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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)

Noam Wasserman · 6 HN comments
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Amazon Summary
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.
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Hacker News Stories and Comments

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Read the Founder's Dilemma[1].

Don't "look for a cofounder".

Collaborate with friends and loose connections on projects ("date") and escalate from there. (Don't undershoot "loose".)

You need to be friends[2].

Get hitched when you're sure.



Probably to find your first user. Get feedback from them on your prototype. Startups aren't fungible so more info on your startup would help. Additionally there is a wealth of resources on the Internet: some of my favorites:

How to Start a Startup: Watch the whole series, or you might regret it

Lean Startup: Get this book. If you're not a reader become one. Don't skim it; read it.

Founder's Dillemma: Read the whole book before you go get married to a cofounder

I have the Lean Startup and I must admit I'm guilty of skimming lol. Thanks for the info/advice. I really appreciate it.
I knew it. Happy to help.
Seconded! In the meanwhile, Founder's Dilemmas is a great read (
If you find this interesting, Wasserman expanded his thesis into a book[0], an academic study of startups. Highly recommended.


A good read for those interested in this topic i.e. the pros and cons of finding a co-worker through something like "founder dating" VS. with friends/relatives VS. with coworkers is "The Founder's Dilemmas"[1] by Noah Wasserman.

If you'd just like a preview/synopsis of the book, there's a podcast[2] of the author's talk at Stanford, which covers all the broad strokes and key points.



Great post. It's not often you see founders share how they arrived at their equity split.

I highly recommend The Founder's Dilemmas by Noam Wasserman ( The book is very data driven. Noam uses the data he collected over the last 10 years to backup the different scenarios he discusses. Chapter 6 talks about equity split and Noam talks about the difference between 50/50 hand-shake splits, 50/50 designed splits, 51/49 splits, and other splitting scenarios. I got the audiobook and it's an easy listen/read over the weekend. For me, this is not just a "one man's opinion" book. Its data driven nature makes it a must read.

Other parts of the book talks about different co-founder options (family, friends, co-workers, life partners), role divisions and funding choices.

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