forever supporter — while also being transparent and tough with the founders when needed."
The opening story of the book is about successful VC David Hornik, managing partner of August Capital who has invested in the likes of Splunk and Evite and "was initially passed over by a founder because Hornik was too nice but [he] eventually got to be part of the deal and more," So said.
"Sometimes being helpful doesn't get you anything in return, which is what happened to Hornik at first — he didn't get the deal," explained So. "While the book has a happy ending for this example with Hornik, that's not always the case. But it doesn't matter. Givers don't sweat about getting anything in return."
2. "The Business of Venture Capital: Insights from Leading Practitioners on the Art of Raising a Fund, Deal Structuring, Value Creation, and Exit Strategies" byMahendra Ramsinghani
Jeremy Harrison is the founder and CEO of Hustle Life, a website that helps future entrepreneurs find their perfect side hustle. Harrison admitted that he knew very little about venture capital when he first started as an entrepreneur. That's when he discovered "The Business of Venture Capital."
He pointed out that the book does double duty as a comprehensiveresource on the topic for industry veterans, while also being accessible to those with no business background.
"The book is great for two types of people: those that are interested in getting intoventure capital, and also for entrepreneurs who want an in-depth understanding of what motivates VCs," Harrison said.
3. "Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies" by Chris Yeh and Reid Hoffman
Formerly on the strategic teams of McKinsey and Motorola, VC and entrepreneur Oksana Malysheva is now the CEO and managing partner of Sputnik ATX, an accelerator program that funds startup companies out of Austin, Texas.
One of the books that she ends up recommending most often for this industry is "Blitzscaling."
"Investing in and running a venture-backed business is a completely different game from almost anything one typically learns about business," she said. "Until Reid published his book, very few people have been able to sensibly explain how, and so it really was a 'secret sauce' known to a select few. Now this problem has been solved!"
4. "Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers" by Tim Ferriss
Malysheva also told Business Insider that "Tools of Titans" is on her nightstand at all times.
The book is broken into roughly three sections — "Healthy," "Wealthy," and "Wise" — and, Malysheva shared, "Tim Ferris collected advice from the absolute gurus in a variety of fields: from the most prominent VCs to Olympians, artists, actors, and writers. I can literally open it on any page, read for 10 to 15 minutes, and walk away inspired."
5. "Grit: The Power of Passion and Perseverance" by Angela Duckworth
Duckworth's popular New York Times bestseller is another one on Malysheva's must-read list for VCs. The managing partner first picked this book up for inspiration as a parent, and it quickly became the opening read of the Sputnik ATX startup curriculum.
"Starting a company is a long, hard journey, and grit is one of the most important ingredients for any startup founder," she explained. "It is the trait that can be built up, and Angela does a phenomenal job breaking down exactly what it is and how anyone can grow it."
6. "The Mom Test: How to Talk to Customers and Learn If Your Business Is a Good Idea When Everyone Is Lying to You" by Rob Fitzpatrick
"As a VC, this is the book you want every entrepreneur you invest in to read," Malysheva observed about "The Mom Test." She explained that anyone who ever launches a product or company must talk to their customers to make it better, but noted that "almost everyone does it incorrectly."
"We love our products, we breathe our products, and we pitch them all the time — including in customer interviews, which is exactly the wrong thing to do!" she said. "When we do that, the person on the other end is sympathetic and tells us what we want to hear, not what we need to hear. And off we go wasting our time and money building something they do not need; they were just too polite to tell us so."
Malysheva added that by reading this practical book, you will fix a lion's share of these errors. "I end up recommending it to a lot of entrepreneurs, and I always hear, 'I wish I read this earlier!'" she said.
7. "Man's Search for Meaning" by Viktor Frankl
"As an entrepreneur,you're going to have tremendous ups and insane downs, and in those dips that you think everything is over — reach for this book," Malysheva said of Frankl's book."This book is breathtaking and inspiringfor the toughest moments. It is without fail helping me discover light and strength again."
She added that Frankl survived the worst of humanity in aNazi death camp, yet still found the power to give us reminders like, "Everything can be taken from a man but one thing: the last of human freedoms — to choose one's attitude in any given set of circ*mstances, to choose one's own way," she said.
"If he could find strength, light, and love living through what he went through, so can I, so can we all; we must choose it," Malysheva concluded.
