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The Founder's Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup (The Kauffman Foundation Series on Innovation and Entrepreneurship, 13) Hardcover – March 25, 2012
Often downplayed in the excitement of starting up a new business venture is one of the most important decisions entrepreneurs will face: should they go it alone, or bring in cofounders, hires, and investors to help build the business? More than just financial rewards are at stake. Friendships and relationships can suffer. Bad decisions at the inception of a promising venture lay the foundations for its eventual ruin. The Founder's Dilemmas is the first book to examine the early decisions by entrepreneurs that can make or break a startup and its team.
Drawing on a decade of research, Noam Wasserman reveals the common pitfalls founders face and how to avoid them. He looks at whether it is a good idea to cofound with friends or relatives, how and when to split the equity within the founding team, and how to recognize when a successful founder-CEO should exit or be fired. Wasserman explains how to anticipate, avoid, or recover from disastrous mistakes that can splinter a founding team, strip founders of control, and leave founders without a financial payoff for their hard work and innovative ideas. He highlights the need at each step to strike a careful balance between controlling the startup and attracting the best resources to grow it, and demonstrates why the easy short-term choice is often the most perilous in the long term.
The Founder's Dilemmas draws on the inside stories of founders like Evan Williams of Twitter and Tim Westergren of Pandora, while mining quantitative data on almost ten thousand founders.
People problems are the leading cause of failure in startups. This book offers solutions.
- Print length480 pages
- LanguageEnglish
- PublisherPrinceton University Press
- Publication dateMarch 25, 2012
- Dimensions6.25 x 1.5 x 9.25 inches
- ISBN-100691149135
- ISBN-13978-0691149134
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Editorial Reviews
Review
"Winner of the 2013 Silver Medal Book Award in Entrepreneurship, Axiom Business"
"Finalist for the 2013 George R. Terry Book Award, Academy of Management"
"[A] seminal work. . . . Sure to be required reading in business school curricula, this illuminating and captivating read will also appeal to aspiring entrepreneurs or founders who want to make better decisions in existing ventures." ― Publishers Weekly
"[A] first-aid manual to help resuscitate ailing start-ups."---Jessica Bruder, journalist, author, and adjunct professor at Columbia University's Graduate School of Journalism, You're the Boss blog, New York Times
"Wasserman illustrates his findings with real world examples that translate into immediately applicable advice. But rather than creating a prescriptive list of commandments that would be impossible to follow, he adopts a more holistic approach. Encouraging entrepreneurs to study how others have handled similar challenges in the past, his insights highlight the common ground found in seemingly unique situations." ― ForeWord
"Harvard Business School professor Noam Wasserman is one of the writers and teachers who best captures the high stakes decisions that entrepreneurs face every day."---Scott Kirsner, Boston Globe
"There are plenty of books, lots with stories, anecdotes, and suggestions, but none that are particularly systematic about going through all of the issues. Noam's book is the first I've read--and he totally nails it."---Brad Feld, Feld Thoughts
"[T]he definitive book on the topic. . . . If you are a founder or thinking about becoming one, you should read this book."---Dharmesh Shah, OnStartups.com
"This is a serious book for a serious endeavor: creating a company from scratch that can be a world-beater and life-changer. . . . Wasserman's book is a towering guide to making these decisions thoughtfully and purposefully. Every founder should read it--and take the time to digest its rich data and lessons."---Jeff Bussgang, Seeing Both Sides
"Wasserman's book is on track to take as lofty a position in the entrepreneurial literature as HBS's Clayton Christensen's The Innovator's Dilemma did in the field of technological change."---Peter Cohan, Forbes
"Highly recommended for those who plan to embark or are already living the entrepreneurial lifestyle, it can serve as a guide to very tough situations for founders to evaluate the best possible way out."---Bernard Leong, SGEntrepreneurs
"Ten years of extensive research combined with winning case studies make this a trustworthy source not only for the potential startup owner but also for the classroom." ― Library Journal
"[A] must-read for anyone thinking of creating a startup, who is currently involved with one or who is an investor/advisor in the startup ecosystem."---Dilip James, Business Standard
"This book, upon release, becomes the single-most indispensible guide for founders of startups. Comingling research, straight talk, and a human voice--so often lacking in books with an academic bent--Dilemmas totally rocks as a business school required read and a founder's gripping, absolute must-read. Turning the last page, anyone with an entrepreneurial femur in their body will be fully armed with a battery of knowledge that can make or break a passionate first or even fifteenth venture. Do not start a startup without this book."---Ted Sturtz, New York Journal of Books
