11 Epic Side Hustle Success Stories

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11 Epic Side Hustle Success Stories

Millions of people are looking for ways to make money outside of a traditional job. For some people, a side hustle might be needed to make a small amount of extra spending money. For others, it may be a way to make an extra $1,000 per month to pay the bills. But for some people, a side hustle turns into something truly special.

If you’ve got a side hustle or if you’re considering your options, you might enjoy learning about a handful of people who achieved amazing success with their own side hustles. 

Side Hustle Success Stories

Jason Saddler, I Wear Your Shirt

On January 1, 2009, Jason Saddler started out on a side hustle that would eventually earn more than $1 million, just for wearing t-shirts. On that day, he charged a company $1 to wear their shirt and post a photo on his website, IWearYourShirt.com. Each day of the year, the price went up by $1 until he was paid $365 by the sponsor on December 31st. 

Jason got a lot of publicity for his creative business and was able to increase his prices. He scaled the business by hiring other people to wear shirts for him and by having multiple sponsors each day. In addition to wearing the shirt, he would photograph himself in the shirt, share the picture through social media, and host a brief video chat on his website where he would talk about the business.

The story of Jason and his successful business was featured on The Today Show, CBS Evening News, and Forbes. All of the publicity, of course, led to more sponsors.

Jason ran the business from 2009 until 2013 when he decided to move on to other projects. During that run, Jason and his team created more than 3,000 videos and took more than 12,000 photos for sponsors.

Alex Tew, The Million Dollar Homepage

In 2005 Alex Tew was worried about racking up debt as a result of enrolling in business school. He brainstormed creative ways to make money and came up with the idea of The Million Dollar Homepage. The simple website would include 1 million pixels that would be sold to sponsors for $1 each. 

Alex was able to create the website in just two days. Advertisers would have to purchase at least 100 pixels (10×10 block) and they would get an advertisement and a link. Of course, the more pixels an advertiser purchased, the bigger the ads would be.

He started by approaching friends and family to purchase the pixels, which helped him to earn a few thousand dollars. Alex used that money to get a professionally-written press release, which was picked up by the BBC and The Guardian, resulting in a windfall of publicity.

Quickly reaching thousands of visitors every day, the site started making money immediately. After one month he had made $250,000 and in less than five months all of the pixels were sold. Alex auctioned the final 1,000 pixels on eBay, bring the grand total to $1.04 million in just five months.

Ryan Kaji, Ryan’s World

Ryan Kaji got his start on YouTube when he was just three years old with his parents posting videos of Ryan unboxing toys. The YouTube channel that was originally called Ryan ToysReview is now called Ryan’s World and it has expanded to include some educational videos, like science experiments. The channel currently has more than 27 million subscribers.

In 2018 and 2019, Ryan was the highest-earning YouTube star, earning a reported $22 million in 2018 and $26 million in 2019 (according to Forbes). 

At just nine years old, Ryan’s empire has grown to include toys and his own show.

Joel Young, Jump Start Video

In 2013, Joel Young and his wife Jenna were about $50,000 in debt. As part of his work as a pastor, Joel hired a freelancer on Fiverr.com to record a voiceover for the church. That led him to wonder if he could do voiceovers himself as a way to make some extra money and pay off debt. 

Joel made $400 in his first month on Fiverr, much more than he and Jenna were anticipating. After working to grow the business by with late nights and working whenever he was able, Joel’s side hustle income eventually caught up to the salary he was making as a pastor. In 2015 he left his job to pursue the side hustle full-time.

From 2013 – 2019, Joel made over $1.5 million from his work on Fiverr and was featured on CNBC. He also runs Jump Start Video, a company that creates explainer videos for clients. Many of Joel’s voiceover clients also needed help creating videos, so offering the video services was a natural choice for his business. 

Between the revenue from Fiverr and from his own website, Joel’s business now earns more than $50,000 per month in profit (source).

Brian Winch, Cleanlots

Brian Winch is living proof that a business doesn’t need to be glamorous in order to be successful. Brian has been earning a six-figure income by picking up trash since the 1980s. It originally began as a side hustle in 1981. Brian wasn’t happy with the income he was making from his full-time job, so he explored ideas of ways to make some extra money. When he was a kid, Brian helped his dad with some side jobs, including picking up trash at a shopping plaza.

After reaching out to a few real estate management companies, Brian was quickly able to land work cleaning up trash at three local strip malls. He picked up some additional clients and Brian’s trash cleaning side hustle was bringing in more money than his full-time job after just two months! Brian continued to grow the business by outsourcing most of the work. Now, he bills about $650,000 of work per year.

With a few decades of success in the industry, Brian teaches others how to build their own trash cleaning business through his book Cleanlots. Unlike most other types of businesses, there is no particular skill or experience needed to start or run this business. You need very little equipment, it’s quick and easy to get started, and the work can be done around your existing schedule (part-time or full-time). Brian calls it “America’s simplest business“.

Elan Lee, Exploding Kittens

Elan Lee is a successful video game developer who also created the card game Exploding Kittens. Elan worked with Matthew Inman and Shane Small on Exploding Kittens, which became one of the most successful Kickstarter campaigns ever, raising more than $8 million (their funding goal was $10,000).

