8 Amazing REAL STORIES on Side Hustles That Turned Into Full-Fledged Businesses

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Have you ever wondered what it’s like to actually run a side hustle, and how it plays out in real life?

We’ve compiled 8 amazing stories of real people who run their own side hustles; be it to earn extra cash or pursue their passions. 

If you still doubt the idea of getting tangible results from your side hustle, we hope these inspirational stories will change your mind.

1. Gene, Greenpal

In most cases, working in a startup is like getting punched in the face every day and working at a corporate job is like getting waterboarded.

I was a corporate sales manager for Dell Computers and I co-founded a company GreenPal, which has been described as Uber for lawn care.

We launched GreenPal as a side hustle just to see if anyone would use this type of service before actually really putting real money into the website.

For two years this little “hobby” started gaining steam and I realized the potential that it had. Having to leave a very well paid corporate job was very difficult and doing both really consumed my time. My corporate life started at 7am-4pm, Mon-Fri, while my side hustle started at 4:30pm-9pm, Mon-Fri, Saturday, 8am-6pm, and Sunday, 10am-4pm.

 After 5 years of doing both, I took a leap of faith and quit my job and went full time with GreenPal.

GreenPal Rev in 2018 – $15M
Projected Rev in 2019 – $30M

My grandfather who barely spoke English told me this…”There are 3 8-hour workdays in 24 hours…pick which two you want to work and you will be successful.”

2. Ryan Sprance, Kaihatsu Media

I am a perfect example of how a side hustle can pay off. Back in March of 2013 while I was working in a leadership role for Apple, I started a curated men’s blog on Flipboard called The Stylish Man.

At first I would curate articles in other publications that were related to men’s style and health. In August of 2015 I expanded that to Instagram and spent 15 hours a day learning the platform and trying to understand the algorithms and finding the best content to post.

I was able to build two accounts to a combined 300,000 followers. Brands kept asking me how I built such a large following and in March 2016, I stated to tell them “you hire me to run your account”.
I kept doing it as a side hustle while earning just $1,000 a month extra. In May of 2018 I was fired from my full time corporate role (for having a side business).

I have since grown that business from $3,500 in April of 2018 to over $70,000 a month in recurring revenue. I now have 8 employees in 4 counties and we are on track for 2019 to break $1,000,000 in revenue in just 16 months.

My partnerships have allowed me to expand and last month I signed on to be an Associate Producer for Amazon Prime series called The Social Movement.

I used the profits from the business to branch out to real estate investing. This month, I am partnership with a larger digital data agency to create a second agency with a focus on travel and hospitality.

So as you can see, my side hustle was well worth it. The key is not to seek out a side hustle that will make you money. If you do that, you will fail because most of the work to build the business is hard and not rewarding. If you chase the money, you will quit well before you achieve success.

When you follow your passion and what you actually love and figure out how to make that a business, you have a fighting chance to succeed!

3. Shawn Breyer, Atlanta House Buyers

When I graduated from college, I was introduced to Rich Dad, Poor Dad. From reading that, I knew that I wanted to buy rental properties for my retirement plan. After a few months, I bought my first duplex, renovated it, and managed the tenants. Later that year, I bought my second rental property. With renovations, repairs, and maintenance, I knew it would take a while to buy our next rental property. So, I decided to start wholesaling real estate on the side. My goal was to build capital for rental properties and to have a source of off-market, discounted properties that I could buy.

Most people get into the business by cold calling or sending postcards to homeowners. I had zero desire to cold call or spend thousands of dollars on direct mail, so I started a website to generate inbound leads online. I studied and implemented SEO and backlink building for a year before I got my first deal from the website. Now that I’ve seen the power of having a lead generation machine, I have reinvested 50% of the income from the properties we flip back into the website.

Now that we have built some momentum, we are consistently doing multiple deals per month. I still have my 9-5 engineering job that my family lives off of. We invest all of the money from the side business back into the business and into rental properties now. We have bought a couple of rental properties and now we have several hundred dollars in cash flow coming in each month. At the moment, nothing life-changing has occurred, but the plan is working. We are able to find rental properties that we can buy for 50% of their value and the business is generating enough capital to buy at least two per year.

Looking ahead, we will continue to purchase rental properties and build up our passive income. Once we have enough rental income to cover our living expenses, I will quit the engineering job and go full time into the business.

4. Jeff, JMoriartyMarketing.com, dogchristmasstockings.com

I started a few side hustles over the years. I was in the digital marketing industry, which opened my eyes to how successful you could become online.

I thought why not make extra money on nights and weekends. I started at first working as a marketing consultant on the side, earning more and more clients from forums, Facebook groups and word of mouth.

Eventually I was able to leave my job to do it 100% of the time. Now I have more freedom and am making twice as much as I did at my old job.

With this work, I even started another side hustle business selling stockings (www.dogchristmasstockings.com). It’s only about 10k a year, but a nice side business that changes things up a bit. Maybe one day it won’t be a side hustle anymore either!