"[S]obering. . . . Professor Wasserman provides a great deal of data and stories about high-potential technology and life-sciences startups. His book offers much more information than most entrepreneurs can handle at once, but it is probably essential for them to know."---Harvey Schachter, Globe & Mail
"Wasserman presents a series of entrepreneurship vignettes and case studies, drawn from a massive 10,000-founder survey he created. Due to the size of this business start-up survey, several of the stories, including accounts from founders of Blogger, Sittercity, and SmarTix, should prove fresh to readers. Much of the advice in the book governs key decisions founders have to make and factors that can cause decisions to turn out well or badly. . . . [T]his work includes valuable, unique content." ― Choice
"[A] uniquely valuable resource for any entrepreneur."---Terrence Murray, Financialist
"The Founder's Dilemmas can't prevent entrepreneurs from repeating the mistakes of their predecessors; we all know how well human beings learn from history. But it's a worthwhile, prudent read for anyone considering or engaging in entrepreneurship. In pointing out the patterns, the common quandaries and routes, The Founder's Dilemmas can eliminate one headache along the path of business-building."---Tamara Micner, LSE Politics and Policy blog
"The guru on this subject is Noam Wasserman, who wrote an insightful book called The Founder's Dilemmas."---Luke Johnson, BusinessDay
Review
"The Founder's Dilemmas is required reading for entrepreneurs, venture capitalists, and the professionals who work with them. Few entrepreneurs appreciate the far-reaching implications of decisions they need to make at the beginning of a startup venture. Most founders make these critical decisions based on their gut instincts; backed up by data covering ten thousand founders, Noam Wasserman shows that the most common choices made at the outset of a new venture are often the wrong ones. This book also shines a light on the difficult conversations that entrepreneurs need to have with their colleagues and with their investors, and makes plainspoken, commonsense recommendations that facilitate this dialogue."―Pascal Levensohn, founding partner of Levensohn Venture Partners and member of the board of directors of the National Venture Capital Association (2007―2011)
"The Founder's Dilemmas will change the way we think about the internal dynamics that can make or break startup companies. Drawing on substantial research and considerable insight into practice, Wasserman uncovers the inner lives of startups, exploring the personal and professional conflicts that founders encounter on their entrepreneurial journeys. His book will appeal to academics and practitioners alike."―Thomas Hellmann, University of British Columbia
"The research that Noam Wasserman has assembled here can help entrepreneurial companies who want to prepare well for their future. The Founder's Dilemmas is a must-read for anyone thinking about starting a business."―Timothy C. Draper, founder of Draper Fisher Jurvetson
"Looking at the real-life founder issues of many accomplished entrepreneurs, Noam Wasserman draws insights that are both universal and timeless. If you're thinking of starting a new venture, do your homework and read this first."―Jeremy Stoppelman, CEO and cofounder of Yelp
"Noam Wasserman takes you through every major issue in a startup and shows you how to handle it in a prescriptive, logical way. The Founder's Dilemmas is for everyone thinking about starting a serious company, with their eye on a big prize, and for the people who invest in those companies."―Paul Maeder, chairman of the National Venture Capital Association, founder and general partner of Highland Capital Partners
"If you're starting a new company, you probably already know that a crazy variety of land mines await you. What if you had a map that showed exactly where they are and how to avoid them? Wasserman's recommendations are backed up by rigorous research―a rare thing in books about entrepreneurship―and his stories and anecdotes serve as accessible illustrations of situations faced by thousands of companies. Having seen these dilemmas derail countless startups, I wish every entrepreneur and prospective founder would read this book."―Eric Ries, author of The Lean Startup
"Every entrepreneur faces trade-offs when founding and growing their company. As we discovered at YouTube, those early decisions have far-reaching impacts and lead to unforeseen pitfalls down the road. Noam Wasserman uses vivid anecdotes and deep research to expertly outline the key early choices that define a startup, making The Founder's Dilemmas an invaluable alternative to real-world trial and error."―Chad Hurley, founder-CEO of YouTube
"[A] wonderful book. . . . It's a must read before you have even one more discussion with anyone about starting a company with them."―Melinda Thomas, Entrepreneur-in-Residence for the City of New York
"The Founder's Dilemmas fills an important gap in the entrepreneurship literature by providing an in-depth treatment of the people problems that confront all new business founders. Wasserman argues that people problems are responsible for a significant portion of startup failures, and that entrepreneurs tend to underestimate their potentially dangerous long-term effects. In this pathbreaking book, he grounds the analysis of these problems in both richly textured case examples and rigorously developed concepts and theories."―Ari Ginsberg, director of the Berkley Center for Entrepreneurial Studies at New York University's Stern School of Business
