7 Business Books That Helped Me Start My $16,000 Side Hustle

Greg Reading.jpg

If you’ve read any of my previous blog posts, I’m sure you know that I’m an avid reader (and rereader) of business books. For every book I’ve read, I make sure to take at least one major concept and integrate it into how I’m running my business.

In my first year, 2018, I made a little over $8,000 running my Resume Writing business and this year, as of July 21st, I have already surpassed $8,000. I owe a lot of that to reading and listening to podcasts. I’m going to do another post of my favourite business podcasts, but for now, let’s talk literature.

Tiny Disclaimer: I am a registered Amazon Affiliates member, so if you click through these links and purchase the book, I will get a (laughably small) commission. However, I’m only recommending books I have read and which have significantly helped me get this side hustle running and growing!


1. Rich Dad Poor Dad: What the Rich Teach Their Kids about Money that the Poor and Middle-Class Do Not by Robert T. Kiyosaki

How it made me feel: This is the first business-related book I ever read and it got me FIRED UP! Rich Dad Poor Dad opened my eyes to the possibility that I was headed down a seriously wrong path if I wanted to gain any kind of financial independence. It also made me feel a little overwhelmed by how much work I had ahead of me, but that’s why I kept on reading more business books!

What it taught me: This book taught me many of the mistakes most people make when they think they’re building towards a sound financial future, and why most people work they’re whole lives only to live a modest retirement with frequent financial headaches.

When to read this: Read this if you’re starting to feel like the track you’re on might not lead to the life you’re dreaming about.

Times I’ve read it: 3

Check it out!


2. The 4-Hour Work Week: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss

How it made me feel: This is the Mecca of all business books for a budding entrepreneur. I still get butterflies when I see this on my bookshelf. Tim Ferriss has designed a blue print for not only creating financial freedom, but also creating a time-flexible lifestyle that I (and many others) so desperately want. Tim’s step-by-step guide also makes me think… I can do this!

What it taught me: Tim’s “Definition”, “Elimination”, “Automation”, “Liberation” formula helped me to craft a vision of what I want my life to be and craft a plan of how to get there.

This book taught me how to work smart and not hard and stop wasting the enormous amount of time when I thought I was being “productive”. It has also made me far more efficient in the workplace and a much higher-performing employee (bonus!).

When to read this: When you’ve decided you want to make a change in your work/financial situation but you don’t know where to start.

Times I’ve read it: 3

Check it out!


3. You Are a Badass at Making Money: Master the Mindset of Wealth by Jen Sincero

How it made me feel: This book gave me permission to pursue a better financial lifestyle. It talks about the limiting mindset many of us have around money and the psychological reason many of us have chosen to take a safe, timid financial path. This book oscillates between giving me that heavy feeling on my chest and energizing blasts of hope and empowerment.

What it taught me: Sincero helped me identify my negative relationship with money and put me on a path to re-examine my financial mindset and open me up to the possibilities which I am able to pursue.

It also empowered me to share exact dollar amounts when talking about money (see title of this blog) which has helped me to have much more meaningful discussions about money with more people.

When to read this: If you’ve ever felt a bit icky thinking about or talking about money.

Times I’ve read it: 3

Check it out!


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

How it made me feel: Chris Guillebeau has this innate gift to make the process of starting a business seem simple and possible. He fills this book with a dozens of real world examples of people who started a business, investing roughly $100, and grew it into something big. While other books made me feel excited (and occasionally overwhelmed) The $100 Start Up gave me my first sense of calm.

What it taught me: This book taught me where to start! Guillebeau walks you through defining your idea, crafting a one-page business plan, and how to start making money with a minimal investment (as a side, the initial investment in my business was about $220 for web hosting and an email service, so this definitely helped).

When to read this: When you’ve decided you want to start your own business but before you know exactly what you’re going to do.

Times I’ve read it: 1.5 (just skimmed it the second time)

Check it out!


5. The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg

How it made me feel: When you’re starting a business while still working a full-time job and trying to have a life, finding time, energy, and willpower to get things off the ground (or expand) can be daunting. Charles Duhigg breaks down the psychology of habit forming and how we can use that to construct a life where working towards our goals is automatic. For a more detailed look at how I’ve incorporated the lessons from this book, see my blog How I Make $1,000 per Month Riding the Subway.

What it taught me: Duhigg’s research taught me how to build time into my daily schedule for business development without needing to use up precious willpower to get to work. He helped me discover how to work, when to work, and how to reward myself so that I can handle all the clients I do (coming up on 100!) while still driving the business forward and not letting it take over my entire life!

When to read this: Read this if you’ve started a business and if you’re having trouble finding time and energy for the rest of the commitments in your life.

Times I’ve read it: 1… plus I listened to him walk through the concepts in a podcast.

Check it out!


6. Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World by Gary Vaynerchuk

How it made me feel: Gary Vee (as the author likes to be known), is probably the most high energy public-figure/entrepreneur out there. I picked up this book during the third month of my business (March 2018) when I famously made exactly $0. This book is focused on content marketing through social media and it had me saying, “Aha!” and “Ohhhhhhh!” a lot. Lots of good revelations about how to build trust with your audience through providing high-value content online.

What it taught me: Jab, Jab, Jab, Right Hook is full of screenshots of actual social media ads which real companies have used. Gary Vee breaks down each ad and tells you why they are good and bad. This book got me back on track and helped me to start bringing in clients who weren’t in my inner circle through social media marketing.

When to read this: If you have started a business and you’re ready to expand your client/customer base.

Times I’ve read it: 1

Check it out!


7. Rules for Focused Success in a Distracted World Deep Work by Cal Newport

How it made me feel: This book gave me two very distinct feelings. First, it made me feel like I had superpowers. By following Newport’s advice, I have been able to find my flow-state and get a load of high-concentration work done in a short period of time. Second, it made me understand that we have natural limits to our concentration and that I shouldn’t feel bad when I start to lose my focus.

What it taught me: Cal Newport taught me how to structure my workflow so that I can really drill down and do deep, concentration-intensive work, and still have plenty of time for family, friends, and relaxation.

When to read this: Whether you have a business or not, read this one if you’ve got a lot on your plate!

Times I’ve read it: 2

Check it out!

Let me know if you found this helpful! And please comment with any business books you think I should read next!