Essential Reading for Startup CTOs

2020, Nov 09 — 13 minute read

Being a great CTO requires insight and vision in both technology and business. You have to be the perfect combination of a software engineer, manager, and entrepreneur. Besides technical skills, you need knowledge of marketing, project management, and product development. It’s a tough job, but one of the ways I learned to cope was reading…a lot.

Even in the internet era, it can be difficult to find reading material online that’s actually useful. After reading hundreds of books over the past few years, I decided to compile my top picks for startup Chief Technology Officers.

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Early-Stage

These books will be best for early-stage CTOs tasked with building an MVP and finding product-market fit. Some of these are classics, but they’re all still applicable today.

Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers

Although Crossing the Chasm is a bit old, it’s not dated. The book is relevant to the high-tech industry today and shows you how fundamentally new products get introduced to the marketplace. Most interestingly, it shows you how to leap early adopters to the mainstream market.

“This book changed my life and the lives of my clients. I bought it in April 1999 and skimmed it. But it was not until April 2009 that I dug in to learn its secrets. I was simply amazed. The most basic point of this book is that the tactics that serve you well at one stage will sink you in the next, so you better orient yourself properly before shouting and writing big checks.”

The Innovator’s Dilemma

The Innovator’s Dilemma is the best-known work of Clayton Christensen, a Harward professor who coined the term “disruptive technologies.” This book explains how big, successful companies can quickly lose their market leadership as new competitors rise and become dominant in the market. The Economist named the book one of the six most important business-related books ever written.

“I picked up this book after hearing the “innovator’s dilemma” alluded to in several interviews by different CEOs. After reading this interesting piece on business strategy, it is no surprise why executive level management teams enjoy quoting this book. Innovator’s Dilemma is a thoroughly researched investigation into an age-old business phenomenon: How do businesses who were once dominant players in their industry get displaced by smaller, upcoming rivals?”

The Lean Startup

In this classic startup book, Eric Ries talks about his startup’s failure, caused by spending too much time and energy on the initial product launch. The book helps entrepreneurs in companies of all sizes to adapt and adjust to new technologies before it’s too late. Ries provides a scientific approach to developing new ideas in an age where markets change rapidly and quick adaptation is of great importance.

I wrote more about applying lean methods to software startups recently, and while the examples in Ries’ book are now pretty old, the general philosophy still works.

“I have been running a software business for 30 years, and, after reading this book, my eyes were opened to the “system” for starting and growing a business. Eric provides the core processes for identifying, developing, and refining products and the key metrics to use for growing your business. I really appreciated his concepts of validated learning vs. the typical “gut” approach to decision making. I also got a lot of value out of his disdain for vanity metrics. I now feel like I have a framework for improving and growing my business. This book is an excellent resource for anyone looking to create products that create value.”

Zero to One

Written by legendary entrepreneur and investor Peter Thiel, this book teaches you the most critical skill that a startup founder must have - learning to think for himself. He mentions how the next Bill Gates or Larry Page won’t win by mercilessly fighting the competition. Instead, they will win by escaping the competition since their businesses will be unique.

“For starters, going from zero to one or intensive (vertical) progress means doing new things. Vertical progress is harder to imagine because it requires doing something no one else has done. In short, doing new things is wiser than copying things that work. Thiel is best in questioning conventional thinking, for he advises a start-up must question received ideas and rethink business from scratch.”

Getting Real: The Smarter, Faster, Easier Way to Build a Successful Web Application

Packed with unconventional approaches to software design, this book is a source of ideas for anyone working on a web application. It has inspired me to try different approaches to solving familiar problems and taught me to build better, cleaner code overall.

“Not everything in this book will apply to every situation. Our team works for the government as contractors; we are required to produce a lot of documentation to fulfill our contractual obligations. Outside of our paper deliverables, though, this book is spot on with software development. Getting Real isn’t full of theories - it’s full of techniques that work. I know this from my experience. The book was a great help in giving that knowledge to my coworkers as well.”

Founders at Work: Stories of Startups’ Early Days

Founders at Work is a collection of interviews with people who founded well-known technology companies. It includes interviews with Steve Wozniak, Max Levchin, Sabeer Bhatia, and other entrepreneurs who made a big impact on the market. I really liked their stories and how they climbed to the top from seemingly simple ideas.

“This book is perfect for anyone interested in entrepreneurship, technology startups, technology companies in general, and business books in general. I’ve read the book once already and now I’m in the middle of reading it a second time. I wish there were an audio version of it.”

Technical Challenges

One of your most visible roles as a CTO is to solve challenging technical problems as your company grows. Once you’ve built your MVP and started to scale, you have to figure out how to maintain growth and deal with more data and users. In this section, I will include some books that help CTOs solve technical problems.