"This book offers a rich understanding of the central personal dilemmas that entrepreneurs uniquely face. These dilemmas are tied to particular choices for entrepreneurs that can have subtle and unexpected ramifications. I don't know of any other book that comes close to examining these specific and important issues."―Kathleen M. Eisenhardt, Stanford University, coauthor of Competing on the Edge: Strategy as Structured Chaos
From the Inside Flap
"This book provides the rare combination of practical advice and scholarly research. It gets to the heart of the people issues that can bedevil every, and I do mean every, startup. Issues such as founder motivations, equity splits, and equity control can make or break a company. I guarantee that the price of this book is approximately one-thousandth of what you'll pay lawyers to clean up your mess if you don't read it."--Guy Kawasaki, author of Enchantment and former chief evangelist of Apple
"The Founder's Dilemmas is required reading for entrepreneurs, venture capitalists, and the professionals who work with them. Few entrepreneurs appreciate the far-reaching implications of decisions they need to make at the beginning of a startup venture. Most founders make these critical decisions based on their gut instincts; backed up by data covering ten thousand founders, Noam Wasserman shows that the most common choices made at the outset of a new venture are often the wrong ones. This book also shines a light on the difficult conversations that entrepreneurs need to have with their colleagues and with their investors, and makes plainspoken, commonsense recommendations that facilitate this dialogue."--Pascal Levensohn, founding partner of Levensohn Venture Partners and member of the board of directors of the National Venture Capital Association (2007--2011)
"The Founder's Dilemmas will change the way we think about the internal dynamics that can make or break startup companies. Drawing on substantial research and considerable insight into practice, Wasserman uncovers the inner lives of startups, exploring the personal and professional conflicts that founders encounter on their entrepreneurial journeys. His book will appeal to academics and practitioners alike."--Thomas Hellmann, University of British Columbia
"The research that Noam Wasserman has assembled here can help entrepreneurial companies who want to prepare well for their future.The Founder's Dilemmas is a must-read for anyone thinking about starting a business."--Timothy C. Draper, founder of Draper Fisher Jurvetson
"Looking at the real-life founder issues of many accomplished entrepreneurs, Noam Wasserman draws insights that are both universal and timeless. If you're thinking of starting a new venture, do your homework and read this first."--Jeremy Stoppelman, CEO and cofounder of Yelp
"Noam Wasserman takes you through every major issue in a startup and shows you how to handle it in a prescriptive, logical way.The Founder's Dilemmas is for everyone thinking about starting a serious company, with their eye on a big prize, and for the people who invest in those companies."--Paul Maeder, chairman of the National Venture Capital Association, founder and general partner of Highland Capital Partners
"If you're starting a new company, you probably already know that a crazy variety of land mines await you. What if you had a map that showed exactly where they are and how to avoid them? Wasserman's recommendations are backed up by rigorous research--a rare thing in books about entrepreneurship--and his stories and anecdotes serve as accessible illustrations of situations faced by thousands of companies. Having seen these dilemmas derail countless startups, I wish every entrepreneur and prospective founder would read this book."--Eric Ries, author of The Lean Startup
"Every entrepreneur faces trade-offs when founding and growing their company. As we discovered at YouTube, those early decisions have far-reaching impacts and lead to unforeseen pitfalls down the road. Noam Wasserman uses vivid anecdotes and deep research to expertly outline the key early choices that define a startup, making The Founder's Dilemmas an invaluable alternative to real-world trial and error.&quo
From the Back Cover
"This book provides the rare combination of practical advice and scholarly research. It gets to the heart of the people issues that can bedevil every, and I do mean every, startup. Issues such as founder motivations, equity splits, and equity control can make or break a company. I guarantee that the price of this book is approximately one-thousandth of what you'll pay lawyers to clean up your mess if you don't read it."--Guy Kawasaki, author of Enchantment and former chief evangelist of Apple
"The Founder's Dilemmas is required reading for entrepreneurs, venture capitalists, and the professionals who work with them. Few entrepreneurs appreciate the far-reaching implications of decisions they need to make at the beginning of a startup venture. Most founders make these critical decisions based on their gut instincts; backed up by data covering ten thousand founders, Noam Wasserman shows that the most common choices made at the outset of a new venture are often the wrong ones. This book also shines a light on the difficult conversations that entrepreneurs need to have with their colleagues and with their investors, and makes plainspoken, commonsense recommendations that facilitate this dialogue."--Pascal Levensohn, founding partner of Levensohn Venture Partners and member of the board of directors of the National Venture Capital Association (2007--2011)
