16 books every small business owner should read

I don’t know where I’d be in my freelance business without other entrepreneurs’ knowledge. When you’re running a small business, this kind of expertise is crucial. There are so many moving parts, and you need advice from folks who’ve been there.

While you can get a lot of insights from blog posts and newsletters—I absolutely look to those types of content—books have a depth of knowledge other formats just can’t beat. So I asked small business owners and leaders what they think are the best books for small business owners. Here’s what they said.

The best small business books

Books about running a small business

These are the books you might think of first when looking for reads on small business. They help entrepreneurs figure out the best operations for themselves and their employees.

The E-Myth Revisited

Many of the folks I consulted brought up The E-Myth Revisited by Michael E. Gerber. It tackles the titular “E-Myth”—that everyone is automatically an entrepreneur—and shares processes to grow into that role.

This book gave founder and CEO of Bloomfilter, Erik Severinghaus, “a wake-up call,” he told me: “Many people believe if you start a business, you automatically know how to run one. Michael Gerber strongly challenges this idea.” He continued:

“His book made me understand I was too busy with daily tasks and missing the larger goal. Learning to focus on growing my business, not just doing work in it, changed everything for me. Organizing systems and processes may seem dull, but it is what stops the chaos and helps you grow without problems.”

The E-Myth Revisited is also indispensable for Rustin Yasavolian, CEO of Masina Diamonds. Rustin told me: “It is a book I highly recommend every entrepreneur read if you are trying to grow your business from a small mom-and-pop shop. The book essentially talks about things like how to create processes and operational handbooks that small business owners might not typically think about.”

Subscribed

On-and-off talks of a recession have business owners looking to switch up their models and diversify their income. Subscribed by Tien Tzuo, the CEO of the subscription SaaS Zuora, explains how a subscription model could serve your business.

Sara Jensen, Principal at Brighter Messaging LLC, explains the book like this: 

“Subscribed is an examination of the subscription economy, and specifically how many businesses are moving to a subscription-based pricing structure. The book is full of unexpected examples that show how you don’t have to be a company like Netflix or Spotify to implement a subscription-like model in your business.”

Delivering Happiness: A Path to Profits, Passion, and Purpose

Zappos CEO Tony Hsieh’s book, Delivering Happiness: A Path to Profits, Passion, and Purpose, explores people-first business operations. While the book centers around Tony’s journey to becoming a successful CEO, it also emphasizes the importance of alternative corporate models that prioritize people.

“Number one on my personal list is Delivering Happiness: A Path to Profits, Passion, and Purpose by Tony Hsieh,” Andriy Bogdanov, Founder of One Day Tours Portugal, told me. “This book‘s author shares his experience as an entrepreneur and provides insights into how Zappos.com was created. He also explains how making a good product or providing a high-quality service as a company founder is essential.”

Measure What Matters

Making priorities and measuring your success can make or break your small business, but it doesn’t necessarily come naturally. In Measure What Matters, John Doerr introduces an objectives and key results (OKR) system that supports these two skills.

Stefano Lodola, owner of Think Languages, considers this book one of his most valuable reads as an entrepreneur:

“This book really made me stop and think: does what we do really matter? It’s very straightforward and simple, yet it imparts powerful lessons to help startups maintain focus while keeping the team aligned to achieve maximum results. The book emphasizes accountability by encouraging measuring, logging, and reviewing every aspect of operations. It kind of forced me to look at how I allot my time in the business and what everyone on my team is prioritizing.”

While this book focuses on OKRs over KPIs, you can adjust this KPI dashboard to fit the metrics you measure through this book‘s tips. Then, you can track it over time to see how your operations perform.

The Regenerative Business

Business growth has its ebbs and flows, even when you’re having an overall upward trend—I definitely discovered this in my first few years of running a freelance business. Carol Sanford suggests that we embrace these bumps and valleys like the changing seasons in her book The Regenerative Business.

Katie Sarna, co-founder and CEO of Santa Cruz Fungi, had a new perspective on growth after reading this book. Katie told me:

“It taught me that, like trees, businesses need to align with the seasons. Periods of rest, like winter, are absolutely necessary.

