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Measure What Matters audiobook cover

Measure What Matters by John Doerr

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I was all gung-ho on OKRs for a while and when this book came out, I picked it up right away. While the stories are great, I kind of wanted more out of it. Really what the book did for me was whet my appetite to read about Andy Grove. 

I’ve since backed off my initial excitement for OKRs after hearing some strong counter arguments from startup CEOs, including my partner at SpringTime, Jeff Gardner. Hearing how OKRs work against the direction of a company and its path to growth was enlightening. 

Regardless, if you want to learn about OKRs this has a number of interesting stories about how they’ve been implemented in successful companies, as well as clear guidelines and definitions. Dig in!


Genre: Business, Non-Fiction, Startups
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Startup CEO by Matt Blumberg

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I really want to be able to strongly recommend this to most of the startups I work with on a daily basis, but it’s not for early stage startups. I have to keep in mind that this series of startup books originated with Brad Feld from Foundry Group, a venture firm that invests in Series A & B rounds. The vast majority of the startups I see and work with are at the angel and seed level of capital and growth. As such, advice such as annual 360 reviews is not the most critical advice I would offer early stage startups.

The title may have been better as “Scale-up CEO” and targeting companies that have found a scalable, repeatable business model. 

With the idea in mind that this is for “scale-up” executives, then I heartily recommend it. But for me and my audience, it’s something to aspire towards. 


Genre: Business, Non-Fiction, Startups
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Founder’s Dilemmas, The by Noam Wasserman

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I had the pleasure of seeing Noam speak at Techstars in Boulder, and I was deeply impressed by his research. If you are in the startup world, this is a must-read. Forget the link-bait articles and the CB Insights surveys that all say the same shit. The Founder’s Dilemmas is based absolutely massive research, over many years. He’s done this work not to get you to pay for a subscription, but to help founders understand the pitfalls of others in the hopes they can avoid repeating the mistakes. Go read it.

Publisher’s 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 10,000 founders. People problems are the leading cause of failure in startups. This book offers solutions.


Genre: Business, Non-Fiction, Startups
Startup Communities audiobook cover

Startup Communities by Brad Feld

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Ah, the “Boulder Thesis”. Startup Communities is essential reading for anyone in the startup world, especially if you’re in the startup world outside of the Bay Area. I’ve read this book quite a few times, and have heartily recommended it over and over again. It has become such an important part of startup community development that many of the terms, ways of thinking, and even the phrase “Boulder Thesis” have become part of the startup lexicon. If you’re in the startup world and you haven’t read it, go grab it now.


Genre: Non-Fiction, Startups
Subjects: Rich’s Reco’s
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Venture Deals by Brad Feld, Jason Mendelson

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Note: this review is for an older edition of the book—they’re on the third edition now.

I don’t offer many conditional reviews, but this review is predicated on the fact that you want to learn more about startup venture financing. It’s a dry subject, and if you’re not into it, or it’s not relevant to you, then skip this book.  However, if you are in the startup world and you want to know about venture capital from the experts, then this is a must. It’s just OK as an audio book, and I got a copy of the print book (print! so old fashioned) to be able to review the parts with math. 


Genre: Business, Non-Fiction, Startups
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