In 2015 Elan had the idea for the game that eventually became Exploding Kittens. The Kickstarter campaign went live about three weeks later. In the past few years, the company has created a few other games like Bears vs. Babies, You’ve Got Crabs, Throw Throw Burrito, and On a Scale of One to T-Rex. They also have plans for an in-person gaming convention called Burning Cat.

Ashley Mason, Dash of Social

Ashley Mason wasn’t like most college students. In 2016, at the age of 19, she started a marketing firm Dash of Social. While running a blog as a teenager, Ashley had developed some skills with social media that she was able to use to promote her blog and attract visitors. She realized that those skills could be valuable, so she started Dash of Social in order to help clients promote their own businesses.

For the next three years, Ashley worked at growing Dash of Social while she was a full-time college student. She gave up the free time that many college students enjoy and dedicated early mornings and late nights to her school work and to growing her business.

In 2019, three years after launching Dash of Social, Ashley graduated college and smoothly transitioned into running the business full-time. While her peers were searching for jobs and trying to secure interviews, Ashley didn’t need to rely on anyone else to give her a job because she started a business in college.

At the age of 23, Ashley earns a six-figure income running a business that she loves. She also started Student to CEO to help other students develop their own ideas into a successful business.

Sophia Amoruso, Nasty Gal

In 2006, Sophia Amoruso started an eBay shop called Nasty Gal Vintage, selling vintage clothing and other items. The business grew rapidly before she was reportedly banned from eBay in 2008 for including links in feedback to customers. 

Following her success on eBay, Sophia began selling items on her own website, Nasty Gal. Inc Magazine named Nasty Gal one of the fastest-growing companies in 2012, and the site reached $100 million in annual sales at its peak. In 2016, Nasty Gal filed for bankruptcy before being sold for $20 million.

Following Nasty Gal, Sophia started Girlboss Media in 2017. Netflix also created a series called Girlboss based on Sophia and her early days of selling on eBay.

Rob & Melissa Stephenson, Flea Market Flipper

Rob Stephenson grew up with six sisters. With seven kids to provide for, his mom relied on yard sales and thrift stores to buy clothes and toys, as well as some items to resell for extra money. After getting married in 2007, Rob and his wife Melissa continued with the hobby of buying and reselling. 

When their first daughter was born, Melissa cut back on the hours at her job and Rob became more active with flipping as a consistent way to make money. After gradually growing their business for a few years, Rob left his job to become a full-time flipper.

On average, they spend about 20-25 hours per week working on their business. That involves a few hours shopping at yard sales and flea markets and about 15 hours cleaning, fixing, listing items for sale, and shipping items that are sold (most of their items are sold on eBay). 

What started as a hobby has grown into a six-figure income that allows Rob and Melissa to stay at home with their three kids. Today, Rob and Melissa run Flea Market Flipper, where they teach others how to build their own successful reselling business.

Christian Lander, Stuff White People Like

Stuff White People Like was a blog (still online but no longer active) started in January of 2008 by Christian Lander, a white Canadian. The blog took a satirical approach, writing about things that white people like. Blog posts covered things like dinner parties, standing still at concerts, picking their own fruit, and frisbee sports.

Although the blog received plenty of criticism from those who found it to be racist or offensive, it also drew huge interest from people who thought it was funny and entertaining. In its first year, the blog received more than 40 million visitors.

Following the success of the blog, Christian Lander received a book deal that reportedly paid him a $300,000 advance. The Book Stuff White People Like: A Definitive Guide to the Unique Taste of Millions was on the New York Times bestseller list for several months.

Clint Proctor, Wallet Wise Guy

Today, Clint Proctor is a full-time freelance writer and editor, and also the founder of Wallet Wise Guy. While Clint earns a six-figure income today, that wasn’t always the case. For seven years, Clint worked full-time as a pastor. 

Before he started a career in the ministry, Clint became interested in personal finance as a senior in high school. That interest developed into a passion during his 20’s until he eventually decided he wanted to make a career transition and work in a role that involved finance.

While he was still in his role as a pastor, Clint got started as a freelance writer for personal finance websites and blogs. He landed his first client in November of 2018 and he wanted to grow his business quickly in order to be able to make it a full-time income. 

Many people have turned a freelancing side hustle into a full-time income, but what makes Clint’s story unique and special is the fact that he was able to leave his job in June of 2019, just seven months after taking on his first client. And to make it even more impressive, Clint was able to earn five figures per month less than a year after taking that first client.

Clint went from a modest income as a pastor to a six-figure income as a freelancer in just one year, with no prior experience. In the past few years, Clint has worked with clients like Credit Karma, Business Insider, The College Investor, and others.

After achieving success as a freelancer, Clint teamed up with fellow freelancer Ashley Barnett to create the course Freelance Writing for Bloggers with the purpose of helping bloggers to use their existing skills to earn income as a freelance writer.

Final Thoughts

While your own side hustle may not make you millions of dollars or lead to a book deal, it’s always helpful to get some inspiration by seeing what others have been able to accomplish. One key thing that all of these people have in common is that they took action and they made it happen. If you’re interested in starting your own side hustle, be sure to check out this list of more than 150 side hustle ideas.

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