Experts Share Their First Side Hustle

First Side Hustle: 33 Experts Share Their First Side Hustle

As readers and anyone in the private Personal Profitability Facebook group (join the email list to get the link instantly) know, side income is my favorite way to improve anyone’s financial situation. You won’t get rich by budgeting, because real wealth comes from income. Plus, everyone has the ability to earn more – unless you face some work restrictions, like being on a visa while living abroad.

It turns out I’m not the only one who believes inside hustling to grow wealth. The experts agree that side hustling is one of the best ways to grow your income and achieve your own Personal Profitability. To help you follow in the path of other successful entrepreneurs, I asked them how they started their first side hustle. The stories were great, some even started as children!

If they can do it, you can do it, and it’s never too late to start side hustling. Read on below to learn what these experts did as their first side hustle.

What is a side hustle?

According to Entrepreneur magazine, a side hustle is:

A side hustle is a way to make some extra cash that allows you flexibility to pursue what you’re most interested in. It can also be your true passion – a chance to delve into fashion, travel or whatever it is you care about the most without quitting your day job.

My first side hustle

You probably already know that side hustling has changed my life immeasurably, but what got me started on the path to side hustling? Depending on your definition of side hustle, my first side hustle was back when I was a Cub Scout, hustling to sell popcorn. As a Boy Scout, I sold Gold C and Entertainment coupon books. I was super competitive, and always set the annual sales record for my troop. I got a portion of the sales to use for Boy Scout activities, and paid for my summer camp, campouts, ski trips, and more with a few weeks of book sales.

I’ve had lots of side hustles since. From custom bracelets to niche sites to freelance writing, which led me to full-time self-employment, I’m a side hustle addict. But enough about me! Let’s see what my friends and other bloggers, podcasters, and entrepreneurs have to say.

33 experts share their first side hustle

First Side Hustle: Online

The internet is a great place to start side hustling, as the startup costs are often quite low compared to the potential payoff. You can register a domain and get website hosting starting at about $50 per year, and it only takes five minutes to get your first website up and running at your own .com. You can also market your online services on a freelance site like Fiverr.

Ruby from A Journey We Love: worked as a book reviewer on UpWork. Reviewed self-published books on Amazon, Goodreads, and other websites after reading them, and ghost-wrote articles on personal finance and travel on various websites or clients.

Joe from Pod to Pod started the first email newsletter covering the Podcast Industry.

Speaking of podcasts, Blake from The Blake & Sal Show got started with his first side hustle by podcasting! It only took about five years, and Blake says, “after five years of podcasting we may actually make some money. Or not.”

Gee from My Online Biz Journey got started with one of my favorite first side hustles: selling textbooks on eBay! According to Gee, “Back in 2004-2005, I was in college and had learned about eBay as an auction site to buy fairly discounted products. However, the big moment came when I learned I could list my used college textbooks on eBay. It was always fun for me when I got the notification that I had made a sale – I made around $200 a semester doing this. Great extra change for a college student!”

Another first side hustle using Ebay from Robert of The College Investor: “I started selling stuff on eBay when I was in high school. I started with my own junk (like old video games and CDs/DVDs) and eventually started going to estate and garage sales to find stuff I could resell.”

Caitlin Pyle, a hugely successful entrepreneur, got her start online back in 2014 with proofreading, but she was hustling even sooner than that – in 2007. “I started proofreading on the side in 2007. My skills became a blog and online course platform in 2014 — also began that as a side hustle!! That first blog has since evolved into a multimillion-dollar media company with multiple blogs and online courses.”

Curious what personal finance experts first side hustles were? Their answers might surprise you!

Kali from Going Beyond Wealth didn’t wait for anyone when she decided to start her own freelancing writing business: “I always wanted to be a writer, but struggled to find a “writing job” out of college. Eventually, I stopped waiting for some faceless company or anonymous hiring manager to give me permission and started hunting for freelance jobs on my own. It started small and humble — we’re talking 600-word articles at content mills I got paid $15 a pop for, and sketchy Craigslist posts looking to pay writers or editors $5 an hour — but I took what I could get from the beginning and consistently worked my way up not just to better-quality gigs and higher-paying work, but ultimately, to my own business that I run today.” The hustle starts humble and can clearly lead to amazing opportunities!

Dan from Growella didn’t start at the bottom – he went right to the top with wMUsers. wMUsers was a specialized software user community for consultants that generated revenue through job postings and enhanced memberships. It was acquired after 30 months.” Not bad!

Joseph from My Work From Home Money first got started as a freelance investment analyst: I completed stock research reports for financial advisors and investment firms. I had to write up a 40-page research report to use as a portfolio example but it paid off when I was invited to speak at a Bloomberg conference in New York. Take the time to create something really awesome to show what you can do for clients.

Now, this one is seriously clever: Jim Wang from Wallet Hacks capitalized on inefficiencies in casino gaming – “my first side hustle was chasing online casino promotions. They used to match your deposit (put in $100, get $100 in free cash) as long as you put a multiple of that amount into play. If the multiple was 10 times, you had to bet $1000 to get the cash-out. I learned how to play blackjack and would sign up to dozens of casinos a week for the money. I made a small fortune in college and it taught me how inefficiencies are everywhere and I just had to look hard enough.”

First Side Hustle: Offline

ESI from ESI Money focused on the bigger picture with this first side hustle: paying off debt! ESI got started writing for magazines – not online! As ESI tells it, “I started a magazine freelance writing business (marketing) and personal finance pieces (back when people still read magazines). We put all profits against our mortgage and paid off all our debts in six years!” Now that’s a hustle!

Emmitt from The Billionaire Lifestyle took a rather challenging first side hustle to share with us – electronic repair! Emmitt repaired and refurbished consumer electronics to make some extra cash. 

Not every side hustle begins with a purpose! Melissa from Melissa the Coach started her business on accident, but made it work! As she tells it, “I own and operate a pet and places sitting business in my town. Started by accident but ran with it and made it a success!”

Stephanie from Healthy, Savvy and Wise had a pretty tough sounding first side hustle: proofreading legal transcripts! "Any court case or deposition requires a court reporter to type up a transcript of every word uttered, and I was the final set of eyes before the attorneys got them in their hot little hands. You haven't lived until you learn to proofread verbatim's a hoot!"

Andrew from Family Money Plan took a skill he had, knowledge about musical instrument, and capitalized on it: "I worked in the music industry, so I knew the values of musical instruments. I used to go to the pawn shops and buy the under priced instruments that I found, clean them up and resell them. The mark up on them was anywhere between 50% to 300% depending on what you could find."

What do you do if you want to stay at home with your child but still need to make money? Start your own babysitting/daycare like Caroline Vencil: "I ran a daycare in my house for up to 5 kids each weekday. It was exhausting, but I got to stay at home with my son and still get to make money without leaving the house."
First Side Hustle: 33 Experts Share Their First Side Hustle
Scroll to Top