The Best Books to Read Before Starting a Small Business

So, you've got that entrepreneurial itch. Maybe it's a brilliant idea that won't let you sleep, a desire for more autonomy, or a yearning to solve a problem you see in the world. It’s a prospect that is incredibly daunting yet often romanticized. If it’s your first business or didn’t grow up with entrepreneurial role models, you may not know where to start. If you’ve had a failed business in your past, you may be understandably reluctant to take a risk.

Before you dive headfirst into a business plan, I recommend reading a few books that can make the decision a little easier and, if you do start a business, help you build a foundation for a successful venture.

Think of these books not just as guides, but as your wise, more experienced co-founders willing to offer advice, temper your expectations, and inspire new ideas without demanding equity. They won't give you all the answers, but they will pose the right questions to ask yourself before taking the leap.

The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It by Michael E. Gerber

After my first business failed – an edgy, award-winning women’s magazine called Nervy Girl that I ran for three years that enjoyed a healthy measure of success and notoriety in Portland and beyond – the original iteration of this book (The Emyth) practically leaped out at me from the shelves of Powells Books while I was wandering the aisles in despair over the demise of a business I had nurtured like a child. I devoured it in less than a day and fervently wished I had read it before starting Nervy Girl. It is practically a rite of passage for aspiring entrepreneurs. Gerber challenges the common misconception that being good at a technical skill (like baking a great cake or being a fantastic designer) automatically makes you good at running a business. He argues that most small business owners are "technicians" suffering from an "entrepreneurial seizure."

Why read it? The E-Myth Revisited forces you to think about building a system that can run without you, rather than just creating another job for yourself. (You’d like to take the occasional vacation or weekend getaway, right?) It introduces the crucial difference between working in your business and working on your business. If you're hoping for more freedom, this book will show you why structure, not just passion, is key.

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear

In his popular blog, Clear writes, “(If) you completely ignored your goals and focused only on your system, would you still succeed? For example, if you were a basketball coach and you ignored your goal to win a championship and focused only on what your team does at practice each day, would you still get results? I think you would.” He continues, “Goals are good for setting a direction, but systems are best for making progress.”

Though not strictly a business book, Atomic Habits is foundational for anyone considering entrepreneurship. Running a business demands immense discipline, consistency, and the ability to set and achieve goals. Clear's framework for building tiny, incremental habits that lead to remarkable results is invaluable. He explains how to design simple systems that make good habits inevitable and bad habits impossible, a crucial skill for navigating the demanding, often unstructured world of business ownership.

Why read it? Starting a business is a marathon, not a sprint. This book will teach you how to design your environment for success and ensure that the daily grind contributes meaningfully to your long-term vision. Think of it as building the personal operating system you'll need to sustain your entrepreneurial journey.

The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries

If you're an innovator or considering a tech-driven venture, The Lean Startup is essential. Ries champions the concept of "validated learning," where you test your business hypotheses by building a Minimum Viable Product (MVP) and iterating rapidly based on customer feedback, rather than spending years perfecting something no one wants. The core idea is to test your assumptions about what customers truly want, allowing you to pivot or persevere based on real-world data, thereby reducing risk and significantly increasing your chances of building something the market actually needs. It's a pragmatic guide to navigating uncertainty and fostering continuous innovation.

Why read it? This book teaches you to fail fast, learn faster, and adapt. It's a pragmatic antidote to the common pitfall of pouring resources into a product or service without truly understanding market demand. It's about managing risk and increasing your odds of success in an uncertain environment.

Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine by Mike Michalowicz

For many entrepreneurs, profit is an afterthought, what's left over at the end. Michalowicz advocates for paying yourself and setting aside profit first, before expenses. This simple yet profound shift in mindset can fundamentally change your business's financial health.

By challenging the conventional accounting formula (Sales - Expenses = Profit) Michalowicz proposes a counter-intuitive yet highly effective approach: Sales - Profit = Expenses. By advocating for setting aside a predetermined percentage of every deposit for profit first, before paying bills, Michalowicz helps aspiring entrepreneurs build immediate financial discipline.

Why read it? Money matters. This book demystifies cash flow management and provides a simple, actionable system that ensures your business is designed to be profitable from day one, alleviating common fears about money management and charting a clear path to financial viability. It's easy to read and offers a clear, disciplined approach to ensuring your venture actually makes money, rather than just breaking even or constantly chasing revenue.

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

I often tell my clients, “If you read $100 Startup and you don’t want to start a business, you probably shouldn’t.” Guillebeau writes his entrepreneurial books with an infectious, optimistic tone that assumes you are indeed going to start a successful business and thereby create a life for yourself with more flexibility and autonomy.

The $100 Startup also shatters the myth that you need massive investment to launch a successful venture. Guillebeau highlight real-world examples of individuals who built profitable businesses from minimal upfront costs, often by leveraging existing skills and passions. It focuses on identifying the intersection of what you love, what you're good at, and what people will pay for, guiding you to find market gaps and create value quickly.

Why read it? More than just a how-to guide, $100 Startup is a motivational manifesto for aspiring entrepreneurs looking to create financial freedom and a meaningful livelihood without unnecessary risk or debt.

Building a StoryBrand: Clarify Your Message So Customers Will Listen by Donald Miller

Building a StoryBrand helps you craft marketing messages that truly resonate. An indispensable guide to mastering the art of communication and customer connection, this book reveals a powerful, seven-part StoryBrand framework for crafting clear, compelling messages that resonate deeply with your target audience.

Miller argues that businesses often make the mistake of positioning themselves as the hero, when in reality, customers are the heroes seeking a guide to help them solve their problems. Understanding this fundamental shift helps you clarify your brand's unique value, attract the right clients, and build a marketing strategy that genuinely speaks to their needs and desires—a crucial skill for turning an idea into a thriving enterprise.

Why read it? You might have the best product or service in the world, but if you can't articulate its value in a way that captures attention and connects with your audience, you'll struggle. Building a Storybrand helps you cut through the noise, clarify your mission, and speak directly to your ideal customer's needs and desires.

Embarking on the entrepreneurial journey is a profound decision, one that demands more than just a brilliant idea. It requires foresight, discipline, financial acumen, and a deep understanding of your potential customers. These six books offer more than just theories; they provide practical frameworks, mindset shifts, and real-world strategies that significantly minimize your entrepreneurial risk.

By investing time in these pages, you're building the foundational knowledge that will inform whether starting a business is the right path for you, right now. They won't guarantee success, but they should provide you with a robust mental framework, realistic expectations, and actionable strategies, so you can launch a startup with wisdom and a greater chance of thriving.

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Kristin Schuchman, MSW is a business coach, career counselor, and author based in Portland, Oregon who works with creative and mission-driven professionals. She writes resumes and coaches individuals seeking support for career indecision, next steps, work re-entry, advancement, starting a business, and work-life-balance. She offers a free 30-minute Zoom or phone session and presently works with clients in-person in Portland and remotely. You can find her books The DIY Website Workbook and Jump Start: How to redirect a career that has stalled, lost direction or reached a crossroads on Amazon.