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!

How I Successfully Pretended to Run a Business for the Last 18 Months

It’s time to get something off my chest. For the past year and a half, I’ve been pretending to run a business. What I do isn’t running a business. I’ve created an avenue for self employment. It’s not scalable, and therefore in my eyes… not a business. I would love to transform this into a business, and here’s how I’m going to do it!

How I Make $1,000 per Month Riding the Subway

Me on the first day the subway came all the way to my work! Sorry for the dramatic Insta-filter ;)

Me on the first day the subway came all the way to my work! Sorry for the dramatic Insta-filter ;)

Hi, my name is Greg Langstaff and I make a little over a $1,000 every month riding the subway. Am I really good at riding the subway? After all these years, I’d like to think so. But no, I’m not just getting paid for sitting here looking pretty (notice I said “here” because I’m writing this on the subway). 

As many of you know, in January of 2018, I launched my resume writing and interview coaching business. And if you’ve been following closely, you’ll know that over the first little while, I had some ups and downs, including earning $820 in my second month and then $0 in my third.

After nearly a year of experimenting with various marketing and promotional tactics including organic Facebook content, word-of-mouth, paid Google and Facebook Ads, and registering with the Career Professionals of Canada, I started to experience a reliable flow of candidates that would earn me anywhere from $1,000 to $1,400 per month. 

Lots of Clients… Not a lot of Time

The challenging part was, when would I write all those resumes and cover letters? I still have  an 8:30am to 4:30pm job and I also live with my girlfriend, Ariana, who I like to spend time with in the evenings, so I can’t just work into the night. I also try to hit the gym 3-4 times a week and I don’t miss a Raptors game if I can help it. Also, friends. They take up time too!

It takes me anywhere from 1.5 to 4 hours to write a resume (depending on my familiarity with the industry and how useful my phone call with the client was). Cover letters take another 45 minutes or so and then an additional chunk of time for the LinkedIn makeover. I’ve been working with 5-7 clients per month so as you can tell, the time adds up. 

So not wanting to give up any aspect of my life, or cut back on clients (and income), I scoured my schedule in search of a time when I could get this writing done. I tried waking up at 6:00am to start writing, but after even two days that turned me into a zombie. I tried doing work at home on the weekends, but that just made me sad. I tried working on lunch breaks at work and that had some success but it just wasn’t quite enough time. 

Then… a Miracle 

I tried writing during my commute. Every morning I walk 8 minutes to the subway station in downtown Toronto, sit down for 40 minutes and arrive just steps from my office. The subway is fairly empty because I’m leaving downtown when most people are coming in, so there is always a seat. 

Right there, I found 1 hour and 20 minutes per day (nearly 7 hours per week) for writing. That’s more than enough to get through 1.5, even two clients a week without even touching my social life. Between that time and the odd lunch break here and there, I’ve managed to almost completely avoid letting writing interfere with my home or social life. 

Building the Habit

Writing first thing in the morning or after a tough day of work wasn’t easy at first. I’m somewhat of a morning person but after work, my brain often feels like mashed potatoes. 

However, I’m a big believer in habit forming. I have read The Power of Habit by Charles Duhigg twice (weird brag, I know), and using the tactics in his book, I was able to completely take the willpower out of writing on the subway. There is literally no decision making process at all. 

When I get on subway. 

  1. Sit down.

  2. Turn off music/podcast. 

  3. Open laptop. 

  4. Start typing. 

When I arrive at my station: 

  1. Hit save. 

  2. Close laptop. 

  3. Exit train 

*(oh damn, as I was writing that line, I literally arrived at my stop and had to exit the train. Now I’m continuing to write this a couple days later. Welcome to this meta/behind the scenes tangent. Okay back to what I was saying). 

What Makes a Habit Stick

According to Duhigg, there are four essential elements to building a successful habit. Here are mine. 

The Cue: A recurring event that triggers the desired behaviour (e.g. waking up is the cue for brushing your teeth). My cue is getting into the subway.

The Behaviour: The thing you want to do. For me, this is writing resumes or blog posts or whatever is on tap. 

The Reward: This is the reason for doing what we do. For brushing your teeth, it’s a clean mouth and a nice smile. For me, it’s clearing out my to-do list and having a free schedule. 

