The best books for startup success from someone with big startup wins and equally big disasters

Anyone who might ever be involved in raising funds for a startup should read Feld and Mendelson’s famous book, Venture Deals. This includes entrepreneurs, CFOs, legal and financial advisors, board members, and investors. The authors have long been pivotal players in Boulder, Colorado’s vibrant startup ecosystem. Their many engaging and illuminating talks to entrepreneurship classes and groups can be found on YouTube. Venture Deals is the best book out there for learning VC fundraising fundamentals – the players, terminology, processes, strategies, etiquette, deal documentation, best practices, and the implications of taking VC money. According to a study by CB Insights, “Running out of Money” is the second most common reason for startup failure. Venture Deals can help startups and startup advisors increase their odds for fundraising success by providing insiders’ insights for winning strategies. 

See, Solve, Scale provides a proven three-part framework for entrepreneurial success called the “See, Solve, Scale Entrepreneurial Process.” Author Danny Warshay has been a Professor of Entrepreneurship at Brown University for 15+ years. Previously, after earning his Harvard MBA, Warshay spent time in brand management at Procter & Gamble, followed by several years launching, growing, and exiting startups in software, advanced materials, consumer products, and media. 

See, Solve, Scale unpacks key concepts from Warshay’s Brown University course on entrepreneurship. Warshay has also taught these concepts internationally to entrepreneurship organizations, private companies, non-profits, governmental agencies, and non-governmental organizations. His teachings have broad applicability to solving all types of problems and improving the functioning and results of almost any kind of organization, not just startups. 

Key lessons in the book include the importance of bottom-up research, being anthropological and empathetic and finding and validating an unmet need or problem to solve, recognizing and overcoming organizational forces that inhibit innovation, techniques to help individuals and organizations break through cognitive “fixedness” in devising solutions to address an identified need, iterating toward the ideal solution, or value proposition, before scaling, and scaling a sustainable model for long-term viability and impact. See, Solve, Scale is equal parts entrepreneurship framework for success and illustrative examples of how elements of the framework have been deployed successfully by entrepreneurs or botched to their startup’s injury.

I love Dave Parker’s book, Trajectory: Startup – Ideation to Product/Market Fit, because it provides a clear, but detailed roadmap to guide entrepreneurs through and over all of the necessary steps and obstacles to entrepreneurial success. The nature and degree of the best practices and practical insights laid out in Trajectory: Startup is somewhat similar, but even more granular, to that found in my own book but for the business side of things instead of the legal, governance, or regulatory side.

There is a lot of intellectual and procedural handholding in these pages, including checklists, to-do lists, and template forms for gathering and analyzing research and data, that first-time entrepreneurs will find indispensable and that even experienced entrepreneurs will find illuminating and useful. In the book’s Introduction, Parker summarizes what he hopes to help aspiring entrepreneurs do: create value with your product or service; decide on primary and secondary revenue models from the list of fourteen that are right for your business model; deliver value and make money using your positioning, marketing, methods and sales model; and capture value.

I just recommended Trajectory: Startup to the CEO of a new startup that recently hired me as their general counsel. She liked it so much that she reached out to Parker and is meeting with him for some one-on-one consulting. Trajectory: Startup is well-written, easy to ready, and a comprehensive, one-of-a-kind primer on entrepreneurship that will no doubt help countless entrepreneurs and startups chart a straighter, faster road to success.

Pitch Anything is an established work in the pitching and negotiation book categories. It is not perfect, but it is one of the best books for introducing entrepreneurs to the importance of pitching, selling, and negotiating persuasively. Entrepreneurs must pitch to attract co-founders and early team members, to obtain early stage funding, to close customers and other commercial partners, to close later stage funding rounds, and, ultimately, to go public or exit in a sale. While Pitch Anything is a good book, the brashness of some of its advice, particularly around what Klaff calls “frames,” do not fit all persons or situations. Some contexts require full-on Machiavellian tactics; others warrant more of a “Winning Friends and Influencing People” approach. Nonetheless, it is useful to understand which situation you are in and the available plays to run.

Armed with those caveats, I suggest readers of Pitch Anything read Chapter 1 first for its neuroscience theories and to internalize Klaff’s strong pitching framework: "Set the Frame, Tell the story, Reveal the intrigue, Offer the price, Nail the hookpoint, Get the deal." Then I suggest readers skip to Chapter 4, "Pitching Your Big Idea" and then Chapter 6, "Eradicating Neediness." To me, these Chapters 1, 4, and 6 have the broadest applicability to modern, global startups. Readers should then circle back to the more aggressive content in Chapter 2, "Frame Control," Chapter 3, "Status," and Chapter 5, "Frame Stacking and Hot Cognitions." At the risk of offending Klaff, Chapters 7 and 8 do not add much.

The second most common reason startups fail is that they run out of money. Sometimes this is because startups misjudge demand for their products, but equally often it’s due to unsuccessful fundraising. Angel Investing: Start to Finish provides critical insights into the thinking of sophisticated angel investors – key sources of early-stage fundraising dollars for many startups. This book is co-authored by Joe Wallin, one of the top startup and venture capital attorneys in the U.S. Few attorneys are capable of providing better fundraising counsel to startups than Wallin, and this book clearly reflects Joe’s deep experience on both sides of fundraising – representing investors and representing startups. 

Entrepreneurs should read this book carefully to understand the guidance angel investors receive from attorneys like Wallin and from their fellow angel investors or angel groups. Doing so will help entrepreneurs anticipate angel investors’ tough questions, negotiate term sheets, and maintain strong relationships with their investors. Fundraising is one of a startup founder’s hardest tasks and there is simply no such thing as too much knowledge or preparation. With this book, an entrepreneur can know more than many angel investors.