“As a small business owner, there’s always pressure, both external and internal, to keep growing and producing, but this book reassured me that it’s critical to take breaks. It’s a good reminder that a tree isn’t always fruiting and that my business won’t wither away if I step back to take care of myself.”

Books about small business leadership

Even when you have a solid system for running your business, you need the skills to lead the people involved. These books offer three unique perspectives on leadership for people in small businesses.

Built to Last

Our typical notion of a leader is the face of the group who handles all of the decisions. Jim Collins challenges that notion in Built to Last, where he shares the results of a six-year project at Stanford University that examined leadership at top companies like Walmart and 3M. According to Scott Shrum, President and COO at Hennessey Digital, Jim introduces two types of leaders: 

• Time tellers, the singular leaders that we often think of

• Clock builders, leaders who build teams that generate ideas together

“For my whole career, this lesson has shaped how I’ve led and built teams. I never want to be ‘the leader with all the answers,'” Scott told me. “I strive to build teams that can figure out things and generate new ideas on their own. It’s very easy to get seduced by the idea of the celebrity CEO who generates all the great ideas and calls all the shots, but the leaders I really admire are the clock builders.”

Quiet: The Power of Introverts in a World That Can’t Stop Talking

Good leadership involves bringing people with different backgrounds and personalities together. Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain offers leaders perspective for guiding introverts.

Here’s what Lucas Botzen, CEO of Rivermate, took away from the book:

“It helped me understand the great variety of personality types that exist within our team, together with the special strengths that introverts bring along with them. Because we are bringing about an enabling environment that values quiet leadership and sober contributions, we’ve been able to harness the full potential of every team member. This leads to more innovative and balanced decision-making.”

I Got There

In I Got There, JeVon McCormick describes how he became a CEO while facing racism, abuse, incarceration, and unemployment. He shares the challenges he faced as well as the steps he took to get to where he is now.

“McCormick’s story is inspiring, but it also provides readers with plenty of useful advice for leading a team,” says Eric Pines, CEO of Pines Federal. Eric cites JT’s advice to focus on people. “We don’t focus on what’s best for us—we focus on what’s best for the people we represent. The beautiful thing is that, in the end, that’s what ends up being best for our firm as well: positive reviews, word-of-mouth referrals, and the energy that comes from using our knowledge and skills to help people.”

Books about mindset for small business owners

It takes many shifts in mindset to go from employee to business owner. As someone behind a freelance business, I still work on changing my mindset every day. These books suggest new mindsets on broad and narrow levels.

Mindset

Psychologist Carol Dweck Ph.D. introduced the concept of the growth mindset in her book Mindset. She compares people with a fixed mindset, where you believe abilities are fixed, with those who have a growth mindset, where you believe you can develop your abilities. Using these concepts, she explains how to succeed using a growth mindset over a fixed mindset.

Noah Lydiard, CEO of Conductor, told me: “This writing covers a lot about growth and fixed mindsets—thinking you can keep learning more and getting better helps teams be creative and strong. This type of thinking is very important in creating a culture at Conductor, where we see challenges as opportunities to learn and get better.”

Never Split the Difference

If you need to learn how to negotiate, you can’t get a more qualified teacher than a former FBI negotiator. In Never Split the Difference, Chris Voss takes FBI negotiating tactics to the business world. While his experience comes from a cutthroat environment, much of his advice relies on emotional intelligence and empathy.

According to Matt Aird, Owner & CTO at Offices.co, this book “helped overhaul how I handle important discussions, whether with potential partners or during deal negotiations and high-stakes sales.” Matt told me:

“His strategies about active listening, emotional intelligence (EQ), and securing a win-win outcome (rather than the compromise we’re always told to seek) were particularly poignant and stuck with me. Another of the most valuable takeaways was the concept of tactical empathy. Understanding the counterparty’s emotions and viewpoint can create a significant advantage in negotiations, leading to better outcomes for our deals and each party.”

The Work

Entrepreneurship offers plenty of challenges that have you question why you do what you do. The Work by Wes Moore explores the author’s and others’ stories to find purpose in what we do.

