Karl Hughes

Karl Hughes

The Best Startup Books for Founders

The Best Startup Books for Founders

As a startup founder, you get pulled in a million different directions from the moment you start your company. It can be overwhelming to have to learn so many new skills at once: raising funds, hiring a team, managing people.

Before I started Draft.dev earlier this year, I spent almost a decade working with startups, reading, and preparing myself to run a business. I worked with some great people, met fantastic mentors, and read some outstanding books that gave me the confidence to go out on my own. In this post, I’ll give you my list of the best startup books available today.

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Early-Stage Startups

This category includes books for people who are just starting out. If you are building your first product or raising the first round of funding, these books will provide you with a good starting point.

Founders at Work: Stories of Startups’ Early Days

What I love about this book is that it shows you how several popular technology companies started out. The book is a collection of interviews with founders of Paypal, Hotmail, Apple, and other giants of our era. It’s interesting to see where they got the ideas that eventually made them household names and how they recovered from various difficulties along the way.

“If you’re thinking about entrepreneurship you should read this book to get familiar with the possibilities, both the positives and the challenges. From the success arrived by a detour to the success of following a dedicated plan. There’s much to absorb and it’s just plain interesting.”

The Innovator’s Dilemma

Written by the Harward professor and businessman Clayton Christensen, The Innovator’s Dilemma is one of the most important business books on the market. It explains how mammoth, successful companies can lose market leadership in a blink of an eye as new competitors rise and become dominant in emerging segments of their market.

“Christensen shows that successful innovation is not unpredictable. This comes with the recognition, however, that “data only exist about the past” and hence what is working in the present for leading firms need not apply to disruptive firms of the future. This paradigm necessarily applies to all companies and is not exclusive to technological ones.”

The Lean Startup

We live in an age where technology changes rapidly and quickly changes the market around it. This means that sometimes, you have to move fast to avoid getting swallowed up by innovation. In The Lean Startup, Ries talks about his own business failure and how he spent too much time on the initial product launch instead of focusing on validating the market.

“This book focuses on giving an overview of Lean methods and convincing you why you should use them. It uses a lot of examples, mainly from startups. Some of the best examples come from the author’s own experience, and his company continues to do well.”

Zero to One: Notes on Startups, or How to Build the Future

Zero to One book cover

I don’t love Peter Thiel’s politics, but I do like how he pushes readers to think for themselves. He explains that you don’t necessarily have to fight the competition to be the leader in the market. Instead, by thinking out of the box and creating a brand new market, you can become a leader with no competition at all. With a unique idea, you can escape the rivals and focus completely on your unique value proposition.

“Let me assure you that Zero to One is worth reading, even if you’re not engaged in the world of startups and venture capital. It’s worth reading in the same way a triple espresso is worth drinking: it makes you feel superhuman, at least for the moment. You can almost hear the caffeine coursing through your veins as you absorb the ideas.”

The Art of the Start

Although named “The Art of the Start,” this book covers various business areas, including the art of launching, positioning, socializing, and marketing your startup. In 13 easy-to-read chapters, Guy Kawasaki talks about crucial topics for startup founders like finding a business idea, finding the right co-founder, writing a vision statement, and defining your business model.

“Never assume you’re done. Recruiting doesn’t stop when a candidate accepts your offer, nor when he resigns from his current employer, nor on his last day at his current employer—not even after he starts at your organization. In actuality, recruiting never stops. Every day is a new contract between a startup and an employee.”

The Startup Owner’s Manual

With over a hundred charts, graphs, and valuable checklists, this book helps startup founders in many ways. For example, it teaches you how to avoid “deadly sins” that lead your business to failure and how to drive your company to repeatable and scalable profits. The methods in this book were created by Steve Blank, a famous Silicon Valley startup, and were tested by him for more than a decade.

“Best entrepreneur book period. If you liked Lean Startup (another great read/education) you’ll love this one by Steve Blank. He taught those guys. I love how the author really reset your approach and lays out a clear plan on how to test and scale.”

Note: If you’re an early-stage startup founder learning about content marketing, I helped create a course at thisisgoodmarketing.com just for you. Learn everything you need to know about building a repeatable content marketing funnel that actually drives new business.

