How Entrepreneurs First Got Interested In Being Their Own Boss

10 May 2011 Start-Up

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Entrepreneurs aren’t born with the idea to go work for themselves. Well, some are. But many entrepreneurs find themselves building a business out of life circumstances. We found out how some entrepreneurs first got interested in being their own boss. Some responses we expected but some we didn’t. Who would have thought farming makes you entrepreneurial? We didn’t.

Grew Up With It

1. I Liked The Challenge

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I grew up in a family business and saw my father work with customers, help them and make decisions about the business. I liked the idea of the challenge of finding a product or service (the idea), putting it together and getting in front of potential customers (the marketing plan), getting them to buy and use it (sales and fulfillment) and making money from it. It started with t-shirts, then college dorm room lofts, now software and Internet businesses.

I’m an entrepreneurial thrill-seeker and currently run a venture capital-funded startup called RealPractice which provides new client leads and a marketing, client development and practice management SaaS platform for attorneys and other professionals.

Carey Ransom, RealPractice

2. Father Successfully Exited From Company

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Growing up my father owned a business that he eventually sold. After college I found myself intrigued by the teachings of Mark Victor Hansen, Robert G. Allen and many others. By incorporating my passion of public relations and marketing with my interest in helping others dreams come true, I was able to start building a stream of income that I could be passionate about and proud to leave as a legacy for the next generation in my family.

Ebony Grimsley, Above Promotions Company

3. Watched My Mom, A Successful Entrepreneur

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I started a video production company two years ago. I got into business simply because my mother is a well known successful entrepreneur and watching her as I grow up has influenced me to do the same and taught me how to make smart decisions.

Travis Woodward, Dinosaur Studios

Did “Stuff” As A Kid

4. First Start As High School Sophomore


I have been interested in entrepreneurship since I was a kid and always dreamed up different businesses I’d like to start. I started my first real company when I was a high school sophomore in 1999 fixing computers and teaching computer basics to older adults in my community. After graduating college and not being able to find a job, I got frustrated with the state of the job market and decided to hire myself! I started out freelance copy writing, and that quickly segued into a small business-oriented marketing and creative firm that I’ve been running since 2009!

Amanda Sage, Gong Gong Communications

5. I Played Bank In Highschool


I first became interested in entrepreneurship as I facilitated transactions for friends in high school using spare pocket change. Always having an appreciation for customer need, creation of value and customer development I became a lender to kids who didn’t have money to buy candy after school.

Listening to peoples need, pains and problems helped me appreciate how to help people by recognizing the value in executing solutions. It came from listening thoughtfully to those around me followed by a little research and elbow grease.

Devon George, DMV Capital Corp

6. We Mowed Lawns


When we were 12 and 10, my brother and I borrowed my father’s lawnmower to cut two of our neighbors’ lawns, which brought our weekly income to a grand total of $10/week. As we grew up, we built our business to 17 lawns in early high school, 50 lawns and a truck during our later high school years, and then over 100 lawns into our college summers. I learned the value of working for yourself: flexibility, ability to be your own boss, room for creativity, making more money than at typical summer jobs, and managing real life customer relationships at a young age.

After I graduated from Babson College in May of 2010 where I concentrated in Entrepreneurship, I started my own internet marketing and social media agency – Roominate Marketing – in the Boston area, where we act as the online brand and voice for a handful of clients through social networks, blogging, and search engine results. Entrepreneurship, to me, is more than just working for yourself, however, it is about working hard, being creative and flexible in any situation or job position you hold.

Henry O’Loughlin, Roominate Marketing, LLC.

7. Sold Headbands In Grade School


I first became interested in entrepreneurship when I was in grade school. I was reprimanded for making and selling headbands to my classmates because school was for learning, not for having a business.

I am now in business school :) and was inspired to make business my profession after a missions trip to a third-world country, where I saw the impact small businesses could have on a familys financial situation. I am learning a lot now that I hope to one day put to use to help people…mostly I am learning that success in business is driven by creativity and hard work.

