Enroll in my FREE 5-day course and learn how to start and grow a successful email list!
Subscribe for valuable weekly articles to help you start and grow a thriving online business.
If there’s such a thing as a “stereotypical serial entrepreneur,” then I’m curious to know whether I fit the mold.
I certainly fit the definition!
According to Business Dictionary:
“An entrepreneur who continuously comes up with new ideas and starts new businesses. As opposed to a typical entrepreneur, who will often come up with an idea, start the company, and then see it through and play an important role in the day to day functioning of the new company, a serial entrepreneur will often come up with the idea and get things started, but then give responsibility to someone else and move on to a new idea and a new venture.”
And while that is exactly what I do, I’m not really sure that I’m your average serial entrepreneur. Mostly, because I’m a lot younger than most. In fact, just last week I celebrated my 24th birthday.
But, I’ll be the first to admit that I started young. I remember a few little “businesses” I had when I was 8 or 9 years old: selling mail-order flower bulbs door-to-door, setting up shop to sell my Easter candy to the neighborhood children, and organizing the “Animal Club” (wherein we rescued various critters).
Eventually, I moved on to bigger (and more long-lasting) ventures. Twenty-four is a bit of a special year for me because it marks the 10 year anniversary of the first “real” company I started — one that is still alive and well today.
Here’s a rundown of 6 businesses I successfully started before I turned 24:
1) Northwest School of Music
At age 14 I started my first “real business” — and it was actually unintentional. I was looking for a job (but not finding anyone who wanted to hire a high school freshman), when a friend approached me and asked if I’d be interested in teaching her to play the flute.
I’d been studying piano for a number of years, and then had taken up the flute a few years later. But teach? I wasn’t sure about that at all!
I stuttered something out to the effect of, “Well, I really don’t know…” and my friend responded, “Great! When can we start?”
Suffice to say: she really liked my teaching style. She started telling all her friends what a good teacher I was, and soon I had several families calling me up, asking for music lessons for their children.
After several months of success with this, I gained enough confidence that I began to advertise my services as a music teacher. And the rest is history!
My studio grew steadily until I hit 50 students when I was about 18. That was as many as I could handle myself, so at age 19 I started hiring other teachers to take over some of the classes.
Not too long later, I leased a larger studio space in Oregon’s capital city and hired several more teachers. Eventually, I handed over most of the administrative work to an office staff as well.
Northwest School of Music continues to grow every month! We currently employ seven teachers and provide a variety of classes, including piano, voice, guitar, strings, and woodwinds.
2) Aptus Creative Marketing
At age 15 I taught myself how to create my first website. From that point on, I learned a new web design program just about every year (everything from Wix, Squarespace, and WordPress to CSS and HTML).
What became Aptus Creative Marketing followed a very different growth pattern from most of my other ventures. Unlike many, when I studied something for a few years, then jumped into creating a company, with web design I practiced for about five years on my own, then spent a few more years doing pro bono work for family and friends. It was only then that I felt my services were truly high enough quality to start offering to the public and actually charging for.
Today, I offer custom, fully responsive websites for small businesses that are looking to attract more customers online. I build my websites with WordPress (which I LOVE!) because it’s easy to use and so flexible that it really makes anything possible.
Most of my clients are authors, service-based entrepreneurs (such as coaches or branding experts), or “infopreneurs” who sell courses.
I really enjoy doing web design work, because I love being able to provide such a valuable tool for entrepreneurs to use to grow their online businesses. Done right, your website can be more valuable than any employee!
3) Divine Mobile Salon
After studying hair styling and makeup artistry for two years, at age 18 I started a “mobile” salon that offered beauty services for brides.
On the day of the wedding, I’d visit the bride’s home or wedding venue, and provide them with a fancy hairstyle and professional makeup. It was convenient for them, helped reduce the chaos of their wedding, and quite profitable for me.
I also worked with a local photographer, providing hair and makeup services for really fun, dramatic photo shoots!
This business was SO much fun, but unfortunately not something I could very well hire others to do for me. Because I was the hair/makeup artist, unless I wanted to grow it into a big company (which would have required me to invest significantly more time) it could only exist as long as I had the hours to trade for the dollars.
When I was about 21, I started seriously studying business strategy and marketing, as well as expanding my web design work. That was when I realized what I really wanted to do long-term.
So, while the mobile salon was certainly profitable, I chose to close it so that I could focus more on growing my personal brand and spend my energy studying marketing and web design.
4) Quintessential Investments
When I was 17 I started a real estate investment firm.
Yeah, I did that.
Yeah, it was weird and kind of crazy.
And NO, it didn’t go very well at first! I was really young to be doing something like that and didn’t know very much about it.
I’d read several books about real estate investing, had several thousand dollars saved up, and just decided to jump in with both feet.
(Yes, it was crazy!)
I roped my boyfriend (now husband) into it (he thought it was crazy too, but he was also in love with me, so he went along with it), and together we started flipping mobile homes.