Growth Stage Startups

Books in this category will teach you how to grow your business from the first few customers to wider adoption. These will also help you sell high-dollar products and scale your sales to the next level.

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

I first read this classic over a decade ago. It explains the way products move to progressively more mainstream markets and how you can cross the “chasm” from early adopters to these lucrative mass markets. Although technology changes rapidly, the principles in Crossing the Chasm can still be applied in the software industry today.

“The author’s emphasis is on distinguishing between the selling and marketing tactics for the early innovators versus mainstream customers. There is a chasm between the innovators and mainstream market and the author dedicates the book outlining the various steps a high tech company should perform to successfully navigate through the chasm.”

Hacking Growth: How Today’s Fastest-Growing Companies Drive Breakout Success

Ever wonder why Facebook unseated early entrants like MySpace to become the number one social network? Or how Uber succeeded despite seeming to have no chance against New York’s Yellow Cabs? With the proper methodology - known as “growth hacking” - they became the giants of our era. Sean and Morgan’s stories inspired me, and I recommend this book to any founder who will handle marketing.

“The authors walk the reader through each stage of building a growth machine, give examples from real companies, and, the best part, they apply this process to a hypothetical scenario/product so you can see what it would look like from beginning to end.”

The Hard Thing About Hard Things

This book is a collection of stories from the career of Ben Horowitz, one of the most respected entrepreneurs of Silicon Valley. It reveals problems that he faced during his journey from being a founder to becoming an investor. It analyzes difficulties that confront leaders every day, related to management, selling, investment, and staying balanced.

“If you’re planning to start a company, whether it’s a high-tech company or the kinds of companies that I started and ran, read this book. If you’re going to be someone in charge of anything in any kind of a company, read this book.”

Great at Work: How Top Performers Do Less, Work Better, and Achieve More

Early in my career, I worked too much on too many projects. It took me nearly a decade to figure out that putting hours into the right things was the key. This book debunks the myth of multitasking, talks about coordinating between priorities, and reveals how to make your work time more productive.

“With the massive amount of business books published every year, it’s tough to find a book with some original ideas. This book is one of those. What’s great about it is that there isn’t a lot of fluff and the book gets to the points of what can help one become a great performer. I would recommend this book to any leader out there who wants to help his or her team grow and become more, with less of the wrong kind of work.”

Hiring and Management

At some point in running a business, you will have to build a team of professionals around you. You will likely move into management, which requires an entirely new set of skills. These books helped me out, and I’m sure you will find them useful, too.

Recruit Rockstars: The 10 Step Playbook to Find the Winners and Ignite Your Business

I learned the hard way that many business-related problems have their roots in poor hiring practices. Instead of hiring consistent A-players, many startup founders rush to assemble half-hearted teams that are bound to fail. Hyman shows his ten practical steps to recruiting top talent in this book. My favorite part was about choosing employees based on data instead of gut feeling, and I used this to create my first hiring rubric at Draft.dev.

“This is the recruitment guide that every startup needs to read. It’s especially valuable for people who might not have a background in recruiting but find themselves in a position where they need to hire the best. Recruit Rockstars is a clear and concise guide that won’t waste your time and gives you the recruitment background you need. I can’t recommend this book enough!”

High Output Management

Written by the former chairman of Intel, this book shows startup founders how to build highly productive teams that lead the company to peak performance. Management isn’t about posturing or power-struggles. It’s about getting results.

High Output Management book

“The author emphasizes the importance of judging managers based on the output that they achieve, which is an accumulation of the outputs of the people that work for them. He also focuses on the importance of continuing to improve yourself and strive to be better. He rightly points out that nobody owes you a job.”

True North: Discover Your Authentic Leadership

Running a business requires you to be an authentic leader and make hard decisions. True North teaches you how to follow your internal compass and create a personal leadership development plan. It’s based on interviews with over a hundred of today’s top leaders, and I strongly recommend it to every startup founder.

“Bill George begins by explaining that leadership follows from understanding your ‘True North’ (purpose). While this may seem obvious, it’s actually not very often practiced. Many people want to be leaders just to be important or climb the ranks in a company. Often people want to be leaders because that seems to be what one ought to aspire to. Bill George uses the lift stories of other iconic leaders and shows how the best cases of leadership are derived from following your True North.”