Laura Florek, LinkedIn Profile

8. Through Entrepreneurship Class

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My name is C. Harley Ellis, I am 14 years old (I started my company last year at 13 years of age), I live in Southern California, and I run a small business I call Micro-Kites; I make and sell miniature kites. I am taking a class/entrepreneurship class through my charter school class called “Life Skills”. The project for the year was to create your own business; create a product, website, business e-mail, market the product, logo design, business cards, bookkeeping, business bank account, etc.

My business has become very successful and I am currently retailing my Micro-Kites in 6 stores here in North County, San Diego (7-11 Store, Encinitas Surfboards, San Elijo State Beach Camp Store, Thinker Things Toy Store, and 2 Geppetto’s Toy Stores), I have sold over 600 Micro-Kites in a very short time.

Harley Ellis, Micro Kites

9. Was A (Candy) Smuggler In School


I was entrepreneurial at a very young age. We didn’t have much money, my mother told me to go sell some kool-aid in the summer, and shovel walks in the winter. In grade school I smuggled candy in hollow book to sell (The nuns did not approve.) And continued this path.

John Schulte, National Mail Order Association (NMOA)

Couldn’t Stand Corporate

10. Because I Didn’t Fit In With Corporate

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Even as a kid, I could never see myself in a regular job. I was too hyper-active, always thought outside-the-box, was bored in school, and I thought that no career would really be for me. After college, I had no idea what to do with myself, so I went to law school and got a top-market job on Wall Street. Even that was just a higher-octane version of the jobs I’d always dreaded. So, my best friend and I started our own
business, quit our day jobs and never looked back. If you don’t think you “fit” anywhere, chances are you just need to create your own custom niche.

Jordan Harbinger, The Art of Charm, Inc.

11. Because My Boss Sucked

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I had a ‘great corporate job’ and then I got a new boss. He knew nothing about me or my whole division of the company, yet he’s now my boss and he will largely control my career for the foreseeable future. My previous boss was great! But this guy let’s just say if it was 10,000 years ago I would have just killed him and taken his stuff (and he and I both knew it).

So I immediately began preparing to leave corporate life and purchased an existing business one year later.

I have since declared myself unemployable and have three companies!

Shawn M. Miller, Performance Institute

11. Having To Ask For Bathroom Breaks Sucked


I didn’t like being stuck to a desk, having to ask for bathroom breaks! I loved my financial career but it was too much of the same routine with too many politics and not enough creativity. I knew I was good at organizing, project management and loved ‘all things pretty’ so jumped at the opportunity to leave finance when it presented itself and go out on my own. At first I applied the financial premise’ maximize your returns’ to real estate and did staging, but then technology make it possible to take that same concept and apply it to both the buy and sell side. 8 years later is the only affordable online platform for personalized interior design.

Kelly Fallis,

No Choice But To Be Entrepreneurs

12. No Car, No Job

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My name is Carlton, I’m 14 years old, and I am an entrepreneur. I got into the business due to the fact that, since I don’t own a car, it’s difficult for me to get a summer job. My dad does have an internet business, so I worked with him to make a mobile App guide for the town my grandparents live in, Cullman, Alabama. The website is With this job I’m able to work my own hours, anytime anyday, I’m my own boss, and I’m always crossing my fingers on making a little money.

Carlton Ragsdale, Cullman Life

13. Couldn’t Find A J-O-B


Quite simply, I couldn’t find a job. I was a recent grad with a very strange resume and intolerance for bad bosses. So I started my business as a typing service, total startup cost $200, and grew it into the marketing and publishing consulting company serving clients around the world that it is today. I’ve also managed to write eight books, most recently Guerrilla Marketing Goes Green: Winning Strategies to Improve Your Profits and Your Planet ( category best seller list for 13 months).