"The Founder's Dilemmas will change the way we think about the internal dynamics that can make or break startup companies. Drawing on substantial research and considerable insight into practice, Wasserman uncovers the inner lives of startups, exploring the personal and professional conflicts that founders encounter on their entrepreneurial journeys. His book will appeal to academics and practitioners alike."--Thomas Hellmann, University of British Columbia
"The research that Noam Wasserman has assembled here can help entrepreneurial companies who want to prepare well for their future.The Founder's Dilemmas is a must-read for anyone thinking about starting a business."--Timothy C. Draper, founder of Draper Fisher Jurvetson
"Looking at the real-life founder issues of many accomplished entrepreneurs, Noam Wasserman draws insights that are both universal and timeless. If you're thinking of starting a new venture, do your homework and read this first."--Jeremy Stoppelman, CEO and cofounder of Yelp
"Noam Wasserman takes you through every major issue in a startup and shows you how to handle it in a prescriptive, logical way.The Founder's Dilemmas is for everyone thinking about starting a serious company, with their eye on a big prize, and for the people who invest in those companies."--Paul Maeder, chairman of the National Venture Capital Association, founder and general partner of Highland Capital Partners
"If you're starting a new company, you probably already know that a crazy variety of land mines await you. What if you had a map that showed exactly where they are and how to avoid them? Wasserman's recommendations are backed up by rigorous research--a rare thing in books about entrepreneurship--and his stories and anecdotes serve as accessible illustrations of situations faced by thousands of companies. Having seen these dilemmas derail countless startups, I wish every entrepreneur and prospective founder would read this book."--Eric Ries, author of The Lean Startup
"Every entrepreneur faces trade-offs when founding and growing their company. As we discovered at YouTube, those early decisions have far-reaching impacts and lead to unforeseen pitfalls down the road. Noam Wasserman uses vivid anecdotes and deep research to expertly outline the key early choices that define a startup, making The Founder's Dilemmas an invaluable alternative to real-world trial and error.&quo
About the Author
Product details
- Publisher : Princeton University Press; unknown edition (March 25, 2012)
- Language : English
- Hardcover : 480 pages
- ISBN-10 : 0691149135
- ISBN-13 : 978-0691149134
- Item Weight : 1.81 pounds
- Dimensions : 6.25 x 1.5 x 9.25 inches
- Best Sellers Rank: #492,401 in Books (See Top 100 in Books)
- #568 in Starting a Business (Books)
- #3,033 in Entrepreneurship (Books)
- #4,589 in Business Management (Books)
- Customer Reviews:
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About the author

"LIFE IS A STARTUP": #1 AMAZON BESTSELLER IN ENTREPRENEURSHIP
"THE FOUNDER'S DILEMMAS" -- #1 AMAZON BESTSELLER IN NEW BUSINESS ENTERPRISES, #1 IN MANAGEMENT, #1 IN BUSINESS SYSTEMS & PLANNING, #2 IN POPULAR ECONOMICS
Dr. Noam Wasserman is bestselling author of The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup (2012, Princeton Univ. Press) and Life Is a Startup: What Founders Can Teach Us about Making Choices and Managing Change (2018, Stanford Univ. Press). He was a professor at Harvard Business School for 13 years and is now founding director of the Founder Central initiative at the University of Southern California and the Lemann Chair in Entrepreneurship.
Noam created HBS’s most popular entrepreneurship elective, “Founder’s Dilemmas,” for which he won HBS’s Faculty Teaching award and USC’s Golden Apple teaching award. He also won the Academy of Management’s Impact on Practice award and its Innovation in Entrepreneurship Pedagogy award.
He was a Principal at a firm where he founded and led the Groupware Practice, and worked as a venture capitalist. Noam received a PhD and MBA from Harvard University, a BSE (Penn Engineering), and a BS (Wharton).
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The book is both comprehensive as well as a true reflection of the early start-up world from the human perspective. Nine times out of ten, the "technology" or the "market" or just the "idea" are at the center of the entrepreneurs mind, while the most important, in fact the first and pivotal piece of the puzzle receives too far attention - the founder. No founder is looking further ahead than 3, 6, 9 or 12 months - early stage ventures are simply in too tumultuous a stage of development for that. Furthermore rarely do they think about the strategic interpersonal issues that are so often overlooked - I know I didn't. But they should. And this book provides an approach that structures the thought process.
Prof. Wasserman has done what few people (certainly not stressed entrepreneurs) could have done: he's asked the meta questions. Not to sound philosophical but it's a tough question to ask "why do we do what we do", and "what do we want [to achieve]". Even constricted to the startup space it's still a momentous question to answer but taking a data-centric approach has crystallized at least a framework within which Prof. Wasserman goes about exploring the motivations behind the people. That's what it's really about. What do the people (the founders) want?