The Architecture of Open-Source Applications

I worked with many programmers throughout the years and noticed that many of them make the same mistakes over and over again. One of the best ways to avoid repeating the mistakes of the past is to learn about them. In this book, the authors of 25 well-known open-source applications talk about their software architecture and its evolution over time. It’s a fascinating deep dive into the minds of some brilliant people.

“The book is an excellent collection of architectural/structural sketches of major open-source projects. Many of them are written by the developers or maintainers of these projects and provide invaluable insight into why these projects are structured the way they are. The description of each project is an individual chapter and can be read in isolation.“

How to Make Sense of Any Mess: Information Architecture for Everybody

Being a CTO, I often encounter problems that seem impossible. Sometimes, I’m not even sure where to start. However, Covert’s book helped me a lot by explaining how to properly break big problems into smaller chunks and solve them step-by-step.

“This is an essential read for knowledge workers because it is the essence of what knowledge workers do. We don’t all need to be IA professionals, but if you do something like engineering or computer programming, this book is part of the “soft skills” we all talk about.”

Clean Code Series by Robert Martin

Every year, companies spend many hours and even resources on fixing the poorly-written code. In this classic series, Martin explains the difference between good and bad code and provides a totally different view on making an efficient program.

“I’ve been programming for about 17 years and consider myself above average programmer. Yet, this book made me feel like I’m actually a horrible coder. I’ve always gotten my tasks done but I didn’t pay attention to refactoring to clean up the code. I’m already behind and got a demo coming up in a few days. As I’m reading my guilty verdicts on all his ‘bad code’ examples, it inspires me to care about ‘coding’ yet again. It can be fun, and it’s not all about getting the job done.”

Note: I wrote a long review of Clean Code back in 2015, but that review holds up.

Designing Data-Intensive Applications: The Big Ideas Behind Reliable, Scalable, and Maintainable Systems

Every application becomes a data-intensive application if it grows large enough, and building these data-rich applications can be a very tricky job. In this book, Martin Kleppmann explains that although software keeps changing, the principles for handling data remain the same. He also talks about the architecture of well-known websites.

“If you are interested in distributed systems or scalability, this book is a must-read for you. It gives you a high-level understanding of different techniques, including the idea behind it, the pros and cons, and the problem it is trying to solve. A great book for practitioners who want to learn all the essential concepts quickly.”

Scaling Up

If you are already making some money but you’re struggling to hire and build a large team, the books in this section will help. These books talk about growing your business, raising money, and building a scalable team structure.

Startup Engineering Management

This book is a must-read for all engineers who are offered a management job at a startup - CTOs included. Being an engineer and manager himself, Piaw explains his process for putting together a team, hiring top-notch engineers, and picking engineering leaders. It’s a very tactical book for engineers and managers of all levels.

“This book is a short but practical guide for engineering team managers on how to run an effective team through different obstacles and problems that may arise in the real world when developing products in a fast-changing environment.”

High Output Management

Who can provide better tips on how to run a company than the former chairman and CEO of Intel? In High Output Management, he shows you how to create highly productive teams and motivate them to work at their peak performance. It’s an excellent choice for any CTO who wants to make their time as productive as possible, especially as their role starts to cover more team-management and analyzing marketing trends.

“Grove’s success is undebatable. This book shows his underlying philosophy of individualism and optimism was key in shaping the man he was and everything he achieved. Highly recommended for anyone who manages anything or even just interacts with people. So unless you literally live in a cave, this book will be a benefit.”

Peopleware: Productive Projects and Teams

Although this book is over 20 years old, it holds up for modern CTOs. In eight chapters, DeMarco and Lister provide many useful insights and explain that the main issues of software development are of a human, not technical nature.

“I cannot overstate just how great this book is! DeMarco and Lister don’t mess around. They go right to the heart of the project and team management and tell you exactly what makes one company succeed while so many others fail: it’s not technology, it’s people.”

Note: I wrote a longer review of Peopleware in 2015, which you can find here.

The Phoenix Project

The book is about Bill, an IT manager at Parts Unlimited. The company’s most important project is over budget and late, so the CEO assigns him the task of fixing the mess in less than three months. Otherwise, Bill’s department will be outsourced. It’s a fast-paced story that illustrates many devops and agile principles that most books present as mere theory.

“For me, the most important take-away is the distinction between planned work and unplanned work, and how destructive the unplanned type can be when unfettered. I’ve always known this intuitively, and indeed was the very stuff I fought on a daily basis while doing DevOps at Amazon, but until this book, have never been able to articulate it in such simple, effective terms.”