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs

This is, by far, one of the best books about management I have ever read. It explains a specific goal-setting system of “Objectives and Key Results,” which creates a unified management plan throughout your organization. Looking to OKRs as their guide, employees are empowered to make better decisions and operate with more autonomy.

“Anyone who wants to understand what makes Silicon Valley tick will learn a lot from this book. So many of the giants from the last fifty years are captured in these pages – as relayed by John, their commitment and ambition shine through.”

Personal Development

Running a business can be an all-consuming endeavor. While a little stress is okay, it can be a challenge to stay mentally and physically healthy if you ignore all your friends and work 80 hours every week. Knowing more about your psychology can help. Here are some of the books that have helped me maintain personal balance while running a business.

Mindset: The New Psychology of Success

Mindset book cover

I heard of Carol Dweck’s theory almost a decade ago, but it took me some time to finally read the book and see what it’s all about. Mindset reveals the importance of how we think about our abilities and how this perception directly influences our success in business, school, and even relationships.

“If you’re looking for a better understanding of how your mindset - either growth or fixed - affects your opinions, self-worth, outlook on the world, personal limitations, and the trajectory of your life - read this book. There were so many examples in the book of celebrities, corporate leaders, and sports legends displaying the different mindsets and showing the results of these mindsets - it was fascinating to read.”

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

Slack busts some of the most popular myths by showing readers that working more hours is not always the key to success. Sometimes, you simply need a certain degree of freedom in your company to let it grow. For example, by designing workloads that allow employees to think and innovate, you can minimize fear, promote creativity, and produce growth.

“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

Nudge, written by the winner of the Nobel Prize in Economics, Richard H. Thaler, reveals how even the smallest decisions that we make daily can affect our lives in general. Incomplete information often leads entrepreneurs to make bad decisions or suffer from biases that lead them down unsustainable paths. This book is about setting your life up to make better decisions in every aspect.

Nudge book cover

“Nudge is about the decisions we make. Our surroundings have a bigger impact on our decision making than we are willing to admit. Simple changes to our environment can have a huge impact both positively and negatively.”

How to Win Friends and Influence People

In any business - especially if you are a startup founder - it’s crucial to know how to influence people. This book taught me various ways to win people to my way of thinking and change them without causing resentment. Some of these tricks seem basic, but it takes serious practice to do this regularly.

“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.”

Exit Planning

Starting a business is a great way to escape fixed working hours and have more freedom. However, many startup founders struggle to get their business to this point. They often find that their business only grows when they actively spend 40 to 80 hours per week in it. Whether you actually plan to sell your startup or not, every entrepreneur should run their business like they’re preparing to exit.

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

The key to preparing your startup for an exit is to make sure the business can thrive without you. In Built to Sell, John Warrilow talks about his personal experience selling his business and shares some secrets for creating a scalable company that is valuable to potential buyers.

“An excellent business book that’s both fun to read and full of valuable insights. Whereas other business books are laden with jargon and often unattainable examples, “Built to Sell” is a practical and relatable read on how to grow (and sell) a successful service business.”

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

The Emyth Revisited book cover

Although the original was written almost 20 years ago, this book is still a fantastic choice for business owners of any size. It offers practical advice on systemizing your business and building a work plan that will allow employees to succeed even when you are not around. Gerber also reveals how to start working ON instead of IN your business, which is essential if you want your company to grow.

“I knew of the struggle between the inner technician, manager, and entrepreneur but never had the framework to understand it. If you’re a person who has the marketable, technical talent and is self-employed or thinking of being self-employed, I’d say invest in this book and save yourself some inner turmoil.”

Before The Exit: Thought Experiments For Entrepreneurs

The hard thing about “exiting” is that you can’t actually “practice” it.

It’s a process that might take years or even decades. Besides, there are many irreparable mistakes that a business owner can make, which makes the exiting process overwhelmingly complicated. This book opened my eyes in various ways, and I’m sure it will be helpful for you, too.

“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

Just because I’m running a business doesn’t mean I’ve stopped reading. If you’re looking for more good material, check out my post on the best books for startup CTOs or some of the books that are next on my list:

If you know of any other books that might be suitable for startup founders, please let me hear about them on Twitter. I can’t wait to hear your recommendations.

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