My Early History as an Entrepreneur

Despite mostly cutting myself off from parental financing in high school, I’ve actually only had a “real� job for less than a year total in my life. I attribute this not to any great genius on my part, but rather to habit. It was what I was used to doing. I knew that I couldn’t get a job when I was a kid, and probably didn’t think too highly of them even back then, but I figured that there must be some way for me to make money on my own.

Tynan Park

I jumped in head first when I was ten, and, as a result, got in way over my head. One of they joys of my childhood was visiting a small amusement park in New Hampshire called “Canobie Lake Park�. I only got to go once or twice per summer, though, and I figured other kids were probably in the same boat. How great would it be if I opened up an amusement park in my neighborhood?

First I dug up my parents back yard (without permission) and made a miniature golf course. I put buckets of water in holes to serve as water features, made and flattened mounds of dirt to make grades, and fashioned parts of a croquet set into obstacles.

We had a rather steep driveway, so I raided my father’s lumber pile and built a track down the driveway that would serve as a roller coaster. I don’t remember exactly how it worked, but the car was a skateboard and I had tied a rope to it to pull it back up once the passenger reached the bottom.

Those were the main features, but I enlisted my neighborhood friends and together we also set up a few carnival style contests. We got one of the parents to bring us to the drug store to buy candy to give away as prizes.

Once the amusement wonderland was complete, I went off to sell tickets which I had drawn on cut out bits of blank paper. My pitch I delivered door to door:

“Hi, my name is Tynan and I have built an amusement park. It will be open every day for the next month and tickets are one dollar. Would you like to buy some?�

Most people were confused and asked if it was for a charity. When I said that I would be keeping the money, they would usually say no. A few said yes, though. After half an afternoon of hard work I sold $20 worth of tickets, which was about a billion dollars in 1992 10-year-old-dollars.

When I got back from my tough day as a salesman, I was delighted to see that one man had actually brought his daughter to the park. I proudly accepted his tickets and guided him to the golf course. He held his daughter’s arms as she swung the putter. All of us kids followed them around on the course, determined to make sure that they had a good time. When she finally completed the course we gave her a handful of candy and one of my brother’s stuffed animals, even though we hadn’t discussed and official mini-golf prize policy.

Once our first and only customer left, though, things went to hell fast. I discovered that one of the kids had eaten all of our prize candy. Infuriated, I shut down Tynan park twenty nine days early. I felt bad about not giving refunds, but didn’t remember who bought tickets and who didn’t. If you have a ticket, I’m happy to give you a refund now.

The Newton

I’m actually skipping a critical step in my path towards entrepreneurship, but the story isn’t all that exciting. My best friend and I made a bunch of friendship bracelets and sold them all summer long. This may sound like a cash cow to you, but the only thing I remember buying with the proceeds was a big cactus, which was later washed down a drain when I was camping out for Star Wars and a storm came through.

This story is about the first time I was able to make enough money to buy something more substantial than a potted succulent.

In graphic design class in high school I sat next to a really white kid. He was the kind of white that can only come from a place like Kentucky, and can only be preserved through complete abstinence from the sun.

We struck up a conversation about the Wacom tablet the class had, which is a digital pad that you draw on with a stylus and it magically translates your art to the screen.

“I have something like that at home. It’s called an Apple Newton, and it’s basically a portable computer that you write on with a pen. I’ll bring it in some time.�

A few days later, he brought it in. An Apple Newton 110. In case you don’t know, the Newton was a precursor to the Palm Pilot, which was a precursor to your iPhone.

He offered to loan it to me for a few days, and if I wanted to buy it he would sell it for $60. I took him up on the loan and fell in love with the thing over the weekend. It didn’t do much, but, man, was it neat.

I went online to see how much a Newton was worth. The 110 was worth around $60, as he’d priced it. Something was peculiar, though. His Newton had a clear plastic shell, while every other one I saw was black. I searched for “clear Newton�, and was shocked by what I read.

The clear Newtons were very rare and were given exclusively to Apple execs. They were worth hundreds, and hard to find even at that price. I brought $60 into school the next day and paid for my treasure.

I immediately went to the Newton Users Forum, where there was a forum for buying and selling Newtons. I posted an ad saying that I would like to trade my super-rare clear Newton 110 for a 120, 130, or maybe even the legendary Newton 2000. I had no idea I’d be making a business out of this — I just didn’t care about the color of the Newton and wanted to get the best one I could.

Emails flooded in. Most people were offering a 130, but one girl said she desperately wanted the clear one and would give me her 2000 in trade. I responded to her and the person with the best 130, and emailed both of them several times over the next few days. All of a sudden, at the verge of agreeing to the final terms, the girl with the 2000 changed her mind.

I couldn’t figure out why she had cold feet all of a sudden. I had my heart set on the 2000 and couldn’t imagine settling for a 130 anymore. I started deleting all of the Newton emails other than hers and the best 130. Their emails were next to each other in my inbox, and I noticed something: both of them had the same last name.

He was her father. As soon as I realized what was up I emailed him and told him that I was going to hold out for a 2000, and that if his daughter wanted it, she would have to trade hers. He was angry, but he finally caved.

Suddenly getting a shiny Newton wasn’t all that exciting anymore– I could make a business out of this. Back then eBay existed, but wasn’t popular. There were a few classifieds sites, like Classifieds2000.com, as well as item-specific classifieds like the Newton forum, but most people didn’t know about all these places.

Bouncing back and forth between the different auction sites, classifieds, and forums, I managed to trade up my Newton until I had a stock of Palm Pilots and laptops, which I would keep flipping. For four or five years, up until I started gambling professionally, I made my income buyng and selling small computers and PDAs. The money was great, but the most exciting part was being young and having access to all the toys and gadgets I lusted after.

I probably could have carried on without Tynan Park, but I sometimes wonder what would have happened if I hadn’t gotten such a good deal on that Newton. Maybe I’d be a manager at Wal-Mart.