The power of the framework lies in it's simplicity: you can be either rich, or you can be in control of your venture, almost never both, notable exceptions notwithstanding.
That's it. Nothing more and nothing less.
Few founders I have spoken to, have had that clear a framework in mind, much less have been able to articulate it (myself included). Eventually one comes to a realization of what it is that one wants, but often than not, one is in a situation that is suboptimal, and could have been solved better if those motivations / questions were properly known and answered.
This is truly a book written for founders. It must be mandatory reading in every incubator of which so many should be popping up; every VC should buy a case of the books and give every founding team (better late than never!); and every business plan contest should distribute this book to their contestants (charge an extra fee or do it free but do it!).
The problem is that of seven start-ups only two will be operating in a year later! That is a 71% failure rate. Imagine if close to all business that started succeeded, and went on to employ only five people. In a short time our “national scar,” unemployment, would be on the way down and prosperity on the way up.
Naom Wasserman has assembled superb data from his research on over 10,000 new businesses that were set to grow large. His research focused exclusively on businesses that were intended to grow large, not on lifestyle businesses intended only to keep the founder comfortable. He also accessed a wide range of reliable data from other sources to formulate this book.
What makes Wasserman’s book so unusual is his focus on a fact over research overlooks. More business start-ups fail because of internal problems caused by the founders’ errors of judgement than by external causes. If founders in the initial stages could make better decisions, many more businesses would be saved, and more would thrive.
Wasserman has identified clear a set of dilemmas facing founders. Choices have to be made between alternatives with no choice obviously better than another. All come with significant upsides and downsides. Solved appropriately, the founders will survive to face the next dilemma. Fail, and there could be no next dilemma.
“This book’s central message is that these founding decisions need to be made by design, not by default,” say Wasserman.
There are four primary founding decisions that make up the content of the book. Each dilemma is analysed, and its implications made clear. This clarity will help you, and those you care about make better, safer decisions.
At the “Pre-founding” stage, there are a set of dilemmas regarding when to launch the start-up. There are at least three major areas of considerations. If you do not have enough money, it may be wise to work for someone else until you do. Perhaps you should you borrow money and start right now? If you delay the start of the business, will you have missed the wave?
There is no one right answer to this question, and it requires the consideration of a number of factors. Are you able to ensure the security of your family (if you are responsible for one?) If you have savings or a retrenchment package will that suffice? Does your life-partner earn sufficiently to support the family? If she does, is she completely committed to your success to pay her part while you play yours? If not, the strain of founding the business may exhaust your strength and shatter your relationship. Are you locked in the golden handcuffs of a secure job?
These and many more profound and difficult questions need probing and honest answers.
Once you have made the decision to start a business, you face the “Founding Team Dilemmas” . Are you able to start a business alone or should you have others doing this with you? There are always skills that are required, but cannot reside in one person. Then there may be a need to work with another person who has your commitment to the success of the venture.
The need to work with others raises the “Relationship Dilemma” of to attract. Will the business work best if you team up with friends, family, acquaintances or strangers? Should you seek someone you have actually worked with before?
The “Role Dilemma” follows from this. What are the positions each one of you should assume in the new business?
How should each person be rewarded for their contribution to the venture? If you reward with more equity than is deserved, you cannot take it back when this becomes apparent. “Reward Dilemmas” are especially dangerous at the beginning of a business when there is nothing tangible. Giving away half of nothing but a promise is easy. However, when the business makes money, paying dividends to someone who never deserved it takes on a different hue. Few mistakes sour relationships more profoundly.
Beyond the dilemmas of the founding team are the “Investor Dilemmas.” Most businesses require funding to take off in a meaningful way.
You can turn to family and friends, “angel” investors, or venture capitalists. Accessing each these sources become progressively harder, and each poses its dilemmas.
For example, when take money from you pensioned parents, you do this believing you will succeed. Five of seven businesses never succeed causing great harm to people close to you. Borrowing from family and friends is best when it is a gift that come with love, not an investment.
Angel investors are investors but tend not to be professional investors. They are often people who have money and are prepared to “take a punt” on what looks like a “good idea” in exchange for equity and a high return. As with all investors, you will be required give up a portion of your business to the investor in exchange for the support.
At every stage there are dilemmas that if not confronted and not addressed thoughtfully, will do more damage to the fledgling business than problems that come from external forces.
Self-inflicted wounds can be avoided. Forewarned is forearmed. Read Wasserman’s profound book.
Readability Light ---+- Serious
Insights High +---- Low
Practical High -+--- Low
*Ian Mann of Gateways consults internationally on leadership and strategy and is the author of Strategy that Works.

