10 Best Books for Starting a Side Business in 2021

10 Best Books for Starting a Side Business in 2021

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This is my list of the 10 best books for starting a side business. As a young entrepreneur who has started three businesses and worked closely with other small business owners, I understand it can be hard to know where to start, so this list contains both practical and inspirational works.

Most of them are points of access to experts currently practicing in the field of business and who have much, much more to offer you after you’ve finished their books. Pick one or two to read, get fired up, and start building your side business!

The $100 Startup – Chris Guillebeau

Written by a serial entrepreneur and world-traveler with an ever-widening following, this is the go-to book for anyone who wants to learn how to make money from no money.

It’s a practical handbook with advice for the everyday entrepreneur: real people with real day jobs, families, and bills. The core message of the book is twofold: action, however small, always beats endless planning; and the key to big success is not big debt, a fancy business plan, or tons of employees, but rather to start small, right where you are.

It helped take me from big plans that went nowhere to small actions that went somewhere. Success in business followed – I even wrote an article about how I started my own side business with no cash investment, following Guillebeau’s advice.

Get your copy at 100startup.com.

100 Side Hustles – Chris Guillebeau

If you’re hungry for more inspiration after The $100 Startup, check out Guillebeau’s side hustle idea book. The stories within, selected from those featured on his remarkably prolific Side Hustle School podcast, are bound to inspire you to seek out your own niche.

If you’re ready to get started right away, you can also check out our article, 45 Ways to Supplement Your Income Creatively.

Get your copy of 100 Side Hustles here.

Titan: The Life of John D. Rockefeller, Sr. – Ron Chernow

In any field, we can learn much from extreme examples. John D. Rockefeller, perhaps the richest man ever to live, is about as extreme an example any aspiring business person can find.

Born into poverty in rural New York at the dawn of the industrial age, later labeled by some as a robber baron and the world’s most generous philanthropist by others — whatever your feelings on the famous oil tycoon, we have much to learn from an exploration of his lifelong practice of business and pursuit of money.

My biggest takeaways from this book were questions for myself, rather than answers – what is the moral purpose of money? How much is enough? At the end of my life, whether I die rich or poor, what will be the parts of my story that really mattered?

Pick up a copy of the book here.

The Personal MBA – Josh Kaufman

A perennial but up-to-date classic. The author asserts that spending $100,000 on a university MBA is a poor investment, and the book is intended as a starting point for the reader’s alternative (and almost free) business education. It does that very well.

The book breaks down the major pieces of a business system at any scale, from ideation to delivery of value, and from the creation of efficient systems to marketing and sales. Organized into neat, encyclopedic sections, it’s more useful than entertaining, but not at all dry. Each entry is designed to give you all the knowledge you need to ask deeper questions and includes links to online resources to help you learn more about almost every aspect of business.

The book is accompanied by a frequently updated website, www.PersonalMBA.com, which has helped earn it an enduring place on many lists of best books for starting a side business. Pick up a copy here.

Crushing It: How Great Entrepreneurs Build Their Business and Influence-and How You Can, Too – Gary Vaynerchuk

Vaynerchuk is a social media, YouTube, and podcasting sensation, as well as a best-selling author. He’s known for his inspirational style and go-getter attitude. The hard-working son of immigrants who made his first fortune building the family wine business, he now also owns VaynerX, a modern-day media, and communications company.

If there’s one thing Vaynerchuk trades on, it’s attention. Anyone who dreams of one day ruling a social media empire, or just wants to know how to get their work to stand out against the local competition, should check out this book or any of the prolific author’s other (mostly free) content. Check out the book here.

The Side Hustle: How to Turn Your Spare Time into $1,000 a Month or More – Nick Loper

The author gathered the material for this book from hundreds of interviews conducted on his show, Side Hustle Nation, which I’m a big fan of. 

What I love about Nick Loper’s work, and that of the people he interviews is that the numbers are seldom obscured by the hype. Nick and the hustlers he speaks with are mostly regular people, many of whom have now quit their jobs to pursue their side business full time and genuinely want to share the lessons they’ve learned that earned them their financial freedom. They’re willing to tell you just how much they spent on equipment or advertising, and how much money they made on sales last year, and especially about their big mistakes.

The Side Hustle takes you through three business models you can use as starting points, through the eyes of these everyday people who’ve used them successfully. Check out the book here.

In my opinion, some of the best books for starting a side business don’t deal with the practical knowledge of day-to-day tasks, but on the mindsets that help you succeed.

Jocko Willink is a decorated Navy SEAL officer, best-selling author, and successful businessman. The coauthors’ premise is that the key to freedom and success in business and on the battlefield is personal responsibility — you take credit for your own failures and reap the rewards of your own successes.

Check out the book here. But if the written words of the warrior-author aren’t enough to get you moving, check out Jocko’s famously motivating YouTube videos and podcast library, available for free.

The 4-Hour Workweek: Escape 9-5, Live Anywhere and Join the New Rich – Timothy Ferriss

Timothy Ferriss’s popular book makes some pretty bold claims about what is possible with business and lifestyle design. Personally, I think it’s worth a read just for exposure to a different way of life, and a different pace of living. At the very least, this exploration of business efficiency and alternative work styles should leave you with the question: is my business serving me, or am I serving it?

Get the book here.

Folks, This Ain’t Normal – Joel Salatin

If this list has one inclusion that’s dictated by my personal bias, this would be it. It’s not, strictly speaking, a business book, but rather an equally humorous and pleading exploration of what used to matter in life, through the eyes of a modern-day farmer, author, speaker, and businessman.

As a businessman myself who is guilty of many 80-hour workweeks chasing after the almighty dollar, I found this book to be a deeply refreshing reminder of every human being’s simple roots. Joel Salatin asserts that what we are missing is not more money and faster pleasures, but a deeper relationship with our communities, centered around the earth that sustains the most widely practiced human industry: food production.

Get the book here.

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

Perhaps one of the longest-running titles on lists of best books for side businesses, this is a great place to start if you’ve got a passion for your side business, but not so much for the numbers behind it. The book boils down to a pretty simple concept, echoing Chris Guillebeau’s thoughts in The $100 Startup: Don’t accrue tons of expenses in order to earn a profit; earn a profit before you spend tons of money on expenses.

This is an especially important lesson for small business owners just starting out, and well worth the time spent reading the book to ingrain it into memory. Get the book here.

Bonus – Make Your Bed: Little Things That Can Change Your Life…And Maybe the World – Admiral William H McRaven

The shortest book on this list is also the simplest and perhaps the most powerful. Admiral McRaven says “If you want to change the world, start off by making your bed.”

The idea is that all unfathomably big, incredibly difficult achievements begin with little, simple steps. It’s true for soldiers, lovers, and entrepreneurs.

If you don’t want to read the book, watch the commencement speech the book was based on.

Then get out there and go change your world!

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