Shel Horowitz, Green And Profitable

14. Couldn’t Return To Old Job


I first got into entrepreneurship out of necessity. When I gave birth to my daughter I knew that I couldn’t return to my job as a full-time high school English teacher. I needed to find or invent something that would offer me the flexibility I needed to balance a family and a career. So I decided to start an online business, Castle Ink that addressed an issue that I faced as a teacher: the high price of ink cartridges, especially for those like me that do a lot of printing.

Lauren Elward, Castle Ink

15. No Room For Growth


At age 31 while in process of a divorce I took my 2 daughters and with no child support or alimony moved 70 miles away and started my own business. At the new location I was offered a salaried position at a higher pay then I had ever had before but realized they were hiring me at “the top of the ladder” leaving me no place to grow. So with no other source of income, I opted for my own business. I built the business to a $200 million dollar asset management and financial planning practice and recently sold the business. I am now a national speaker to help business owners do a better job for their clients and improve their bottom line and help individuals live a successful life and realize their dreams.

Nancy Butler, Above All Else, Success in Life and Business®

16. Because Of My Son

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When my only son was diagnosed with Autism at age three, I made a commitment to myself to raise awareness of this condition. As former marketer, my first thought was to develop and sell a product from which a percentage of the proceeds would be donated to Autism related organizations. It was while researching this concept that I realized that I was not alone in my quest to develop a product with a “for a cause” purpose. I found that there are thousands of charities selling cause-related products as a means of fundraising that are struggling to be noticed. It was this realization that led me to create, a one-stop online shopping mall offering ONLY “Products That Give Back.” Currently, hosts over 50 nonprofits representing over 240 “Products That Give Back.”

Filomena Laforgia, Filanthropists


17. Lessons From Farming

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I am the second oldest of nine children from a diversified farm in Southcentral North Dakota. Nothing represents entrepreneurial values and personality traits needed for success more than farming.

Each corporate job I had after graduate school I quickly found myself using these same observations and skills to start divisions and departments before venturing out on my own where I founded, grew and sold a DJ company, a publishing company and an event company. Today I freelance consult and write.

Observing and working alongside my entrepreneurial parents was and is the foundation of my entrepreneurial success.

Linda Leier Thomason, Thomason Enterprises, Inc.

Just Fell Into It

18. Good Actually Comes Out Of Gaming


Evil Controllers started in 2007 out of Adam Coe’s dorm room when he modified his own Xbox controllers for his own pleasure. When friends started wanting his modifications, he realized the potential for business with no entrepreneurial experience and started selling controllers on eBay. When this proved lucrative, dropped out of college to start the now 4 year old business with his older brother in charge of business operations. The entrepreneurship just kind of fell into his lap in combination with his talents and insights for customizing and re-progamming video game controllers. Evil Controllers is now the leader in the custom controller industry with products ranging from programming mods to aesthetic customizations to a line of accessible controllers for people with limited mobility.

Adam and Jonah Coe, Evil Controllers, LLC

19. I Invented A Game


I fell into it. I was a practicing lawyer and teaching at N.Y.U. I invented a game to teach my own children what it’s like to be a lawyer. I gave the game to my husband as a Father’s Day gift. It was not intended to be mass-produced. However, when the game was played around others, it was always suggested that I “do something with it.” My initial marketing research (albeit haphazardly) was done.

Tina Nelson,

Other Reasons

20. Out Of Frustration

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It was early in my high school career when I realized that entrepreneurship was what I was searching for in life. By discovering that the world around me was sometimes flaky and all-talk, it frustrated me and drove me to accomplish things. I wondered then why people did not pursue more of their ideas and dreams. Out of curiosity, I picked up a couple magazines one by one: Inc, Fast Company, and Entrepreneur Magazine and saw people who actually followed their dreams and took it to the next level by developing them into tangible realities. I’ve just turned twenty now and I am following my dreams by working with a startup company called Agent Anything.

