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

Who am I?

I have worked with startups since 2000, when I joined ShareBuilder, ultimately sold to Capital One in a $9.5 billion deal – one of my five successful startup exits to date. I am currently an officer of seven startups. Startups drive global job creation and problem-solving innovation. But 90% fail, often for preventable reasons. I am helping entrepreneurs beat those odds. I wrote Startup Law and Fundraising to help entrepreneurs build on a solid foundation, avoid common legal and regulatory mistakes, and fund their vision. My books are used globally in law and MBA schools, and I speak constantly on entrepreneurship-related topics, including recently to groups in Istanbul, Ramallah, and Tehran. 


I wrote...

Startup Law and Fundraising for Entrepreneurs and Startup Advisors

By Paul A. Swegle,

Book cover of Startup Law and Fundraising for Entrepreneurs and Startup Advisors

What is my book about?

Entrepreneurship is chaotic. Some chaos drives innovation. But legal chaos rocks startups to their foundations, dashing dreams, jeopardizing jobs and investments, causing liabilities, and slowing innovation. Swegle wrote Startup Law and Fundraising for Entrepreneurs and Startup Advisors to help startups avoid these pitfalls, including the pitfall of struggling to grow a poorly funded business. 

This is a practical book meant to help entrepreneurs and their advisors: build on a solid foundation; avoid costly legal and regulatory mistakes; and raise the money needed for stability, innovation, and operational success. Startup Law and Fundraising is read in by entrepreneurs, lawyers, CFOs, investors, and others across the globe interested in business, business law, and startup fundraising. Its pages cover an unmatched range of startup-focused concepts, tips, traps, strategies, and best practices. 

The books I picked & why

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Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist

By Brad Feld, Jason Mendelson,

Book cover of Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist

Why this book?

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. 

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist

By Brad Feld, Jason Mendelson,

Why should I read it?

1 author picked Venture Deals as one of their favorite books, and they share why you should read it.

What is this book about?

Help take your startup to the next step with the new and revised edition of the popular book on the VC deal process-from the co-founders of the Foundry Group

How do venture capital deals come together? This is one of the most frequent questions asked by each generation of new entrepreneurs. Surprisingly, there is little reliable information on the subject. No one understands this better than Brad Feld and Jason Mendelson. The founders and driving force behind the Foundry Group-a venture capital firm focused on investing in early-stage information technology companies-Brad and Jason have been involved in hundreds of venture…


See, Solve, Scale: How Anyone Can Turn an Unsolved Problem Into a Breakthrough Success

By Danny Warshay,

Book cover of See, Solve, Scale: How Anyone Can Turn an Unsolved Problem Into a Breakthrough Success

Why this book?

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.

See, Solve, Scale: How Anyone Can Turn an Unsolved Problem Into a Breakthrough Success

By Danny Warshay,

Why should I read it?

1 author picked See, Solve, Scale as one of their favorite books, and they share why you should read it.

What is this book about?

Inspired by Brown University's beloved course - The Entrepreneurial Process - Danny Warshay's See, Solve, Scale is a proven and paradigm-shifting method to unlocking the power of entrepreneurship.

The Entrepreneurial Process, one of Brown University's highest-rated courses, has empowered thousands of students to start their own ventures. You might assume these ventures started because the founders were born entrepreneurs. You might assume that these folks had technical or finance degrees, or worked at fancy consulting firms, or had some other specialized knowledge. Yet that isn't the case. Entrepreneurship is not a spirit or a gift. It is a process that…


Trajectory: Startup – Ideation to Product/Market Fit

By Dave Parker,

Book cover of Trajectory: Startup – Ideation to Product/Market Fit

Why this book?

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.

Trajectory: Startup – Ideation to Product/Market Fit

By Dave Parker,

Why should I read it?

1 author picked Trajectory as one of their favorite books, and they share why you should read it.

What is this book about?

Listed #1 in "The 13 Best Business Books of 2021" by HubSpot

Have a startup idea? Want to launch it fast?

People often spend years on working on startup ideas that fail-and they could have known long before, had they asked the hard questions earlier. Five-time tech founder Dave Parker has been there, and in Trajectory: Startup he offers a path to get you from ideation to launch and revenue in just six months.

With a track record of starting companies from scratch, raising both angel and venture capital, and participating in eight exits as founder, operator, and board member,…


Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal

By Oren Klaff,

Book cover of Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal

Why this book?

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.

Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal

By Oren Klaff,

Why should I read it?

2 authors picked Pitch Anything as one of their favorite books, and they share why you should read it.

What is this book about?

Gold Medal Winner--Tops Sales World's Best Sales and Marketing Book

"Fast, fun and immensely practical."
-JOE SULLIVAN, Founder, Flextronics

"Move over Neil Strauss and game theory. Pitch Anything reveals the next big thing in social dynamics: game for business."
-JOSH WHITFORD, Founder, Echelon Media

"What do supermodels and venture capitalists have in common?They hear hundreds of pitches a year. Pitch Anything makes sure you get the nod (or wink) you deserve."
-RALPH CRAM, Investor

"Pitch Anything offers a new method that will differentiate you from the rest of the pack."
-JASON JONES, Senior Vice President, Jones Lang LaSalle

"If you…


Angel Investing: Start to Finish

By Joe Wallin, Pete Baltaxe,

Book cover of Angel Investing: Start to Finish

Why this book?

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.

Angel Investing: Start to Finish

By Joe Wallin, Pete Baltaxe,

Why should I read it?

1 author picked Angel Investing as one of their favorite books, and they share why you should read it.

What is this book about?

Angel Investing: Start to Finish is the most comprehensive practical and legal guide written to help investors and entrepreneurs avoid making expensive mistakes.

Angel investing can be fun, financially rewarding, and socially impactful. But it can also be a costly endeavor in terms of money, time, and missed opportunities. Through the successes, failures, and collective experience of the authors you’ll learn how to navigate the angel investment process to maximize your chances of success and manage downside risks as an investor or entrepreneur.

You’ll learn how:

Lead investors evaluate deals Lawyers think through term sheets To keep perspective through losses…


5 book lists we think you will like!

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And, 3 books we think you will enjoy!

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