Book Review: The Great CEO Within

My five star review

A version of this book review originally appeared on Venture Patterns. Since then the author has published a much more detailed guide to his methods. I’m still absorbing it.

The Great CEO Within gets my Five Star book review.

In my first startup, I learned many of these items although it took years, talking to many people, and reading many books.  I wish I had been able to read this one book instead!

I read Great CEO Within in two sittings and it instantly became one of my top 3 recommendations for startup founders. If you are a first-time founder of a company of 20 people or less, I recommend making it a priority to read this book now. Yes, like over the holidays.

The book is a tactical and detailed look at how to run a tech startup.  The audience is most technically oriented first-time founders without much experience with management. Much of what it says will be applicable to a different audience, but the further you get from the less it may apply to you. For the experienced startup leader, the book can be a reminder and checklist of best practices.

Matt Mochary, the author, was a VC and then founded Totality which he sold quickly in the first dotcom boom. More recently he developed a coaching practice working with CEOs of tech startups like Coinbase, Plaid, Reddit, Brex, OpenAI, Flexport, and others. The book summarizes what he learned from experts, other books, and coaching these CEOs.

It very well summarizes the Silicon Valley body of knowledge of how to run a tech startup.  It is something you can learn but there is precious little time for training when you are in the middle of it. Having a resource that summarizes so much in one place, is extremely valuable. If you adopt these approaches, while not all employees will be familiar with them, they are accepted enough that other management, board, and employees will be less likely to be pushed back compared to something you invent on your own.

The book is strongly opinionated. The voice is definitive in presenting one way of doing things. That can be helpful as a first-time exec who has a lot to learn.  Of course, we all know and I suspect the author would agree that there is more than one way to do things. But many of the things described here are way better than anything you’ll figure out on your own while doing 20 other things.  It’s useful to take his recommendation as to the starting point until you develop your own point of view.

I have implemented many of the ideas in the book previously but not all. Given the success I’ve had with the ones I’ve used, I would like to try the others, as well.  For example, I have not used the RAPID decision-making process or writing-heavy prep for meetings.

What does the book cover?  Things like:

1. Beginning (getting to product-market fit and keeping a team very small before that)

2. Individual Habits (things like GTD, being present, expressing gratitude, and taking care of personal health)

3. Group Habits (decision making, impeccable agreements, issue identification, and conflict resolution, company culture, etc.)

4. Infrastructure (tools like online file folders – yes it gets this tactical)

5. Collaboration (org structure, accountability, and transparency)

6. Processes (fundraising, recruiting and sales/marketing)

Here are some of the big things it does not cover enough.  No book is perfect!

1. Diversity: From experience, I can share that it is easier to build a diverse team the earlier you start.

2. Remote or Virtual Teams: The book did not say enough about managing remote teams.

3. Purpose: While there is some discussion of a 10-year company vision, I think there could be more said about identifying and communicating about a company’s purpose.

On the more tactical side, the book does not cover much in-depth on the following areas as the assumed audience likely knows it, or it is less important in the B2B software world. One book can’t cover everything.  You should know so you’re not expecting too much given my glowing review.  

1. DevOps

2. Agile or another approach to managing software development.  Although there is some on the role of a product manager and why it should be an independent function in the company

3. Press / Media 

4. Compliance

5. Consumer Marketing

6. Collections

There are some areas where I disagree with the book. Some worth mentioning right now would include:

1. Sleep – While the author does advocate for exercise, meditation, and personal health, he seems to embrace a low sleep approach.  It seemed like he almost advocated sleeping for 3 to 6 hours. I’ve heard enough interviews with Dr. Matthew Walker (author of Why We Sleep) to think that more sleep is important for most people.

2. Disciplined Entrepreneurship over Lean Startup – I think the Disciplined Entrepreneurship book is wonderful but if I had to pick, I think the Lean Startup approaches apply in more places and gives a larger framework/mental model compared to the DE approach.

3. Governance – There is a brief mention in favor of super-voting founder shares. I believe that a more balanced governance model is often better to drive accountability, represent different interests, and avoid the risk of a founder losing touch with reality. A reasonable debate to be had here.

4. Going Public – The book is a fairly negative ongoing public and argues that staying as a private company is better. I think the discussion is more nuanced depending on the company and the situation.

I had the thought that it would be great to extend this work even further.  I wonder if anyone has:

1. Cataloged and/or created the template documents that support the recommendations here and published them in one place?

2. Created a list of the software tools that support the practices here and are the recommended software tool kit. 

As it might be helpful, here are some of the key books referenced.  Reading the sourcebook can be helpful, although Great CEO Within can give you a great place to start. Think of the time you can save!

1. Getting Things Done

2. One Minute Manager

3. 15 Commitments of Conscious Leadership

4. Who

5. Never Split the Difference (I read Getting More and Getting to Yes and have not read all of this one)

6. Predictable Revenue

7. Unconventional Success

8. Disciplined Entrepreneurship

9. Nonviolent Communication 

10. High Output Management

Thank you to Thomas Smyth for introducing me to the book.