8 Founders Share Their Very First Business Ideas -- And How It Helps Them Today

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1. Start a business with people different than you.

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2. Listen to your gut

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3. Engage with customers

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Charity: Water

4. Execute on ideas

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5. The nuts and bolts of running a business

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6. How to scale a company

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7. Learned what it took to run a marketplace

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8. Talk directly to people

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Staff Writer. Covers media, tech, startups, culture and workplace trends.

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

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 called it Furance Surf. 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

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

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


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.'


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


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


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


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


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