5. Daniel Chan, Bay Area Dinner Show

Quit a job in tech close to 20 years ago to come back full circle entertaining for tech’s most influential billionaires. It was a real struggle when I first started off. I had to take pretty much any show, which meant I started off at the bottom with birthday parties. I was pretty much an overpaid babysitter more than a magician or balloon twister starting off making $75, then raising my rates slowly $250 per hour and leveling off there for many years.

At one time I was doing close to 300 shows a year and I was a fixture at birthday parties, libraries, and school events. I’ve done an estimated 5000 plus shows in the Bay Area. Now I’m close to closing a chapter of going out to entertain. My show’s reach the level where it’s a destination and people are driving an hour or two coming to see me in San Francisco. I’ve gone from Dan Chan Magic Man to Dan Chan Master Magician and regularly entertain for Bay Area billionaires. Now, one of the PayPal mafia is helping me launch my career.

Before I was a full-time magician, I was a pre-IPO Silicon Valley employee. I worked alongside Elon Musk and Peter Thiel at the PayPal offices in Palo Alto. I was a PayPal employee with a side hustle performing magic, pick-pocketing, and fire juggling on the side. The other employees would gather around my desk to watch me perform my close-up miracles during lunch. The few times there was the opportunity to entertain at a lucrative high profile gig I would call in sick.

Initially, I thought PayPal was the dream job. However when reality set in, I hated the job. It was boring. I wanted the job to have the pedigree on my resume. I had only vested 13 months of my options when I decided to jump ship. When I left to pursue my dream, I gave up approximately 3/4 of my stock options.

Since I’ve moved on from PayPal, I’ve performed for many companies in Silicon Valley and has been nominated “Silicon Valley’s Favorite Magician” by Buzzfeed.

My wife, Katherine, is blessed with the skill of twisting balloons. She can make almost ANYTHING just by looking at a picture and has twisted life-size superheroes, life-size motorcycles, and even parade floats – with ONLY balloons and markers. Kat is also my beautiful onstage assistant.

My son, James, has the extraordinary ability to juggle balls, clubs, and flaming torches! He can juggle up to 5 balls, pass up to 8 balls with his father, and can juggle three burning torches. He also does world class magic, in fact he’s performing at corporate events regularly!

Like James, my daughter, Grace, can juggle up to 4 balls, can pass up to 7 balls, and can do the best math and memory illusions.

And then there’s me. I do world-class sleight of hand, pickpocketing, and iPhone illusions. I’ve performed for many companies in Silicon Valley and has been nominated “Silicon Valley’s Favorite Magician” by Buzzfeed.

6. Lyn Alden, lynalden.com

I work full time as an engineer but have a side hustle as an independent equity analyst.

My primary career has always involved a mix of technical and business aspects, and due to my natural interest in numbers and spreadsheets, I ventured into equity analysis as a side hustle, and have been doing it for the past nine years.

I perform analysis on various companies, including technology companies, for various financial publications. In addition, I started my own website which provides various research, model portfolios, spreadsheet tools, and digital books to help others learn how to invest.

On my own website, I have written a few dozen evergreen articles about investing, and have a free newsletter that comes out every 6 weeks that serves as one of my primary. My approach is be a source of anti-hype; a place where readers can get an objective analysis on investment ideas and updates on the economic cycle without hyperbole, unverifiable performance claims, or hard sales pitches. It has tens of thousands of monthly readers, with many of them being retirees, working professionals, high net worth individuals, and fund managers.

Part of what makes my analysis fairly unique is that I approach things from an engineering perspective rather than someone purely within the finance sector. This has been a profitable way to repackage my skill set into a side hustle. For example, an engineering approach to problem solving is to break the system down into its subcomponents and then solve them individually, before putting them back together into a complete solution. I take this methodology to the investment world, and it seems to connect with a lot of people. Readers often tell me that it helps to have someone explain financial jargon to them in plain English.

I write a weekly column for FEDweek about the Thrift Savings Plan, which is the primary investment retirement plan for federal civilian and military personnel, and have been doing so for nearly three years. For that column, I provide context and analysis of what is driving the stock market, what the risks are, and coach readers through behavioral biases that can negatively impact their investment returns (like buying at the top and selling at the bottom).

I also contribute research on a contract basis to two paid investment services, including one focused on dividends and one focused on trading.

The thing that makes me most proud is the feedback I get and conversations I have with thousands of readers via email. People share with me their life stories, their goals, their concerns, and it’s fascinating and rewarding to connect with them.

7. Kyle Isaacson, Ike Scientific

I am currently in the last year of my PhD in Bioengineering at the University of Utah, where I am required to perform research (40 hrs per week) for the university. In March, I started my own freelance science consulting firm, Ike Scientific LLC. This is strictly a side gig, where I work outside of my normal hours.

