In mythology, the path to American entrepreneurship is paved with lemonade stands.
In reality, entrepreneurs are a whole lot more creative than that--and from a very young age. We asked a number of business owners to tell us exactly how they got on the road to being their own boss, and yes, they've made some serious money babysitting and delivering newspapers, selling fruit from the backyard, and tutoring. But that's just the beginning. The answers we got ranged from selling rocks to selling beer--with, obviously, varying levels of success.
Here are some of the more unexpected business ideas we heard.
Entrepreneur: Barry Schuler, managing director, DFJ Growth; former chairman/CEO, AOL; founder, Medior
"I went door to door in our neighborhood offering to develop rolls of film with same-day service, using the darkroom in our basement. After I proved I could do it, and figured out how much to charge, I made some flyers at the school mimeograph machine. I didn't get much response until I added a testimonial. Then I ended up getting so much business I was able to buy my dream camera--a Nikon F1."
Selling beer (at age 5)
Entrepreneur: Rachel Hofstetter, founder of Guesterly, a startup that makes custom photobooks for weddings
"I saw the leftover beer from my parents' summer cookouts, knew adults liked beer, and dragged the coolers out onto the road and sold beer for 5 cents a bottle. That business was shut down three hours later when my mom realized what I was up to. I went on to charge neighborhood kids to use my family's computer, another venture that was promptly shut down when my parents found out."
Demonstrating products at trade shows
Entrepreneur: Rachel ten Brink, co-founder of Scentbird, a subscription perfume service
"When I was a teenager, I organized a few friends and created an 'agency' to demonstrate products at trade shows in Costa Rica, where I'm from. It was successful for a little while, but teenagers are flaky and I ended up covering lots of shifts myself. That meant hours on my feet, and it was exhausting."
Making and selling shoelaces
Entrepreneur: Jeni Britton Bauer, founder of Jenis Splendid Ice Creams
"I started lots of businesses growing up. I did have a lemonade stand, but I thought that was very boring. I had a shoelace business where I was making shoelaces and I sold a ton of them at recess. I also had other kids on other recesses selling them for me. Our principal looked like Tom Selleck, which I loved. But he asked me to stop selling the shoelaces at school."
"My sister and I started as entrepreneurs at 5 and 6 years old. We didn't really know what to sell, so we resorted to selling rocks on our driveway to cars passing by. I have to say it was a tough sell--not very much demand."
Making and selling hats
Entrepreneur: Matt Benedetto, founder of Eastern Collective, a maker of outdoor-style tech accessories
"When I was about 12, my mom got me some yarn and crochet hooks for Christmas. We were an avid skiing family, so she thought it would be fun to teach me how to crochet winter beanies. Friends at the mountain began asking about them, because they wanted one themselves. I could eventually make a full beanie in 90 minutes, so I crocheted hats for friends for $15 apiece. Over the summer I made a website with a PayPal button and text field, so anyone could write out the colors and pattern they wanted for their hat and I would ship it to them. I advertised on skiing forums. When I was 15, I felt like I was going to crochet my hands to early arthritis, so I researched on Alibaba and began outsourcing my beanie production to Asia."