8. "The Great CEO Within: The Tactical Guide to Company Building" by Matt Mochary, Alex MacCaw, and Misha Talavera
Jake Saper, partner at leadingventure capital firm Emergence Capital, selected "The Great CEO Within" as his top VC book pick. Mochary, who has an MBA from Kellogg School of Management, has coached several successful tech startups, including Coinbase and Reddit.
"This is a highly tactical and practical guide to being the CEO of a high-growth tech company," Saper said. "The author, Matt Mochary, is a seasoned CEO coach who has developed a system for each key process in running a company. It's a terrific distillation of best practices we've shared with our CEOs over the years."
9. "Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist" by Brad Feld and Jason Mendelson
Tim Schigel, managing partner of early-scale investor Refinery Ventures, has been in venture capital since 1998.
The entrepreneur characterized "Venture Deals" as "a great primer for anyone new to venture investing."
Schigel explained that the book helps to demystify the world of venture, which has historically been secretive and full of technical and legal jargon. This can make it intimidating for a founder trying to attract capital.
"The more the founder understands the decision-making criteria of VCs, the better," said Schigel, pointing toward Feld and Mendelson's book as a solution. "VCs are like any other service provider. Founders need to do their research and find the best investors who understand their business, can help them grow, and connect them with later-stage funding sources."
10. "Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets" by Al Ramadan, Dave Peterson, Christopher Lochhead, and Kevin Maney
Schigel emphasized that in order to understand how to evaluate and support founders and hypergrowth startups, "Play Bigger" can help with understanding the most important variable in startup success: market timing.
"If you're operating in a large, growing market, you have the opportunity to 'ride the wave' to success," Schigel explained. "However, even the best talent and greatest product cannot overcome unfavorable market dynamics."
He continued that "Play Bigger"clearly illustrates that in today's environment, there is only one winner, and then everyone else.
"It's even more important to become the 'Category King," Schigel said. "The authors share that success is not about first to market, but rather first to properly define the problem. This book will help founders frame their vision, providing valuable insights about category design to better architect their strategy.
11. "Peak: How Great Companies Get Their Mojo from Maslow" by Chip Conley
Schigel also recommended "Peak" for your VC toolkit to help understand the motivations and framework for employees, customers, and investors.
"Your business plan may make perfect sense on your Excel spreadsheet, but throw in the human element and rational thinking goes out the window," said Schigel. "Leaders play the role of therapist and cheerleader. Humans are not rational, so understanding motivations that lead to behavior is supremely important. Chip Conley does a masterful job mapping the motivations for employees, customers, and investors and then integrates them into a holistic roadmap."
12. "Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs" by John Doerr
Schigel said "Measure What Matters" is a great introduction to objectives and key results, better known as OKRs, which are strategic ways to set goals.
Author John Doerr first learned how to create OKRs while working for Andrew Grove at Intel and then passed the methodology to Google in the early days of the company. Schigel shared that he has been using OKRs since 2008, and the Refinery's portfolio companies also use OKRs to improve their ability to plan and set priorities.
"OKRs are meant to be simple as well as aspirational," said Schigel. "It's amazing to see what happens when teams wrestle through competing priorities to identify and track the one or two key initiatives that will dramatically impact their business."
13. "High Growth Handbook" by Elad Gil
Schigel pointed to "High Growth Handbook" as your "complete compendium for growth strategies and tactics."
"Elad Gil draws on his experiences at companies including Airbnb, Twitter, Google, Instacart, Coinbase, Stripe, and Square," Schigel said. "The book covers everything from inception to fundraising from early to later stage and exit."
He added that this truly is a handbook to be referenced often for specific ideas and solutions to some of the most vexing problems that entrepreneurs face.
14. "The Titanic Effect: Successfully Navigating the Uncertainties that Sink Most Startups" by Todd Saxton, M. Kim Saxton, and Michael Cloran
Kim Saxton, clinical professor of marketing at Indiana University's Kelley School of Business, recommended her own book: "The Titanic Effect."
She and her coauthors wrote "The Titanic Effect" based on 20 years' experience working with and researching successful startups, failed startups — even the decisions made in launching the Titanic, one of the largest startup failures to date. They noticed patterns of faulty decisions founders made, called "icebergs."
"The book shows how these decisions lead to hidden debt, like the part of the iceberg under the water," Saxton explained. "It gives startup founders ideas about how to navigate through these icebergs."
