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My Startup Reading List

Startup founders often share what they read. I share what works. These books keep might aligned and ready. I read and revisit them often.

Published: January 19, 2025

I have noticed that many startup founders often say they are too busy to read. When I hear this statement, I know the feeling, but understand it be a hedge. They are busy, and reading for fun is a beach activity. It can feel like a luxury.

But, when founders talk to each other about what they read, I hear something very different. Founders read for effect and impact. They read to learn. A different mindset can change a go to market strategy. It can radically change how a founding teams approach their belief in what is possible.

So here is my reading list.


1. “Never Split the Difference” - Chris Voss

I found this book in the months right after we graduated from the 2018 TechStars Boston program. A number of the founders from the program moved from the WeWork in Fort Point to GSV Labs in the downtown area. As we exited the program, we all went through an adjustment period. During the TechStars we tried out a suite of tools and products. When the trial periods were over, we had to make the call; ‘keep’ or ‘dump’. Getting out of a contract is not fun, but it can be done! Getting a complete refund from a pre-paid contract is even less fun.

This book gave me an approach to negotiations that I have used ever since.

I read random capture from this book every time I enter a negotiation. I find that even a short read can make a difference. It gets me back a listening mode that yields better results.

Get it on Amazon!

TLDR: Chris Voss was an FBI hostage negotiator. Some years ago the FBI figured out they were loosing too many hostages when negotiations failed. They came up with a better way. This book is the results. It's a power tool for startup founders.

2. “Venture Deals” - Brad Feld & Jason Mendelson

Simple book, easy read, but a dense topic. Brad and Mendelson break down terms sheets, and tease apart each component, from two sides: From the VC/Investor side, and the startup founder. I have found that this book got me to rethink the entire fundraising process.

In the past I took the approach that we needed to tell a complete store to the investor. This back and forth narrative got me to think about the entire process as a negotiation. As a sharing of interests. As a process of understanding what the investors were looking for.

A startup founder needs to understand investment theory. I read parts of this book every time I talk to an investors. It gets me into their mindset. It took me years to understand that the investment thinking was not founder thinking.

Get it on Amazon!

TLDR: Investors seek returns. It all comes down to control or economics.

3. “Meditations” - Marcus Aurelius

Again, simple book, long term utility. Founders have to believe in the impossible. When everyone else says something is impossible, they have to believe it is possible. As with the Voss book I carry this book in laptop bad. I got the paper back, so I could make notes in it. Its a working reference. I add dates and topics to the margins, and it helps me remember that there is a burden in doing things that are not easy.

Something about the fact that a man 2k years ago was thining words that are still relevant is helpful. And seeing my margin notes from past struggles reminds me to keep things in perspective.

Get it on Amazon!

What make the list?

Nothing goes onto my long term reading list if it does not provide persistent utility. If I am not re-reading it on a regular basis, it does not make the cut. For the Voss book, I read it every three month on schedule. That seems to be cadence I need to keep the concepts fresh.