Matthew Fishman, Agent Anything

21. Just Went For It


I decided to “go for it” and become an entrepreneur when an idea I had for a board game was submitted to my MBA class at UCLA. All students were required to develop a business on paper and present our ideas to a panel of real financial investors. When the investors actually wanted to fund my business and my series of presentations became standing room only, I thought to myself ‘ Wow, I might actually have a real business here’ and Zobmondo!! was born. Thirteen years later we are a $6 million company and I’m still an independent entrepreneur.

Randy Horn, Zobmondo!! Entertainment

From The TBF Community

22. Not Sure, But Glad

Personally I have no recollection at all of how I decided to start something, yet here I am 3 years later with a writing agency :/


23. Always Interested

Haha, things happen quickly! I’ve always been interested in it, I believe that I’ve been an entrepreneur from the start, just the interest in business waited till my teenage years. I love accomplishing something awesome, that lots of people can enjoy, so I find event organizing really cool, so I plan to start dabbling a little this year along with my online company.

My online business is going great, so far I’d say I’m very good at being in the right places at the right times, where opportunities quite simply reveal themselves.

Cec, BlueSnow Media

24. Watched My Favorite Uncle

I think I got into the business because I had an uncle who was a professional in the industry and he was one of my favourite uncles. As such, I spent a lot of time with him when I was younger and I just saw him doing his job and thought it would be a cool thing to do myself. Then I researched it, looked into it to see if it was a profitable venture and off I went

benwmsonline, Premiere Entertainment UK

25. Lots Of Free Time Being Homeschooled

It was easy for me. I was around 11 or so and I had a computer. Homeschooled with no one really to do anything with. I had a lot of free time and thought ‘hey, why not start a website?’


26. Sold Dollar Store Items For More

Watching my dad suffer daily from the 9-5 (for the past few months it’s actually been 9-7) day job is not something I’m interested in doing for the rest of my life. Nor am I interested in working for someone else, working hard to put money into his/her pocket.

Also, money and the things it can do fascinates me. At an early age I was always into making money. My first profitable venture was at the tender age of 10, where I bought items from the dollar store and sold them to my class mates for more.


27. Bad At Filling Out Job Applications

I’m just really, really awful at filling out job applications.


28. Work For Other People… NOT

The reason for me is that I don’t want to work for other people for the rest of my life, I don’t want to have somebody above me telling me what to do. I also want to be able to work when I want to and the rewards are much better after the years of hard work.


29. Love The Projects

It happened so fst but originally I thought it would be easy because I wouldn’t have to work as much as other people. Boy was I wrong.

Anyways, today I still do it because I simply love the projects I get to work on.


30. Started Making Websites

I just felt like being more productive with my time, and I started making websites. I didn’t actually know that it was entrepreneurship.


31. Attended Class With Mom

I’ve always been interested in it, I believe that I’ve been an entrepreneur since 9 years old when my mother started at The Women Business School in Washington DC. After school I would attend class with her.Also I think it hard wired in every American it the so called “American Dream” Everyone once to be a business owner but not everyone can.


32. Idea Of Working For Yourself

Havent actually found or started anything yet. But I like the idea of working for yourself


33. Heard From Others

Well for me I was just enjoying youtubing like many other people.
Then I saw this one guy Duncan Maile aka Mobilephone2003 doing PC software related videos. I was so impressed how he did this and saw how tons of kids (yes, mostly kids with high pitched voices) made their own channel that was very similar. I also tried that, without being an exact copycat.


34. Pulled Off Of A Job

Around 1 year ago I was supposed to get a job set in stone.. luckily for me I got put off while I was getting job training “some other kid got picked even though I was better” (this person also stole from the organization). I needed spending money so I started working online and never looked back!


Created By:

Chief Community Officer at TeenBusinessForum. I believe that successful and ethical entrepreneurs make the world a better place. To make that a reality, I help empower teen entrepreneurs that will be the next generation of business leaders.


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