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17 Founders Share How Their Very First Business Idea Helps Them Today These leaders caught the entrepreneurial bug early.

By Nina Zipkin

Sensay | Getty Images

An integral part of being an entrepreneur is not being afraid to try and fail. And the earlier you realize this, the better off you will be.

For many of the most successful founders, they had a mind for business when they were very young. And even though they obviously didn't get very far with that first playground hustle, it set them on the path to where they are today.

We asked 17 entrepreneurs to tell us about their very first ventures and what they learned from their experiences. Here is what they had to say.


Start a business with people different than you.

Name: Jeff Chapin
Company: Casper
Business idea: In grad school, we were all surfers in New England. We made a dry glove for surfing and it still exists. Eventually I peeled out. We were all very much the same people, and you really should start a business with people different from yourself. There are a lot of reasons for that, but I'll boil it down to two. One, since there are so many different things that need to get done, it's incredibly helpful to be able to divide and conquer, Second, I believe you don't need more than one expert on any one topic. We all have opinions on everything, and we all share them and listen to them, but we each get a final say on our own area of the business. It helps us make decisions quickly and move faster.

Read more about Chapin: Behind a $100 Million Mattress Startup, Casper Co-Founder Shares Advice on Finding Success as an Entrepreneur


Listen to your gut

Name: Oliver Kharraz
Company: Zocdoc
Business idea: The first business was right out of high school, pre-internet, email companies. Back when email took five days to get from Munich to Los Angeles, I was running one of those services in the early 90s. I realized that the internet was coming, and I had two choices: to either double down on the company and dropout of college or sell the company and finish college. I opted for the latter, a great decision. It protected me from too much money early on in life, and shortly thereafter, the internet bubble inflated. It was a great experience.

Read more about Kharraz: This Founder Says to Succeed You Need to Question Everything

Charity: Water

Engage with customers

Name: Scott Harrison
Company: Charity: Water
Business idea: I sold Christmas cards door-to-door in the country. I didn't make much money, but I learned how to knock on the door of a stranger with a smile.

Read more about Harrison: Everyone Can Adopt This Founder's One-Step Productivity Advice


Execute on ideas

Name: Daniella Yacobovsky
Company: BaubleBar
Business idea: I don't know if this qualifies as a business itself, but one of the jobs I had when I was a senior in college was at restaurant on campus called Pod. I noticed that whenever we had events that came up every year the reservations were a mess and eventually would degrade into mass chaos. So, I had an idea for events planning and reservations. Before graduation, I was able to roll out a system that we kept the restaurant on. It was the first year that everything was on schedule and everyone across the restaurant knew what was happening.

It was a really fun moment for me. It gave me a taste and flavor for recognizing a problem and having an idea for being able to solve it, being able to grab the bull by the horns and start to roll out an idea.

Read more about Yacobovsky: This Co-Founder of BaubleBar's Secret for Inspiration? Always 'Keep Your Eyes Peeled.'


The nuts and bolts of running a business

Name: Ryan Holmes
Company: Hootsuite
Business idea: I was a huge paintball fan as a kid, but it's an expensive hobby. In high school, my brother and I had the idea of starting our own paintball field near our home in British Columbia. It was a crash course in business -- everything from marketing to pricing and filing your taxes.

Read more about Holmes: How Following His Heart Led This Entrepreneur to Start a Multi-Billion Dollar Company


How to scale a company

Name: Matt Ehrlichman
Company: Porch
Business idea: The first one I can remember and did something with was a company called All Star Camps. When I was 14 years old, I started a multi-sports camp for elementary-aged children. Over the course of the next five years, I built it up, scaled it and had different sites across Western Washington. It was also one of the best jobs, because you're playing sports with kids during your summer break.

It also solidified for me that it's what I love to do: building a company like that is tremendously fun.

Read more about Ehrlichman: How This Founder Uses His Competitiveness to Succeed in Business


Learned what it took to run a marketplace

Name: Jack Groetzinger
Company: SeatGeek
Business idea: In high school I ran a small company that edited people's college essays. I built relationships with a few retired English teachers. Folks who were applying to college and needed help editing an essay would submit their work via our website and then we would hook them up with an English teacher who would work with them to make it better. That was back in 2001 and 2002 and was a marketplace. SeatGeek is a marketplace, so it gave me exposure to the power of being able to connect people on the internet.

Read more about Groetzinger: The Simple Trick This CEO Uses to Prevent Burnout


Talk directly to people

Name: Aaron Hirschhorn
Company: DogVacay
Business idea: I was also personal trainer and a jujitsu instructor. I probably learned the most there about how to interact with people one-on-one and again finding individual motivation. I had another idea for a business, before DogVacay, which was around a marketplace for personal trainers and massage therapists which was actually a pretty good idea, probably a little early. We really didn't have enough velocity to get a good product out, iterate on it and get customers.

Read more about Hirschhorn: This CEO Says the Key to Being a Good Boss Is Getting Out of the Way

Courtesy of Boxed

Always be present for when opportunity strikes.

Name: Chieh Huang
Company: Boxed
Business idea: When I was in fifth grade I sold candy to all the kids on the block. I saw how much they loved the ice cream truck, but it only came around once a day. So, being outside with the kids from the neighborhood, I was always around. That was my start.

Read more about Huang: The Surprising Reason Why This Founder Says Not to Be Afraid of the Competition

Courtesy of Lyft

Things are often more complicated than they appear.

Name: John Zimmer
Company: Lyft
Business idea: There is a white pineapple that is native to Nicaragua that I tried with the community I was staying with. After my trip there, I thought it would both benefit people there who wanted to export [the pineapple], as well as people in the states who hadn't tried it.