“As an entrepreneur, finding meaning in your work isn’t just a nice-to-have—it’s a necessity,” Eric Pines says. This book‘s knowledge helped him learn from his job change from in-house counsel to law firm owner to help his wife be closer to her family:

“It was difficult to leave a secure position—especially with five young children at home—but it was the best decision for my family. Not only were we able to be closer to family, but I was able to do something that I felt more connected to, which made me more whole as a professional and as a partner and father.”

Think and Grow Rich for Women

While researching this piece, most of the recommendations I got were for books written by men. The male-centric business world is partly why Sharon Lechter wrote Think and Grow Rich for Women, the modern woman’s take on the 1937 book Think and Grow Rich. In this book, she studies successful women of the past, present, and future to help women thrive.

Hanna Olivas, co-founder and CEO of She Rises Studios, tells me that this book helped her make moves in her industry: “It has provided me with valuable insights and strategies to leverage my personal power, create success, and make a significant impact in my field.”

Strategize to Win

Becoming a small business owner is one of the biggest career changes you can make. Carla A. Harris’s Strategize to Win offers advice for anyone trying to make a major career change, whether they work for themselves or someone else.

Here’s how Eric Pines describes the book: “[Harris] shows you how to attract the kinds of opportunities you want, first by clearly defining your goals and what you have to offer, then by building relationships and making changes as necessary. [She] offers practical advice and examples for everything from resilience to navigating interpersonal conflict.”

Harris’s advice about talking with as many people as possible about your career aspirations especially stood out to Eric. It reminded him of time spent abroad for law school where talking with strangers from all sorts of backgrounds gave him opportunities he never imagined.

Books about building a small business’s finances

Your approach to finance also needs to change when you own a small business. These books will help you keep your business’s money in shape.

Chillpreneur

Think of this book as a combination of mindset and financial advice. In Chillpreneur, Denise Duffield-Thomas teaches you how to have a “millionaire mindset” and the right tools for your business. She explains how to hustle less and earn more doing work that means something to you.

“This book is like the 4-Hour Workweek, but for someone driven by doing more meaningful work,” says Emily Cassel Copeland, Founder and CEO of WMNûp. “This was amazing to listen to as an audiobook for me, to calibrate and start to shift my perspective to know it was actually possible to build and lead a business with greater ease and less hustle, grind, and stress when I first read it years ago. Especially great for women entrepreneurs who want to hear business advice from a fellow woman’s perspective and vantage point.”

Profit First

Another popular pick among the business leaders I talked to was Mike Michalowicz’s Profit First. As the title implies, the book suggests a financial approach where you take profits from your finances first, then establish expenses.

R.J. Weiss, founder of The Ways to Wealth, found this book insightful as someone with a financial planning background:

“I assumed managing business finances would be similar to personal finance, but I was very wrong. The method of allocating profit before expenses helps prevent many good companies from failing due to poor cash flow management. Implementing these strategies has significantly improved my business’s financial health and stability, which has been up and down since 2016.”

Laura Milroy, founder of Laura Milroy Media, also considers Profit First influential to her business’s growth. She told me: “It shows a very realistic way of managing your business finances and helps emerging entrepreneurs to manage their money in the right places so they don’t make the big mistakes that could put their business in jeopardy.”

If this budgeting style resonates with you, try entering it into one of Zapier’s small business budget templates. You can also use the templates on their own if you’re looking for other budgeting systems.

Simple Numbers, Straight Talk, Big Profits!

In Simple Numbers, Straight Talk, Big Profits!, Greg Crabtree and Beverly Blair Harzog break down finances for small businesses. The two authors identify the top numbers to follow and how to make smart decisions based on them.

Gretchen Roberts, CEO of financial firm Red Bike Advisors, keeps this book on her desk as a reference for good finance management—a high form of praise. She says, “One of the best tips in the book is to pretend you’re the NFL and establish a salary cap to achieve good pretax profit. It’s a simple calculation: You determine expected revenue and non-salary costs, and then cap the salaries to achieve your desired profit margin.”

Put these ideas into action

If one of these books gives you new ideas for your business, don’t forget to put them to work in your tech stack too. Use the knowledge you got from these books using free small business software to try new operations without touching your budget. And then automate your small business operations so you can focus on the work that matters.

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This was originally published as a guest post from Eric Pines, CEO of Pines Federal in June 2022. The most recent update was in August 2024.