Just four months in, I am pulling in nearly $4,000 per month (and my revenues have doubled each month). Obviously, the money is providing me a nice financial cushion as I finish out my studies; however, the mental stimulation I receive by running a business has proven more beneficial as it has helped me stay motivated through my many day-to-day struggles. Unlike most other student side gigs, this freelance position requires high qualifications, but also requires high-pressure interactions with clients.

This gig is helping me achieve my professional goals by providing me with entrepreneurial experience, an expanded professional network, and greater understanding of technology needs in industry. I hope that my experience is what you are searching for.

I decided to start the gig when I attended a financial self-reliance course offered by my church. One of the main tips expressed was to look for other sources of income. I had become increasingly more bored with my current research. (In academic research, you occasionally need to work on projects that have no real, meaningful purpose.)

As I’m in my last year of my PhD, I decided to see if I could leverage my nine years of schooling into something lucrative. On a whim, I decided to post my services to a freelance website. I saw that others were offering consulting services for as low as $20/hr. I wanted to stand out, so I placed my price at $500! Remarkably, I had received two requests for interviews within the first day! Obviously, most of my gigs are for short, one- or two-hour speed sessions where I provide them with the information that I need, but I have found two clients with whom I’ve developed longer-term contracts. Still, I only work maybe ten “billable” hours per month (often at a slightly reduced rate), but overall, the gig has proven highly lucrative.

Soon after scoring a few consulting agreements, I began to realize that I needed to make myself look professional (due to the high hourly rate). I quickly set up an LLC, purchased a URL, and made a website. I’ve been working on creating backlinks to improve SEO. As of right now, it is very possible that I could take this gig full-time upon graduation if I really want to. Currently, I’m not yet sure about the direction of the company.

The gig has many pros and cons. As I currently work for the university as a researcher, I have kept my freelance business a secret from my professor that I work for. As such, I am only able to work for Ike Scientific during off-hours (I work for the university M-F 9am-5pm). Therefore, I end up using a lot of time that people normally use to catch up on life to run my business. By running the business though, I have gained many skills regarding running a business (accounting, legal, marketing, operations, invoicing, etc.) and have made myself much more valuable to the private sector in the future.

Additionally, consulting is not an easy business. Clients can be demanding, and finding the right clients that are willing to work with my schedule can be difficult. Maintaining strong customer-client relationships with my limited schedule can be a challenge. Many clients expect you to solve problems that they have been working on for a few months (or even years). You are expected to be able to solve their problems, and do it quickly. As I live in a small apartment, I don’t have the ability to perform chemical reactions and other scientific experiments (I cannot legally use my university lab); therefore, all consultation and contract work must be done via phone, video chat, or computer work.

My advice for other students considering starting a side hustle: Do it! Don’t wait. If I would have started my gig earlier, I probably would have enough money to purchase a house already. Then again, don’t rush into it either. Make sure that you know exactly the work that will be required of you and how you are going to get paid. Your time will be stretched, but you can make it work with proper planning; the financial rewards are worth it.

8. Logan Allec, Money Done Right

I launched my personal finance blog Money Done Right in February 2017 as a side hustle.  At the time, it was called Millennial Money Club, but I rebranded it to Money Done Right in July 2017.

Within a year of starting my business, my blog was netting over $10,000 monthly, which was enough for us to get by financially. So, on March 15, 2018, I quit my corporate CPA job.

For years, I had been a CPA and tax consultant at a “Big 4” accounting firm.

At my job, I helped large companies save money on taxes, but what I was really passionate about personal finance.

This is why I started my blog – because I loved learning and writing about personal finance.

The year after starting my business was crazy. I had just gotten married, and now I was juggling a full-time corporate job in which I routinely worked upwards of 60 hours weekly, a two-hour one-way commute, and now this new business.

My wife was not happy that I was away so much; I would often leave the house before she woke up and come back after she went to sleep. I would spend the little free time that I had working on my blog.

Something had to give : I either had to give up on my marriage, my business, or my job, and I chose the latter.

My business has grown exponentially since I’ve gone full-time. I’ve been able to bring on new partners to promote on my blog as well as new contractors and employees.

Personally, my life is much better since going full-time as well.

At a high level, I love that I’m able to leverage my CPA background to help people make smarter financial decisions.

Not only do I enjoy the work itself – managing a team of writers and building relationships with brands with products and services that I know will be useful to my writers – but I also enjoy the fact that the Internet does most of the legwork for me.

What I mean by this is that because my business generates revenue from web traffic, I don’t actually have to “work” on any given day in order to make money that day; the traffic will still come regardless of whether I am present or not.

At this stage of my life, the flexibility of owning an Internet business means everything to me. My wife and I just welcomed our first child into the world, and the fact that I can take a break from work basically whenever I want to spend time with and care for him is truly a new parent’s dream.


As you can see by these examples, side hustles can be manifested in various shapes and forms, from people from all walks of life.

The question now is, are YOU ready to kickstart your own side hustle?

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