We thought how were we going to ship it. There were four of us that worked on it. We went to the idea of dried fruit because of the shipping difficulties, and it ended up that we were not successful in bringing it to market.

I learned a lot about how something that may seem simple is very complicated. At the time I was naive in what I thought it meant to start something. It was just a dose of reality around if you want to make something happen, you have to fully commit yourself. I think that's what Logan and I have done with Lyft. It's basically our life's world. I learned a lot about the commitment required to fully deliver.

Read more about Zimmer: Lyft Co-Founder John Zimmer: 'You Should Never Veer Off the Path of Your Own Values'
Courtesy of Randi Zuckerberg

If you have a problem, other people might too.

Name: Randi Zuckerberg
Company: Zuckerberg Media
Business idea: A snow-shoveling subscription service when I was in middle school. I grew up in New York, and I was making a little bit of pocket money shoveling our own walkway. I then thought, 'what if I went door to door and say, here's my price for today, or you could pre-order for the entire season.' If it snows a lot, you'll get a good deal, but it if it doesn't, that's the risk you take. I had a few houses our block that took me up on it, mostly because the cute neighborhood kid had an idea, but now I see all the subscription services out there, and I think I was a little ahead of my time.

Read more about Zuckerberg: Why Everyone Can Use Randi Zuckerberg's Number One Focus Tip
Courtesy of Katrina Lake

Don’t go into business unless you’re truly passionate about your idea.

Name: Katrina Lake
Company: Stitch Fix
Business idea: In business school one of the areas that interested me was hunting and fishing. I thought it was kind of interesting and not a lot of technology has been applied to retailing in that category. I did a trip where I rented a car in Boston and drove to New Hampshire. We went to some hunting and fishing shops and one was a gun shop. I remember talking to the guy who ran it to understand his pain points. Hours into that trip, I realized I was not super passionate about the category. I can't imagine devoting my whole life to it. For me it was an epiphany that when you start a company, this is a lifelong thing.

Read more about Lake: Stitch Fix Founder Explains Why the Worst Piece of Advice She Ever Got Was to Raise A Lot of Money
Courtesy of Duolingo

Lessons from bad ideas are just as valuable as the ones from good ideas.

Name: Luis von Ahn
Company: Duolingo
Business idea: I actually had what I thought was a pretty serious business idea when I was about 12. I also thought I was the first person to have this idea, and I thought it was a great idea. Neither of those were true. The idea was to see if you could generate electricity through motion.

I thought this would allow us to make gyms for free. Connect the exercise equipment to the power grid. Anyone who is exercising would be generating electricity, and I would be able to sell that electricity to the power company. Therefore I don't have to charge anyone to come exercise. My gym would be free and everybody else's gym would be expensive, so I would be able to take over the gym world.

It turns out this a pretty common bad idea. The reason it doesn't work is because humans are pretty crappy at generating electricity. The amount of electricity you could generate this way is worth nothing. There is an even bigger problem. Gyms make their money from people who don't show up, and for this idea you need people to show up.

Read more about von Ahn: Why This Founder Says the Worst Advice He Ever Got Was to Listen to His Users
Courtesy of G Adventures

How to make a business model work for you.

Name: Bruce Poon Tip
Company: G Adventures
Business idea: When I was a kid, you had to be 12 in order to have a paper route, but I wanted a paper route when I was 10. By the time I was 12, realized that it would be better to get multiple routes in different areas in the city with different, competing newspapers. I contracted the paper routes out to 11- and 10-year-olds to deliver the papers, and I split the profits with them. It went on until I got caught -- it was a couple of years. It was a little newspaper empire.

Read more about Poon Tip: I Was About to Shut Down My Business but I Changed My Mind. Here's Why.
Courtesy of Ayah Bdeir

How to know when to walk away.

Name: Ayah Bdeir
Company: LittleBits
Business idea: I had my first business idea when was in high school. Me and two friends started The Kids Workshop. I grew up in Beirut, and a lot of the activities for kids were around carnivals. I remember my friends and I were like, why can't it be something more creative than just tossing the ball on a bunch of bottles?

So we ended up doing The Kids Workshop, and it was different arts and crafts stations that kids would sit at, make something and then take home. We did it two years in a row. The first year we had 300 people show up, and the second year we had 1,000 people. I realized it was going to become a career, and I had to finish school, so I stopped.

Read more about Bdeir: This Successful Entrepreneur Explains Why Revenue Is Not the Most Important Thing (and What Is)
Courtesy of Rodan + Fields

How to meet an untapped need.

Name: Dr. Katie Rodan
Company: Rodan + Fields
Business idea: My first business started at age 13 selling purses. I was inspired after seeing a purse that I loved but couldn't afford at a trendsetting store for teenagers in Los Angeles. After learning to source the materials wholesale I used my sewing skills to figure out how to design and make the purse even better. I ended up supplying a store called The Light Brigade with my purses until I went off to college.

Read more about Dr. Katie Rodan: Want to Build a Billion-Dollar Business? Here Are 2 Simple Ideas That Helped These Two Skincare Heavyweights.

Courtesy of Kathryn Minshew

How to connect with an audience that truly gets your product.

Name: Kathryn Minshew
Company: The Muse
Business idea: When I was 13 years old, I decided I wanted to produce plays, so that my friends and I could perform in them. But I knew that if we didn't find a captive audience, it would just be our parents pity watching us.

I realized there were two populations of people who would probably be thrilled to see productions by 13 year olds: those with children and people in senior citizens homes. So I founded a group called Star Workz Children's Theatre. Over the next six years we produced plays for audiences from three to 300. We did a show once literally only three kids showed up.

Read more about Minshew: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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