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Northport High School alumnus Gregg Kaplan is an expert in the field of business, finding success with both startups and well-established companies. In 2002, he founded Redbox, leading it to earn over $2 billion in revenue. He has also worked for McDonald’s Corporation, Streamline.com, and Dentologie. We were able to speak with him about his time in high school, what his journey was like after high school, and his advice for students at Northport High School today.

If you were teleported back in time to Northport High School, what would be the first place you would go and why?

I think I would go to the tennis courts.  I played on the JV tennis team and have many fond memories of playing on those courts with teammates and having a lot of fun.

What were your favorite classes at Northport High School and why?

I had so many great teachers and classes, but there is one teacher and class which stands out for me after all these years.  During my senior year, I took AP English which was taught by Mr. William Sequin.  At the time, the class had the reputation for being very tough and it sure was.  Up until that time, I had been able to get good grades all through high school without working that hard, but Mr. Sequin had a different approach.  Right from the first paper, he was a tough critic and a hard grader.  During the first couple months of that class, I got the worst grades I had ever gotten in high school.  Rather than getting discouraged, I ended up working harder in that class than any class I had ever taken and by the spring, I was getting significantly better grades.  My lesson from that class was that hard work matters…a lot…and I incorporated that incredibly poignant lesson into my approach to college, my first job, and the rest of my career.  Years after graduation from Northport, I did have an opportunity to share with Mr. Sequin what a deep impact his teaching had on me and the appreciation I had for the level of care he must have had to be so tough.

Professionally, what were your goals during your high school years and how did those change over time? 

When I was in high school, I thought I was going to be a lawyer.  I didn’t really know what being a lawyer was like, but it sounded interesting.  As college progressed, I became more interested in business, which led to me going into investment banking after college.  I then went to business school and graduated from business school in 1997, at the beginning of the Internet boom.  There were tons of startups being created then and it whet my appetite for entrepreneurship.  This led to me joining a string of startups and ultimately to me starting Redbox.

How did you get the idea for Redbox? Did it relate in any way to your time renting movies as a high school student?

After being a part of two startups, I was recruited to McDonalds Corporation and asked to help them start new businesses.  Soon after my arrival, the CEO of McDonalds asked me to check out a little project that had just started called “Vending”.  It was an attempt by McDonalds to get into innovative vending concepts.  After spending some time with the small team, I concluded that the concept of innovative vending was interesting and promising but that the small team they had created were not the right folks to run this project.  The CEO asked me to take over the project and build my own team, which I did, bringing in entrepreneurial folks that I knew from previous startups.  We gave the project a name – Redbox – and over the next 11 years, built it from scratch to 45,000 kiosks, $2 billion in revenue and 2,500 employees.

Back to your question about the idea for Redbox, it wasn’t my idea.  At that time, 2002, there were a bunch of companies trying to create DVD rental kiosks.  We took that idea and ended up doing it much better than any of the competitors.

I didn’t have the idea as a high school student about renting DVDs out of a kiosk, but I did work as a check out clerk in an early video rental store (before the creation of DVDs) in Commack.

Did you have any ideas for businesses in high school that you tried in Northport?

I don’t recall starting any businesses myself in high school, but I did start a fun business in college at the University of Michigan.  I had read before my sophomore year that students at some big college football stadiums would bring bags of marshmallows and have marshmallow fights in the student section.  A roommate and I ran with that idea and went to Meijers (a big Walmart-like superstore in Michigan) and bought many cases of Marshmallows.  As I recall, our costs were something like 10 or 15 cents a bag.  We then sold the marshmallows for $1 per bag outside of Michigan Stadium.  The business took off and I recall that we each made $500+ in the first few games.  It was time to buy some more marshmallows at Meijers and we decided it was time to exit the business because other students copied our idea and were selling marshmallows right next to us outside the stadium.  It turned out to be great timing, because a few weeks later the University of Michigan outlawed bringing marshmallows into the stadium because they were getting stuck on the astroturf.  This probably led to my first lesson of business – know when to get out.

What advice do you have for students looking to go into business?

For now, do great at school and absorb everything you can.  Get great grades, get into a quality college and engage in the learning.  All the fundamentals – writing, reading, logical thinking, math – are instrumental in business.  You will have plenty of time to learn finance, marketing and operations, but these are all easier to absorb once you have the fundamentals down.

My other advice about business is to have a growth and learning mindset.  There is much to learn, so you should approach business with curiosity (about all there is to learn), with humility (about all the mistakes you will make) and with a self-awareness which allows you to continually adjust, learn and improve.

What would you say to your high school self?

It’s all going to work out.  Enjoy the ride.