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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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The Founder's Dilemmas audiobook cover

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
The Rise of The Creative Class audiobook cover

The Rise of The Creative Class by Richard Florida

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I picked up this book because Brad Feld referenced it once or twice in Startup Communities. Five and a half years later, I’m trying to write a review for it. I vaguely recall nodding my head quite a bit in agreement research and feeling hope from the conclusions. However, I didn’t go back and re-read it. As much as I want to read a book that’s backed by research, sometimes the research is too much of the narrative and I want suggested action. In 2013 I was just getting started as an ecosystem leader/builder. With a few years of experience in that realm under my belt now, I may go back and give this a re-read. Until then, three stars just because I want the gameplan book (Startup Communities) not the research book (this one).


Genre: Business, Economics, Non-Fiction
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Crossing the Chasm by Geoffrey A. Moore

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It’s hard to believe this was only released in 2012, because it instantly became part of the common language of tech startups everyone. It was brought up so frequently that by the time I read it in 2013, I assumed it had been around for a decade already. Regardless, it’s a great framework. If all you need is to understand the terminology or the framework, then a YouTube explainer video should do the trick. If, after watching that you want to dive in then by all means—it will be worth your time.


Genre: Business, Non-Fiction
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