Building Great Software Engineering Teams

After almost a decade of building teams for various high-growth companies, Tyler decided to put his knowledge on paper and help people in similar situations. He talks about how to find great candidates, create an effective hiring process, and manage your people for optimal, long-term cooperation. It’s a very tactical book for engineering leaders and startup CTOs.

“Excellent for anyone who wants to make a difference and create the best Sw Eng teams! A MUST for recruiters, hiring managers, and engineers.”

Personal Development

Startup success is not just about making money and growing your business. Sometimes, you have to slow down and work on yourself. The books in this section have helped me stay (mostly) sane, healthy and form better relationships inside and outside my startups.

How to Win Friends and Influence People

Whether it’s in business or in personal life, influence can be crucial. In this book, Dale Carnegie provides very useful tips on how to make people like you and start thinking your way, as well as how to change people without arousing resentment.

“Dale Carnegie’s advice has remained constant and applicable across the years for a reason. It’s simple, and his techniques make perfect sense. If you’re anything like me, you’ll be kicking yourself when you see how you could have handled situations differently. I’m being transformed from a socially awkward, timid, and defensive person to someone that seems collected and confident.”

How to Fail at Almost Everything and Still Win Big

In this funny memoir, Scott Adams explains how he went from run-of-the-mill office worker to professional speaker, entrepreneur, and Dilbert creator. Along the way, he offers his advice for personal and career success. I liked this book so much that I read it twice!

“As Adams says, you shouldn’t take life advice from a cartoonist, but I did. I would enjoy reading more of his books as he is an interesting and outside-the-box thinker. Though it’s not an earth-shattering-revelation tome, I give it 5 stars for ease and likeliness of success.”

Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency

Despite popular belief, more efficiency is not always the answer. If you want your company to become more responsive and agile, you need to give smart people more space and time to think. It’s a revolutionary book that will provide you with a brand-new model for achieving effectiveness.

“Slack is an outstanding management book full of wisdom about corporate culture, change, failure, learning, quality, risk management, productivity, and managing people.”

Nudge: Improving Decisions about Health, Wealth, and Happiness

We make choices every day - whether it’s what to have for lunch or how to invest our money. Written by the winner of the Nobel prize in Economics, Richart H. Thaler, Nudge explains how no choice is ever presented neutrally. However, by knowing how people think and the forces that influence them, you can prompt them to make better decisions.

These principles work whether you’re influencing an employee to perform better or convincing yourself to work out every day.

“In this great book, Thaler and Sunstein walk you through the architectures of choice. They present the issues and provide possible solutions. From cafeterias to retirement plans to organ donors, this is a great book about how we can adjust environments to better our lives and the lives around us.”

Exit Planning

One of the most often overlooked elements of running a startup is planning to leave it someday. Whether you want to sell for a big revenue multiple or simply move on to new projects someday, you need to create a business that can prosper even if you are not around. For CTOs, this means letting go and using your organization and delegation skills more than you’re used to.

Built to Sell: Creating a Business That Can Thrive Without You

Many technologists start their businesses because they want more freedom and possibly riches. However, most startup CTOs end up working all the time because the company doesn’t run without them. In this book, John Warrillow provides a useful guide for making a company that can thrive when you’re not around.

“Not only does it very effectively demonstrate what to do VS what you shouldn’t do, it shows that you can always implement these types of changes to make sure you’re more prepared to sell and at the same time make your company more successful.”

The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It

One of the most common entrepreneurial traps is believing that because you are a great technician, you will be a great business owner. Gerber debunks this myth and provides insight into creating systems that will allow your team to succeed without you. This is another one that I’ve read multiple times.

“This book literally changed my life. I own a small service business with around 15 employees. I had been struggling for years doing all managerial work myself so that it was done up to my standards. We did great work but at the expense of my sanity!”

Before The Exit: Thought Experiments For Entrepreneurs

Exiting your business provides new challenges that most CTOs never think about. If you know them in advance, selling a business can be fun and profitable. In Before the Exit, Andrews presents a series of interesting experiments that will help you plan your future after you sell your company.

“Every active entrepreneur should consider these thought experiments as they build and grow their businesses. For myself, I can tell this will be one of those books I see myself coming back to as I move from one growth stage of my business to another.”

Next on My List

The books above helped me grow from engineer to manager to CTO, but learning is a never-ending process. Here are a few of the books that I’m planning to read next in case you’re interested:

I also wrote another list of books for startup founders recently. You might want to check those out foe even more recommendations.

If you know other good books that could help startup CTOs, please let me know about them on Twitter. I look forward to hearing your recommendations.