The idea was that we would buy run-down old mobile homes for cash, fix them up, then finance them to people who needed low-cost housing.
But that’s not exactly what ended up happening. We’d buy them, but before we could even START fixing them, someone would want to buy them from us (financed). So we’d sell them, because why do a whole lot of work to make just a little bit more money?
(As for what didn’t go so well: mostly, we weren’t organized enough at all. We kept terrible records and it made for some messy situations. Slowly, slowly we learned.)
This was fun and profitable, but also scary and stressful. Mostly just because I knew I didn’t know what I was doing. And the more I learned, the more I realized that I didn’t know what I was doing.
So, we paused. And it was a good choice, because I really feel like I might have gotten us into [big] trouble if we’d just kept at it right then. We needed to slow down, spend more time learning, and be more careful.
This business still very much exists and actively manages a few rental units we have since purchased. Down the road, we will be purchasing more properties, but at the moment I’m more focused on growing my web design and business strategy companies.
5) SORTED Life-Organization Consultancy
Guys, this is such a side hustle! It’s never been my full-time thing and it never will be, but it’s such an integral part of who I am that I don’t want to let go of it.
In 2014 Quintessential Investments bought three town houses as an investment property. We were supposed to move in immediately, so we gave notice on our apartment.
Then, after we’d signed all the papers and become the official owners, we were handed the “rental agreements” for the current tenants… and discovered that they had year-long leases! (We’d be told they had month-to-month rental agreements.)
This was a big problem because it meant we didn’t have anywhere to live. So we went and stayed with my parents for a month, then rented a different apartment temporarily.
It was exciting, to say the least.
Long story short (because this whole story is really getting a bit longer than I intended), we had to live with all our stuff boxed up in storage for several months.
And we discovered that we REALLY liked living with less.
Specifically, having less stuff cluttering up our lives allowed me to actually notice my (crazy) schedule. And finally get it sorted.
All this led to a number of epiphanies about my relationship with material stuff, what I really “needed,” happiness (or the lack thereof), and how much easier life could be with less — of everything!
So I wrote a book about it: Sorted: Freedom Through Structure
“Sorted” was published in May of 2016, and took off like crazy. In the first three days it was downloaded over 10,000 times, and since then it’s gone on to sell over 15,000 copies.
This unexpected success unintentionally started yet another business: my life-organization consultancy.
Basically what happened is that all these readers suddenly wanted to connect (and get advice from) the author. So I started offering consulting services to help people simplify their lives, declutter their homes, and create routines to keep things running smoothly.
It’s very satisfying work, and I LOVE me some organizing. But like I said before, it’s just a great side-hustle, and I don’t plan to turn it into anything more.
6) Gillian Perkins International
When I turned 23 was when I really started asking myself some hard questions.
What was I doing with my professional life?
What was my career? Did I even have one? Did I want to have one?
Why was I starting all of these different, relatively unrelated businesses?
And I realized that there were two main reasons for starting so many companies:
- I was looking for something that I really loved. I was starting these businesses because I didn’t know what I wanted and I was trying to figure it out.
- I love business! I love the science of startups. Planning businesses, developing strategy and marketing make me so happy!
These realizations provided the information I needed to finally be able to launch my personal brand as Gillian Perkins (GP), which is all about business training (especially strategy and marketing) for startup entrepreneurs!
After years of rambly, disjointed blogs and countless unrelated business ventures, GP is the culmination of all my experience starting, starting, and starting again.
Everything I’ve learned about branding, marketing, sales funnels, creating products, systems, and management all come together under one, beautiful roof.
One of my favorite things about GP is that it marries so beautifully with my “day job” of web design. Every online startup needs a great website and a strategy to grow. I often get clients who come to me for a web design who then, later, end up hiring me as a consultant to help them come up with a business plan or marketing strategy.
My personal brand is still definitely in it’s beginning stages, but I’m so excited to see where it goes from here.
The End of an Era
These past ten years have had a lot of ups and downs. They’ve been exciting, fun, and hard.
On the one hand, you might say they’ve been all over the place. But, to the contrary, I actually feel like everything I’ve done has led me quite perfectly to where I am now.
Interested in a FREE 30-minute strategy session to design a plan to reach your biggest
for the next year?
I'd love to do this with you!
Grab the first two chapters of my #1 international bestseller FREE right now!
Gillian Perkins is a WordPress web designer, business strategist, and #1 internationally bestselling author. She geeks out about all things entrepreneurial and loves helping people turn their interests into income.
Gillian is also the founder and executive director of Northwest School of Music. She lives in beautiful, green Oregon with her husband and two young children.
Download the Workbook!
The EASIEST Business Plan Ever
"Failing to plan is planning to fail."
- Benjamin Franklin
Download the free workbook now, and in less than 30 minutes you can create a plan for online business SUCCESS!