An Internal Driver: It’s the subconscious driver that motivates us to continue with the habit. The internal driver for brushing your teeth is that satisfying tingly feeling you get after you’re done. For me writing in the subway, it’s relief from the fear of people yelling at me for not delivering their documents on time (if you’ve read my “How I Paid off $12,000 of Debt in Six Months while Enjoying Guilt-Free Spending” blog, you know the fear of being yelled at has always been a great motivator for me). 

Final Thought

Life’s good! I had a problem and I solved it! Onto the next one :)

If you know anyone who’s struggling to form a good habit or make a lasting change (or find a time to write), send them this blog. I’d really appreciate it and hopefully they will too!

Starting My Own Business: 10-Months In!

Greg Balloons

Dear Mom... and whoever else decides to read this blog <3

Ten months ago today, I launched Greg Langstaff - Resume Writer & Interview Coach! Believe it or not, I'm still standing :) 

Since January 8th, I have served 43 clients (plus five currently in process) and I owe a great deal of that success to all of you who supported me. Thank you to anyone who passed my name onto some who needed help, or shared my promotional content online, or simply asked me how the business was going. Without you, I am but a lonely man posting memes on his Facebook page.

For all those following along the journey, here's how the first ten months have gone :)

The Money

I don’t think enough people share the cold hard numbers when they talk about their businesses, but like a good resume, I want to show you my specific and measurable accomplishments.

My initial goal was to make a modest $1,000 this year. I went onto hit that in February so I set a new goal of $5,000. I've honestly stopped keeping track of how much money I've made exactly (I guess I'll have to figure that out before tax season), but I can tell you that I'm somewhere north of $6,000. 

The Commitment

At the six month-mark (after some eye-opening spring travelling with Ariana), I decided that I liked running this business enough that it was time to commit. Here's a quick summary of what committing looks like for me: 

July: I registered as a Sole Proprietor with the Government of Ontario. 

August: I applied for and was accepted to the Futurpreneur Mentorship program for young entrepreneurs. I now have a great mentor who is helping me expand my business. 

September: Record-high month in revenue generation at roughly $1,200. 

October: I became a card-carrying member of the Career Professionals of Canada. 

November: I am studying for my Certified Resume Strategist designation which I hope to have by the end of this year. 

Lessons Learned

The first ten months have definitely dropped some knowledge into my lap. I've done my best to categorize those lessons for you. 

Marketing: You can get it for free, and you can pay for it too. 

I've had great success in posting useful content in my social media just to generate awareness in my business and tossing out the occasional sales pitch. To be honest, the content generation does get challenging, and I've been guilty of disappearing for weeks on end. It's a lot of work and I also worry about over-saturating my newsfeed and wearing out my welcome. 

I'm also starting to dabble in paid marketing (this is where it's great to have an experienced mentor). I’ve done a bit of Facebook and now I’m messing around with Google Ads a bit, which has proven to be fairly successful so far.

Service Excellence: I’ve also found that the best way to find new clients is to do a damn good job with the ones you have! About 20% of my clients have been referred by other satisfied clients. That's not a bad ROI for just doing your job with a smile... also it's nice to genuinely help people, but that’s not as measurable ;) 

People are Amazing: There are a lot of really great people out there. I'm so lucky to get to spend a hour on the phone with each of my clients, hearing all about their incredible lives. I have learned so much about so many different professions that I would have never learned if I hadn't started this business. Talking to people has been my absolute favourite part. 

What's Next?

Here's a quick taste of some upcoming initiatives for my business.

Certification: As mentioned above, I'm currently studying to become a Certified Resume Strategist. Just reading the textbook as already validated a lot of my earlier work and given me more confidence in my ability to help my clients. 

More Succinct Marketing Plan: Some of you may have heard that I recently moved in with my beloved, Ariana. And you may know that she is a digital marketing professional. So between Ariana and my mentor, I feel great about the direction my marketing strategy is heading in. 

Video Course: I've been talking about this for a long time now, but I swear I'm going to do it!

Thanks for reading! If you're thinking about starting a business or you recently started one and you want to talk, hit me up!